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PiHKAL#62 DOB; SI#52 DOB
62
Variant: N α β R4 R5 skeleton isomers all
Analogues: 10 3 2 82 3 16 19 135

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 62065; ChemSpider: 55902; Drugs Forum: DOB; Erowid: DOB; Wikipedia: 2,5-Dimethoxy-4-bromoamphetamine

Shulgin Index: #52 DOB; Table: 5 Page: 340 Row: 28

See also PiHKAL: #8 ARIADNE
#10 B
#22 2C-C
#26 2C-F
#39 2C-T
#52 DESOXY
#54 2,5-DMA
#64 DOC
#65 DOEF
#67 DOI
#72 E
#124 META-DOB
#156 4-TM
#162 TMA-6
See also Pharmacology notes I: p. 152, DOB
p. 171, DOB: Enantiomeric effects
See also Pharmacology notes II: p. 226, DOB

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011.

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Shulgin, AT. Profiles of psychedelic drugs. 10. DOB. J. Psychoactive Drugs, 1 Jan 1981, 13 (1), 99. 775 kB. doi:10.1080/02791072.1981.10471457

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

Barfknecht, CF; Nichols, DE. Potential psychotomimetics. Bromomethoxyamphetamines. J. Med. Chem., 1 Jan 1971, 14 (4), 370–372. 377 kB. doi:10.1021/jm00286a026 Rhodium

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Shulgin, AT; Sargent, T; Naranjo, C. 4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog. Pharmacology, 1 Jan 1971, 5 (2), 103–107. 1030 kB. doi:10.1159/000136181

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Shulgin, AT. DOB and other possible prodrugs. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 May 2005.

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Sargent, T; Kalbhen, DA; Shulgin, AT; Stauffer, H; Kusubov, N. A potential new brain-scanning agent: 4-77Br-2,5-dimethoxyphenylisopropylamine (4-Br-DPIA). J. Nucl. Med., 1 Jan 1975, 16 (3), 243–245. 443 kB.

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Pigott, A; Frescas, SP; McCorvy, JD; Huang, X; Roth, BL; Nichols, DE. trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family. Beilstein J. Org. Chem, 0000, 8, 1705–1709. 298 kB. doi:10.3762/bjoc.8.194

McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. doi:10.1021/jm00212a001

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

McKenna, DJ; Saavedra, JM. Autoradiography of LSD and 2,5-dimethoxyphenylisopropylamine psychotomimetics demonstrates regional, specific cross-displacement in the rat brain. Eur. J. Pharmacol., 13 Oct 1987, 142 (2), 313–315. 263 kB. doi:10.1016/0014-2999(87)90121-X

Rasmussen, K; Glennon, RA; Aghajanian, GK. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Eur. J. Pharmacol., 2 Dec 1986, 132 (1), 79–82. 267 kB. doi:10.1016/0014-2999(86)90014-2

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Sargent, T; Kalbhen, DA; Shulgin, AT; Braun, G; Stauffer, H; Kusubov, N. In vivo human pharmacodynamics of the psychodysleptic 4-Br-2,5-dimethoxyphenylisopropylamine labelled with 82Br or 77Br. Neuropharmacology, 1 Jan 1975, 14 (3), 165–174. 1157 kB. doi:10.1016/0028-3908(75)90001-5

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Costa, JL; Wang, AY; Micke, GA; Maldaner, AO; Romano, RL; Martins-Júnior, HA; Neto, ON; Magg, MF. Chemical identification of 2,5-dimethoxy-4-bromoamphetamine (DOB). Forensic Sci. Int., 20 Dec 2007, 173 (2–3), 130–136. 285 kB. doi:10.1016/j.forsciint.2007.02.018

Schultz, DM; Prescher, JA; Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem., 1 Jan 2008, 16 (11), 6242–6251. 228 kB. doi:10.1016/j.bmc.2008.04.030

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Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Delliou, D. 4-Bromo-2,5-dimethoxyamphetamine: Psychoactivity, toxic effects and analytical methods. Forensic Sci. Int., 1 May 1983, 21 (3), 259–267. 1358 kB. doi:10.1016/0379-0738(83)90131-7

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

10 N analogues:
127
Analogue 1: Adding Methyl at N

METHYL-DOB
N-Me-DOB
M-154
4-Bromo-2,5-dimethoxy-N-methylamphetamine

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-N-methylpropan-2-amine

Formula: C12H18BrNO2 Molecular weight: 288.18082 g/mol InChI Key: GURVSGCCXMIFMQ-UHFFFAOYSA-N

InChI=1S/C12H18BrNO2/c1-8(14-2)5-9-6-12(16-4)10(13)7-11(9)15-3/h6-8,14H,5H2,1-4H3

PubChem CID: 10085486; ChemSpider: 8261023; Wikipedia: Methyl-DOB

Shulgin Index: See #52 DOB; Table: 5 Page: 340 Row: 30

See also Pharmacology notes II: p. 208, METHYL-DOB

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

445
Analogue 2: Adding Benzyl at N

DOB-NB
NB-DOB

IUPAC: N-Benzyl-1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine

Formula: C18H22BrNO2 Molecular weight: 364.27678 g/mol InChI Key: DCFUPFLURXVSAC-UHFFFAOYSA-N

InChI=1S/C18H22BrNO2/c1-13(20-12-14-7-5-4-6-8-14)9-15-10-18(22-3)16(19)11-17(15)21-2/h4-8,10-11,13,20H,9,12H2,1-3H3

PubChem CID: 10021657; ChemSpider: 8197230

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

444
Analogue 3: Adding Phenylbutyl at N

IUPAC: N-[1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-yl]-4-phenylbutan-1-amine

Formula: C21H28BrNO2 Molecular weight: 406.35652 g/mol InChI Key: QNUVDOAEGMVOPH-UHFFFAOYSA-N

InChI=1S/C21H28BrNO2/c1-16(23-12-8-7-11-17-9-5-4-6-10-17)13-18-14-21(25-3)19(22)15-20(18)24-2/h4-6,9-10,14-16,23H,7-8,11-13H2,1-3H3

PubChem CID: 10431435; ChemSpider: 8606862

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

443
Analogue 4: Adding Ethyl at N

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-N-ethylpropan-2-amine

Formula: C13H20BrNO2 Molecular weight: 302.2074 g/mol InChI Key: SMLWLIUZFXEVAQ-UHFFFAOYSA-N

InChI=1S/C13H20BrNO2/c1-5-15-9(2)6-10-7-13(17-4)11(14)8-12(10)16-3/h7-9,15H,5-6H2,1-4H3

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

384
Analogue 5: Adding 2-Methoxybenzyl at N

DOB-NBOMe
NBOMe-DOB
4-Bromo-2,5-dimethoxy-N-(2-methoxybenzyl)amphetamine

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)propan-2-amine

Formula: C19H24BrNO3 Molecular weight: 394.30276 g/mol InChI Key: VIURPEKIEYLSKF-UHFFFAOYSA-N

InChI=1S/C19H24BrNO3/c1-13(21-12-14-7-5-6-8-17(14)22-2)9-15-10-19(24-4)16(20)11-18(15)23-3/h5-8,10-11,13,21H,9,12H2,1-4H3

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

Anon. Personal communication of unpublished research. 1 Dec 2011.

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

383
Analogue 6: Adding 2-Hydroxybenzyl at N

DOB-NBOH
NBOH-DOB
4-Bromo-N-(2-hydroxybenzyl)-2,5-dimethoxyamphetamine

IUPAC: 2-({[1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-yl]amino}methyl)phenol

Formula: C18H22BrNO3 Molecular weight: 380.27618 g/mol InChI Key: RBWFJWZWKNOCJU-UHFFFAOYSA-N

InChI=1S/C18H22BrNO3/c1-12(20-11-13-6-4-5-7-16(13)21)8-14-9-18(23-3)15(19)10-17(14)22-2/h4-7,9-10,12,20-21H,8,11H2,1-3H3

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

2417
Analogue 7: Adding Dimethyl at N

N,N-Me-DOB
D-367
4-Bromo-2,5-dimethoxy-N,N-dimethylamphetamine

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine

Formula: C13H20BrNO2 Molecular weight: 302.2074 g/mol InChI Key: WXXRIBGUTSDGNE-UHFFFAOYSA-N

InChI=1S/C13H20BrNO2/c1-9(15(2)3)6-10-7-13(17-5)11(14)8-12(10)16-4/h7-9H,6H2,1-5H3

PubChem CID: 13781100; ChemSpider: 23240374

Shulgin Index: See #52 DOB; Table: 5 Page: 340 Row: 31

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

2429
Analogue 8: Adding Hydroxy at N

DOB-OH

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-N-hydroxypropan-2-amine

Formula: C11H16BrNO3 Molecular weight: 290.15364 g/mol InChI Key: MLKRRZYMIHQRHE-UHFFFAOYSA-N

InChI=1S/C11H16BrNO3/c1-7(13-14)4-8-5-11(16-3)9(12)6-10(8)15-2/h5-7,13-14H,4H2,1-3H3

7129
Analogue 9: Adding Acetyl at N

N-Acetyl-DOB
DOB-Ac

IUPAC: N-[1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-yl]acetamide

Formula: C13H18BrNO3 Molecular weight: 316.19092 g/mol InChI Key: JANVRHMWBQIUAH-UHFFFAOYSA-N

InChI=1S/C13H18BrNO3/c1-8(15-9(2)16)5-10-6-13(18-4)11(14)7-12(10)17-3/h6-8H,5H2,1-4H3,(H,15,16)

PubChem CID: 559931; ChemSpider: 486754

Shulgin Index: See #52 DOB; Table: 5 Page: 340 Row: 29

7151
Analogue 10: Adding n-Propyl at N

N-Pr-DOB

IUPAC: N-[1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-yl]propan-1-amine

Formula: C14H22BrNO2 Molecular weight: 316.23398 g/mol InChI Key: UGQKMZIPUUQGHA-UHFFFAOYSA-N

InChI=1S/C14H22BrNO2/c1-5-6-16-10(2)7-11-8-14(18-4)12(15)9-13(11)17-3/h8-10,16H,5-7H2,1-4H3

PubChem CID: 13547420; ChemSpider: 23117226

Shulgin Index: See #52 DOB; Table: 5 Page: 341 Row: 1

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Three α analogues:
20
Analogue 1: Removing Methyl at α

2C-B
4-Bromo-2,5-dimethoxyphenethylamine

IUPAC: 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine

Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: YMHOBZXQZVXHBM-UHFFFAOYSA-N

InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 98527; ChemSpider: 88978; Drugs Forum: 2C-B; Erowid: 2C-B; Wikipedia: 2C-B

Shulgin Index: #18 2C-B; Table: 5 Page: 340 Row: 23

See also PiHKAL: #9 ASB
#10 B
#14 BOD
#16 BOHD
#22 2C-C
#23 2C-D
#25 3C-E
#30 2C-G-5
#32 2C-H
#33 2C-I
#34 2C-N
#39 2C-T
#41 2C-T-4
#43 2C-T-7
#50 4-D
#65 DOEF
#72 E
#118 MDPR
#122 MEM
#170 5-TOET
See also TiHKAL: #5 α,O-DMS #37 5-MeO-DIPT  
See also Pharmacology notes I: p. 172, 2C-B: Trials
See also Pharmacology notes II: app. 2, Abuse week
p. 204, 2C-B
p. 211, 2C-B
p. 279, 2C-B
p. 303, 2C-B
p. 305, 2C-B
p. 309, 2C-B
p. 323, 2C-B

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Caudevilla-Gálligo, F; Riba, J; Ventura, M; González, D; Farré, M; Barbanoj, MJ; Bouso, JC. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. J. Psychopharmacol., 1 Jul 2012, 26 (7), 1026–1035. 586 kB. doi:10.1177/0269881111431752

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

Shulgin, AT. 2,5-Dimethoxy-4-bromophenethylamine (2C-B). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 7 Feb 2003.

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Boer, D; Gijzels, MJ; Bosman, IJ; Maes, RAA. More data about the new psychoactive drug 2C-B. J. Anal. Toxicol., 0000, 23 (3), 227–228. 190 kB. doi:10.1093/jat/23.3.227

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Páleníček, T; Fujáková, M; Brunovský, M; Horáček, J; Gorman, I; Balíková, M; Rambousek, L; Syslová, K; Kačer, P; Zach, P; Bubeníková-Valešová, V; Tylš, F; Kubešová, A; Puskarčíková, J; Höschl, C. Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats. Psychopharmacology, 1 Jan 2013, 225 (1), 75–93. 1079 kB. doi:10.1007/s00213-012-2797-7

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36

McLean, TH; Parrish, JC; Braden, MR; Marona-Lewicka, D; Gallardo-Godoy, A; Nichols, DE. 1-Aminomethylbenzocycloalkanes: Conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J. Med. Chem., 1 Jan 2006, 49 (19), 5794–5803. 522 kB. doi:10.1021/jm060656o

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Carmo, H; Hengstler, JG; Boer, D; Ringel, M; Remião, F; Carvalho, F; Fernandes, E; Reys, LA; Oesch, F; Bastos, ML. Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology, 5 Jan 2005, 206 (1), 75–89. 273 kB. doi:10.1016/j.tox.2004.07.004

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

185
Analogue 2: Substituting Ethyl for Methyl at α

4C-DOB
1-(2,5-Dimethoxy-4-bromophenyl)-2-aminobutane

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine

Formula: C12H18BrNO2 Molecular weight: 288.18082 g/mol InChI Key: QQPRORAZQWLMTQ-UHFFFAOYSA-N

InChI=1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3

PubChem CID: 12140147; ChemSpider: 23256805

Shulgin Index: See #52 DOB; Table: 5 Page: 341 Row: 7

See also PiHKAL: #8 ARIADNE    

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1125 kB. doi:10.1021/jm00176a010

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

255
Analogue 3: Substituting Carboxy for Methyl at α

α-Carboxy-2C-B
4-Bromo-2,5-dimethoxyphenylalanine

IUPAC: 2-Amino-3-(4-bromo-2,5-dimethoxyphenyl)propanoic acid

Formula: C11H14BrNO4 Molecular weight: 304.13716 g/mol InChI Key: OSOJBJTVFFPDMV-UHFFFAOYSA-N

InChI=1S/C11H14BrNO4/c1-16-9-5-7(12)10(17-2)4-6(9)3-8(13)11(14)15/h4-5,8H,3,13H2,1-2H3,(H,14,15)

PubChem CID: 22326393

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). III. Some derivatives of 3-phenylalanine. Can. J. Chem., 1 Feb 1974, 52 (3), 390–394. 316 kB. doi:10.1139/v74-062

Two β analogues:
442
Analogue 1: Adding Methoxy at β

β-MeO-DOB

IUPAC: 1-(4-Bromo-2,5-dimethoxyphenyl)-1-methoxypropan-2-amine

Formula: C12H18BrNO3 Molecular weight: 304.18022 g/mol InChI Key: JZRYUHHXNUHBTB-UHFFFAOYSA-N

InChI=1S/C12H18BrNO3/c1-7(14)12(17-4)8-5-11(16-3)9(13)6-10(8)15-2/h5-7,12H,14H2,1-4H3

PubChem CID: 58644857

Shulgin Index: See #13 BOD; Table: 5 Page: 341 Row: 5

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

441
Analogue 2: Adding Hydroxy at β

β-HO-DOB

IUPAC: 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)propan-1-ol

Formula: C11H16BrNO3 Molecular weight: 290.15364 g/mol InChI Key: YLLHAHHNKOUOSR-UHFFFAOYSA-N

InChI=1S/C11H16BrNO3/c1-6(13)11(14)7-4-10(16-3)8(12)5-9(7)15-2/h4-6,11,14H,13H2,1-3H3

PubChem CID: 58644855; ChemSpider: 27750072

Shulgin Index: See #13 BOD; Table: 5 Page: 341 Row: 4

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

82 R4 analogues:
3
Analogue 1: Substituting Methylthio for Bromo at R4

ALEPH
DOT
PARA-DOT
4-Methylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-methylthioamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine

Formula: C12H19NO2S Molecular weight: 241.34976 g/mol InChI Key: COBYBOVXXDQRAU-UHFFFAOYSA-N

InChI=1S/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

PubChem CID: 143828; ChemSpider: 126887; Wikipedia: Aleph (psychedelic)

Shulgin Index: #3 ALEPH; Table: 5 Page: 345 Row: 13

See also PiHKAL: #4 ALEPH-2
#39 2C-T
#44 2C-T-8
#45 2C-T-9
#125 META-DOT
#139 ORTHO-DOT
#167 4T-MMDA-2
See also TiHKAL: #2 DBT #46 5-MeS-DMT  
See also Pharmacology notes I: p. 178, ALEPH: Trials
p. 200, Additional detail on PARADOT; additional trials

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon Press, New York, 1 Jan 1978; pp 74–84. 547 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

Jacob, P; Anderson, G; Meshul, CK; Shulgin, AT; Castagnoli, N. Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 1977, 20 (10), 1235–1239. 717 kB. doi:10.1021/jm00220a001

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Nichols, DE; Shulgin, AT. Sulfur analogs of psychotomimetic amines. J. Pharm. Sci., 1 Jan 1976, 65 (1), 1554–1556. 383 kB. doi:10.1002/jps.2600651040 Rhodium.

4
Analogue 2: Substituting Ethylthio for Bromo at R4

ALEPH-2
4-Ethylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-ethylthioamphetamine

IUPAC: 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: MCYCODJKXUJSAT-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 10264356; ChemSpider: 8439835; Wikipedia: Aleph (psychedelic)

Shulgin Index: #4 ALEPH-2; Table: 5 Page: 345 Row: 19

See also PiHKAL: #47 2C-T-15    
See also TiHKAL: #46 5-MeS-DMT    
See also Pharmacology notes I: p. 194, ALEPH-2: Trials
See also Pharmacology notes II: p. 205, ALEPH-2
p. 220, ALEPH-2
p. 318, ALEPH-2

Reyes-Parada, M; Scorza, C; Romero, V; Silveira, R; Medina, JH; Andrus, D; Nichols, DE; Cassels, BK. (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors. N-S. Arch. Pharmacol., 1 Nov 1996, 354 (5), 579–585. 1417 kB. doi:10.1007/BF00170831

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Rezende, MC; Núñez, C; Sepúlveda-Boza, S; Cassels, BK; Hurtado-Guzmán, C. S-Oxidation products of alkylthioamphetamines. Synth. Commun., 1 Jan 2002, 32 (17), 2741–2750. 225 kB. doi:10.1081/SCC-120006041

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

Acuña-Castillo, C; Scorza, C; Reyes-Parada, M; Cassels, BK; Huidobro-Toro, JP. ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2A and 5-HT2C receptor agonist. Life Sci., 17 Nov 2000, 67 (26), 3241–3247. 89 kB. doi:10.1016/S0024-3205(00)00906-1

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Scorza, MC; Reyes-Parada, M; Silveira, R; Viola, H; Medina, JH; Viana, MB; Zangrossi, H; Graeff, FG. Behavioral effects of the putative anxiolytic (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice. Pharmacol. Biochem. Behav., 1 May 1996, 54 (2), 355–361. 504 kB. doi:10.1016/0091-3057(95)02149-3

5
Analogue 3: Substituting Isopropylthio for Bromo at R4

ALEPH-4
4-Isopropylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-isopropylthioamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-ylsulfanyl)phenyl]propan-2-amine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: BCWCXWKCQMBFBQ-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-9(2)18-14-8-12(16-4)11(6-10(3)15)7-13(14)17-5/h7-10H,6,15H2,1-5H3

PubChem CID: 44350301; ChemSpider: 21500994; Wikipedia: Aleph (psychedelic)

Shulgin Index: #5 ALEPH-4; Table: 5 Page: 345 Row: 34

See also PiHKAL: #4 ALEPH-2 #7 ALEPH-7  
See also Pharmacology notes II: app. 5, Untitled
p. 219, ALEPH-4
p. 265, ALEPH-4
p. 266, ALEPH-4
p. 268, ALEPH-4
p. 282, ALEPH-4: Report of experience
p. 294, ALEPH-4
p. 296, ALEPH-4: Report of experience
p. 297, ALEPH-4: Report of experience
p. 300, ALEPH-4
p. 301, ALEPH-4
p. 302, ALEPH-4

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

6
Analogue 4: Substituting Phenylthio for Bromo at R4

ALEPH-6
4-Phenylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-phenylthioamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(phenylsulfanyl)phenyl]propan-2-amine

Formula: C17H21NO2S Molecular weight: 303.41914 g/mol InChI Key: CSOTVYXYZSJOFL-UHFFFAOYSA-N

InChI=1S/C17H21NO2S/c1-12(18)9-13-10-16(20-3)17(11-15(13)19-2)21-14-7-5-4-6-8-14/h4-8,10-12H,9,18H2,1-3H3

PubChem CID: 44719475; ChemSpider: 23552980; Wikipedia: Aleph (psychedelic)

Shulgin Index: See #3 ALEPH; Table: 5 Page: 346 Row: 14

See also PiHKAL: #4 ALEPH-2    
See also Pharmacology notes II: p. 221, ALEPH-6

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

7
Analogue 5: Substituting n-Propylthio for Bromo at R4

ALEPH-7
4-Propylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-n-propylthioamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]propan-2-amine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: XHWDHFUBCVWXDZ-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3

PubChem CID: 11197521; ChemSpider: 9372590; Wikipedia: Aleph (psychedelic)

Shulgin Index: #6 ALEPH-7; Table: 5 Page: 345 Row: 29

See also PiHKAL: #4 ALEPH-2    
See also TiHKAL: #17 4-HO-DIPT    
See also Pharmacology notes II: p. 223, ALEPH-7

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

54
Analogue 6: Removing Bromo at R4

2,5-DMA
DMA
DOH
2,5-Dimethoxyamphetamine

IUPAC: 1-(2,5-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: LATVFYDIBMDBSY-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 62787; ChemSpider: 56526; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17, #36 2,5-DMA; Table: 4 Page: 335 Row: 22

See also PiHKAL: #55 3,4-DMA
#62 DOB
#64 DOC
#67 DOI
#90 IDNNA
#124 META-DOB
#126 METHYL-DMA
See also Pharmacology notes I: p. 57, 2,5-DMA: Subacute evaluation
p. 58, 2,5-DMA: Subjective response
See also Pharmacology notes II: p. 276, 2,5-DMA

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011.

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

61
Analogue 7: Substituting n-Pentyl for Bromo at R4

DOAM
4-Amyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-n-amylamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-pentylphenyl)propan-2-amine

Formula: C16H27NO2 Molecular weight: 265.39108 g/mol InChI Key: VLJORLCVOAUUKM-UHFFFAOYSA-N

InChI=1S/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3

PubChem CID: 12262512; ChemSpider: 10440619; Wikipedia: 2,5-Dimethoxy-4-amylamphetamine

Shulgin Index: #51 DOAM; Table: 5 Page: 344 Row: 6

See also PiHKAL: #64 DOC #66 DOET #71 DOPR
See also Pharmacology notes I: p. 170, DOAM: Trials

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

63
Analogue 8: Substituting n-Butyl for Bromo at R4

DOBU
4-Butyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-n-butylamphetamine

IUPAC: 1-(4-Butyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: NGVDYAULSQKEGW-UHFFFAOYSA-N

InChI=1S/C15H25NO2/c1-5-6-7-12-9-15(18-4)13(8-11(2)16)10-14(12)17-3/h9-11H,5-8,16H2,1-4H3

PubChem CID: 10060720; ChemSpider: 8236274; Wikipedia: 2,5-Dimethoxy-4-butylamphetamine

Shulgin Index: #53 DOBU; Table: 5 Page: 343 Row: 36

See also PiHKAL: #61 DOAM    

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

64
Analogue 9: Substituting Chloro for Bromo at R4

DOC
4-Chloro-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-chloroamphetamine

IUPAC: 1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16ClNO2 Molecular weight: 229.70324 g/mol InChI Key: ACRITBNCBMTINK-UHFFFAOYSA-N

InChI=1S/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 542036; ChemSpider: 472008; Drugs Forum: DOC; Erowid: DOC; Wikipedia: 2,5-Dimethoxy-4-chloroamphetamine

Shulgin Index: #54 DOC; Table: 5 Page: 340 Row: 20

See also PiHKAL: #22 2C-C #39 2C-T  
See also Pharmacology notes I: p. 162, DOC

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Ehlers, D; Schäning, J. Synthese von DOC (2,5-dimethoxy-4-chloramphetamin). Toxichem Krimtech, 2000, 68 (2), 62–68. 185 kB.

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013.

65
Analogue 10: Substituting 2-Fluoroethyl for Bromo at R4

DOEF
4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine

IUPAC: 1-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C13H20FNO2 Molecular weight: 241.3018032 g/mol InChI Key: QLENKWFQUHHBKZ-UHFFFAOYSA-N

InChI=1S/C13H20FNO2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4-6,15H2,1-3H3

PubChem CID: 14201982; ChemSpider: 21106293; Wikipedia: 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 24

See also PiHKAL: #49 2C-T-21    

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Gerdes, JM; Keil, RN; Shulgin, AT; Mathis, CA. High pressure nucleophilic fluoride-ion substitution reactions: formation of fluoroalkylbenzenes. J. Fluorine Chem., 1 Jan 1996, 78 (2), 121–129. 900 kB. doi:10.1016/0022-1139(96)03417-3

Gerdes, JM; Mathis, CA; Shulgin, AT. Synthesis of 1-[2′,5′-dimethoxy-4′-(p-β;-fluoroethyl)phenyl]-2-aminopropane: Studies related to 18F-labeled serotonin receptor ligands. Tetrahedron Lett., 1 Jan 1988, 129 (50), 6537–6540. 268 kB. doi:10.1016/S0040-4039(00)82391-6

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011.

66
Analogue 11: Substituting Ethyl for Bromo at R4

DOET
HECATE
4-Ethyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-ethylamphetamine

IUPAC: 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: HXJKWPGVENNMCC-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3

PubChem CID: 27402; ChemSpider: 25499; Wikipedia: 2,5-Dimethoxy-4-ethylamphetamine

Shulgin Index: #56 DOET; Table: 5 Page: 343 Row: 13

See also PiHKAL: #8 ARIADNE
#14 BOD
#24 2C-E
#61 DOAM
#65 DOEF
#72 E
#85 GANESHA
#162 TMA-6
#170 5-TOET
See also Pharmacology notes I: p. 95, DOET: Subacute evaluation
p. 110, DOET: Subjective response
p. 111, DOET: Subjective response
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 213, DOET

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Ger, A; Ger, D. Triple Goddess of the Night. British Neuroscience Association Bulletin, 1 Mar 2011, 63, 28–30. 234 kB. Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Snyder, SH; Weingartner, H; Faillace, LA. DOET (2,5-dimethoxy-4-ethylamphetamine) and DOM (STP) (2,5-dimethoxy-4-methylamphetamine), new psychotropic agents: Their effects in man. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 247–264. 2550 kB.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB.

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013.

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

67
Analogue 12: Substituting Iodo for Bromo at R4

DOI
4-Iodo-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-iodoamphetamine

IUPAC: 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: BGMZUEKZENQUJY-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 1229; ChemSpider: 1192; Erowid: DOI; Wikipedia: 2,5-Dimethoxy-4-iodoamphetamine

Shulgin Index: #58 DOI; Table: 5 Page: 341 Row: 12

See also PiHKAL: #22 2C-C
#26 2C-F
#33 2C-I
#39 2C-T
#54 2,5-DMA
#62 DOB
#64 DOC
#65 DOEF
#71 DOPR
#72 E
#90 IDNNA
#105 MDDM
#162 TMA-6
See also TiHKAL: #51 PRO-LAD    
See also Pharmacology notes I: p. 173, DOI: Trials

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013.

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol., 1 Jan 2006, 70 (6), 1956–1964. 361 kB. doi:10.1124/mol.106.028720

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Sargent, T; Shulgin, AT; Mathis, CA. Radiohalogen-labeled imaging agents. 3. Compounds for measurement of brain blood flow by emission tomography. J. Med. Chem., 1 Jan 1984, 27 (8), 1071–1077. 1859 kB. doi:10.1021/jm00374a023 Rhodium.

Braun, U; Shulgin, AT; Braun, G; Sargent, T. Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs. J. Med. Chem., 1 Jan 1977, 20 (12), 1543–1546. 1124 kB. doi:10.1021/jm00222a001

Pigott, A; Frescas, SP; McCorvy, JD; Huang, X; Roth, BL; Nichols, DE. trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family. Beilstein J. Org. Chem, 0000, 8, 1705–1709. 298 kB. doi:10.3762/bjoc.8.194

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Schindler, EAD. Behavioral and biochemical distinctions in the pharmacology of two common hallucinogens. Ph. D. Thesis, Drexel University, Philadelphia, PA, USA, 1 Apr 2010. 5870 kB.

Ang, RLL. Molecular basis of the action of hallucinogens. Ph. D. Thesis, New York University, New York, NY, USA, 2010. 2402 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Sargent, T; Budinger, TF; Braun, G; Shulgin, AT; Braun, U. An iodinated catecholamine congener for brain imaging and metabolic studies. J. Nucl. Med., 1 Jan 1978, 19 (1), 71–76. 922 kB.

Sargent, T; Braun, G; Braun, U; Budinger, TF; Shulgin, AT. Brain and retina uptake of a radio-iodine labeled psychotomimetic in dog and monkey. Commun. Psychopharmacol., 1 Jan 1978, 2 (1), 1–10. 1988 kB.

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Fox, MA; French, HT; LaPorte, JL; Blackler, AR; Murphy, DL. The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis. Psychopharmacology, 1 Sep 2010, 212 (1), 13–23. 240 kB. doi:10.1007/s00213-009-1694-1

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioural effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. doi:10.1007/s00213-002-1141-z

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Dawson, BA; Black, DB; Sy, W; Graham, K. 13C NMR of some iodinated methoxy-amphetamines. Magn. Reson. Chem., 1 Sep 1994, 32 (9), 557–558. 171 kB. doi:10.1002/mrc.1260320913

Sargent, T; Shulgin, AT; Mathis, CA. New iodinated amphetamines by rapid synthesis for use as brain blood flow indicators. J. Labelled Compd. Radiopharm., 1 Jan 1984, 19 (11–12), 1307–1308. 84 kB. doi:10.1002/jlcr.2580191102

Braun, G; Shulgin, AT; Sargent, T. Synthesis of 123I-labelled 4-iodo-2,5-dimethoxyphenylisopropylamine. J. Labelled Compd. Radiopharm., 1 Jan 1978, 14 (5), 767–773. 291 kB. doi:10.1002/jlcr.2580140515 Rhodium.

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

McKenna, DJ; Mathis, CA; Shulgin, AT; Sargent, T; Saavedra, JM. Autoradiographic localization of binding sites for 125I-DOI, a new psychotomimetic radioligand, in the rat brain. Eur. J. Pharmacol., 1 Jan 1987, 137 (2–3), 289–290. 232 kB. doi:10.1016/0014-2999(87)90239-1

Huang, X; Nichols, DE. 5-HT2 receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 1 Jan 1993, 238 (2–3), 291–296. 553 kB. doi:10.1016/0014-2999(93)90859-G

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Schindler, EAD; Dave, KD; Smolock, EM; Aloyo, VJ; Harvey, JA. Serotonergic and dopaminergic distinctions in the behavioral pharmacology of (±)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Pharmacol. Biochem. Behav., 1 Mar 2012, 101 (1), 69–76. 722 kB. doi:10.1016/j.pbb.2011.12.002

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Moreno, JL; Holloway, T; Albizu, L; Sealfon, SC; González-Maeso, J. Metabotropic glutamate mGlu2 receptor is necessary for the pharmacological and behavioral effects induced by hallucinogenic 5-HT2A receptor agonists. Neurosci. Lett., 15 Apr 2011, 493 (3), 76–79. 196 kB. doi:10.1016/j.neulet.2011.01.046

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Sy, W. Iodination of methoxyamphetamines with iodine and silver sulphate. Tetrahedron Lett., 24 Sep 1993, 34 (39), 6223–6224. 133 kB. doi:10.1016/S0040-4039(00)73715-4

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

68
Analogue 13: Substituting Methyl for Bromo at R4

DOM
STP
4-Methyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-methylamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: NTJQREUGJKIARY-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3

PubChem CID: 85875; ChemSpider: 77462; Erowid: DOM; Wikipedia: 2,5-Dimethoxy-4-methylamphetamine

Shulgin Index: #60 DOM; Table: 5 Page: 342 Row: 15

See also PiHKAL: #4 ALEPH-2
#8 ARIADNE
#11 BEATRICE
#12 BIS-TOM
#14 BOD
#23 2C-D
#52 DESOXY
#56 DMCPA
#58 DMMDA
#59 DMMDA-2
#61 DOAM
#63 DOBU
#64 DOC
#66 DOET
#67 DOI
#69 Ψ-DOM
#71 DOPR
#79 F-2
#85 GANESHA
#93 IRIS
#123 MEPEA
#125 META-DOT
#127 METHYL-DOB
#142 PEA
#162 TMA-6
#167 4T-MMDA-2
#170 5-TOET
#171 2-TOM
See also TiHKAL: #2 DBT #17 4-HO-DIPT  
See also Pharmacology notes I: p. 84, nor-oxy-4-TMA-2: Subjective response
p. 88, DOM: Subjective response
p. 89, DOM: Subjective response
p. 92, DOM: Subjective response
p. 101, DOM: Animal pharmacology
p. 102, DOM: Subjective response
p. 103, DOM: Subjective response
p. 106, DOM: Subjective response
p. 165, DOM: Enantiomeric effects
See also Pharmacology notes II: p. 212, DOM
p. 216, DOM

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Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

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Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

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Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Oberlender, R; Ramachandran, PV; Johnson, MP; Huang, X; Nichols, DE. Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines. J. Med. Chem., 1 Jan 1995, 38 (18), 3593–3601. 1288 kB. doi:10.1021/jm00018a019

70
Analogue 14: Substituting Nitro for Bromo at R4

DON
4-Nitro-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-nitroamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine

Formula: C11H16N2O4 Molecular weight: 240.25574 g/mol InChI Key: JQJRESSXOVAECC-UHFFFAOYSA-N

InChI=1S/C11H16N2O4/c1-7(12)4-8-5-11(17-3)9(13(14)15)6-10(8)16-2/h5-7H,4,12H2,1-3H3

PubChem CID: 105432; ChemSpider: 95083; Wikipedia: 2,5-Dimethoxy-4-nitroamphetamine

Shulgin Index: #61 DON; Table: 5 Page: 342 Row: 3

See also PiHKAL: #39 2C-T
#54 2,5-DMA
#64 DOC
#72 E
 

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

71
Analogue 15: Substituting n-Propyl for Bromo at R4

DOPR
4-Propyl-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-n-propylamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine

Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: UEEAUFJYLUJWQJ-UHFFFAOYSA-N

InChI=1S/C14H23NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3

PubChem CID: 542051; ChemSpider: 472021; Wikipedia: 2,5-Dimethoxy-4-propylamphetamine

Shulgin Index: #62 DOPR; Table: 5 Page: 343 Row: 32

See also PiHKAL: #36 2C-P    
See also Pharmacology notes I: p. 115, DOPR: Subjective effects
p. 124, DOPR: Subjective effects
p. 132, DOPR: Subjective effects
See also Pharmacology notes II: app. 4, Experiment for Death Valley

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

122
Analogue 16: Substituting Ethoxy for Bromo at R4

MEM
2,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ITZLAXJQDMGDEO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 542053; ChemSpider: 472023; Wikipedia: 2,5-Dimethoxy-4-ethoxyamphetamine

Shulgin Index: #87 MEM; Table: 5 Page: 344 Row: 32

See also PiHKAL: #35 2C-O-4
#72 E
#73 EEE
#74 EEM
#76 EMM
#93 IRIS
#121 MEE
#136 MME
#138 MPM
See also TiHKAL: #19 5-HO-DMT #46 5-MeS-DMT  
See also Pharmacology notes I: p. 78, MEM: Subacute evaluation
p. 80, MEM: Marginal effects
p. 112, MEM: Subjective response
p. 151, MEM
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 229, MEM
p. 260, MEM
p. 270, MEM
p. 380, MEM

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

By, AW; Dawson, BA; Lodge, BA; Neville, GA; Sy, W; Zamecnik, J. Synthesis and spectral properties of 2,5-dimethoxy-4-ethoxyamphetamine and its precursors. J. Forensic Sci., 1 Mar 1990, 35 (2), 316–335. 538 kB. doi:10.1520/JFS12833J

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

138
Analogue 17: Substituting n-Propoxy for Bromo at R4

MPM
2,5-Dimethoxy-4-propoxyamphetamine
2,5-Dimethoxy-4-n-propoxyamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-propoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: YORRDSMCIGRARV-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3

PubChem CID: 542069; ChemSpider: 472038; Wikipedia: MPM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 1

See also PiHKAL: #35 2C-O-4    
See also Pharmacology notes I: p. 82, MPM: Subacute evaluation
See also Pharmacology notes II: p. 257, MPM

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

158
Analogue 18: Substituting Methoxy for Bromo at R4

TMA-2
2,4,5-Trimethoxyamphetamine

IUPAC: 1-(2,4,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: TVSIMAWGATVNGK-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C12H19NO3/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

PubChem CID: 31014; ChemSpider: 28773; Drugs Forum: TMA-2; Erowid: TMA-2; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #118 TMA-2; Table: 5 Page: 344 Row: 23

See also PiHKAL: #35 2C-O-4
#42 Ψ-2C-T-4
#52 DESOXY
#69 Ψ-DOM
#73 EEE
#75 EME
#76 EMM
#93 IRIS
#120 MEDA
#121 MEE
#122 MEM
#136 MME
#138 MPM
#139 ORTHO-DOT
#145 TA
#157 TMA
#162 TMA-6
#167 4T-MMDA-2
#168 TMPEA
See also TiHKAL: #13 Harmaline #19 5-HO-DMT #46 5-MeS-DMT
See also Pharmacology notes I: p. 54, TMA-2: Subacute evaluation
p. 55, TMA-2: Subjective response
p. 56, TMA-2: Subjective response
p. 64, TMA-2: Subjective response
p. 65, TMA-2: Subjective response
p. 72, SARs
p. 108, TMA-2: Subjective response
p. 151, TMA-2
p. 160, TMA-2
p. 161, TMA-2
p. 185, TMA-2: Qualitative description
See also Pharmacology notes II: p. 224, TMA-2

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-@. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. doi:10.1080/02791072.1976.10471846

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Anon. Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

Tsujikawa, K; Kanamori, T; Kuwayama, K; Miyaguchi, H; Iwata, YT; Inoue, H. Analytical profiles for 3,4,5-, 2,4,5-, and 2,4,6-trimethoxyamphetamine. Microgram J., 1 Jan 2006, 4 (1–4), 12–23. 162 kB.

Sargent, T; Shulgin, AT; Kusubov, N. Quantitative measurement of demethylation of [14]C-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharmacol. Commun., 1 Jan 1976, 2 (3), 199–206. 8643 kB.

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

208
Analogue 19: Substituting Fluoro for Bromo at R4

DOF
2,5-Dimethoxy-4-fluoro-amphetamine
4-Fluoro-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16FNO2 Molecular weight: 213.2486432 g/mol InChI Key: NRANUECGGQVXOT-UHFFFAOYSA-N

InChI=1S/C11H16FNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 23844155; ChemSpider: 23108678; Wikipedia: 2,5-Dimethoxy-4-fluoroamphetamine

Shulgin Index: #57 DOF; Table: 5 Page: 340 Row: 18

See also PiHKAL: #14 BOD #22 2C-C #26 2C-F

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

235
Analogue 20: Substituting Isobutyl for Bromo at R4

DOIB
2,5-Dimethoxy-4-(2-methylpropyl)amphetamine
2,5-Dimethoxy-4-isobutylamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]propan-2-amine

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: ZLESHKOTWSWEGW-UHFFFAOYSA-N

InChI=1S/C15H25NO2/c1-10(2)6-12-8-15(18-5)13(7-11(3)16)9-14(12)17-4/h8-11H,6-7,16H2,1-5H3

PubChem CID: 44374984; ChemSpider: 23231800

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 3

See also PiHKAL: #63 DOBU    

Oberlender, RA; Kothari, PJ; Nichols, DE; Zabik, JE. Substituent branching in phenethylamine-type hallucinogens: A comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane. J. Med. Chem., 1 Jan 1984, 27 (6), 788–792. 764 kB. doi:10.1021/jm00372a015

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

236
Analogue 21: Substituting tert-Butyl for Bromo at R4

DOTB
2,5-Dimethoxy-4-(1,1-dimethylethyl)amphetamine
2,5-Dimethoxy-4-tert-butylamphetamine

IUPAC: 1-(4-tert-Butyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: RUAUPNFNQOGIFF-UHFFFAOYSA-N

InChI=1S/C15H25NO2/c1-10(16)7-11-8-14(18-6)12(15(2,3)4)9-13(11)17-5/h8-10H,7,16H2,1-6H3

PubChem CID: 12262514; ChemSpider: 10440072

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 5

See also PiHKAL: #63 DOBU    
See also Pharmacology notes I: p. 100, DOTB: Subacute evaluation

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

237
Analogue 22: Substituting sec-Butyl for Bromo at R4

DOSB
2,5-Dimethoxy-4-(1-methylpropyl)amphetamine
2,5-Dimethoxy-4-sec-butylamphetamine

IUPAC: 1-[4-(Butan-2-yl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: VEQUTPSVRQTUHR-UHFFFAOYSA-N

InChI=1S/C15H25NO2/c1-6-10(2)13-9-14(17-4)12(7-11(3)16)8-15(13)18-5/h8-11H,6-7,16H2,1-5H3

PubChem CID: 146057; ChemSpider: 128843

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 4

See also PiHKAL: #63 DOBU    

Oberlender, RA; Kothari, PJ; Nichols, DE; Zabik, JE. Substituent branching in phenethylamine-type hallucinogens: A comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane. J. Med. Chem., 1 Jan 1984, 27 (6), 788–792. 764 kB. doi:10.1021/jm00372a015

Oberlender, R; Ramachandran, PV; Johnson, MP; Huang, X; Nichols, DE. Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines. J. Med. Chem., 1 Jan 1995, 38 (18), 3593–3601. 1288 kB. doi:10.1021/jm00018a019

238
Analogue 23: Substituting Amino for Bromo at R4

DONH
DOA
2,5-Dimethoxy-4-aminoamphetamine

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxyaniline

Formula: C11H18N2O2 Molecular weight: 210.27282 g/mol InChI Key: YUGDRVMIVMZKEL-UHFFFAOYSA-N

InChI=1S/C11H18N2O2/c1-7(12)4-8-5-11(15-3)9(13)6-10(8)14-2/h5-7H,4,12-13H2,1-3H3

PubChem CID: 15284796; ChemSpider: 23108725

Shulgin Index: See #61 DON; Table: 5 Page: 341 Row: 30

See also PiHKAL: #64 DOC #66 DOET  

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

239
Analogue 24: Substituting Acetylamino for Bromo at R4

DOAA
2,5-Dimethoxy-4-acetamidoamphetamine

IUPAC: N-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]acetamide

Formula: C13H20N2O3 Molecular weight: 252.3095 g/mol InChI Key: DQGBCNCIAFEAEQ-UHFFFAOYSA-N

InChI=1S/C13H20N2O3/c1-8(14)5-10-6-13(18-4)11(15-9(2)16)7-12(10)17-3/h6-8H,5,14H2,1-4H3,(H,15,16)

PubChem CID: 69390424

Shulgin Index: See #61 DON; Table: 5 Page: 341 Row: 34

See also PiHKAL: #64 DOC    

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

245
Analogue 25: Substituting 1-Hydroxypropyl for Bromo at R4

Hydroxy-DOPR
2,5-Dimethoxy-4-(1-hydroxypropyl)amphetamine

IUPAC: 1-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]propan-1-ol

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: WMEOYAANTKOSDW-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-12(16)11-8-13(17-3)10(6-9(2)15)7-14(11)18-4/h7-9,12,16H,5-6,15H2,1-4H3

PubChem CID: 69396146

See also PiHKAL: #71 DOPR    
See also Pharmacology notes I: p. 198, Hydroxy DOP
246
Analogue 26: Substituting Isopropyl for Bromo at R4

DOIP
2,5-Dimethoxy-4-isopropylamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-yl)phenyl]propan-2-amine

Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: SPKSLAUXKHSASF-UHFFFAOYSA-N

InChI=1S/C14H23NO2/c1-9(2)12-8-13(16-4)11(6-10(3)15)7-14(12)17-5/h7-10H,6,15H2,1-5H3

PubChem CID: 44265275; ChemSpider: 23108724

Shulgin Index: #59 DOIP; Table: 5 Page: 343 Row: 34

See also PiHKAL: #71 DOPR    

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

302
Analogue 27: Substituting Isopropoxy for Bromo at R4

MIPM
2,5-Dimethoxy-4-isopropoxyamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: UEUXKMHRZTVVCQ-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-9(2)18-14-8-12(16-4)11(6-10(3)15)7-13(14)17-5/h7-10H,6,15H2,1-5H3

ChemSpider: 23553121

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 6

See also PiHKAL: #35 2C-O-4 #138 MPM  
303
Analogue 28: Substituting n-Butoxy for Bromo at R4

MBM
4-n-Butoxy-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Butoxy-2,5-dimethoxyphenyl)propan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: QKAUNHGCSPPQBX-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-5-6-7-19-15-10-13(17-3)12(8-11(2)16)9-14(15)18-4/h9-11H,5-8,16H2,1-4H3

PubChem CID: 69456028

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 9

See also PiHKAL: #35 2C-O-4 #138 MPM  
See also Pharmacology notes I: p. 86, MBM: Subacute evaluation
304
Analogue 29: Substituting n-Pentyloxy for Bromo at R4

MAM
4-n-Amyloxy-2,5-dimethoxyamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(pentyloxy)phenyl]propan-2-amine

Formula: C16H27NO3 Molecular weight: 281.39048 g/mol InChI Key: BJNHWPMJOQBFLT-UHFFFAOYSA-N

InChI=1S/C16H27NO3/c1-5-6-7-8-20-16-11-14(18-3)13(9-12(2)17)10-15(16)19-4/h10-12H,5-9,17H2,1-4H3

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 10

See also PiHKAL: #138 MPM    
See also Pharmacology notes I: p. 87, MAM: Subacute evaluation
322
Analogue 30: Substituting n-Hexyl for Bromo at R4

DOHE
DOHx
4-Hexyl-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Hexyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C17H29NO2 Molecular weight: 279.41766 g/mol InChI Key: NICYQFWHLYLNFE-UHFFFAOYSA-N

InChI=1S/C17H29NO2/c1-5-6-7-8-9-14-11-17(20-4)15(10-13(2)18)12-16(14)19-3/h11-13H,5-10,18H2,1-4H3

PubChem CID: 44265170; ChemSpider: 23108583

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 7

See also PiHKAL: #61 DOAM    

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

323
Analogue 31: Substituting Benzyl for Bromo at R4

DOBZ
4-Benzyl-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Benzyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C18H23NO2 Molecular weight: 285.38072 g/mol InChI Key: FQARCNZVKSYIGI-UHFFFAOYSA-N

InChI=1S/C18H23NO2/c1-13(19)9-15-11-18(21-3)16(12-17(15)20-2)10-14-7-5-4-6-8-14/h4-8,11-13H,9-10,19H2,1-3H3

PubChem CID: 24039384; ChemSpider: 23108642

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 9

See also PiHKAL: #61 DOAM    

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

324
Analogue 32: Substituting Cyclopropylmethyl for Bromo at R4

DOCPM
4-Cyclopropylmethyl-2,5-dimethoxyamphetamine

IUPAC: 1-[4-(Cyclopropylmethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C15H23NO2 Molecular weight: 249.34862 g/mol InChI Key: WFKVCOUFNBAEFY-UHFFFAOYSA-N

InChI=1S/C15H23NO2/c1-10(16)6-12-8-15(18-3)13(7-11-4-5-11)9-14(12)17-2/h8-11H,4-7,16H2,1-3H3

PubChem CID: 69454735

See also PiHKAL: #63 DOBU    
2078
Analogue 33: Substituting Cyclopropylmethylthio for Bromo at R4

ALEPH-8
4-Cyclopropylmethylthio-2,5-dimethoxyamphetamine

IUPAC: 1-{4-[(Cyclopropylmethyl)sulfanyl]-2,5-dimethoxyphenyl}propan-2-amine

Formula: C15H23NO2S Molecular weight: 281.41362 g/mol InChI Key: FZWXHXVQKMVIAF-UHFFFAOYSA-N

InChI=1S/C15H23NO2S/c1-10(16)6-12-7-14(18-3)15(8-13(12)17-2)19-9-11-4-5-11/h7-8,10-11H,4-6,9,16H2,1-3H3

See also PiHKAL: #44 2C-T-8    
2084
Analogue 34: Substituting Cyclohexylthio for Bromo at R4

ALEPH-5
4-Cyclohexylthio-2,5-dimethoxyamphetamine

IUPAC: 1-[4-(Cyclohexylsulfanyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C17H27NO2S Molecular weight: 309.46678 g/mol InChI Key: UKUSQTYEWXTIBG-UHFFFAOYSA-N

InChI=1S/C17H27NO2S/c1-12(18)9-13-10-16(20-3)17(11-15(13)19-2)21-14-7-5-4-6-8-14/h10-12,14H,4-9,18H2,1-3H3

PubChem CID: 69396745

See also PiHKAL: #4 ALEPH-2    
2085
Analogue 35: Substituting Allylthio for Bromo at R4

ALEPH-16
4-Allylthio-2,5-dimethoxyamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(prop-2-en-1-ylsulfanyl)phenyl]propan-2-amine

Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: LJESJFBTHSFCLG-UHFFFAOYSA-N

InChI=1S/C14H21NO2S/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h5,8-10H,1,6-7,15H2,2-4H3

PubChem CID: 69396918

See also PiHKAL: #4 ALEPH-2    
2088
Analogue 36: Substituting 2-Fluoroethylthio for Bromo at R4

ALEPH-21
4-(2-Fluoroethylthio)-2,5-dimethoxyamphetamine

IUPAC: 1-{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}propan-2-amine

Formula: C13H20FNO2S Molecular weight: 273.3668032 g/mol InChI Key: XVRGKTXSWAENLK-UHFFFAOYSA-N

InChI=1S/C13H20FNO2S/c1-9(15)6-10-7-12(17-3)13(18-5-4-14)8-11(10)16-2/h7-9H,4-6,15H2,1-3H3

PubChem CID: 69393297

See also PiHKAL: #49 2C-T-21    
5381
Analogue 37: Substituting Trifluoromethyl for Bromo at R4

DOTFM
2,5-Dimethoxy-4-(trifluoromethyl)amphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]propan-2-amine

Formula: C12H16F3NO2 Molecular weight: 263.2561496 g/mol InChI Key: WPGOTSORDNBMHP-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2/c1-7(16)4-8-5-11(18-3)9(12(13,14)15)6-10(8)17-2/h5-7H,4,16H2,1-3H3

PubChem CID: 10400521; ChemSpider: 8575959; Wikipedia: 2,5-Dimethoxy-4-trifluoromethylamphetamine

Shulgin Index: #63 DOTFM; Table: 5 Page: 343 Row: 2

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Huang, X; Roth, BL; Gudelsky, GA; Nash, JF. 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: A potent serotonin 5-HT2A/2C agonist. J. Med. Chem., 1 Jan 1994, 37 (25), 4346–4351. 873 kB. doi:10.1021/jm00051a011

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

2328
Analogue 38: Substituting Phenylbutyl for Bromo at R4

2,5-Dimethoxy-4-phenylbutylamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(4-phenylbutyl)phenyl]propan-2-amine

Formula: C21H29NO2 Molecular weight: 327.46046 g/mol InChI Key: WFHQKLDPRBJNSJ-UHFFFAOYSA-N

InChI=1S/C21H29NO2/c1-16(22)13-19-15-20(23-2)18(14-21(19)24-3)12-8-7-11-17-9-5-4-6-10-17/h4-6,9-10,14-16H,7-8,11-13,22H2,1-3H3

PubChem CID: 10592333; ChemSpider: 8767707

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2196
Analogue 39: Substituting Ethynyl for Bromo at R4

DOYN
4-Ethynyl-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Ethynyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H17NO2 Molecular weight: 219.27958 g/mol InChI Key: XSBAOBBZMYENRL-UHFFFAOYSA-N

InChI=1S/C13H17NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h1,7-9H,6,14H2,2-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 22

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

2197
Analogue 40: Substituting Cyano for Bromo at R4

DOCN
4-Cyano-2,5-dimethoxyamphetamine

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxybenzonitrile

Formula: C12H16N2O2 Molecular weight: 220.26764 g/mol InChI Key: ULNMEZQBQBLXMC-UHFFFAOYSA-N

InChI=1S/C12H16N2O2/c1-8(14)4-9-5-12(16-3)10(7-13)6-11(9)15-2/h5-6,8H,4,14H2,1-3H3

PubChem CID: 23900148; ChemSpider: 23108720

Shulgin Index: #55 DOCN; Table: 5 Page: 343 Row: 8

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

2323
Analogue 41: Substituting Phenylpropyl for Bromo at R4

DOPh3
2,5-Dimethoxy-4-phenylpropylamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(3-phenylpropyl)phenyl]propan-2-amine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: XKCYCNKOOGOHIQ-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-15(21)12-18-14-19(22-2)17(13-20(18)23-3)11-7-10-16-8-5-4-6-9-16/h4-6,8-9,13-15H,7,10-12,21H2,1-3H3

PubChem CID: 44265227; ChemSpider: 23108650

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 10

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2325
Analogue 42: Substituting 2-Phenylethyl for Bromo at R4

2,5-Dimethoxy-4-phenethylamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(2-phenylethyl)phenyl]propan-2-amine

Formula: C19H25NO2 Molecular weight: 299.4073 g/mol InChI Key: WZUGJMKNNAADLQ-UHFFFAOYSA-N

InChI=1S/C19H25NO2/c1-14(20)11-17-13-18(21-2)16(12-19(17)22-3)10-9-15-7-5-4-6-8-15/h4-8,12-14H,9-11,20H2,1-3H3

PubChem CID: 10542174; ChemSpider: 8717565

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2329
Analogue 43: Substituting (4-Chlorophenyl)propyl for Bromo at R4

4-(4-Chlorophenylpropyl)-2,5-dimethoxyamphetamine

IUPAC: 1-{4-[3-(4-Chlorophenyl)propyl]-2,5-dimethoxyphenyl}propan-2-amine

Formula: C20H26ClNO2 Molecular weight: 347.87894 g/mol InChI Key: NBVUSYYQRXPQSV-UHFFFAOYSA-N

InChI=1S/C20H26ClNO2/c1-14(22)11-17-13-19(23-2)16(12-20(17)24-3)6-4-5-15-7-9-18(21)10-8-15/h7-10,12-14H,4-6,11,22H2,1-3H3

PubChem CID: 10831543; ChemSpider: 9006843

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2330
Analogue 44: Substituting (4-Methoxyphenyl)propyl for Bromo at R4

2,5-Dimethoxy-4-(4-methoxyphenylpropyl)amphetamine

IUPAC: 1-{2,5-Dimethoxy-4-[3-(4-methoxyphenyl)propyl]phenyl}propan-2-amine

Formula: C21H29NO3 Molecular weight: 343.45986 g/mol InChI Key: QQVQBSXATXKAAM-UHFFFAOYSA-N

InChI=1S/C21H29NO3/c1-15(22)12-18-14-20(24-3)17(13-21(18)25-4)7-5-6-16-8-10-19(23-2)11-9-16/h8-11,13-15H,5-7,12,22H2,1-4H3

PubChem CID: 10807330; ChemSpider: 8982635

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

390
Analogue 45: Substituting Ethenyl for Bromo at R4

DOVI
DOV
4-Ethenyl-2,5-dimethoxyamphetamine

IUPAC: 1-(4-Ethenyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H19NO2 Molecular weight: 221.29546 g/mol InChI Key: RDOMWNSTCLMGGA-UHFFFAOYSA-N

InChI=1S/C13H19NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h5,7-9H,1,6,14H2,2-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 20

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

2416
Analogue 46: Substituting Acetyl for Bromo at R4

DOAC
4-Acetyl-2,5-dimethoxyamphetamine

IUPAC: 1-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanone

Formula: C13H19NO3 Molecular weight: 237.29486 g/mol InChI Key: NWWLLPGDGZOZAT-UHFFFAOYSA-N

InChI=1S/C13H19NO3/c1-8(14)5-10-6-13(17-4)11(9(2)15)7-12(10)16-3/h6-8H,5,14H2,1-4H3

PubChem CID: 23983771

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 26

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

2415
Analogue 47: Substituting Carboxy for Bromo at R4

DOCA
4-Carboxy-2,5-dimethoxyamphetamine

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxybenzoic acid

Formula: C12H17NO4 Molecular weight: 239.26768 g/mol InChI Key: FRWTXPXOPHGXDE-UHFFFAOYSA-N

InChI=1S/C12H17NO4/c1-7(13)4-8-5-11(17-3)9(12(14)15)6-10(8)16-2/h5-7H,4,13H2,1-3H3,(H,14,15)

PubChem CID: 44265203; ChemSpider: 23108623

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 10

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Ho, B; Tansey, LW. Analogs of amphetamine. 4. Synthesis of metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). J. Med. Chem., 1 Feb 1971, 14 (2), 156–157. 316 kB. doi:10.1021/jm00284a018

Ho, B; Estevez, V; Tansey, LW; Englert, LF; Creaven, PJ; McIsaac, WM. Analogs of amphetamine. 5. Excretory metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) in rats. J. Med. Chem., 1 Feb 1971, 14 (2), 158–160. 371 kB. doi:10.1021/jm00284a019

2414
Analogue 48: Substituting Hydroxy for Bromo at R4

DOOH
4-Hydroxy-2,5-dimethoxyamphetamine

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: XZYTWVYCADLTTI-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-11(15-3)9(13)6-10(8)14-2/h5-7,13H,4,12H2,1-3H3

PubChem CID: 44265202; ChemSpider: 23108622

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 11

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

2413
Analogue 49: Substituting Propylaminocarbonyl for Bromo at R4

DOCONHP
2,5-Dimethoxy-4-(propylaminocarbonyl)amphetamine

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxy-N-propylbenzamide

Formula: C15H24N2O3 Molecular weight: 280.36266 g/mol InChI Key: VZDOPLQWWABTDV-UHFFFAOYSA-N

InChI=1S/C15H24N2O3/c1-5-6-17-15(18)12-9-13(19-3)11(7-10(2)16)8-14(12)20-4/h8-10H,5-7,16H2,1-4H3,(H,17,18)

PubChem CID: 44265221; ChemSpider: 23108641

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 27

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

2412
Analogue 50: Substituting Propanoyl for Bromo at R4

DOCOE
2,5-Dimethoxy-4-propanonylamphetamine

IUPAC: 1-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]propan-1-one

Formula: C14H21NO3 Molecular weight: 251.32144 g/mol InChI Key: ACCIWGPKICCJMA-UHFFFAOYSA-N

InChI=1S/C14H21NO3/c1-5-12(16)11-8-13(17-3)10(6-9(2)15)7-14(11)18-4/h7-9H,5-6,15H2,1-4H3

PubChem CID: 44265278; ChemSpider: 23108731

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 28

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

2411
Analogue 51: Substituting Butoxycarbonyl for Bromo at R4

DOCEB
4-Butoxycarbonyl-2,5-dimethoxyamphetamine

IUPAC: Butyl 4-(2-aminopropyl)-2,5-dimethoxybenzoate

Formula: C16H25NO4 Molecular weight: 295.374 g/mol InChI Key: DHCQOPOFDPDJGB-UHFFFAOYSA-N

InChI=1S/C16H25NO4/c1-5-6-7-21-16(18)13-10-14(19-3)12(8-11(2)17)9-15(13)20-4/h9-11H,5-8,17H2,1-4H3

PubChem CID: 44265214; ChemSpider: 23108630

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 30

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

2410
Analogue 52: Substituting Propoxycarbonyl for Bromo at R4

DOCEP
2,5-Dimethoxy-4-propoxycarbonylamphetamine

IUPAC: Propyl 4-(2-aminopropyl)-2,5-dimethoxybenzoate

Formula: C15H23NO4 Molecular weight: 281.34742 g/mol InChI Key: WCFHJUFPNNTMGG-UHFFFAOYSA-N

InChI=1S/C15H23NO4/c1-5-6-20-15(17)12-9-13(18-3)11(7-10(2)16)8-14(12)19-4/h8-10H,5-7,16H2,1-4H3

PubChem CID: 15128244; ChemSpider: 23108640

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 29

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

2409
Analogue 53: Substituting n-Octyl for Bromo at R4

DOOC
2,5-Dimethoxy-4-n-octylamphetamine

IUPAC: 1-(2,5-Dimethoxy-4-octylphenyl)propan-2-amine

Formula: C19H33NO2 Molecular weight: 307.47082 g/mol InChI Key: YJEXIKLCPDHVQC-UHFFFAOYSA-N

InChI=1S/C19H33NO2/c1-5-6-7-8-9-10-11-16-13-19(22-4)17(12-15(2)20)14-18(16)21-3/h13-15H,5-12,20H2,1-4H3

PubChem CID: 44265204; ChemSpider: 23108624

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 8

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

7183
Analogue 54: Substituting Dimethylamino for Bromo at R4

DONMM

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxy-N,N-dimethylaniline

Formula: C13H22N2O2 Molecular weight: 238.32598 g/mol InChI Key: ZIJPPBTWERGKCU-UHFFFAOYSA-N

InChI=1S/C13H22N2O2/c1-9(14)6-10-7-13(17-5)11(15(2)3)8-12(10)16-4/h7-9H,6,14H2,1-5H3

PubChem CID: 10466736; ChemSpider: 8642147

Shulgin Index: See #61 DON; Table: 5 Page: 341 Row: 33

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

7234
Analogue 55: Substituting Fluoromethyl for Bromo at R4

DOFM

IUPAC: 1-[4-(Fluoromethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C12H18FNO2 Molecular weight: 227.2752232 g/mol InChI Key: ZKRHJAGMXZBOMW-UHFFFAOYSA-N

InChI=1S/C12H18FNO2/c1-8(14)4-9-5-12(16-3)10(7-13)6-11(9)15-2/h5-6,8H,4,7,14H2,1-3H3

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 34

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

7254
Analogue 56: Substituting Hydroxymethyl for Bromo at R4

DOHM

IUPAC: 4-(2-Aminopropyl)-2,5-dimethoxybenzaldehyde

Formula: C12H17NO3 Molecular weight: 223.26828 g/mol InChI Key: DNFAIVPALXHIOA-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-8(13)4-9-5-12(16-3)10(7-14)6-11(9)15-2/h5-8H,4,13H2,1-3H3

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 4

7267
Analogue 57: Substituting n-Heptyl for Bromo at R4

DOHP

IUPAC: 1-(4-Heptyl-2,5-dimethoxyphenyl)propan-2-amine

Formula: C18H31NO2 Molecular weight: 293.44424 g/mol InChI Key: OTDMGXQPXDCJNK-UHFFFAOYSA-N

InChI=1S/C18H31NO2/c1-5-6-7-8-9-10-15-12-18(21-4)16(11-14(2)19)13-17(15)20-3/h12-14H,5-11,19H2,1-4H3

PubChem CID: 10469663; ChemSpider: 8645074

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 17

7268
Analogue 58: Substituting n-Nonyl for Bromo at R4

DONO

IUPAC: 1-(2,5-Dimethoxy-4-nonylphenyl)propan-2-amine

Formula: C20H35NO2 Molecular weight: 321.4974 g/mol InChI Key: IAURWCWNBAOSLI-UHFFFAOYSA-N

InChI=1S/C20H35NO2/c1-5-6-7-8-9-10-11-12-17-14-20(23-4)18(13-16(2)21)15-19(17)22-3/h14-16H,5-13,21H2,1-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 18

7275
Analogue 59: Substituting 2-Hydroxyethyl for Bromo at R4

DOEH

IUPAC: 2-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XXLDJSGSZKURAM-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)6-11-8-12(16-2)10(4-5-15)7-13(11)17-3/h7-9,15H,4-6,14H2,1-3H3

PubChem CID: 14201978; ChemSpider: 21415075

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 25

7353
Analogue 60: Substituting 2-Hydroxypropoxy for Bromo at R4

M(2OP)M

IUPAC: 1-[4-(2-Aminopropyl)-2,5-dimethoxyphenoxy]propan-2-ol

Formula: C14H23NO4 Molecular weight: 269.33672 g/mol InChI Key: PLZQGTLBVBLWRF-UHFFFAOYSA-N

InChI=1S/C14H23NO4/c1-9(15)5-11-6-13(18-4)14(7-12(11)17-3)19-8-10(2)16/h6-7,9-10,16H,5,8,15H2,1-4H3

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 3

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

7354
Analogue 61: Substituting 3-Hydroxypropoxy for Bromo at R4

M(3OP)M

IUPAC: 3-[4-(2-Aminopropyl)-2,5-dimethoxyphenoxy]propan-1-ol

Formula: C14H23NO4 Molecular weight: 269.33672 g/mol InChI Key: UJYMLOWSDODCLN-UHFFFAOYSA-N

InChI=1S/C14H23NO4/c1-10(15)7-11-8-13(18-3)14(9-12(11)17-2)19-6-4-5-16/h8-10,16H,4-7,15H2,1-3H3

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 4

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

7361
Analogue 62: Substituting Benzyloxy for Bromo at R4

MBZM

IUPAC: 1-[4-(Benzyloxy)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C18H23NO3 Molecular weight: 301.38012 g/mol InChI Key: BUQHFKLOPGDEDI-UHFFFAOYSA-N

InChI=1S/C18H23NO3/c1-13(19)9-15-10-17(21-3)18(11-16(15)20-2)22-12-14-7-5-4-6-8-14/h4-8,10-11,13H,9,12,19H2,1-3H3

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 11

7404
Analogue 63: Substituting n-Butylthio for Bromo at R4

ALEPH-19

IUPAC: 1-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C15H25NO2S Molecular weight: 283.4295 g/mol InChI Key: GHEFZUSLOGYDQM-UHFFFAOYSA-N

InChI=1S/C15H25NO2S/c1-5-6-7-19-15-10-13(17-3)12(8-11(2)16)9-14(15)18-4/h9-11H,5-8,16H2,1-4H3

PubChem CID: 11450018; ChemSpider: 9624870

Shulgin Index: See #3 ALEPH; Table: 5 Page: 346 Row: 4

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

7413
Analogue 64: Substituting n-Pentylthio for Bromo at R4

ALEPH-S-amyl

IUPAC: 1-[2,5-Dimethoxy-4-(pentylsulfanyl)phenyl]propan-2-amine

Formula: C16H27NO2S Molecular weight: 297.45608 g/mol InChI Key: QJIMRIAYMMVZRY-UHFFFAOYSA-N

InChI=1S/C16H27NO2S/c1-5-6-7-8-20-16-11-14(18-3)13(9-12(2)17)10-15(16)19-4/h10-12H,5-9,17H2,1-4H3

PubChem CID: 11461761; ChemSpider: 9636601

Shulgin Index: See #3 ALEPH; Table: 5 Page: 346 Row: 13

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

7415
Analogue 65: Substituting Phenethylthio for Bromo at R4

ALEPH-S-PhEt

IUPAC: 1-{2,5-Dimethoxy-4-[(2-phenylethyl)sulfanyl]phenyl}propan-2-amine

Formula: C19H25NO2S Molecular weight: 331.4723 g/mol InChI Key: DLCYMWYHXKNVOC-UHFFFAOYSA-N

InChI=1S/C19H25NO2S/c1-14(20)11-16-12-18(22-3)19(13-17(16)21-2)23-10-9-15-7-5-4-6-8-15/h4-8,12-14H,9-11,20H2,1-3H3

Shulgin Index: See #3 ALEPH; Table: 5 Page: 346 Row: 15

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

7416
Analogue 66: Substituting Methylsulfonyl for Bromo at R4

ALEPH sulfone

IUPAC: 1-[2,5-Dimethoxy-4-(methylsulfonyl)phenyl]propan-2-amine

Formula: C12H19NO4S Molecular weight: 273.34856 g/mol InChI Key: YDLBFQHWQNHGES-UHFFFAOYSA-N

InChI=1S/C12H19NO4S/c1-8(13)5-9-6-11(17-3)12(18(4,14)15)7-10(9)16-2/h6-8H,5,13H2,1-4H3

PubChem CID: 542054; ChemSpider: 472024

Shulgin Index: See #3 ALEPH; Table: 5 Page: 346 Row: 16

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

473
Analogue 67: Substituting 2,2,2-Trifluoroethyl for Bromo at R4

DOTFE

IUPAC: 1-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]propan-2-amine

Formula: C13H18F3NO2 Molecular weight: 277.2827296 g/mol InChI Key: OZFGHDLWUVVAPY-UHFFFAOYSA-N

InChI=1S/C13H18F3NO2/c1-8(17)4-9-5-12(19-3)10(6-11(9)18-2)7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

469
Analogue 68: Substituting 2,2,2-Trifluoroethoxy for Bromo at R4

MTFEM

IUPAC: 1-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]propan-2-amine

Formula: C13H18F3NO3 Molecular weight: 293.2821296 g/mol InChI Key: LFPUPGGEYLURDG-UHFFFAOYSA-N

InChI=1S/C13H18F3NO3/c1-8(17)4-9-5-11(19-3)12(6-10(9)18-2)20-7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

468
Analogue 69: Substituting 2,2-Difluoroethoxy for Bromo at R4

MDFEM

IUPAC: 1-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C13H19F2NO3 Molecular weight: 275.2916664 g/mol InChI Key: AXKORAKXKXDBAF-UHFFFAOYSA-N

InChI=1S/C13H19F2NO3/c1-8(16)4-9-5-11(18-3)12(6-10(9)17-2)19-7-13(14)15/h5-6,8,13H,4,7,16H2,1-3H3

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

467
Analogue 70: Substituting 2-Fluoroethyoxy for Bromo at R4

MFEM

IUPAC: 1-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C13H20FNO3 Molecular weight: 257.3012032 g/mol InChI Key: HCQYGRWXRUZBGI-UHFFFAOYSA-N

InChI=1S/C13H20FNO3/c1-9(15)6-10-7-12(17-3)13(18-5-4-14)8-11(10)16-2/h7-9H,4-6,15H2,1-3H3

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

1514
Analogue 71: Substituting Bromomethyl for Bromo at R4

DOBM

IUPAC: 1-[4-(Bromomethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C12H18BrNO2 Molecular weight: 288.18082 g/mol InChI Key: QQVJWPHCOPXKEU-UHFFFAOYSA-N

InChI=1S/C12H18BrNO2/c1-8(14)4-9-5-12(16-3)10(7-13)6-11(9)15-2/h5-6,8H,4,7,14H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1515
Analogue 72: Substituting Chloromethyl for Bromo at R4

DOMCl

IUPAC: 1-[4-(Chloromethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C12H18ClNO2 Molecular weight: 243.72982 g/mol InChI Key: KSWPNSXPMSQFIL-UHFFFAOYSA-N

InChI=1S/C12H18ClNO2/c1-8(14)4-9-5-12(16-3)10(7-13)6-11(9)15-2/h5-6,8H,4,7,14H2,1-3H3

PubChem CID: 10967899; ChemSpider: 9143110

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Harms, A; Ulmer, E; Kovar, K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm. Pharm. Med. Chem., 16 Jun 2003, 336 (3), 155–158. 69 kB. doi:10.1002/ardp.200390014

1516
Analogue 73: Substituting 2-Chloroethyl for Bromo at R4

DOCET

IUPAC: 1-[4-(2-Chloroethyl)-2,5-dimethoxyphenyl]propan-2-amine

Formula: C13H20ClNO2 Molecular weight: 257.7564 g/mol InChI Key: SEPPDGJRABVPLK-UHFFFAOYSA-N

InChI=1S/C13H20ClNO2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4-6,15H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1517
Analogue 74: Substituting 3,3,3-Trifluoropropyl for Bromo at R4

DOTFPR

IUPAC: 1-[2,5-Dimethoxy-4-(3,3,3-trifluoropropyl)phenyl]propan-2-amine

Formula: C14H20F3NO2 Molecular weight: 291.3093096 g/mol InChI Key: UNQHBLWLHZUVEJ-UHFFFAOYSA-N

InChI=1S/C14H20F3NO2/c1-9(18)6-11-8-12(19-2)10(7-13(11)20-3)4-5-14(15,16)17/h7-9H,4-6,18H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1518
Analogue 75: Substituting Sulfanylmethyl for Bromo at R4

DOHSM

IUPAC: [4-(2-Aminopropyl)-2,5-dimethoxyphenyl]methanethiol

Formula: C12H19NO2S Molecular weight: 241.34976 g/mol InChI Key: ZGLINLFLHGVUND-UHFFFAOYSA-N

InChI=1S/C12H19NO2S/c1-8(13)4-9-5-12(15-3)10(7-16)6-11(9)14-2/h5-6,8,16H,4,7,13H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1519
Analogue 76: Substituting 2-Methylthioethyl for Bromo at R4

DOMSM

IUPAC: 1-{2,5-Dimethoxy-4-[(methylsulfanyl)methyl]phenyl}propan-2-amine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: IXJATGGDEBTDAQ-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/c1-9(14)5-10-6-13(16-3)11(8-17-4)7-12(10)15-2/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 69399016

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1520
Analogue 77: Substituting Methoxymethyl for Bromo at R4

DOMOM

IUPAC: 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IACSUTUTFQAPTC-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-10-6-13(17-4)11(8-15-2)7-12(10)16-3/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 10934687; ChemSpider: 9109923

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Harms, A; Ulmer, E; Kovar, K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm. Pharm. Med. Chem., 16 Jun 2003, 336 (3), 155–158. 69 kB. doi:10.1002/ardp.200390014

1521
Analogue 78: Substituting Formylamino for Bromo at R4

DONCO

IUPAC: N-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]formamide

Formula: C12H18N2O3 Molecular weight: 238.28292 g/mol InChI Key: HDSLNYKIIRTSHE-UHFFFAOYSA-N

InChI=1S/C12H18N2O3/c1-8(13)4-9-5-12(17-3)10(14-7-15)6-11(9)16-2/h5-8H,4,13H2,1-3H3,(H,14,15)

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1522
Analogue 79: Substituting Propanoylamino for Bromo at R4

DONCOE

IUPAC: N-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]propanamide

Formula: C14H22N2O3 Molecular weight: 266.33608 g/mol InChI Key: OAMVCVFHVFIINA-UHFFFAOYSA-N

InChI=1S/C14H22N2O3/c1-5-14(17)16-11-8-12(18-3)10(6-9(2)15)7-13(11)19-4/h7-9H,5-6,15H2,1-4H3,(H,16,17)

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1523
Analogue 80: Substituting (Trifluoroacetyl)amino for Bromo at R4

DONCOTFM

IUPAC: N-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]-2,2,2-trifluoroacetamide

Formula: C13H17F3N2O3 Molecular weight: 306.2808896 g/mol InChI Key: RDORIUNLTWAGRE-UHFFFAOYSA-N

InChI=1S/C13H17F3N2O3/c1-7(17)4-8-5-11(21-3)9(6-10(8)20-2)18-12(19)13(14,15)16/h5-7H,4,17H2,1-3H3,(H,18,19)

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1513
Analogue 81: Substituting Cyanomethyl for Bromo at R4

DOCNM

IUPAC: [4-(2-Aminopropyl)-2,5-dimethoxyphenyl]acetonitrile

Formula: C13H18N2O2 Molecular weight: 234.29422 g/mol InChI Key: YRDVSOCPGNXBIX-UHFFFAOYSA-N

InChI=1S/C13H18N2O2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4,6,15H2,1-3H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1016
Analogue 82: Substituting Hydroxymethyl for Bromo at R4

IUPAC: [4-(2-Aminopropyl)-2,5-dimethoxyphenyl]methanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: PJNXHBSMCHLAFM-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)4-9-5-12(16-3)10(7-14)6-11(9)15-2/h5-6,8,14H,4,7,13H2,1-3H3

Ho, B; Tansey, LW. Analogs of amphetamine. 4. Synthesis of metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). J. Med. Chem., 1 Feb 1971, 14 (2), 156–157. 316 kB. doi:10.1021/jm00284a018

Ho, B; Estevez, V; Tansey, LW; Englert, LF; Creaven, PJ; McIsaac, WM. Analogs of amphetamine. 5. Excretory metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) in rats. J. Med. Chem., 1 Feb 1971, 14 (2), 158–160. 371 kB. doi:10.1021/jm00284a019

Three R5 analogues:
6429
Analogue 1: Removing Methoxy at R5

4-Br-2-MA

IUPAC: 1-(4-Bromo-2-methoxyphenyl)propan-2-amine

Formula: C10H14BrNO Molecular weight: 244.12826 g/mol InChI Key: YWONMRKCBJPFCM-UHFFFAOYSA-N

InChI=1S/C10H14BrNO/c1-7(12)5-8-3-4-9(11)6-10(8)13-2/h3-4,6-7H,5,12H2,1-2H3

PubChem CID: 13547422; ChemSpider: 23153503

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 326 Row: 29

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

1524
Analogue 2: Substituting Cyano for Methoxy at R5

5-Cyano-DOB

IUPAC: 5-(2-Aminopropyl)-2-bromo-4-methoxybenzonitrile

Formula: C11H13BrN2O Molecular weight: 269.13772 g/mol InChI Key: WIHMCRXNPQQVQL-UHFFFAOYSA-N

InChI=1S/C11H13BrN2O/c1-7(14)3-8-4-9(6-13)10(12)5-11(8)15-2/h4-5,7H,3,14H2,1-2H3

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

1525
Analogue 3: Substituting Formylamino for Methoxy at R5

5-HOCA-DOB

IUPAC: N-[5-(2-Aminopropyl)-2-bromo-4-methoxyphenyl]formamide

Formula: C11H15BrN2O2 Molecular weight: 287.153 g/mol InChI Key: WJOYVFIIUIQYOR-UHFFFAOYSA-N

InChI=1S/C11H15BrN2O2/c1-7(13)3-8-4-10(14-6-15)9(12)5-11(8)16-2/h4-7H,3,13H2,1-2H3,(H,14,15)

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

16 skeleton analogues:
5384
Analogue 1: With Benzocyclobutanylmethanamine skeleton

TCB-2
2C-BCB
(4-Bromo-3,6-dimethoxy-1,2-dihydrocyclobutabenzene-1-yl)methanamine

IUPAC: 1-(3-Bromo-2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine

Formula: C11H14BrNO2 Molecular weight: 272.13836 g/mol InChI Key: MPBCKKVERDTCEL-UHFFFAOYSA-N

InChI=1S/C11H14BrNO2/c1-14-9-4-8(12)11(15-2)7-3-6(5-13)10(7)9/h4,6H,3,5,13H2,1-2H3

PubChem CID: 16046239; ChemSpider: 13174651; Wikipedia: TCB-2

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Fox, MA; French, HT; LaPorte, JL; Blackler, AR; Murphy, DL. The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis. Psychopharmacology, 1 Sep 2010, 212 (1), 13–23. 240 kB. doi:10.1007/s00213-009-1694-1

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

McLean, TH; Parrish, JC; Braden, MR; Marona-Lewicka, D; Gallardo-Godoy, A; Nichols, DE. 1-Aminomethylbenzocycloalkanes: Conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J. Med. Chem., 1 Jan 2006, 49 (19), 5794–5803. 522 kB. doi:10.1021/jm060656o

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

2220
Analogue 2: With 1-(2,3-Dihydro-1H-inden-1-yl)methanamine skeleton

2CB-Ind

IUPAC: 1-(5-Bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine

Formula: C12H16BrNO2 Molecular weight: 286.16494 g/mol InChI Key: HCLPGYNQMVSQIM-UHFFFAOYSA-N

InChI=1S/C12H16BrNO2/c1-15-10-5-9(13)12(16-2)8-4-3-7(6-14)11(8)10/h5,7H,3-4,6,14H2,1-2H3

PubChem CID: 16086368; ChemSpider: 17245022; Wikipedia: 2CB-Ind

McLean, TH; Parrish, JC; Braden, MR; Marona-Lewicka, D; Gallardo-Godoy, A; Nichols, DE. 1-Aminomethylbenzocycloalkanes: Conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J. Med. Chem., 1 Jan 2006, 49 (19), 5794–5803. 522 kB. doi:10.1021/jm060656o

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

5553
Analogue 3: With Phenylethyl-cyclic-amine skeleton

2CLisaB

IUPAC: 2-[2-(4-Bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

Formula: C19H22BrNO2 Molecular weight: 376.28748 g/mol InChI Key: FUQOBJZWVZVGDO-UHFFFAOYSA-N

InChI=1S/C19H22BrNO2/c1-22-18-12-17(20)19(23-2)11-15(18)8-10-21-9-7-14-5-3-4-6-16(14)13-21/h3-6,11-12H,7-10,13H2,1-2H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

396
Analogue 4: With Phenylethyl-cyclic-amine skeleton

pip-2C-B

IUPAC: 1-[2-(4-Bromo-2,5-dimethoxyphenyl)ethyl]piperidine

Formula: C15H22BrNO2 Molecular weight: 328.24468 g/mol InChI Key: HCAIUSZHAJZMDI-UHFFFAOYSA-N

InChI=1S/C15H22BrNO2/c1-18-14-11-13(16)15(19-2)10-12(14)6-9-17-7-4-3-5-8-17/h10-11H,3-9H2,1-2H3

PubChem CID: 10087864; ChemSpider: 8263401

Shulgin Index: See #18 2C-B; Table: 5 Page: 340 Row: 27

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

922
Analogue 5: With 1-Benzylpiperazine skeleton

2C-B-BZP

IUPAC: 1-(4-Bromo-2,5-dimethoxybenzyl)piperazine

Formula: C13H19BrN2O2 Molecular weight: 315.20616 g/mol InChI Key: OHXVYXBOJDDYJS-UHFFFAOYSA-N

InChI=1S/C13H19BrN2O2/c1-17-12-8-11(14)13(18-2)7-10(12)9-16-5-3-15-4-6-16/h7-8,15H,3-6,9H2,1-2H3

PubChem CID: 43090477; ChemSpider: 26234933; Wikipedia: 2C-B-BZP

Shulgin Index: See #79 MDBP; Table: 9 Page: 358 Row: 7

Westphal, F; Junge, T; Girreser, U; Stobbe, S; Pérez, SB. Structure elucidation of a new designer benzylpiperazine: 4-Bromo-2,5-dimethoxybenzylpiperazine. Forensic Sci. Int., 30 May 2009, 187 (1–3), 87–96. 859 kB. doi:10.1016/j.forsciint.2009.03.003

7156
Analogue 6: With 2-Amino-1-phenylethanone skeleton

DOB-βk

IUPAC: 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)propan-1-one

Formula: C11H14BrNO3 Molecular weight: 288.13776 g/mol InChI Key: NFDUSHHXFRLENI-UHFFFAOYSA-N

InChI=1S/C11H14BrNO3/c1-6(13)11(14)7-4-10(16-3)8(12)5-9(7)15-2/h4-6H,13H2,1-3H3

ChemSpider: 27749706

Shulgin Index: See #52 DOB; Table: 5 Page: 341 Row: 6

546
Analogue 7: With Phenyl-cyclic-amine skeleton

2CBecca

IUPAC: 4-(4-Bromo-2,5-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Formula: C17H18BrNO2 Molecular weight: 348.23432 g/mol InChI Key: LRHOKFHXSNZVLA-UHFFFAOYSA-N

InChI=1S/C17H18BrNO2/c1-20-16-8-15(18)17(21-2)7-13(16)14-10-19-9-11-5-3-4-6-12(11)14/h3-8,14,19H,9-10H2,1-2H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

547
Analogue 8: With Phenyl-cyclic-amine skeleton

2CJP

IUPAC: 4-(4-Bromo-2,5-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-2-benzazepine

Formula: C18H20BrNO2 Molecular weight: 362.2609 g/mol InChI Key: FQAXYSXGRJQKMV-UHFFFAOYSA-N

InChI=1S/C18H20BrNO2/c1-21-17-9-16(19)18(22-2)8-15(17)14-7-12-5-3-4-6-13(12)10-20-11-14/h3-6,8-9,14,20H,7,10-11H2,1-2H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

550
Analogue 9: With 2,3,4,5-Tetrahydro-1-benzoxepin-4-amine skeleton

BBOX

IUPAC: 8-Bromo-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepin-4-amine

Formula: C11H14BrNO2 Molecular weight: 272.13836 g/mol InChI Key: NVIUTKUAJYDPRH-UHFFFAOYSA-N

InChI=1S/C11H14BrNO2/c1-14-11-5-7-4-8(13)2-3-15-10(7)6-9(11)12/h5-6,8H,2-4,13H2,1H3

PubChem CID: 44567540; ChemSpider: 23340687

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nelson, DL; Nichols, DE. Conformationally restricted tetrahydro-1-benzoxepin analogs of hallucinogenic phenethylamines. Med. Chem. Res., 1 Jan 1995, 5, 651–663. 2040 kB.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

1234
Analogue 10: With Benzyl-cyclic-amine skeleton

IUPAC: 3-(4-Bromo-2,5-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Formula: C18H20BrNO2 Molecular weight: 362.2609 g/mol InChI Key: ACIIXMUSMUSCNA-UHFFFAOYSA-N

InChI=1S/C18H20BrNO2/c1-21-17-10-16(19)18(22-2)9-14(17)8-15-7-12-5-3-4-6-13(12)11-20-15/h3-6,9-10,15,20H,7-8,11H2,1-2H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1236
Analogue 11: With Phenyl-cyclic-amine skeleton

IUPAC: 3-(4-Bromo-2,5-dimethoxyphenyl)-1-(2-methoxybenzyl)piperidine

Formula: C21H26BrNO3 Molecular weight: 420.34004 g/mol InChI Key: XCBPFHGQWYIAJG-UHFFFAOYSA-N

InChI=1S/C21H26BrNO3/c1-24-19-9-5-4-7-16(19)14-23-10-6-8-15(13-23)17-11-21(26-3)18(22)12-20(17)25-2/h4-5,7,9,11-12,15H,6,8,10,13-14H2,1-3H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1237
Analogue 12: With Phenyl-cyclic-amine skeleton

IUPAC: 5-(4-Bromo-2,5-dimethoxyphenyl)-2-(2-methoxyphenyl)piperidine

Formula: C20H24BrNO3 Molecular weight: 406.31346 g/mol InChI Key: BDZXVOHNVCEDNQ-UHFFFAOYSA-N

InChI=1S/C20H24BrNO3/c1-23-18-7-5-4-6-14(18)17-9-8-13(12-22-17)15-10-20(25-3)16(21)11-19(15)24-2/h4-7,10-11,13,17,22H,8-9,12H2,1-3H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1238
Analogue 13: With Benzyl-cyclic-amine skeleton

IUPAC: 2-(4-Bromo-2,5-dimethoxybenzyl)-6-(2-methoxyphenyl)piperidine

Formula: C21H26BrNO3 Molecular weight: 420.34004 g/mol InChI Key: KMVGLBONODPTDY-UHFFFAOYSA-N

InChI=1S/C21H26BrNO3/c1-24-19-10-5-4-8-16(19)18-9-6-7-15(23-18)11-14-12-21(26-3)17(22)13-20(14)25-2/h4-5,8,10,12-13,15,18,23H,6-7,9,11H2,1-3H3

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem. Neurosci., 2012. 1060 kB. doi:10.1021/cn3000668

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1075
Analogue 14: With Phenyl-cyclic-amine skeleton

IUPAC: 2-(4-Bromo-2,5-dimethoxyphenyl)morpholine

Formula: C12H16BrNO3 Molecular weight: 302.16434 g/mol InChI Key: OUTZYBJUJMETRJ-UHFFFAOYSA-N

InChI=1S/C12H16BrNO3/c1-15-10-6-9(13)11(16-2)5-8(10)12-7-14-3-4-17-12/h5-6,12,14H,3-4,7H2,1-2H3

PubChem CID: 11429275; ChemSpider: 9604151

1028
Analogue 15: With 2-Amino-1-phenylethanone skeleton

bk-2C-B

IUPAC: 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone

Formula: C10H12BrNO3 Molecular weight: 274.11118 g/mol InChI Key: HFYJGAIOBIDRPX-UHFFFAOYSA-N

InChI=1S/C10H12BrNO3/c1-14-9-4-7(11)10(15-2)3-6(9)8(13)5-12/h3-4H,5,12H2,1-2H3

PubChem CID: 11288812; ChemSpider: 9463799

938
Analogue 16: With Phenyl-cyclic-amine skeleton

IUPAC: 3-(4-Bromo-2,5-dimethoxyphenyl)piperidine

Formula: C13H18BrNO2 Molecular weight: 300.19152 g/mol InChI Key: ULJHXMHMDJQESG-UHFFFAOYSA-N

InChI=1S/C13H18BrNO2/c1-16-12-7-11(14)13(17-2)6-10(12)9-4-3-5-15-8-9/h6-7,9,15H,3-5,8H2,1-2H3

19 isomers:
18
Isomer 1

4-Br-3,5-DMA
4,3,5-DOB
4-Bromo-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-bromoamphetamine

IUPAC: 1-(4-Bromo-3,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: FAVLJTSHWBEOMA-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(14-2)11(12)10(6-8)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 208044; ChemSpider: 180279; Wikipedia: 4-Bromo-3,5-dimethoxyamphetamine

Shulgin Index: See #52 DOB; Table: 5 Page: 349 Row: 11

See also Pharmacology notes I: p. 197, 4-Br-3,5-DMA

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Barfknecht, CF; Nichols, DE. Potential psychotomimetics. Bromomethoxyamphetamines. J. Med. Chem., 1 Jan 1971, 14 (4), 370–372. 377 kB. doi:10.1021/jm00286a026 Rhodium

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

124
Isomer 2

META-DOB
m-DOB
5-Bromo-2,4-dimethoxyamphetamine

IUPAC: 1-(5-Bromo-2,4-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: YFSLPSITQIUFQK-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)11(15-3)6-10(8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 143750; ChemSpider: 126826; Wikipedia: Meta-DOB

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 30

See also PiHKAL: #53 2,4-DMA #55 3,4-DMA #62 DOB

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 36161 kB. Rhodium.

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

195
Isomer 3

2C-B-2-EtO
2CB-2ETO
4-Bromo-2-ethoxy-5-methoxyphenethylamine

IUPAC: 2-(4-Bromo-2-ethoxy-5-methoxyphenyl)ethanamine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: FLMAKYQLBBLIAH-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-3-15-10-7-9(12)11(14-2)6-8(10)4-5-13/h6-7H,3-5,13H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 346 Row: 21

See also PiHKAL: #20 2C-B    
198
Isomer 4

N-Me-2-Br-DMPEA
2-Bromo-4,5-dimethoxy-N-methylphenethylamine

IUPAC: 2-(2-Bromo-4,5-dimethoxyphenyl)-N-methylethanamine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: FHDOOUJHFQIHAM-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-13-5-4-8-6-10(14-2)11(15-3)7-9(8)12/h6-7,13H,4-5H2,1-3H3

PubChem CID: 60697533; ChemSpider: 27209759

See also PiHKAL: #20 2C-B    
287
Isomer 5

o-DOB
ORTHO-DOB
2-Bromo-4,5-dimethoxyamphetamine

IUPAC: 1-(2-Bromo-4,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: JPDVAVONMYSOMF-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-10(14-2)11(15-3)6-9(8)12/h5-7H,4,13H2,1-3H3

PubChem CID: 141685; ChemSpider: 124999

Shulgin Index: See #52 DOB; Table: 5 Page: 344 Row: 16

See also PiHKAL: #124 META-DOB    

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Barfknecht, CF; Nichols, DE. Potential psychotomimetics. Bromomethoxyamphetamines. J. Med. Chem., 1 Jan 1971, 14 (4), 370–372. 377 kB. doi:10.1021/jm00286a026 Rhodium

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

2166
Isomer 6

5,2,3-DOB
5-Br-2,3-DMA
5-Bromo-2,3-dimethoxyamphetamine

IUPAC: 1-(5-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: ZJJIBYZWBGZMEZ-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)6-10(14-2)11(8)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 69396115; ChemSpider: 26472392

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 4

See also PiHKAL: #124 META-DOB    
2168
Isomer 7

6,2,3-DOB
6-Br-2,3-DMA
6-Bromo-2,3-dimethoxyamphetamine

IUPAC: 1-(6-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: OATUVSAOMSEFGM-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-9(12)4-5-10(14-2)11(8)15-3/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69396333

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 16

See also PiHKAL: #124 META-DOB    

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

2169
Isomer 8

3,2,6-DOB
3-Br-2,6-DMA
3-Bromo-2,6-dimethoxyamphetamine

IUPAC: 1-(3-Bromo-2,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: IBSXXLIDLPNKKF-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-10(14-2)5-4-9(12)11(8)15-3/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69390368

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 22

See also PiHKAL: #124 META-DOB    

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

2170
Isomer 9

2,3,5-DOB
2-Br-3,5-DMA
2-Bromo-3,5-dimethoxyamphetamine

IUPAC: 1-(2-Bromo-3,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: IGMMJULXSJSRCB-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(14-2)6-10(15-3)11(8)12/h5-7H,4,13H2,1-3H3

PubChem CID: 69396730

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 16

See also PiHKAL: #124 META-DOB    

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

374
Isomer 10

4,2,6-DOB
Ψ-DOB
4-Bromo-2,6-dimethoxyamphetamine

IUPAC: 1-(4-Bromo-2,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: LLTVNYHNUJIHOU-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(14-2)5-8(12)6-11(9)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 158251; ChemSpider: 139237

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 15

See also PiHKAL: #162 TMA-6    

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

391
Isomer 11

2C-B-M
4-Bromo-2,5-dimethoxy-N-methylphenethylamine

IUPAC: 2-(4-Bromo-2,5-dimethoxyphenyl)-N-methylethanamine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: ZRTYZUYYGULHEW-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-13-5-4-8-6-11(15-3)9(12)7-10(8)14-2/h6-7,13H,4-5H2,1-3H3

PubChem CID: 9970546; ChemSpider: 8146138

Shulgin Index: See #18 2C-B; Table: 5 Page: 340 Row: 24

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

6977
Isomer 12

4,2,3-DOB

IUPAC: 1-(4-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: VERVNXXUCNQDRY-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(12)11(15-3)10(8)14-2/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69730008

Shulgin Index: See #52 DOB; Table: 5 Page: 337 Row: 27

7005
Isomer 13

3,2,4-DOB

IUPAC: 1-(3-Bromo-2,4-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: DLPXDUUHKRKZAS-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(14-2)10(12)11(8)15-3/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 338 Row: 5

7011
Isomer 14

2,3,4-DOB

IUPAC: 1-(2-Bromo-3,4-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: MYNGUVCYHDQOCQ-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(14-2)11(15-3)10(8)12/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 338 Row: 11

7060
Isomer 15

3-DOB

IUPAC: 1-(3-Bromo-2,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: HCZXNFSMGJKVHO-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(14-2)6-10(12)11(8)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 12626552; ChemSpider: 23115301

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 10

Rasmussen, K; Glennon, RA; Aghajanian, GK. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Eur. J. Pharmacol., 2 Dec 1986, 132 (1), 79–82. 267 kB. doi:10.1016/0014-2999(86)90014-2

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

7420
Isomer 16

2C-B-5-EtO

IUPAC: 2-(4-Bromo-5-ethoxy-2-methoxyphenyl)ethanamine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: OOAVAHXKEKAQFF-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-3-15-11-6-8(4-5-13)10(14-2)7-9(11)12/h6-7H,3-5,13H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 346 Row: 20

7574
Isomer 17

3,4,5-DOB

IUPAC: 1-(3-Bromo-4,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: ZCCTYRNKQKAYJU-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)11(15-3)10(6-8)14-2/h5-7H,4,13H2,1-3H3

PubChem CID: 60907710; ChemSpider: 26495735

Shulgin Index: See #52 DOB; Table: 5 Page: 349 Row: 24

7730
Isomer 18

2,3,6-DOB

IUPAC: 1-(2-Bromo-3,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: NJFHFMVZHWXSEF-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-9(14-2)4-5-10(15-3)11(8)12/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 30

7772
Isomer 19

2,4,6-DOB

IUPAC: 1-(2-Bromo-4,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: QEZQLIBEVDLHCE-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(12)5-8(14-2)6-11(9)15-3/h5-7H,4,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 22

Show all 135 analogues and isomers Show only the 10 N analogues Show only the three α analogues Show only the two β analogues Show only the 82 R4 analogues Show only the three R5 analogues Show only the 16 skeleton analogues
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