PiHKAL • info | explore | 3-DOB; 1-(3-Bromo-2,5-dimethoxyphenyl)propan-2-amine

One α analogue:
2,3,5-MBM 7059	Analogue 1: Removing Methyl at α 2,3,5-MBM IUPAC: 2-(3-Bromo-2,5-dimethylphenyl)ethanamine Formula: C10H14BrN Molecular weight: 228.12886 g/mol InChI Key: PKHDQEALKJDESR-UHFFFAOYSA-N InChI=1S/C10H14BrN/c1-7-5-9(3-4-12)8(2)10(11)6-7/h5-6H,3-4,12H2,1-2H3 Shulgin Index: See #18 2C-B; Table: 5 Page: 339 Row: 9

Five R3 analogues:

2,5-DMA

Analogue 1: Removing Bromo at R3

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

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

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

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

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

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

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

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; 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

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

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

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

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

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:10.1039/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

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.

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.

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

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

TMA-4

160

Analogue 2: Substituting Methoxy for Bromo at R3

TMA-4
2,3,5-Trimethoxyamphetamine

IUPAC: 1-(2,3,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: MJIBJXKJBRLSQA-UHFFFAOYSA-N

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

PubChem CID: 602804; ChemSpider: 523988; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #120 TMA-4; Table: 5 Page: 339 Row: 22

See also PiHKAL:	#42 Ψ-2C-T-4	#135 MMDA-3b	#136 MME	#158 TMA-2	#161 TMA-5

See also Pharmacology notes I:	p. 61, TMA-4: Subacute evaluation p. 72, SARs

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

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

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. 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. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

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

3-DON

7061

Analogue 3: Substituting Nitro for Bromo at R3

3-DON

IUPAC: 1-(2,5-Dimethoxy-3-nitrophenyl)propan-2-amine

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

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

PubChem CID: 126982; ChemSpider: 112754

Shulgin Index: See #61 DON; Table: 5 Page: 339 Row: 11

3-DOM

7062

Analogue 4: Substituting Methyl for Bromo at R3

3-DOM

IUPAC: 1-(2,5-Dimethoxy-3-methylphenyl)propan-2-amine

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

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

PubChem CID: 12626548; ChemSpider: 23187896

Shulgin Index: See #60 DOM; Table: 5 Page: 339 Row: 12

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

3,2,5-DOET

7063

Analogue 5: Substituting Ethyl for Bromo at R3

3,2,5-DOET

IUPAC: 1-(3-Ethyl-2,5-dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 57486947

Shulgin Index: See #56 DOET; Table: 5 Page: 339 Row: 13

19 isomers:

4-Br-3,5-DMA

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

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

DOB

Isomer 2

DOB
4-Bromo-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-bromoamphetamine

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

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

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.

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

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; 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

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.

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

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

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

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

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

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

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.

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. Profiles of psychedelic drugs. 10. DOB. J. Psychoactive Drugs, 1 Jan 1981, 13 (1), 99. 775 kB.

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.

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

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

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.

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.

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

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.

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

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

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

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

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

META-DOB

124

Isomer 3

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

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.

2C-B-2-EtO; 2CB-2ETO

2C-B-2-EtO; 4-Bromo-2-ethoxy-5-methoxyphenethylamine

195

Isomer 4

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

2-Bromo-4,5-dimethoxy-N-methylphenethylamine

198

Isomer 5

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

o-DOB; ORTHO-DOB

287

Isomer 6

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

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.

5,2,3-DOB; 5-Br-2,3-DMA

5,2,3-DOB; 5-Bromo-2,3-dimethoxyamphetamine

2166

Isomer 7

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

6,2,3-DOB; 6-Br-2,3-DMA

6,2,3-DOB; 6-Bromo-2,3-dimethoxyamphetamine

2168

Isomer 8

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

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.

3,2,6-DOB; 3-Br-2,6-DMA

3,2,6-DOB; 3-Bromo-2,6-dimethoxyamphetamine

2169

Isomer 9

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

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.

2,3,5-DOB; 2-Br-3,5-DMA

2,3,5-DOB; 2-Bromo-3,5-dimethoxyamphetamine

2170

Isomer 10

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

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.

4,2,6-DOB; Ψ-DOB

4,2,6-DOB; 4-Bromo-2,6-dimethoxyamphetamine

374

Isomer 11

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

2C-B-M

391

Isomer 12

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; Angeles, JDL; 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

4,2,3-DOB

6977

Isomer 13

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

3,2,4-DOB

7005

Isomer 14

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

2,3,4-DOB

7011

Isomer 15

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

2C-B-5-EtO

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

3,4,5-DOB

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

2,3,6-DOB

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

2,4,6-DOB

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