PiHKAL • info | explore | PiHKAL#122 MEM; SI#87 MEM

Two α analogues:

2C-O-2

2068

Analogue 1: Removing Methyl at α

2C-O-2
2C-O-2
2,5-Dimethoxy-4-ethoxyphenethylamine

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

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

InChI=1S/C12H19NO3/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 57474251

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 31

See also PiHKAL:	#35 2C-O-4

4C-EtO

334

Analogue 2: Substituting Ethyl for Methyl at α

4C-EtO
1-(4-Ethoxy-2,5-dimethoxyphenyl)-2-aminobutane
4-Ethoxy-α-ethyl-2,5-dimethoxyphenethylamine

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

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: IFHFZYCBFHDQCO-NSHDSACASA-N

InChI=1S/C14H23NO3/c1-5-11(15)7-10-8-13(17-4)14(18-6-2)9-12(10)16-3/h8-9,11H,5-7,15H2,1-4H3/t11-/m0/s1

ChemSpider: 25042426

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 33

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

One R2 analogue:

EEM

Analogue 1: Substituting Ethoxy for Methoxy at R2

EEM
2,4-Diethoxy-5-methoxyamphetamine

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

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

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

PubChem CID: 44719558; ChemSpider: 21106297; Wikipedia: EEM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 34

See also PiHKAL:	#73 EEE	#122 MEM

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

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

81 R4 analogues:

ALEPH

Analogue 1: Substituting Methylthio for Ethoxy 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

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.

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

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

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

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

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

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.

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.

ALEPH-2

Analogue 2: Substituting Ethylthio for Ethoxy 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

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

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

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

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

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

ALEPH-4

Analogue 3: Substituting Isopropylthio for Ethoxy 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

ALEPH-6

Analogue 4: Substituting Phenylthio for Ethoxy 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

ALEPH-7

Analogue 5: Substituting n-Propylthio for Ethoxy 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

2,5-DMA

Analogue 6: Removing Ethoxy 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

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

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

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

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.

DOAM

Analogue 7: Substituting n-Pentyl for Ethoxy 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

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.

DOB

Analogue 8: Substituting Bromo for Ethoxy at R4

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.

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

DOBU

Analogue 9: Substituting n-Butyl for Ethoxy 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

See also Pharmacology notes I:	p. 166, DOBU p. 167, DOBU

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

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

DOC

Analogue 10: Substituting Chloro for Ethoxy 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

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.

DOEF

Analogue 11: Substituting 2-Fluoroethyl for Ethoxy 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

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

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

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

DOET

Analogue 12: Substituting Ethyl for Ethoxy 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

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

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.

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

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

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.

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

DOI

Analogue 13: Substituting Iodo for Ethoxy 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

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

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.

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.

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

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

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

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.

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

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

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

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

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

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

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.

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.

DOM

Analogue 14: Substituting Methyl for Ethoxy 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. 84.1, nor-oxy-4-TMA-2 (XV-198) 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

Standridge, RT; Howell, HG; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane. J. Med. Chem., 1 Jan 1976, 19 (12), 1400 –1404. 730 kB. doi:10.1021/jm00234a010

Barfknecht, CF; Caputo, JF; Tobin, MB; Dyer, DC; Standridge, RT; Howell, HG; Goodwin, WR; Partyka, RA; Gylys, JA; Cavanagh, RL. Congeners of DOM: Effect of distribution on the evaluation of pharmacologic data. 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 16–26. 502 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

Hollister, LE; Macnicol, MF; Gillespie, HK. An hallucinogenic amphetamine analog (DOM) in man. Psychopharmacology, 1 Jan 1969, 14 (1), 62–73. 667 kB. doi:10.1007/BF00401535

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

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

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of &alpha-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Fantegrossi, WE; Harrington, AW; Eckler, JR; Arshad, S; Rabin, RA; Winter, JC; Coop, A; Rice, KC; Woods, JH. Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats. Psychopharmacology, 1 Sep 2005, 181 (3), 496–503. 182 kB. doi:10.1007/s00213-005-0009-4

Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. doi:10.1016/S0091-3057(99)00178-1

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

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

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. Stereospecific requirements for hallucinogenesis. J. Pharm. Pharmacol., 1 Jan 1973, 25 (3), 271–272. 226 kB.

Shulgin, AT. Profiles of psychedelic drugs. 5. STP. J. Psychedelic Drugs, 1 Jan 1977, 9 (2), 171–172. 755 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.

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.

McKenna, DJ; Guan, AM; Shulgin, AT. 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine. Pharmacol. Biochem. Behav., 1 Jan 1991, 38 (3), 505–12. 783 kB. doi:10.1016/0091-3057(91)90005-M

Nichols, DE; Pfister, WR; Yim, GKW. LSD and phenethylamine hallucinogens: New structural analogy and implications for receptor geometry. Life Sci., 1 Jan 1978, 22 (24), 2165–2170. 323 kB. doi:10.1016/0024-3205(78)90567-2

Weintraub, HJR; Nichols, DE; Makriyannis, A; Fesik, SW. Conformational energy differences between side chain alkylated analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 1980, 23 (3), 339–341. 452 kB. doi:10.1021/jm00177a030

Kothari, PJ; Hathaway, BA; Nichols, DE; Yim, GKW. Synthesis and serotonin-like activity of 2-amino-5,8-dimethoxy-6-methyl-1,2-dihydronaphthalene. J. Med. Chem., 1 Jan 1981, 24 (7), 882–884. 464 kB. doi:10.1021/jm00139a022

Jacob, JN; Nichols, DE. Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue. J. Med. Chem., 1 Jan 1982, 25 (5), 526–530. 732 kB. doi:10.1021/jm00347a009

Nichols, DE. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: Entactogens. J. Psychoactive Drugs, 1 Jan 1986, 18 (4), 305–313. 10675 kB.

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

Chambers, JJ; Kurrasch-Orbaugh, DM; Nichols, DE. Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: Effects on 5-HT2A/2C receptor affinity. Bioorg. Med. Chem. Lett., 1 Jan 2002, 12 (15), 1997–1999. 100 kB. doi:10.1016/S0960-894X(02)00306-2

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.

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.

Coutts, RT; Malicky, JL. The synthesis of four possible in vitro metabolites of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Feb 1974, 52 (3), 395–399. 299 kB. doi:10.1139/v74-063

Zweig, JS; Castagnoli, N. Chemical conversion of the psychotomimetic amine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane to 5-hydroxy-2,6-dimethylindole. J. Med. Chem., 1 Jul 1974, 17 (7), 747–749. 438 kB. doi:10.1021/jm00253a019

Zweig, JS; Castagnoli, N. In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. J. Med. Chem., 1 Mar 1977, 20 (3), 414–421. 1182 kB. doi:10.1021/jm00213a020

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034

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

DON

Analogue 15: Substituting Nitro for Ethoxy 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

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.

DOPR

Analogue 16: Substituting n-Propyl for Ethoxy 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

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

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

MPM

138

Analogue 17: Substituting n-Propoxy for Ethoxy 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

TMA-2

158

Analogue 18: Substituting Methoxy for Ethoxy 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. 55.1, 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

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

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

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

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. 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.

Shulgin, AT. Profiles of psychedelic drugs. 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 169. 891 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.

DOF

208

Analogue 19: Substituting Fluoro for Ethoxy 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

DOIB

235

Analogue 20: Substituting Isobutyl for Ethoxy 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

DOTB

236

Analogue 21: Substituting tert-Butyl for Ethoxy 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

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.

DOSB

237

Analogue 22: Substituting sec-Butyl for Ethoxy 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

DONH; DOA

238

Analogue 23: Substituting Amino for Ethoxy 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

DOAA

239

Analogue 24: Substituting Acetylamino for Ethoxy 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

Hydroxy-DOPR

245

Analogue 25: Substituting 1-Hydroxypropyl for Ethoxy 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

DOIP

246

Analogue 26: Substituting Isopropyl for Ethoxy 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

MIPM

302

Analogue 27: Substituting Isopropoxy for Ethoxy 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

MBM

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

303

Analogue 28: Substituting n-Butoxy for Ethoxy 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

MAM

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

304

Analogue 29: Substituting n-Pentyloxy for Ethoxy 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

DOHE

322

Analogue 30: Substituting n-Hexyl for Ethoxy 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

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

DOBZ

323

Analogue 31: Substituting Benzyl for Ethoxy 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

DOCPM

324

Analogue 32: Substituting Cyclopropylmethyl for Ethoxy 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

ALEPH-8

2078

Analogue 33: Substituting Cyclopropylmethylthio for Ethoxy 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

ALEPH-5

2084

Analogue 34: Substituting Cyclohexylthio for Ethoxy 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

ALEPH-16

2085

Analogue 35: Substituting Allylthio for Ethoxy 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

ALEPH-21

2088

Analogue 36: Substituting 2-Fluoroethylthio for Ethoxy 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

DOTFM

5381

Analogue 37: Substituting Trifluoromethyl for Ethoxy 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

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

Nichols, DE; Frescas, S; 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

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

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.

2328

2328

Analogue 38: Substituting Phenylbutyl for Ethoxy 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

DOYN

2196

Analogue 39: Substituting Ethynyl for Ethoxy 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

DOCN

2197

Analogue 40: Substituting Cyano for Ethoxy 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

DOPh3

2323

Analogue 41: Substituting Phenylpropyl for Ethoxy 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

2325

2325

Analogue 42: Substituting Phenethyl for Ethoxy 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

2329

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

2329

Analogue 43: Substituting (4-Chlorophenyl)propyl for Ethoxy 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

2330

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

2330

Analogue 44: Substituting (4-Methoxyphenyl)propyl for Ethoxy 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

DOVI

390

Analogue 45: Substituting Ethenyl for Ethoxy 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

DOAC

2416

Analogue 46: Substituting Acetyl for Ethoxy 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

DOCA

2415

Analogue 47: Substituting Carboxy for Ethoxy 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

DOOH

2414

Analogue 48: Substituting Hydroxy for Ethoxy 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

DOCONHP

2413

Analogue 49: Substituting Propylaminocarbonyl for Ethoxy 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

DOCOE

2412

Analogue 50: Substituting Propanoyl for Ethoxy 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

DOCEB

2411

Analogue 51: Substituting Butoxycarbonyl for Ethoxy 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

DOCEP

2410

Analogue 52: Substituting Propoxycarbonyl for Ethoxy 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

DOOC

2409

Analogue 53: Substituting n-Octyl for Ethoxy 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

DONMM

7183

Analogue 54: Substituting Dimethylamino for Ethoxy 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

DOFM

7234

Analogue 55: Substituting Fluoromethyl for Ethoxy 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

DOHM

7254

Analogue 56: Substituting Hydroxymethyl for Ethoxy 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

DOHP

7267

Analogue 57: Substituting n-Heptyl for Ethoxy 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

DONO

7268

Analogue 58: Substituting n-Nonyl for Ethoxy 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

DOEH

7275

Analogue 59: Substituting 2-Hydroxyethyl for Ethoxy 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

M(2OP)M

7353

Analogue 60: Substituting 2-Hydroxypropoxy for Ethoxy 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

M(3OP)M

7354

Analogue 61: Substituting 3-Hydroxypropoxy for Ethoxy 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

MBZM

7361

Analogue 62: Substituting Benzyloxy for Ethoxy 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

ALEPH-19

7404

Analogue 63: Substituting n-Butylthio for Ethoxy 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

ALEPH-S-amyl

7413

Analogue 64: Substituting n-Pentylthio for Ethoxy 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

ALEPH-S-PhEt

7415

Analogue 65: Substituting Phenethylthio for Ethoxy at R4

ALEPH-S-PhEt

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

Formula: C18H23NO2S Molecular weight: 317.44572 g/mol InChI Key: UJVBIPZRWSFCTC-UHFFFAOYSA-N

InChI=1S/C18H23NO2S/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 #3 ALEPH; Table: 5 Page: 346 Row: 15

ALEPH sulfone

7416

Analogue 66: Substituting Methylsulfonyl for Ethoxy 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

DOTFE

473

Analogue 67: Substituting 2,2,2-Trifluoroethyl for Ethoxy 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

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

MTFEM

469

Analogue 68: Substituting 2,2,2-Trifluoroethoxy for Ethoxy 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

MDFEM

468

Analogue 69: Substituting 2,2-Difluoroethoxy for Ethoxy 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

MFEM

467

Analogue 70: Substituting 2-Fluoroethyoxy for Ethoxy 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

DONCOTFM

1523

Analogue 71: Substituting (Trifluoroacetyl)amino for Ethoxy 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)

DONCOE

1522

Analogue 72: Substituting Propanoylamino for Ethoxy 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)

DONCO

1521

Analogue 73: Substituting Formylamino for Ethoxy 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)

DOMOM

1520

Analogue 74: Substituting 2-Methoxyethyl for Ethoxy 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

DOMSM

1519

Analogue 75: Substituting 2-Methylthioethyl for Ethoxy 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

DOHSM

1518

Analogue 76: Substituting Sulfanylmethyl for Ethoxy 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

DOTFPR

1517

Analogue 77: Substituting 3,3,3-Trifluoropropyl for Ethoxy 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

DOCET

1516

Analogue 78: Substituting 2-Chloroethyl for Ethoxy 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

DOCM

1515

Analogue 79: Substituting Chloromethyl for Ethoxy at R4

DOCM

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

DOBM

1514

Analogue 80: Substituting Bromomethyl for Ethoxy 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

DOCNM

1513

Analogue 81: Substituting Cyanomethyl for Ethoxy 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

One R5 analogue:

MEE

121

Analogue 1: Substituting Ethoxy for Methoxy at R5

MEE
2-Methoxy-4,5-diethoxyamphetamine
4,5-Diethoxy-2-methoxyamphetamine

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

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

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

PubChem CID: 44719591; ChemSpider: 21106337; Wikipedia: MEE (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 28

See also PiHKAL:	#73 EEE	#122 MEM

See also Pharmacology notes I:	p. 79, MEE: Subacute evaluation

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

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

37 isomers:

AEM

Isomer 1

AEM
α-Ethylmescaline
α-Ethyl-3,4,5-trimethoxyphenethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1-(3,4,5-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(3,4,5-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 204932; ChemSpider: 177522; Wikipedia: AEM (psychedelic)

Shulgin Index: #1 AEM; Table: 5 Page: 350 Row: 11

See also PiHKAL:	#157 TMA

See also Pharmacology notes I:	p. 20, AEM: Subacute evaluation

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

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

ASB

Isomer 2

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

IUPAC: 2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 45367; ChemSpider: 41279; Wikipedia: Asymbescaline

Shulgin Index: #8 ASB; Table: 5 Page: 351 Row: 2, #8 ASB; Table: 5 Page: 351 Row: 36

See also PiHKAL:	#148 5-TASB	#163 3-TME	#178 3-T-TRIS

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

3C-E

Isomer 3

3C-E
4-Ethoxy-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 44350137; ChemSpider: 21106237; Wikipedia: 3C-E

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 1

See also PiHKAL:	#72 E

See also Pharmacology notes II:	p. 222, 3C-E

2C-O-4

Isomer 4

2C-O-4
4-Isopropoxy-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropoxyphenethylamine

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

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

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

PubChem CID: 44719510; ChemSpider: 21106225; Wikipedia: 2C-O-4

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 5

EMM

Isomer 5

EMM
2-Ethoxy-4,5-dimethoxyamphetamine
4,5-Dimethoxy-2-ethoxyamphetamine

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

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

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

PubChem CID: 44719565; ChemSpider: 21106299; Wikipedia: EMM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 28

See also PiHKAL:	#73 EEE	#121 MEE	#122 MEM	#136 MME

See also Pharmacology notes I:	p. 60, EMM: Subacute evaluation

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

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.

Isomer 6

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethanamine

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

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

PubChem CID: 15102787; ChemSpider: 10439597; Wikipedia: Isoproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 13

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

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.

MME

136

Isomer 7

MME
2,4-Dimethoxy-5-ethoxyamphetamine

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

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

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

PubChem CID: 44719602; ChemSpider: 21106338; Wikipedia: MME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 26

See also PiHKAL:	#73 EEE	#75 EME	#121 MEE	#122 MEM

See also Pharmacology notes I:	p. 77, MME: Subacute evaluation

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

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.

137

Isomer 8

MP
Metaproscaline
3,4-Dimethoxy-5-propoxyphenethylamine
3,4-Dimethoxy-5-n-propoxyphenethylamine

IUPAC: 2-(3,4-Dimethoxy-5-propoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-4-7-17-12-9-10(5-6-14)8-11(15-2)13(12)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44375097; ChemSpider: 21106345; Wikipedia: Metaproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 5

See also PiHKAL:	#119 ME	#163 3-TME

140

Isomer 9

P
Proscaline
Proscaline
3,5-Dimethoxy-4-propoxyphenethylamine
3,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 15102790; ChemSpider: 10439596; Wikipedia: Proscaline

Shulgin Index: #104 Proscaline; Table: 5 Page: 351 Row: 11

See also PiHKAL:	#72 E #80 F-22	#123 MEPEA #141 PE	#163 3-TME

See also Pharmacology notes II:	p. 209, Proscaline

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

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

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.

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

144

Isomer 10

SB
Symbescaline
3,5-Diethoxy-4-methoxyphenethylamine

IUPAC: 2-(3,5-Diethoxy-4-methoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-4-16-11-8-10(6-7-14)9-12(17-5-2)13(11)15-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44374890; ChemSpider: 21106384; Wikipedia: Symbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 33

See also PiHKAL:	#9 ASB	#163 3-TME

189

1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane

189

Isomer 11

1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane

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

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

InChI=1S/C13H21NO3/c1-5-11(14-15)7-10-8-12(16-3)9(2)6-13(10)17-4/h6,8,11,14-15H,5,7H2,1-4H3

See also PiHKAL:	#8 ARIADNE

4C-TMPEA-6

190

Isomer 12

4C-TMPEA-6
1-(2,4,6-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(2,4,6-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 43565966

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 28

See also PiHKAL:	#8 ARIADNE

BOED

194

Isomer 13

BOED
2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-2-ethoxyethanamine

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

InChI=1S/C13H21NO3/c1-5-17-13(8-14)10-7-11(15-3)9(2)6-12(10)16-4/h6-7,13H,5,8,14H2,1-4H3

See also PiHKAL:	#14 BOD

Coutts, RT; Malicky, JL. The synthesis of analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some ring-methoxylated 1-amino- and 2-aminoindanes. Can. J. Chem., 1 Feb 1974, 52 (3), 381–389. 615 kB. doi:10.1139/v74-061

Z-7.2

Z-7.2; 4-Methyl-2,3,6-trimethoxyamphetamine

244

Isomer 14

Z-7.2
4-Methyl-2,3,6-trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxy-4-methylphenyl)propan-2-amine

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

InChI=1S/C13H21NO3/c1-8-6-11(15-3)10(7-9(2)14)13(17-5)12(8)16-4/h6,9H,7,14H2,1-5H3

See also PiHKAL:	#69 Ψ-DOM

Trichocerine

263

Isomer 15

Trichocerine
Trichocereine
N,N-Dimethylmescaline
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine

IUPAC: N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-14(2)7-6-10-8-11(15-3)13(17-5)12(9-10)16-4/h8-9H,6-7H2,1-5H3

PubChem CID: 420418; ChemSpider: 372161

Shulgin Index: #125 Trichocereine; Table: 5 Page: 350 Row: 25

See also PiHKAL:	#96 M

N-Me-TMA; METHYL-TMA

N-Me-TMA; N-Methyl-3,4,5-trimethoxyamphetamine

288

Isomer 16

N-Me-TMA
METHYL-TMA
N-Methyl-3,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 24257271; ChemSpider: 23900079

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 2

See also PiHKAL:	#126 METHYL-DMA

N-Me-TMA-2; METHYL-TMA-2

N-Me-TMA-2; N-Methyl-2,4,5-trimethoxyamphetamine

289

Isomer 17

N-Me-TMA-2
METHYL-TMA-2
N-Methyl-2,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,5-trimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 69454104

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 24

See also PiHKAL:	#126 METHYL-DMA

See also Pharmacology notes I:	p. 59, N-Me-TMA-2: Subacute evaluation

N-Me-TMA-6; METHYL-TMA-6

N-Me-TMA-6; N-Methyl-2,4,6-trimethoxyamphetamine

290

Isomer 18

N-Me-TMA-6
METHYL-TMA-6
N-Methyl-2,4,6-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,6-trimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 69393054

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 27

See also PiHKAL:	#126 METHYL-DMA

2C-O-7

2069

Isomer 19

2C-O-7
2C-O-7
2,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine

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

InChI=1S/C13H21NO3/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474252

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 35

See also PiHKAL:	#35 2C-O-4

Salbutamol

5549

Isomer 20

Salbutamol
N-tert-Butyl-β,4-dihydroxy-3-(hydroxymethyl)phenethylamine

IUPAC: 4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

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

InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

PubChem CID: 2083; ChemSpider: 1999; Wikipedia: Salbutamol

homo-TMA-2

620

Isomer 21

homo-TMA-2

IUPAC: 4-(2,4,5-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 3839009; ChemSpider: 3064644

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 27

homo-TMA-3

622

Isomer 22

homo-TMA-3

IUPAC: 4-(2,3,4-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 3041182; ChemSpider: 2304487

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 29

homo-TMA-6

623

Isomer 23

homo-TMA-6

IUPAC: 4-(2,4,6-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 3041180; ChemSpider: 2304485

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 30

N,N-Me-β,3,4-TMPEA

6613

Isomer 24

N,N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethanamine

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

InChI=1S/C13H21NO3/c1-14(2)9-13(17-5)10-6-7-11(15-3)12(8-10)16-4/h6-8,13H,9H2,1-5H3

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 13

β-HO-β,N,N-Me-2,5-DMPEA

6870

Isomer 25

β-HO-β,N,N-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)-1-(dimethylamino)propan-2-ol

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

InChI=1S/C13H21NO3/c1-13(15,9-14(2)3)11-8-10(16-4)6-7-12(11)17-5/h6-8,15H,9H2,1-5H3

PubChem CID: 50632; ChemSpider: 45892

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 20

β-HO-N,N-Me-2,5-DMA

6878

Isomer 26

β-HO-N,N-Me-2,5-DMA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1-ol

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

InChI=1S/C13H21NO3/c1-9(14(2)3)13(15)11-8-10(16-4)6-7-12(11)17-5/h6-9,13,15H,1-5H3

PubChem CID: 46240; ChemSpider: 42098

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 28

β-HO-N-Me-2,5-DEPEA

6913

Isomer 27

β-HO-N-Me-2,5-DEPEA

IUPAC: 1-(2,5-Diethoxyphenyl)-2-(methylamino)ethanol

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

InChI=1S/C13H21NO3/c1-4-16-10-6-7-13(17-5-2)11(8-10)12(15)9-14-3/h6-8,12,14-15H,4-5,9H2,1-3H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 13

β-HO-2,5-DEA

6915

Isomer 28

β-HO-2,5-DEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol

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

InChI=1S/C13H21NO3/c1-4-16-10-6-7-12(17-5-2)11(8-10)13(15)9(3)14/h6-9,13,15H,4-5,14H2,1-3H3

PubChem CID: 11253430; ChemSpider: 9428457

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 15

N-Me-TMA-3

7016

Isomer 29

N-Me-TMA-3

IUPAC: N-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine

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

InChI=1S/C13H21NO3/c1-9(14-2)8-10-6-7-11(15-3)13(17-5)12(10)16-4/h6-7,9,14H,8H2,1-5H3

ChemSpider: 21476716

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 16

4C-TMPEA-3

7017

Isomer 30

4C-TMPEA-3

IUPAC: 1-(2,3,4-Trimethoxyphenyl)butan-2-amine

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

InChI=1S/C13H21NO3/c1-5-10(14)8-9-6-7-11(15-2)13(17-4)12(9)16-3/h6-7,10H,5,8,14H2,1-4H3

PubChem CID: 43566032

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 17

4C-HM

7255

Isomer 31

4C-HM

IUPAC: 4-(2-Aminobutyl)-2,5-dimethoxybenzaldehyde

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

InChI=1S/C13H21NO3/c1-4-11(14)5-9-6-13(17-3)10(8-15)7-12(9)16-2/h6-7,11,15H,4-5,8,14H2,1-3H3

PubChem CID: 20315288

Shulgin Index: See #118 TMA-2; Table: 5 Page: 343 Row: 5

BOE

BOE; 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethanamine

7262

Isomer 32

BOE

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethanamine

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

InChI=1S/C13H21NO3/c1-5-9-6-12(16-3)10(7-11(9)15-2)13(8-14)17-4/h6-7,13H,5,8,14H2,1-4H3

PubChem CID: 10331826; ChemSpider: 8507286

Shulgin Index: See #14 BOB; Table: 5 Page: 343 Row: 12

Torres, MA; Cassels, B; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

DOEH

7275

Isomer 33

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

4C-MeO

7327

Isomer 34

4C-MeO

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

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

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

PubChem CID: 43566022

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 27

DESMETHYL-iPr

7570

Isomer 35

DESMETHYL-iPr

IUPAC: 2,6-Dimethoxy-4-[2-(propan-2-ylamino)ethyl]phenol

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

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

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 20

α-MM-M

7609

Isomer 36

α-MM-M

IUPAC: 2-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

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

InChI=1S/C13H21NO3/c1-13(2,14)8-9-6-10(15-3)12(17-5)11(7-9)16-4/h6-7H,8,14H2,1-5H3

PubChem CID: 3029803; ChemSpider: 2295076

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 9

DOMOM

1520

Isomer 37

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