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PiHKAL#14 BOD; SI#13 BOD
14
Variant: β R4 skeleton isomers all
Analogues: 6 7 8 29 50

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

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

InChI=1S/C12H19NO3/c1-8-5-11(15-3)9(6-10(8)14-2)12(7-13)16-4/h5-6,12H,7,13H2,1-4H3

PubChem CID: 44719486; ChemSpider: 21106262; Wikipedia: BOD (psychedelic)

Shulgin Index: #14 BOB; Table: 5 Page: 342 Row: 29

See also PiHKAL: #13 BOB #15 BOH #16 BOHD #17 BOM

See also Transcripts: 4.462, 5.628, 5.628.2

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

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

Six β analogues:
16
Analogue 1: Substituting Hydroxy for Methoxy at β

BOHD
2,5-Dimethoxy-β-hydroxy-4-methylphenethylamine

IUPAC: 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)ethanol

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

InChI=1S/C11H17NO3/c1-7-4-11(15-3)8(9(13)6-12)5-10(7)14-2/h4-5,9,13H,6,12H2,1-3H3

PubChem CID: 44719489; ChemSpider: 21106263; Wikipedia: BOHD (psychedelic)

See also PiHKAL: #14 BOD #57 DME    

Ho, B; Tansey, LW; McIsaac, WM. Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM). J. Med. Chem., 1 Sep 1970, 13 (5), 1022. 99 kB. doi:10.1021/jm00299a071

23
Analogue 2: Removing Methoxy at β

2C-D
LE-25
4-Methyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylphenethylamine

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

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

InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3

PubChem CID: 135740; ChemSpider: 119559; Drugs Forum: 2C-D; Erowid: 2C-D; Wikipedia: 2C-D

Shulgin Index: #20 2C-D; Table: 5 Page: 342 Row: 9

See also PiHKAL: #8 ARIADNE
#14 BOD
#16 BOHD
#20 2C-B
#25 3C-E
#56 DMCPA
#68 DOM
#85 GANESHA
#93 IRIS
 
See also TiHKAL: #16 4-HO-DET      

See also Transcripts: 1.94, 1.175, 2.273, 2.280, 2.285, 2.310, 2.313, 2.316, 5.628, 5.628.2

See also Pharmacology notes I: p. 94, 2C-D: Subacute evaluation
p. 175, 2C-D: Acute trials
See also Pharmacology notes II: p. 273, 2C-D
p. 280, 2C-D
p. 285, 2C-D: Report of experience
p. 310, 2C-D
p. 313, 2C-D
p. 316, 2C-D: Experiment with 2C-D

Meyer, MR; Robert, A; Maurer, HH. Toxicokinetics of novel psychoactive substances: Characterization of N-acetyltransferase (NAT) isoenzymes involved in the phase II metabolism of 2C designer drugs. Toxicol. Lett., 5 Jun 2014, 227 (2), 124–128. 693 kB. doi:10.1016/j.toxlet.2014.03.010

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

Allred, RA. Spectral characterization of 2,4-dimethoxy-3-methylphenethylamine and comparison to 2,5-dimethoxy-4-methylphenethylamine (“2C-D”). Microgram J., 1 Jan 2005, 3 (1–2), 16–26. 107 kB.

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

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

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

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 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. doi:10.1111/j.2042-7158.1985.tb03072.x

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

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

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

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

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

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-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

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

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

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

194
Analogue 3: Substituting Ethoxy for Methoxy at β

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

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

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      

See also Transcripts: 5.628, 5.628.2

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

2065
Analogue 4: Substituting Acetoxy for Methoxy at β

BOAD
β-Acetoxy-2,5-dimethoxy-4-methylphenethylamine

IUPAC: 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)ethyl acetate

Formula: C13H19NO4 Molecular weight: 253.29426 g/mol InChI Key: FTJLCPGTLLANAU-UHFFFAOYSA-N

InChI=1S/C13H19NO4/c1-8-5-12(17-4)10(6-11(8)16-3)13(7-14)18-9(2)15/h5-6,13H,7,14H2,1-4H3

See also PiHKAL: #16 BOHD      

See also Transcripts: 4.462, 5.628, 5.628.2

7211
Analogue 5: Substituting Methyl for Methoxy at β

β-Me-2C-D

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

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

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

ChemSpider: 26706147

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 11

7212
Analogue 6: Substituting Dimethyl for Methoxy at β

β,β-Me-2C-D

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

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

InChI=1S/C13H21NO2/c1-9-6-12(16-5)10(7-11(9)15-4)13(2,3)8-14/h6-7H,8,14H2,1-5H3

PubChem CID: 57486950; ChemSpider: 26711089

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 12

Seven R4 analogues:
13
Analogue 1: Substituting Bromo for Methyl at R4

BOB
β-Methoxy-2C-B
4-Bromo-2,5-β-trimethoxyphenethylamine

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

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

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

PubChem CID: 15185771; ChemSpider: 21106261; Wikipedia: BOB (psychedelic)

Shulgin Index: #13 BOD; Table: 5 Page: 341 Row: 2

See also PiHKAL: #14 BOD #17 BOM    

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

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

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

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

6867
Analogue 2: Removing Methyl at R4

BODM

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

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

InChI=1S/C11H17NO3/c1-13-8-4-5-10(14-2)9(6-8)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 10420680; ChemSpider: 8596110

Shulgin Index: See #14 BOB; Table: 4 Page: 335 Row: 17

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

7161
Analogue 3: Substituting Iodo for Methyl at R4

BOI

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

Formula: C11H16INO3 Molecular weight: 337.15411 g/mol InChI Key: PPHHUNXXWCQIJS-UHFFFAOYSA-N

InChI=1S/C11H16INO3/c1-14-9-5-8(12)10(15-2)4-7(9)11(6-13)16-3/h4-5,11H,6,13H2,1-3H3

PubChem CID: 10449708; ChemSpider: 8625125

Shulgin Index: See #14 BOB; Table: 5 Page: 341 Row: 11

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

7202
Analogue 4: Substituting Nitro for Methyl at R4

BON

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

Formula: C11H16N2O5 Molecular weight: 256.25514 g/mol InChI Key: AACPSSCTUJOCJK-UHFFFAOYSA-N

InChI=1S/C11H16N2O5/c1-16-9-5-8(13(14)15)10(17-2)4-7(9)11(6-12)18-3/h4-5,11H,6,12H2,1-3H3

PubChem CID: 10332628; ChemSpider: 8508087

Shulgin Index: See #14 BOB; Table: 5 Page: 342 Row: 2

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

7262
Analogue 5: Substituting Ethyl for Methyl at R4

BOE

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

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

7322
Analogue 6: Substituting Methoxy for Methyl at R4

BOT

IUPAC: 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethan-1-amine

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: RCJFHHAMXCSUBT-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-14-9-6-11(16-3)10(15-2)5-8(9)12(7-13)17-4/h5-6,12H,7,13H2,1-4H3

PubChem CID: 10399437; ChemSpider: 8574875

Shulgin Index: See #14 BOB; Table: 5 Page: 344 Row: 22

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

7378
Analogue 7: Substituting Propylthio for Methyl at R4

BOPS

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

Formula: C14H23NO3S Molecular weight: 285.40232 g/mol InChI Key: VURRPHKKQVZMGW-UHFFFAOYSA-N

InChI=1S/C14H23NO3S/c1-5-6-19-14-8-11(16-2)10(7-12(14)17-3)13(9-15)18-4/h7-8,13H,5-6,9,15H2,1-4H3

Shulgin Index: See #14 BOB; Table: 5 Page: 345 Row: 28

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

Eight skeleton analogues:
56
Analogue 1: With 2-Phenylcyclopropan-1-amine skeleton

DMCPA
2-(2,5-Dimethoxy-4-methylphenyl)cyclopropylamine

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

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: HYVPPECPQRBJEQ-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-7-4-12(15-3)9(6-11(7)14-2)8-5-10(8)13/h4,6,8,10H,5,13H2,1-3H3

PubChem CID: 3017965; ChemSpider: 2285590; Wikipedia: 4-Methyl-2,5-methoxyphenylcyclopropylamine

Shulgin Index: #41 DMCPA; Table: 5 Page: 342 Row: 27

See also PiHKAL: #142 PEA      
See also TiHKAL: #8 α,N-DMT      

See also Transcripts: 4.497

Nichols, DE; Woodard, R; Hathaway, BA; Lowy, MT; Yim, GKW. Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue. J. Med. Chem., 1 Jan 1979, 22 (4), 458–460. 464 kB. doi:10.1021/jm00190a021

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

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

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; Jadhav, KP; Oberlender, RA; Zabik, JE; Bossart, JF; Hamada, A; Miller, DD. Synthesis and evaluation of substituted 2-phenylcyclobutylamines as analogues of hallucinogenic phenethylamines: Lack of LSD-like biological activity. J. Med. Chem., 1 Jan 1984, 27 (9), 1108–1111. 617 kB. doi:10.1021/jm00375a004

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

5524
Analogue 2: With 1-Benzylcyclopropan-1-amine skeleton

α-CP-2C-D
BL-4358A
1-Amino-1-(2,5-dimethoxy-4-methylbenzyl)cyclopropane

IUPAC: 1-(2,5-Dimethoxy-4-methylbenzyl)cyclopropanamine

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

InChI=1S/C13H19NO2/c1-9-6-12(16-3)10(7-11(9)15-2)8-13(14)4-5-13/h6-7H,4-5,8,14H2,1-3H3

PubChem CID: 54504026

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 22

See also Transcripts: 4.462

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

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.

407
Analogue 3: With 2,3-Dihydro-1H-inden-2-amine skeleton

DOMAI
DOM-AI
2-Amino-4,7-dimethoxy-5-methylindane

IUPAC: 4,7-Dimethoxy-5-methyl-2,3-dihydro-1H-inden-2-amine

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: LBSOVXNUJAVVNS-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-7-4-11(14-2)9-5-8(13)6-10(9)12(7)15-3/h4,8H,5-6,13H2,1-3H3

PubChem CID: 3016787; ChemSpider: 2284673

Shulgin Index: See #60 DOM; Table: 6 Page: 355 Row: 19

Nichols, DE; Barfknecht, CF; Long, JP; Standridge, RT; Howell, HG; Partyka, RA; Dyer, DC. Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP). J. Med. Chem., 1 Jan 1974, 17 (2), 161–166. 718 kB. doi:10.1021/jm00248a004

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

406
Analogue 4: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

DOMAT
DOM-AT
2-Amino-5,8-dimethoxy-6-methyltetralin

IUPAC: 5,8-Dimethoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C13H19NO2/c1-8-6-12(15-2)11-7-9(14)4-5-10(11)13(8)16-3/h6,9H,4-5,7,14H2,1-3H3

PubChem CID: 3016832; ChemSpider: 2284695

Shulgin Index: See #60 DOM; Table: 6 Page: 355 Row: 22

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

Nichols, DE; Barfknecht, CF; Long, JP; Standridge, RT; Howell, HG; Partyka, RA; Dyer, DC. Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP). J. Med. Chem., 1 Jan 1974, 17 (2), 161–166. 718 kB. doi:10.1021/jm00248a004

7228
Analogue 5: With 2-Phenylcyclopropan-1-amine skeleton

DMMCPA

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

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

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

Shulgin Index: See #41 DMCPA; Table: 5 Page: 342 Row: 28

505
Analogue 6: With 2,3-Dihydro-1H-inden-2-amine skeleton

HO-DOMAI

IUPAC: 2-Amino-4,7-dimethoxy-6-methyl-2,3-dihydro-1H-inden-1-ol

Formula: C12H17NO3 Molecular weight: 223.26828 g/mol InChI Key: HXYNJXACCAOMCR-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-6-4-9(15-2)7-5-8(13)11(14)10(7)12(6)16-3/h4,8,11,14H,5,13H2,1-3H3

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

520
Analogue 7: With 2-Phenylcyclopropan-1-amine skeleton

DMMCPA

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-3-methylcyclopropanamine

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

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

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

521
Analogue 8: With 2-Phenylcyclobutan-1-amine skeleton

DMCBA

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

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

InChI=1S/C13H19NO2/c1-8-6-13(16-3)10(7-12(8)15-2)9-4-5-11(9)14/h6-7,9,11H,4-5,14H2,1-3H3

PubChem CID: 146231; ChemSpider: 128990

See also Transcripts: 5.652

Nichols, DE; Jadhav, KP; Oberlender, RA; Zabik, JE; Bossart, JF; Hamada, A; Miller, DD. Synthesis and evaluation of substituted 2-phenylcyclobutylamines as analogues of hallucinogenic phenethylamines: Lack of LSD-like biological activity. J. Med. Chem., 1 Jan 1984, 27 (9), 1108–1111. 617 kB. doi:10.1021/jm00375a004

29 isomers:
72
Isomer 1

E
Escaline
Escaline
4-Ethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-ethoxyphenethylamine

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

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

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

PubChem CID: 38240; ChemSpider: 35053; Wikipedia: Escaline

Shulgin Index: #64 Escaline; Table: 5 Page: 350 Row: 36

See also PiHKAL: #2 AL
#10 B
#25 3C-E
#50 4-D
#51 β-D
#92 IP
#93 IRIS
#99 MAL
#119 ME
#123 MEPEA
#140 P
#141 PE
#143 PROPYNYL
#150 3-TE
#163 3-TME

See also Transcripts: 2.217, 3.365, 3.397

See also Pharmacology notes II: p. 217, Escaline

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

Benington, F; Morin, RD; Clarke, LC. Synthesis of 4-hydroxy- and 4-ethoxy-3,5-dimethoxy-β-phenethylamines. J. Am. Chem. Soc., 1 Nov 1954, 76 (21), 5555–5556. 307 kB. doi:10.1021/ja01650a084

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

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

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

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

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

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

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

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

119
Isomer 2

ME
Metaescaline
3,4-Dimethoxy-5-ethoxyphenethylamine
3-Ethoxy-4,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 44350068; ChemSpider: 21106344; Wikipedia: Metaescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 32

See also PiHKAL: #9 ASB
#137 MP
#163 3-TME
#165 5-TME
#176 3-TSB  

See also Transcripts: 3.409

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

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

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

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

157
Isomer 3

TMA
AMM
EA-1319
3,4,5-Trimethoxyamphetamine

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

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

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

PubChem CID: 31016; ChemSpider: 28775; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #117 TMA; Table: 5 Page: 349 Row: 27

See also PiHKAL: #1 AEM
#14 BOD
#21 3C-BZ
#27 2C-G
#42 Ψ-2C-T-4
#50 4-D
#72 E
#97 4-MA
#100 MDA
#120 MEDA
#132 MMDA
#145 TA
#158 TMA-2
#160 TMA-4
#166 2T-MMDA-3a
See also TiHKAL: #13 Harmaline      

See also Transcripts: 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.72, 1.139, 2.227

See also Pharmacology notes I: p. 8, TMA: Subacute human in vivo tests
p. 9, TMA: Objective response
p. 10, TMA: Objective response
p. 11, TMA: Objective response
p. 12, TMA: Objective response
p. 13, TMA: Subjective response
p. 14, TMA: Subjective response
p. 15, TMA: Subjective response
p. 16, TMA: Subjective response
p. 17, TMA: Subjective response
p. 18, TMA: Subjective response
p. 19, TMA: Subjective response
p. 72, SARs
p. 139, The Pseunut Cocktail
See also Pharmacology notes II: p. 227, TMA: Subjective response

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

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; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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

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

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

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

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

Weil, AT. The use of nutmeg as a psychotropic agent. Bull. Narc., United Nations Office on Drugs and Crime, 1 Jan 1966.

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

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

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

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

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

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

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

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

Peretz, DI; Smythies, JR; Gibson, WC. A new hallucinogen: 3,4,5-Trimethoxyphenyl-β-aminopropane. With notes on the stroboscopic phenomenon. J. Mental Sci., 1 Jan 1955, 101 (423), 317–329. 1559 kB. doi:10.1192/bjp.101.423.317

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. doi:10.1038/210380a0

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Shulgin, AT; Bunnell, S; Sargent, T. The psychotomimetic properties of 3,4,5-trimethoxyamphetamine. Nature, 1 Jan 1961, 189, 1011–1012. 306 kB. doi:10.1038/1891011a0 Rhodium.

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

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

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

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

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

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Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

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

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158
Isomer 4

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 Transcripts: 1.54, 1.55, 1.55.2, 1.56, 1.64, 1.65, 1.72, 1.108, 1.151, 1.160, 1.161, 1.185, 2.224

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

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

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

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

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

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

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

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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

Anon. Report on the risk assessment of TMA-2, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

Glennon, RA; 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

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

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

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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.

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.

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

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. 1188 kB. doi:10.1021/jm00256a016

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

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

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

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

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; 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

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

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

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

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.

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

159
Isomer 5

TMA-3
2,3,4-Trimethoxyamphetamine

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

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

InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31012; ChemSpider: 28771; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #119 TMA-3; Table: 5 Page: 338 Row: 15

See also PiHKAL: #42 Ψ-2C-T-4 #152 2-TIM #158 TMA-2  

See also Transcripts: 1.72, 1.85, 1.85.2

See also Pharmacology notes I: p. 72, SARs
p. 85, TMA-3: Subacute evaluation

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 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

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

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

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

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

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

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

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

160
Isomer 6

TMA-4
2,3,5-Trimethoxyamphetamine

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

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

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

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

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

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

See also Transcripts: 1.61, 1.72

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

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

Glennon, RA; 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

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

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

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

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

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

161
Isomer 7

TMA-5
2,3,6-Trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxyphenyl)propan-2-amine

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

InChI=1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31013; ChemSpider: 28772; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #121 TMA-5; Table: 5 Page: 353 Row: 2

See also PiHKAL: #8 ARIADNE #42 Ψ-2C-T-4 #158 TMA-2  

See also Transcripts: 1.72, 1.97

See also Pharmacology notes I: p. 72, SARs
p. 97, TMA-5: Subacute evaluation

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

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

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

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. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

162
Isomer 8

TMA-6
2,4,6-Trimethoxyamphetamine

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

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

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

PubChem CID: 31015; ChemSpider: 28774; Drugs Forum: TMA-6; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #122 TMA-6; Table: 5 Page: 353 Row: 26

See also PiHKAL: #8 ARIADNE
#42 Ψ-2C-T-4
#69 Ψ-DOM
#122 MEM
#134 MMDA-3a
#158 TMA-2
 

See also Transcripts: 1.72, 1.93, 1.93.2, 1.98, 1.99, 1.150, 1.188, 1.189, 2.253, 5.633, 5.634, 5.679, 5.682

See also Pharmacology notes I: p. 72, SARs
p. 93.1, Subacute evaluation TMA-6 (XVI-21)
p. 98, TMA-6: Subjective response
p. 99, TMA-6: Subjective response
p. 150, TMA-6
p. 188, TMA-6: Qualitative effects
p. 189, TMA-6: Qualitative effects
See also Pharmacology notes II: p. 253, TMA-6

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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

Glennon, RA; 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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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

Chambers, JJ. Use of conformationally-restricted analogues and homology modeling to provide insight into the nature of the 5-HT2A receptor agonist binding site. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2002. 8389 kB.

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

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

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. I. 2,4,6-Trialkoxy-β-phenethylamines. J. Org. Chem., 1 Jan 1954, 19 (1), 11–16. 436 kB. doi:10.1021/jo01366a003

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

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

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

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

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

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

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

Shulgin, AT. Trimethoxylated amphetamine derivatives. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 14 Mar 2002.

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. 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.

262
Isomer 9

METHYL-MESCALINE
M-M
N-Methyl-3,4,5-trimethoxyphenethylamine
N-Methylmescaline

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

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: OTXANOLOOUNVSR-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 138365; ChemSpider: 121990

Shulgin Index: #97 MMDA; Table: 5 Page: 350 Row: 24

See also PiHKAL: #96 M      

See also Transcripts: 1.142

See also Pharmacology notes I: p. 142, Methyl-mescaline

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

2068
Isomer 10

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

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

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      
2214
Isomer 11

N,N-Me-3-DESMETHYL
N,N-Dimethyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 5-[2-(Dimethylamino)ethyl]-2,3-dimethoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: INYMWXUUZSMPQM-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 57478611

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 7

5383
Isomer 12

N,N-Me-DME
Macromerine
β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3

PubChem CID: 165055; ChemSpider: 144706; Wikipedia: Macromerine

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 10

Hodgkins, JE; Brown, SD; Massingill, JL. Two new alkaloids in cacti. Tetrahedron Lett., 1 Jan 1967, 8 (14), 1321–1324. 202 kB. doi:10.1016/S0040-4039(00)90694-4

333
Isomer 13

4C-HO
1-(4-Hydroxy-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-hydroxy-2,5-dimethoxyphenethylamine

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

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: ASFOLEVMZYIHRE-VIFPVBQESA-N

InChI=1S/C12H19NO3/c1-4-9(13)5-8-6-12(16-3)10(14)7-11(8)15-2/h6-7,9,14H,4-5,13H2,1-3H3/t9-/m0/s1

ChemSpider: 25045865

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 12

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

619
Isomer 14

homo-Mescaline

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

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

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

PubChem CID: 614460; ChemSpider: 534098

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 26

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. VI. Mescaline homologs. J. Org. Chem., 1 Dec 1956, 21 (12), 1545–1546. 282 kB. doi:10.1021/jo01118a635

6559
Isomer 15

β-HO-N-iPr-GEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]-2-methoxyphenol

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

InChI=1S/C12H19NO3/c1-8(2)13-7-11(15)9-4-5-10(14)12(6-9)16-3/h4-6,8,11,13-15H,7H2,1-3H3

PubChem CID: 68951; ChemSpider: 62174

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 9

6612
Isomer 16

N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethan-1-amine

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

InChI=1S/C12H19NO3/c1-13-8-12(16-4)9-5-6-10(14-2)11(7-9)15-3/h5-7,12-13H,8H2,1-4H3

PubChem CID: 15612893; ChemSpider: 26711698

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 12

6625
Isomer 17

DMMAOH

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-hydroxy-N-methylpropan-2-amine

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

InChI=1S/C12H19NO3/c1-9(13(2)14)7-10-5-6-11(15-3)12(8-10)16-4/h5-6,8-9,14H,7H2,1-4H3

PubChem CID: 11368108; ChemSpider: 9543025

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 25

6655
Isomer 18

DEE

IUPAC: 2-Amino-1-(3,4-diethoxyphenyl)ethanol

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

InChI=1S/C12H19NO3/c1-3-15-11-6-5-9(10(14)8-13)7-12(11)16-4-2/h5-7,10,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627975

Shulgin Index: See #49 DMPEA; Table: 4 Page: 331 Row: 5

6866
Isomer 19

β-HO-N,N-Me-2,5-DMPEA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-11(14)10-7-9(15-3)5-6-12(10)16-4/h5-7,11,14H,8H2,1-4H3

PubChem CID: 46242; ChemSpider: 42100

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 16

6869
Isomer 20

β-HO-β,N-Me-2,5-DMPEA

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

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

InChI=1S/C12H19NO3/c1-12(14,8-13-2)10-7-9(15-3)5-6-11(10)16-4/h5-7,13-14H,8H2,1-4H3

PubChem CID: 50630; ChemSpider: 45890

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 19

6877
Isomer 21

β-HO-N-Me-2,5-DMA

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

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

InChI=1S/C12H19NO3/c1-8(13-2)12(14)10-7-9(15-3)5-6-11(10)16-4/h5-8,12-14H,1-4H3

PubChem CID: 3027653; ChemSpider: 2293151

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 27

6910
Isomer 22

β,2-HO-N-Me-5-EA

IUPAC: 4-Ethoxy-2-[1-hydroxy-2-(methylamino)propyl]phenol

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

InChI=1S/C12H19NO3/c1-4-16-9-5-6-11(14)10(7-9)12(15)8(2)13-3/h5-8,12-15H,4H2,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 10

6912
Isomer 23

β-HO-2,5-DEPEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)ethanol

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

InChI=1S/C12H19NO3/c1-3-15-9-5-6-12(16-4-2)10(7-9)11(14)8-13/h5-7,11,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627950

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 12

6927
Isomer 24

β-HO-N,N-Me-3,5-DMPEA

IUPAC: 1-(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-12(14)9-5-10(15-3)7-11(6-9)16-4/h5-7,12,14H,8H2,1-4H3

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 27

7217
Isomer 25

N-HO-DOM

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

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

InChI=1S/C12H19NO3/c1-8-5-12(16-4)10(6-9(2)13-14)7-11(8)15-3/h5,7,9,13-14H,6H2,1-4H3

PubChem CID: 597107; ChemSpider: 519067

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 17

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

7569
Isomer 26

DESMETHYL-MM

IUPAC: 4-[2-(Dimethylamino)ethyl]-2,6-dimethoxyphenol

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

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

PubChem CID: 24971842; ChemSpider: 21404060

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 19

1019
Isomer 27

β-HO-DOM

IUPAC: 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)propan-1-ol

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

InChI=1S/C12H19NO3/c1-7-5-11(16-4)9(6-10(7)15-3)12(14)8(2)13/h5-6,8,12,14H,13H2,1-4H3

ChemSpider: 26711720

Ho, B; Tansey, LW; McIsaac, WM. Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM). J. Med. Chem., 1 Sep 1970, 13 (5), 1022. 99 kB. doi:10.1021/jm00299a071

1016
Isomer 28

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

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

InChI=1S/C12H19NO3/c1-8(13)4-9-5-12(16-3)10(7-14)6-11(9)15-2/h5-6,8,14H,4,7,13H2,1-3H3

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

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

701
Isomer 29

N-MeO-3,4-DMA
N,3,4-Trimethoxyamphetamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-methoxypropan-2-amine

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

InChI=1S/C12H19NO3/c1-9(13-16-4)7-10-5-6-11(14-2)12(8-10)15-3/h5-6,8-9,13H,7H2,1-4H3

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

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