PiHKAL • info | explore | PiHKAL#14 BOD; SI#13 BOD

Six β analogues:

BOHD

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

2C-D

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)ethanamine

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 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

BOED

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-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

BOAD

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

β-Me-2C-D

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

β,β-Me-2C-D

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:

BOB

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-methoxyethanamine

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

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, 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

BODM

6867

Analogue 2: Removing Methyl at R4

BODM

IUPAC: 2-(2,5-Dimethoxyphenyl)-2-methoxyethanamine

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, 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

BOI

BOI; 2-(4-Iodo-2,5-dimethoxyphenyl)-2-methoxyethanamine

7161

Analogue 3: Substituting Iodo for Methyl at R4

BOI

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

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, 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

BON

BON; 2-(2,5-Dimethoxy-4-nitrophenyl)-2-methoxyethanamine

7202

Analogue 4: Substituting Nitro for Methyl at R4

BON

IUPAC: 2-(2,5-Dimethoxy-4-nitrophenyl)-2-methoxyethanamine

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, 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

BOE

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

7262

Analogue 5: Substituting Ethyl for Methyl at R4

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

BOT

BOT; 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethanamine

7322

Analogue 6: Substituting Methoxy for Methyl at R4

BOT

IUPAC: 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethanamine

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, 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

BOPS

7378

Analogue 7: Substituting n-Propylthio for Methyl at R4

BOPS

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

Formula: C15H25NO3S Molecular weight: 299.4289 g/mol InChI Key: JWHKQZDRLPNWLP-UHFFFAOYSA-N

InChI=1S/C15H25NO3S/c1-6-7-20-14-9-12(17-3)11(8-13(14)18-4)15(19-5)10(2)16/h8-10,15H,6-7,16H2,1-5H3

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

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

Eight skeleton analogues:

DMCPA

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

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

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

α-CP-2C-D

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

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.

DOMAI; DOM-AI

DOMAI; 2-Amino-4,7-dimethoxy-5-methylindane

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

DOMAT; DOM-AT

DOMAT; 5,8-Dimethoxy-6-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

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

DMMCPA

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

HO-DOMAI

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

DMMCPA

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

DMCBA

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

26 isomers:

Isomer 1

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

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 Pharmacology notes II:	p. 217, Escaline

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

Nichols, DE; 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

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

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

119

Isomer 2

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

IUPAC: 2-(3-Ethoxy-4,5-dimethoxyphenyl)ethanamine

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

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

TMA

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 Pharmacology notes II:

p. 227, TMA: Subjective response

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

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

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

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

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

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

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

Glennon, RA; 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

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

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

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.

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

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

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

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; 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.

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

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

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

TMA-2

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 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

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

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

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

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.

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.

TMA-3

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 Pharmacology notes I:	p. 72, SARs p. 85.1, Subacute evaluation TMA-3 (XVI-13)

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

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

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

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

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

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

TMA-4

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

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

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

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

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

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

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

TMA-5

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

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

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

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

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

TMA-6

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 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

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

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

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

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

METHYL-MESCALINE

262

Isomer 9

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

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

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 Pharmacology notes I:	p. 142, Methyl-mescaline

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

2C-O-2

2068

Isomer 10

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

N,N-Me-3-DESMETHYL

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

N,N-Me-DME; Macromerine

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

4C-HO

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

homo-Mescaline

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

β-HO-N-iPr-GEA

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

N-Me-β,3,4-TMPEA

6612

Isomer 16

N-Me-β,3,4-TMPEA

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

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

DMMAOH

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

DEE

DEE; 2-Amino-1-(3,4-diethoxyphenyl)ethanol

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

β-HO-N,N-Me-2,5-DMPEA

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

β-HO-β,N-Me-2,5-DMPEA

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

β-HO-N-Me-2,5-DMA

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

β,2-HO-N-Me-5-EA

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

β-HO-2,5-DEPEA

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

β-HO-N,N-Me-3,5-DMPEA

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

N-HO-DOM

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

DESMETHYL-MM

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