TiHKAL • info | explore | PiHKAL#168 TMPEA; SI#124 TMPEA-2

One N analogue:

NBOMe-2,4,5-TMPEA

592

Analogue 1: Adding 2-Methoxybenzyl at N

NBOMe-2,4,5-TMPEA
TMPEA-NBOMe

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

Formula: C19H25NO4 Molecular weight: 331.4061 g/mol InChI Key: YWHPPSGTTPXYSD-UHFFFAOYSA-N

InChI=1S/C19H25NO4/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-18(23-3)19(24-4)12-17(14)22-2/h5-8,11-12,20H,9-10,13H2,1-4H3

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 Personal communication of unpublished research. 1 Dec 2011.

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

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

Three α analogues:

TMA-2

158

Analogue 1: Adding Methyl at α

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

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

Trachsel, D. 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

4C-MeO

7327

Analogue 2: Adding Ethyl at α

4C-MeO

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

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

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

PubChem CID: 43566022

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

α-Carboxy-TMA-2

539

Analogue 3: Adding Carboxy at α

α-Carboxy-TMA-2
2,5-Dimethoxy-O-methyltyrosine

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

Formula: C12H17NO5 Molecular weight: 255.26708 g/mol InChI Key: UDNVWGVLPKFPLE-UHFFFAOYSA-N

InChI=1S/C12H17NO5/c1-16-9-6-11(18-3)10(17-2)5-7(9)4-8(13)12(14)15/h5-6,8H,4,13H2,1-3H3,(H,14,15)

PubChem CID: 3929285; ChemSpider: 3151339

One β analogue:

BOT

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

7322

Analogue 1: Adding Methoxy at β

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

Three R2 analogues:

2,4,5-BMM; 6-Br-DMPEA

2,4,5-BMM; 2-Bromo-4,5-dimethoxyphenethylamine

197

Analogue 1: Substituting Bromo for Methoxy at R2

2,4,5-BMM
6-Br-DMPEA
2-Bromo-4,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 820370; ChemSpider: 716761

Shulgin Index: See #18 2C-B; Table: 5 Page: 344 Row: 15

See also PiHKAL:	#20 2C-B

2-Cl-4,5-DMPEA

7314

Analogue 2: Substituting Chloro for Methoxy at R2

2-Cl-4,5-DMPEA

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

Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: DHMSGUTWLHFESS-UHFFFAOYSA-N

InChI=1S/C10H14ClNO2/c1-13-9-5-7(3-4-12)8(11)6-10(9)14-2/h5-6H,3-4,12H2,1-2H3

PubChem CID: 15557188; ChemSpider: 14826767

Shulgin Index: See #19 2C-C; Table: 5 Page: 344 Row: 14

4,5,2-2C-T-7

7330

Analogue 3: Substituting n-Propylthio for Methoxy at R2

4,5,2-2C-T-7

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

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

InChI=1S/C13H21NO2S/c1-4-7-17-13-9-12(16-3)11(15-2)8-10(13)5-6-14/h8-9H,4-7,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 344 Row: 30

One R3 analogue:
TeMPEA 455	Analogue 1: Adding Methoxy at R3 TeMPEA IUPAC: 2-(2,3,4,5-Tetramethoxyphenyl)ethanamine Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: GJKJPCJLMHZZFK-UHFFFAOYSA-N InChI=1S/C12H19NO4/c1-14-9-7-8(5-6-13)10(15-2)12(17-4)11(9)16-3/h7H,5-6,13H2,1-4H3 PubChem CID: 611405; ChemSpider: 531480 Shulgin Index: #114 TeMPEA; Table: 6 Page: 355 Row: 3

81 R4 analogues:

2C-B

Analogue 1: Substituting Bromo for Methoxy at R4

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

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

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

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

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

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

See also PiHKAL:	#9 ASB #10 B #14 BOD #16 BOHD #22 2C-C	#23 2C-D #25 3C-E #30 2C-G-5 #32 2C-H #33 2C-I	#34 2C-N #39 2C-T #41 2C-T-4 #43 2C-T-7 #50 4-D	#65 DOEF #72 E #118 MDPR #122 MEM #170 5-TOET
See also TiHKAL:	#5 α,O-DMS	#37 5-MeO-DIPT

See also Pharmacology notes I:	p. 172, 2C-B: Trials
See also Pharmacology notes II:	app. 2, Abuse week p. 204, 2C-B p. 211, 2C-B p. 279, 2C-B p. 303, 2C-B p. 305, 2C-B p. 309, 2C-B p. 323, 2C-B

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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

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

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

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

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

2C-C

Analogue 2: Substituting Chloro for Methoxy at R4

2C-C
4-Chloro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-chlorophenethylamine

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

Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: CGKQFIWIPSIVAS-UHFFFAOYSA-N

InChI=1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 29979100; ChemSpider: 21106221; Drugs Forum: 2C-C; Erowid: 2C-C; Wikipedia: 2C-C

Shulgin Index: #19 2C-C; Table: 5 Page: 340 Row: 19

See also PiHKAL:	#32 2C-H	#39 2C-T	#64 DOC

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

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

2C-D

Analogue 3: Substituting Methyl for Methoxy at R4

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

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

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

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.

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.

2C-E

Analogue 4: Substituting Ethyl for Methoxy at R4

2C-E
4-Ethyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-ethylphenethylamine

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

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

InChI=1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3

PubChem CID: 24729233; ChemSpider: 21106222; Drugs Forum: 2C-E; Erowid: 2C-E; Wikipedia: 2C-E

Shulgin Index: #21 2C-E; Table: 5 Page: 343 Row: 11

See also PiHKAL:	#23 2C-D #43 2C-T-7	#66 DOET #72 E	#85 GANESHA

See also Pharmacology notes II:	app. 2, Abuse week p. 236, 2C-E

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

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

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

Shulgin, AT. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.

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

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

2C-F

Analogue 5: Substituting Fluoro for Methoxy at R4

2C-F
4-Fluoro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-fluorophenethylamine

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

Formula: C10H14FNO2 Molecular weight: 199.2220632 g/mol InChI Key: QAVFEDRVOUKIPM-UHFFFAOYSA-N

InChI=1S/C10H14FNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 44719499; ChemSpider: 21106223; Wikipedia: 2C-F

Shulgin Index: See #20 2C-D; Table: 5 Page: 340 Row: 17

See also PiHKAL:	#22 2C-C

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

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

2C-H

Analogue 6: Removing Methoxy at R4

2C-H
25H
2,5-Dimethoxyphenethylamine

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

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: WNCUVUUEJZEATP-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3

PubChem CID: 76632; ChemSpider: 69096; Wikipedia: 2C-H

Shulgin Index: #22 2C-H; Table: 4 Page: 335 Row: 7

See also PiHKAL:	#16 BOHD #20 2C-B	#22 2C-C #33 2C-I	#34 2C-N #35 2C-O-4

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

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

Rangisetty, JB; Dukat, M; Dowd, CS; Herrick-Davis, K; DuPre, A; Gadepalli, S; Teitler, M; Kelley, CR; Sharif, NA; Glennon, RA. 1-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character. J. Med. Chem., 1 Jan 2001, 44 (20), 3283–3291. 115 kB. doi:10.1021/jm0100739

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

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

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

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

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-I

Analogue 7: Substituting Iodo for Methoxy at R4

2C-I
Cimbi-88
25I
4-Iodo-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-iodophenethylamine

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

Formula: C10H14INO2 Molecular weight: 307.12813 g/mol InChI Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N

InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 10267191; ChemSpider: 8442670; Drugs Forum: 2C-I; Erowid: 2C-I; Wikipedia: 2C-I

Shulgin Index: #23 2C-I; Table: 5 Page: 341 Row: 8

See also PiHKAL:	#22 2C-C #32 2C-H	#39 2C-T #65 DOEF	#72 E

See also Pharmacology notes I:	p. 179, 2C-I: Trials

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

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

Ettrup, A; Hansen, M; Santini, MA; Paine, J; Gillings, N; Palner, M; Lehel, S; Herth, MM; Madsen, J; Kristensen, J; Begtrup, M; Knudsen, GM. Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers. Eur. J. Nucl. Med. Mol. Imaging, 21 Nov 2010. 752 kB. doi:10.1007/s00259-010-1686-8

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

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

Johnson, MP; Mathis, CA; Shulgin, AT; Hoffman, AJ; Nichols, DE. [125I]-2-(2,5-Dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex. Pharmacol. Biochem. Behav., 1 Jan 1990, 35 (1), 211–217. 724 kB. doi:10.1016/0091-3057(90)90228-A

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

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

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

2C-N

Analogue 8: Substituting Nitro for Methoxy at R4

2C-N
4-Nitro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-nitrophenethylamine

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

Formula: C10H14N2O4 Molecular weight: 226.22916 g/mol InChI Key: ZMUSDZGRRJGRAO-UHFFFAOYSA-N

InChI=1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3

PubChem CID: 10036637; ChemSpider: 8212202; Wikipedia: 2C-N

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 1

See also PiHKAL:	#32 2C-H	#39 2C-T	#72 E

Zuba, D; Sekuła, K; Buczek, A. Identification and characterization of 2,5-dimethoxy-4-nitro-β-phenethylamine (2C-N)–A new member of 2C-series of designer drug. Forensic Sci. Int., 10 Oct 2012, 222 (1–3), 298–305. 588 kB. doi:10.1016/j.forsciint.2012.07.006

2C-O-4

Analogue 9: Substituting Isopropoxy for Methoxy at R4

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

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

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

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

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

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

2C-P

Analogue 10: Substituting n-Propyl for Methoxy at R4

2C-P
4-Propyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-n-propylphenethylamine

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

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

InChI=1S/C13H21NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44350080; ChemSpider: 21106226; Drugs Forum: 2C-P; Erowid: 2C-P; Wikipedia: 2C-P

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 31

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

Fenderson5555. Mechanisms and named reactions in 2C-P synthesis. 7 Jan 2011.

2C-SE

Analogue 11: Substituting Methylseleno for Methoxy at R4

2C-SE
4-Methylseleno-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylselenophenethylamine

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

Formula: C11H17NO2Se Molecular weight: 274.21818 g/mol InChI Key: CXQUHXATPUFGMC-UHFFFAOYSA-N

InChI=1S/C11H17NO2Se/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 44719515; ChemSpider: 21106227; Wikipedia: 2C-SE

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 346 Row: 17

2C-T

Analogue 12: Substituting Methylthio for Methoxy at R4

2C-T
4-Methylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylthiophenethylamine

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

Formula: C11H17NO2S Molecular weight: 227.32318 g/mol InChI Key: UPZMYCMLLQTYEM-UHFFFAOYSA-N

InChI=1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 12315927; ChemSpider: 10438674; Wikipedia: 2C-T

Shulgin Index: #25 2C-T; Table: 5 Page: 345 Row: 12

See also PiHKAL:	#3 ALEPH #30 2C-G-5	#35 2C-O-4 #38 2C-SE	#40 2C-T-2 #49 2C-T-21

See also Pharmacology notes II:	p. 315, 2C-T

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

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.

2C-T-2

Analogue 13: Substituting Ethylthio for Methoxy at R4

2C-T-2
4-Ethylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-ethylthiophenethylamine

IUPAC: 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C12H19NO2S/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: 12074193; ChemSpider: 16787961; Drugs Forum: 2C-T-2; Erowid: 2C-T-2; Wikipedia: 2C-T-2

Shulgin Index: #26 2C-T-2; Table: 5 Page: 345 Row: 17

See also PiHKAL:	#4 ALEPH-2 #35 2C-O-4 #39 2C-T #41 2C-T-4	#43 2C-T-7 #44 2C-T-8 #45 2C-T-9 #46 2C-T-13	#47 2C-T-15 #48 2C-T-17 #49 2C-T-21 #81 FLEA	#87 HOT-2 #118 MDPR

Shulgin, AT. 2C-T-7. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jun 2001.

Stolaroff, MJ; Wells, CW. Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7. In Jahrbuch für Ethnomedizin und Bewußtseinsforschung (Yearbook of Ethnomedicine and the Study of Consciousness); Rätsch, C; Baker, J, Eds., 1 Jan 1993; Vol. 2, pp 99–117. 185 kB.

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

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

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

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

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

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

2C-T-4

Analogue 14: Substituting Isopropylthio for Methoxy at R4

2C-T-4
4-Isopropylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropylthiophenethylamine

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

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

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

PubChem CID: 44350070; ChemSpider: 21106232; Erowid: 2C-T-4; Wikipedia: 2C-T-4

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 33

See also PiHKAL:	#5 ALEPH-4	#35 2C-O-4	#47 2C-T-15

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

2C-T-7

Analogue 15: Substituting n-Propylthio for Methoxy at R4

2C-T-7
4-Propylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-n-propylthiophenethylamine

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

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

InChI=1S/C13H21NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 24728635; ChemSpider: 21106233; Drugs Forum: 2C-T-7; Erowid: 2C-T-7; Wikipedia: 2C-T-7

Shulgin Index: #27 2C-T-7; Table: 5 Page: 345 Row: 26

See also PiHKAL:	#7 ALEPH-7 #35 2C-O-4	#40 2C-T-2 #81 FLEA	#88 HOT-7 #118 MDPR

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

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

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

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

2C-T-8

Analogue 16: Substituting Cyclopropylmethylthio for Methoxy at R4

2C-T-8
4-Cyclopropylmethylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-cyclopropylmethylthiophenethylamine

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

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

InChI=1S/C14H21NO2S/c1-16-12-8-14(18-9-10-3-4-10)13(17-2)7-11(12)5-6-15/h7-8,10H,3-6,9,15H2,1-2H3

PubChem CID: 44350055; ChemSpider: 21106234; Wikipedia: 2C-T-8

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 10

See also PiHKAL:	#81 FLEA	#104 MDCPM

Shulgin, AT. 2C-T-7. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jun 2001.

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

2C-T-9

Analogue 17: Substituting tert-Butylthio for Methoxy at R4

2C-T-9
4-tert-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-tert-butylthiophenethylamine

IUPAC: 2-[4-(tert-Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

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

PubChem CID: 44349799; ChemSpider: 23206245; Wikipedia: 2C-T-9

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 8

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

2C-T-13

Analogue 18: Substituting 2-Methoxyethylthio for Methoxy at R4

2C-T-13
4-(2-Methoxyethylthio)-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-(2-methoxyethylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methoxyethyl)sulfanyl]phenyl}ethanamine

Formula: C13H21NO3S Molecular weight: 271.37574 g/mol InChI Key: PYJLRNOGMKMRTK-UHFFFAOYSA-N

InChI=1S/C13H21NO3S/c1-15-6-7-18-13-9-11(16-2)10(4-5-14)8-12(13)17-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44350108; ChemSpider: 21106228; Wikipedia: 2C-T-13

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 11

See also PiHKAL:	#99 MAL

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

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-15

Analogue 19: Substituting Cyclopropylthio for Methoxy at R4

2C-T-15
SESQUI
4-Cyclopropylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-cyclopropylthiophenethylamine

IUPAC: 2-[4-(Cyclopropylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: HHAPMOUVSYQKLK-UHFFFAOYSA-N

InChI=1S/C13H19NO2S/c1-15-11-8-13(17-10-3-4-10)12(16-2)7-9(11)5-6-14/h7-8,10H,3-6,14H2,1-2H3

PubChem CID: 44719534; ChemSpider: 21106229; Wikipedia: 2C-T-15

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 35

See also PiHKAL:	#48 2C-T-17	#49 2C-T-21

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-17

Analogue 20: Substituting sec-Butylthio for Methoxy at R4

2C-T-17
NIMITZ
4-sec-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-sec-butylthiophenethylamine

IUPAC: 2-[4-(Butan-2-ylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

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

PubChem CID: 44349798; ChemSpider: 21106230; Wikipedia: 2C-T-17

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 6

See also PiHKAL:	#81 FLEA	#89 HOT-17

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

2C-T-21

Analogue 21: Substituting 2-Fluoroethylthio for Methoxy at R4

2C-T-21
4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine

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

Formula: C12H18FNO2S Molecular weight: 259.3402232 g/mol InChI Key: ZBUUUKBTOCTOPW-UHFFFAOYSA-N

InChI=1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 44349972; ChemSpider: 21106231; Drugs Forum: 2C-T-21; Erowid: 2C-T-21; Wikipedia: 2C-T-21

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 23

See also PiHKAL:	#38 2C-SE	#65 DOEF

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

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-CN

200

Analogue 22: Substituting Cyano for Methoxy at R4

2C-CN
2,5-Dimethoxy-4-cyanophenethylamine

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

Formula: C11H14N2O2 Molecular weight: 206.24106 g/mol InChI Key: OGWCKYKYGQORLF-UHFFFAOYSA-N

InChI=1S/C11H14N2O2/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 57474247

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 7

See also PiHKAL:	#22 2C-C

2C-CA; 2C-COOH

2C-CA; 2,5-Dimethoxy-4-carboxyphenethylamine

201

Analogue 23: Substituting Carboxy for Methoxy at R4

2C-CA
2C-COOH
2,5-Dimethoxy-4-carboxyphenethylamine

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

Formula: C11H15NO4 Molecular weight: 225.2411 g/mol InChI Key: CGSVAQGHARVNCH-UHFFFAOYSA-N

InChI=1S/C11H15NO4/c1-15-9-6-8(11(13)14)10(16-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3,(H,13,14)

PubChem CID: 57474249

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 9

See also PiHKAL:	#22 2C-C

2C-TFM

2040

Analogue 24: Substituting Trifluoromethyl for Methoxy at R4

2C-TFM
2C-CF3
4-Trifuouromethyl-2,5-dimethoxyphenethylamine

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

Formula: C11H14F3NO2 Molecular weight: 249.2295696 g/mol InChI Key: LYXGNMLWYONZID-UHFFFAOYSA-N

InChI=1S/C11H14F3NO2/c1-16-9-6-8(11(12,13)14)10(17-2)5-7(9)3-4-15/h5-6H,3-4,15H2,1-2H3

PubChem CID: 10399795; ChemSpider: 8575233; Drugs Forum: 2C-TFM; Wikipedia: 2C-TFM

Shulgin Index: #28 2C-TFM; Table: 5 Page: 343 Row: 1

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

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

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

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

2C-O-2

2068

Analogue 25: Substituting Ethoxy for Methoxy at R4

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

2C-O-7

2069

Analogue 26: Substituting n-Propoxy for Methoxy at R4

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

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

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

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

PubChem CID: 57474252

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

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

2C-O-19

2070

Analogue 27: Substituting n-Butoxy for Methoxy at R4

2C-O-19
2C-O-19
2,5-Dimethoxy-4-n-butoxyphenethylamine

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

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

InChI=1S/C14H23NO3/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3

PubChem CID: 57474253

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 8

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

2C-SE-2

2072

Analogue 28: Substituting Ethylseleno for Methoxy at R4

2C-SE-2
2,5-Dimethoxy-4-ethylselenophenethylamine

IUPAC: 2-[4-(Ethylselanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H19NO2Se Molecular weight: 288.24476 g/mol InChI Key: HUFWOPLGIJKCJU-UHFFFAOYSA-N

InChI=1S/C12H19NO2Se/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: 57474255

See also PiHKAL:	#38 2C-SE

2C-SE-4

2073

Analogue 29: Substituting Isopropylseleno for Methoxy at R4

2C-SE-4
2,5-Dimethoxy-4-isopropylselenophenethylamine

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

Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: UUGAXTBZOCLVOE-UHFFFAOYSA-N

InChI=1S/C13H21NO2Se/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57474257

See also PiHKAL:	#38 2C-SE

2C-SE-7

2074

Analogue 30: Substituting n-Propylseleno for Methoxy at R4

2C-SE-7
2,5-Dimethoxy-4-n-propylselenophenethylamine

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

Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: XMFDSLMFVAJUSR-UHFFFAOYSA-N

InChI=1S/C13H21NO2Se/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474258

See also PiHKAL:	#38 2C-SE

2C-SE-21

2075

Analogue 31: Substituting 2-Fluoroethylseleno for Methoxy at R4

2C-SE-21
2,5-Dimethoxy-4-(2-fluoroethylseleno)phenethylamine

IUPAC: 2-{4-[(2-Fluoroethyl)selanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C12H18FNO2Se Molecular weight: 306.2352232 g/mol InChI Key: XSVWIVWPLWEQOK-UHFFFAOYSA-N

InChI=1S/C12H18FNO2Se/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 57474261

See also PiHKAL:	#38 2C-SE

2C-TE

2076

Analogue 32: Substituting Methyltelluro for Methoxy at R4

2C-TE
2,5-Dimethoxy-4-methyltellurophenethylamine

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

Formula: C11H17NO2Te Molecular weight: 322.85818 g/mol InChI Key: OLHAAXPQNWOKOE-UHFFFAOYSA-N

InChI=1S/C11H17NO2Te/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 57474263

See also PiHKAL:	#38 2C-SE

2C-T-10

2079

Analogue 33: Substituting 2-Pyridylthio for Methoxy at R4

2C-T-10
2,5-Dimethoxy-4-(2-pyridylthio)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(pyridin-2-ylsulfanyl)phenyl]ethanamine

Formula: C15H18N2O2S Molecular weight: 290.38062 g/mol InChI Key: QGMVABLWTNWDAY-UHFFFAOYSA-N

InChI=1S/C15H18N2O2S/c1-18-12-10-14(20-15-5-3-4-8-17-15)13(19-2)9-11(12)6-7-16/h3-5,8-10H,6-7,16H2,1-2H3

PubChem CID: 57474265

See also PiHKAL:	#45 2C-T-9

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2C-T-11

2080

Analogue 34: Substituting 4-Bromophenylthio for Methoxy at R4

2C-T-11
4-(4-Bromophenylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(4-Bromophenyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C16H18BrNO2S Molecular weight: 368.28862 g/mol InChI Key: YSYFWLXCMAVLOQ-UHFFFAOYSA-N

InChI=1S/C16H18BrNO2S/c1-19-14-10-16(15(20-2)9-11(14)7-8-18)21-13-5-3-12(17)4-6-13/h3-6,9-10H,7-8,18H2,1-2H3

PubChem CID: 57474267

See also PiHKAL:	#45 2C-T-9

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2C-T-12

2081

Analogue 35: Substituting 1-Morpholinothio for Methoxy at R4

2C-T-12
2,5-Dimethoxy-4-(1-morpholinothio)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(morpholin-4-ylsulfanyl)phenyl]ethanamine

Formula: C14H22N2O3S Molecular weight: 298.40108 g/mol InChI Key: PHXFPOFFCCVTDK-UHFFFAOYSA-N

InChI=1S/C14H22N2O3S/c1-17-12-10-14(20-16-5-7-19-8-6-16)13(18-2)9-11(12)3-4-15/h9-10H,3-8,15H2,1-2H3

PubChem CID: 57474268

See also PiHKAL:	#45 2C-T-9

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2C-T-14

2082

Analogue 36: Substituting 2-Methylthioethylthio for Methoxy at R4

2C-T-14
2,5-Dimethoxy-4-(2-methylthioethylthio)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-{[2-(methylsulfanyl)ethyl]sulfanyl}phenyl)ethanamine

Formula: C13H21NO2S2 Molecular weight: 287.44134 g/mol InChI Key: YFENVCWPZGGJQO-UHFFFAOYSA-N

InChI=1S/C13H21NO2S2/c1-15-11-9-13(18-7-6-17-3)12(16-2)8-10(11)4-5-14/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474270

See also PiHKAL:	#12 BIS-TOM	#46 2C-T-13

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-5

2083

Analogue 37: Substituting Cyclohexylthio for Methoxy at R4

2C-T-5
4-Cyclohexylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Cyclohexylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C16H25NO2S Molecular weight: 295.4402 g/mol InChI Key: OABFYEYTJSTAMV-UHFFFAOYSA-N

InChI=1S/C16H25NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h10-11,13H,3-9,17H2,1-2H3

PubChem CID: 57474272; ChemSpider: 21375815

See also PiHKAL:	#4 ALEPH-2	#47 2C-T-15

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2C-T-16

2086

Analogue 38: Substituting Allylthio for Methoxy at R4

2C-T-16
4-Allylthio-2,5-dimethoxyphenethylamine

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

Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: BXCMEIZBXNLJKM-UHFFFAOYSA-N

InChI=1S/C13H19NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3

PubChem CID: 12063256

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 1

See also PiHKAL:	#4 ALEPH-2

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-6

2087

Analogue 39: Substituting Phenylthio for Methoxy at R4

2C-T-6
2,5-Dimethoxy-4-phenylthiophenethylamine

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

Formula: C16H19NO2S Molecular weight: 289.39256 g/mol InChI Key: JRDQLJCYERGHDJ-UHFFFAOYSA-N

InChI=1S/C16H19NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3

PubChem CID: 57474275

See also PiHKAL:	#6 ALEPH-6

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2C-T-19

2089

Analogue 40: Substituting n-Butylthio for Methoxy at R4

2C-T-19
4-n-Butylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C14H23NO2S/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3

PubChem CID: 12063257; ChemSpider: 21106235

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 3

See also PiHKAL:	#35 2C-O-4	#49 2C-T-21

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-21.5

2090

Analogue 41: Substituting 2,2-Difluouroethylthio for Methoxy at R4

2C-T-21.5
4-(2,2-Difluouroethylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(2,2-Difluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C12H17F2NO2S Molecular weight: 277.3306864 g/mol InChI Key: LVCSIKISADNGMR-UHFFFAOYSA-N

InChI=1S/C12H17F2NO2S/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3

PubChem CID: 12063258

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 24

See also PiHKAL:	#49 2C-T-21

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-22

2091

Analogue 42: Substituting 2,2,2-Trifluoroethylthio for Methoxy at R4

2C-T-22
2,5-Dimethoxy-4-(2,2,2-trifluouroethylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanamine

Formula: C12H16F3NO2S Molecular weight: 295.3211496 g/mol InChI Key: LDOOFVKAIHFXAR-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2S/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 12063259

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 25

See also PiHKAL:	#49 2C-T-21

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-18

2108

Analogue 43: Substituting Cyclobutylthio for Methoxy at R4

2C-T-18
4-Cyclobutylthio-2,5-dimethoxyamphetamine

IUPAC: 2-[4-(Cyclobutylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C14H21NO2S/c1-16-12-9-14(18-11-4-3-5-11)13(17-2)8-10(12)6-7-15/h8-9,11H,3-7,15H2,1-2H3

See also PiHKAL:	#47 2C-T-15

2C-T-23

2109

Analogue 44: Substituting Cyclopentylthio for Methoxy at R4

2C-T-23
4-Cyclopentylthio-2,5-dimethoxyamphetamine

IUPAC: 2-[4-(Cyclopentylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C15H23NO2S/c1-17-13-10-15(19-12-5-3-4-6-12)14(18-2)9-11(13)7-8-16/h9-10,12H,3-8,16H2,1-2H3

PubChem CID: 57478605

See also PiHKAL:	#47 2C-T-15

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-YN

5378

Analogue 45: Substituting Ethynyl for Methoxy at R4

2C-YN
4-Ethynyl-2,5-dimethoxyphenethylamine

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

Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: MLJHHYIJBZVUEA-UHFFFAOYSA-N

InChI=1S/C12H15NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h1,7-8H,5-6,13H2,2-3H3

PubChem CID: 12063400; ChemSpider: 26234934; Wikipedia: 2C-YN

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 21

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

2C-pEtOH

5396

Analogue 46: Substituting 2-Hydroxyethyl for Methoxy at R4

2C-pEtOH
4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 57474313

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

2C-pKet

5397

Analogue 47: Substituting Acetoxy for Methoxy at R4

2C-pKet
4-Acetoxy-2,5-dimethoxyphenethylamine

IUPAC: Methyl 4-(2-aminoethyl)-2,5-dimethoxybenzoate

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

InChI=1S/C12H17NO4/c1-15-10-7-9(12(14)17-3)11(16-2)6-8(10)4-5-13/h6-7H,4-5,13H2,1-3H3

PubChem CID: 57474315

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

2C-T-3

2177

Analogue 48: Substituting Methallylthio for Methoxy at R4

2C-T-3
4-Methallylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)sulfanyl]phenyl}ethanamine

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

InChI=1S/C14H21NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3

PubChem CID: 12063255

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 9

See also PiHKAL:	#4 ALEPH-2

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-25

2178

Analogue 49: Substituting Isobutylthio for Methoxy at R4

2C-T-25
4-Isobutylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethanamine

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

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

PubChem CID: 12063260

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 5

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-27

2179

Analogue 50: Substituting Benzylthio for Methoxy at R4

2C-T-27
4-Benzylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Benzylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C17H21NO2S/c1-19-15-11-17(16(20-2)10-14(15)8-9-18)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3

PubChem CID: 12063261

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-28

2180

Analogue 51: Substituting 3-Fluoropropylthio for Methoxy at R4

2C-T-28
4-(3-Fluoropropylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(3-Fluoropropyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

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

InChI=1S/C13H20FNO2S/c1-16-11-9-13(18-7-3-5-14)12(17-2)8-10(11)4-6-15/h8-9H,3-7,15H2,1-2H3

PubChem CID: 12063262

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 2

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-30

2181

Analogue 52: Substituting 4-Fluorobutylthio for Methoxy at R4

2C-T-30
4-(4-Fluorobutylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(4-Fluorobutyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C14H22FNO2S Molecular weight: 287.3933832 g/mol InChI Key: BILSBDMCLLFSAV-UHFFFAOYSA-N

InChI=1S/C14H22FNO2S/c1-17-12-10-14(19-8-4-3-6-15)13(18-2)9-11(12)5-7-16/h9-10H,3-8,16H2,1-2H3

PubChem CID: 12063263

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 12

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-31

2182

Analogue 53: Substituting 4-(Trifluoromethyl)benzylthio for Methoxy at R4

2C-T-31
2,5-Dimethoxy-4-[4-(trifluoromethyl)benzylthio]phenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-{[4-(trifluoromethyl)benzyl]sulfanyl}phenyl)ethanamine

Formula: C18H20F3NO2S Molecular weight: 371.4171096 g/mol InChI Key: BDOJPUSYOLIGBS-UHFFFAOYSA-N

InChI=1S/C18H20F3NO2S/c1-23-15-10-17(16(24-2)9-13(15)7-8-22)25-11-12-3-5-14(6-4-12)18(19,20)21/h3-6,9-10H,7-8,11,22H2,1-2H3

PubChem CID: 12063264

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-32

2183

Analogue 54: Substituting 2,3,4,5,6-Pentafluorobenzylthio for Methoxy at R4

2C-T-32
2,5-Dimethoxy-4-(2,3,4,5,6-pentafluorobenzylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(pentafluorobenzyl)sulfanyl]phenyl}ethanamine

Formula: C17H16F5NO2S Molecular weight: 393.371456 g/mol InChI Key: SCZNXZRFVLLJGV-UHFFFAOYSA-N

InChI=1S/C17H16F5NO2S/c1-24-10-6-12(11(25-2)5-8(10)3-4-23)26-7-9-13(18)15(20)17(22)16(21)14(9)19/h5-6H,3-4,7,23H2,1-2H3

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-T-33

2184

Analogue 55: Substituting 3-Methoxybenzylthio for Methoxy at R4

2C-T-33
2,5-Dimethoxy-4-(3-methoxybenzylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(3-methoxybenzyl)sulfanyl]phenyl}ethanamine

Formula: C18H23NO3S Molecular weight: 333.44512 g/mol InChI Key: ADENDGINQJWQOK-UHFFFAOYSA-N

InChI=1S/C18H23NO3S/c1-20-15-6-4-5-13(9-15)12-23-18-11-16(21-2)14(7-8-19)10-17(18)22-3/h4-6,9-11H,7-8,12,19H2,1-3H3

PubChem CID: 12063266

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2C-VI

2198

Analogue 56: Substituting Ethenyl for Methoxy at R4

2C-VI
2C-V
4-Ethenyl-2,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 57474284

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 19

2C-BI-1

2300

Analogue 57: Substituting Phenyl for Methoxy at R4

2C-BI-1
2,5-Dimethoxy-4-phenylphenethylamine

IUPAC: 2-(2,5-Dimethoxybiphenyl-4-yl)ethanamine

Formula: C16H19NO2 Molecular weight: 257.32756 g/mol InChI Key: RMMCNNHGPNUXOX-UHFFFAOYSA-N

InChI=1S/C16H19NO2/c1-18-15-11-14(12-6-4-3-5-7-12)16(19-2)10-13(15)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3

PubChem CID: 57474287

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2C-BI-2

2301

Analogue 58: Substituting 2-Methoxyphenyl for Methoxy at R4

2C-BI-2
2,5-Dimethoxy-4-(2-methoxyphenyl)phenethylamine

IUPAC: 2-(2,2′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WEQGJWJNANPJNP-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-15-7-5-4-6-13(15)14-11-16(20-2)12(8-9-18)10-17(14)21-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 44219736

2C-BI-3

2302

Analogue 59: Substituting 2-Methylphenyl for Methoxy at R4

2C-BI-3
2,5-Dimethoxy-4-(2-methylphenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-2′-methylbiphenyl-4-yl)ethanamine

Formula: C17H21NO2 Molecular weight: 271.35414 g/mol InChI Key: INAUMGJNDBATML-UHFFFAOYSA-N

InChI=1S/C17H21NO2/c1-12-6-4-5-7-14(12)15-11-16(19-2)13(8-9-18)10-17(15)20-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 57474290

2C-BI-4

2303

Analogue 60: Substituting 2-(Trifluoromethyl)phenyl for Methoxy at R4

2C-BI-4
2,5-Dimethoxy-4-[2-(trifluoromethyl)phenyl]phenethylamine

IUPAC: 2-[2,5-Dimethoxy-2′-(trifluoromethyl)biphenyl-4-yl]ethanamine

Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: XCNBZPCBVPDJFY-UHFFFAOYSA-N

InChI=1S/C17H18F3NO2/c1-22-15-10-13(16(23-2)9-11(15)7-8-21)12-5-3-4-6-14(12)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3

PubChem CID: 57474292

2C-BI-5

2304

Analogue 61: Substituting Naphthalen-2-yl for Methoxy at R4

2C-BI-5
2,5-Dimethoxy-4-(naphthalen-2-yl)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(naphthalen-2-yl)phenyl]ethanamine

Formula: C20H21NO2 Molecular weight: 307.38624 g/mol InChI Key: KQKCTYPWGSPYLP-UHFFFAOYSA-N

InChI=1S/C20H21NO2/c1-22-19-13-18(20(23-2)12-17(19)9-10-21)16-8-7-14-5-3-4-6-15(14)11-16/h3-8,11-13H,9-10,21H2,1-2H3

PubChem CID: 57474294

2C-BI-6

2305

Analogue 62: Substituting 3-Methoxyphenyl for Methoxy at R4

2C-BI-6
2,5-Dimethoxy-4-(3-methoxyphenyl)phenethylamine

IUPAC: 2-(2,3′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WMTQTFIOUBEGJW-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-14-6-4-5-12(9-14)15-11-16(20-2)13(7-8-18)10-17(15)21-3/h4-6,9-11H,7-8,18H2,1-3H3

PubChem CID: 57474296

2C-BI-7

2306

Analogue 63: Substituting 3-Nitrophenyl for Methoxy at R4

2C-BI-7
2,5-Dimethoxy-4-(3-nitrophenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-3′-nitrobiphenyl-4-yl)ethanamine

Formula: C16H18N2O4 Molecular weight: 302.32512 g/mol InChI Key: YNWQIUDDSDYOFB-UHFFFAOYSA-N

InChI=1S/C16H18N2O4/c1-21-15-10-14(16(22-2)9-12(15)6-7-17)11-4-3-5-13(8-11)18(19)20/h3-5,8-10H,6-7,17H2,1-2H3

PubChem CID: 57474298

2C-BI-8

2307

Analogue 64: Substituting 4-Methoxyphenyl for Methoxy at R4

2C-BI-8
2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine

IUPAC: 2-(2,4′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: ZALWHJKGZWNFNR-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-14-6-4-12(5-7-14)15-11-16(20-2)13(8-9-18)10-17(15)21-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 57474300

2C-BI-9

2308

Analogue 65: Substituting 4-Butylphenyl for Methoxy at R4

2C-BI-9
4-(4-Butylphenyl)-2,5-dimethoxyphenethylamine

IUPAC: 2-(4′-Butyl-2,5-dimethoxybiphenyl-4-yl)ethanamine

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

InChI=1S/C20H27NO2/c1-4-5-6-15-7-9-16(10-8-15)18-14-19(22-2)17(11-12-21)13-20(18)23-3/h7-10,13-14H,4-6,11-12,21H2,1-3H3

PubChem CID: 57474302

2C-BI-10

2309

Analogue 66: Substituting 4-(Trifluoromethyl)phenyl for Methoxy at R4

2C-BI-10
2,5-Dimethoxy-4-[4-(trifluoromethyl)phenyl]phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4′-(trifluoromethyl)biphenyl-4-yl]ethanamine

Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: BFFLBYIGPNMJQH-UHFFFAOYSA-N

InChI=1S/C17H18F3NO2/c1-22-15-10-14(16(23-2)9-12(15)7-8-21)11-3-5-13(6-4-11)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3

PubChem CID: 57474304

2C-BI-11

2310

Analogue 67: Substituting 4-Phenylphenyl for Methoxy at R4

2C-BI-11
2,5-Dimethoxy-4-(4-phenylphenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-1,1′:4′,1′′-terphenyl-4-yl)ethanamine

Formula: C22H23NO2 Molecular weight: 333.42352 g/mol InChI Key: ZQEKXNJKMUWVBC-UHFFFAOYSA-N

InChI=1S/C22H23NO2/c1-24-21-15-20(22(25-2)14-19(21)12-13-23)18-10-8-17(9-11-18)16-6-4-3-5-7-16/h3-11,14-15H,12-13,23H2,1-2H3

2C-BI-12

2311

Analogue 68: Substituting 1,3-Benzodioxol-5-yl for Methoxy at R4

2C-BI-12
2,5-Dimethoxy-4-(3,4-methylenedioxyphenyl)phenethylamine

IUPAC: 2-[4-(1,3-Benzodioxol-5-yl)-2,5-dimethoxyphenyl]ethanamine

Formula: C17H19NO4 Molecular weight: 301.33706 g/mol InChI Key: QNWIOBZDXFFFLT-UHFFFAOYSA-N

InChI=1S/C17H19NO4/c1-19-15-9-13(16(20-2)8-12(15)5-6-18)11-3-4-14-17(7-11)22-10-21-14/h3-4,7-9H,5-6,10,18H2,1-2H3

PubChem CID: 57474306

2326

2,5-Dimethoxy-4-phenylpropylphenethylamine

2326

Analogue 69: Substituting Phenylpropyl for Methoxy at R4

2,5-Dimethoxy-4-phenylpropylphenethylamine

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

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

InChI=1S/C19H25NO2/c1-21-18-14-17(11-12-20)19(22-2)13-16(18)10-6-9-15-7-4-3-5-8-15/h3-5,7-8,13-14H,6,9-12,20H2,1-2H3

PubChem CID: 10542173; ChemSpider: 8717564

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

2324

2324

Analogue 70: Substituting Phenethyl for Methoxy at R4

2,5-Dimethoxy-4-phenethylphenethylamine

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

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

InChI=1S/C18H23NO2/c1-20-17-13-16(10-11-19)18(21-2)12-15(17)9-8-14-6-4-3-5-7-14/h3-7,12-13H,8-11,19H2,1-2H3

PubChem CID: 10827012; ChemSpider: 9002312

2327

2,5-Dimethoxy-4-phenylbutylphenethylamine

2327

Analogue 71: Substituting Phenylbutyl for Methoxy at R4

2,5-Dimethoxy-4-phenylbutylphenethylamine

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

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

InChI=1S/C20H27NO2/c1-22-19-15-18(12-13-21)20(23-2)14-17(19)11-7-6-10-16-8-4-3-5-9-16/h3-5,8-9,14-15H,6-7,10-13,21H2,1-2H3

PubChem CID: 10805159; ChemSpider: 8980464

2C-IP

2361

Analogue 72: Substituting Isopropyl for Methoxy at R4

2C-IP
Jelena
4-Isopropyl-2,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 57474311; ChemSpider: 27750188

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

2C-EF

370

Analogue 73: Substituting 2-Fluoroethyl for Methoxy at R4

2C-EF
4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H18FNO2 Molecular weight: 227.2752232 g/mol InChI Key: KXPMRPNOYIOXFY-UHFFFAOYSA-N

InChI=1S/C12H18FNO2/c1-15-11-8-10(4-6-14)12(16-2)7-9(11)3-5-13/h7-8H,3-6,14H2,1-2H3

PubChem CID: 44350106; ChemSpider: 21106293

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 23

See also PiHKAL:	#65 DOEF

2C-NH

7179

Analogue 74: Substituting Amino for Methoxy at R4

2C-NH

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

Formula: C10H16N2O2 Molecular weight: 196.24624 g/mol InChI Key: GAEPEBLGEFMUAZ-UHFFFAOYSA-N

InChI=1S/C10H16N2O2/c1-13-9-6-8(12)10(14-2)5-7(9)3-4-11/h5-6H,3-4,11-12H2,1-2H3

PubChem CID: 10330310; ChemSpider: 8505771

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 341 Row: 29

2C-HM

7253

Analogue 75: Substituting Hydroxymethyl for Methoxy at R4

2C-HM

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

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: ZDHYVCBZXIAZEJ-UHFFFAOYSA-N

InChI=1S/C11H15NO3/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-7H,3-4,12H2,1-2H3

PubChem CID: 57486930

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 3

2C-IB

7302

Analogue 76: Substituting Isobutyl for Methoxy at R4

2C-IB

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

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

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

PubChem CID: 57486931

Shulgin Index: See #20 2C-D; Table: 5 Page: 344 Row: 2

2C-TFE

472

Analogue 77: Substituting 2,2,2-Trifluoroethyl for Methoxy at R4

2C-TFE

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

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

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

PubChem CID: 57498513

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

2C-O-22

466

Analogue 78: Substituting 2,2,2-Trifluoroethoxy for Methoxy at R4

2C-O-22

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

Formula: C12H16F3NO3 Molecular weight: 279.2555496 g/mol InChI Key: WXMPTDDEIHHBRM-UHFFFAOYSA-N

InChI=1S/C12H16F3NO3/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 57498514

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

2C-O-21.5

465

Analogue 79: Substituting 2,2-Difluoroethoxy for Methoxy at R4

2C-O-21.5

IUPAC: 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: USTOBZVLZKAMKI-UHFFFAOYSA-N

InChI=1S/C12H17F2NO3/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3

PubChem CID: 57498515

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

2C-O-21

464

Analogue 80: Substituting 2-Fluoroethyoxy for Methoxy at R4

2C-O-21

IUPAC: 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H18FNO3 Molecular weight: 243.2746232 g/mol InChI Key: QFEAVTWEYZNLIS-UHFFFAOYSA-N

InChI=1S/C12H18FNO3/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 57498516

2C-A

2C-A; 2,5-Dimethoxy-4-astatophenethylamine

2474

Analogue 81: Substituting Astato for Methoxy at R4

2C-A
2,5-Dimethoxy-4-astatophenethylamine

IUPAC: [4-(2-Aminoethyl)-2,5-dimethoxyphenyl]astatine

Formula: C10H14AtNO2 Molecular weight: 390.22366 g/mol InChI Key: ULHVWCPOZNGWMU-UHFFFAOYSA-N

InChI=1S/C10H14AtNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

See also PiHKAL:	#33 2C-I

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

Four R5 analogues:
24 5392	Analogue 1: Removing Methoxy at R5 24 2,4-DMPEA 2,4-Dimethoxyphenethylamine IUPAC: 2-(2,4-Dimethoxyphenyl)ethanamine Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: YDTQAPOROITHCN-UHFFFAOYSA-N InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)10(7-9)13-2/h3-4,7H,5-6,11H2,1-2H3 PubChem CID: 417604; ChemSpider: 369665 Shulgin Index: #47 2,4-DMPEA; Table: 4 Page: 327 Row: 9 Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB. Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol., 1 Jan 2006, 70 (6), 1956–1964. 361 kB. doi:10.1124/mol.106.028720
2,4,5-MMB 7079	Analogue 2: Substituting Bromo for Methoxy at R5 2,4,5-MMB IUPAC: 2-(5-Bromo-2,4-dimethoxyphenyl)ethanamine Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: FEAKOSWVJXEIIK-UHFFFAOYSA-N InChI=1S/C10H14BrNO2/c1-13-9-6-10(14-2)8(11)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 PubChem CID: 143750; ChemSpider: 126826 Shulgin Index: See #18 2C-B; Table: 5 Page: 339 Row: 29
5-NH2-2,4-DMPEA 7101	Analogue 3: Substituting Amino for Methoxy at R5 5-NH2-2,4-DMPEA IUPAC: 5-(2-Aminoethyl)-2,4-dimethoxyaniline Formula: C10H16N2O2 Molecular weight: 196.24624 g/mol InChI Key: HUJXOQJDJLWIEV-UHFFFAOYSA-N InChI=1S/C10H16N2O2/c1-13-9-6-10(14-2)8(12)5-7(9)3-4-11/h5-6H,3-4,11-12H2,1-2H3 PubChem CID: 10035582; ChemSpider: 8211147 Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 340 Row: 1
2,4,5-2C-T-7 7504	Analogue 4: Substituting n-Propylthio for Methoxy at R5 2,4,5-2C-T-7 IUPAC: 1-[2,4-Dimethoxy-5-(propylsulfanyl)phenyl]propan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: WPEOSQBUHPSLAM-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-6-18-14-8-11(7-10(2)15)12(16-3)9-13(14)17-4/h8-10H,5-7,15H2,1-4H3 Shulgin Index: See #27 2C-T-7; Table: 5 Page: 348 Row: 4

One R4,5 analogue:

2C-2; 2C-MMDA-2

2C-2; 2-Methoxy-4,5-methylenedioxyphenethylamine

298

Analogue 1: Substituting Methylenedioxy for Dimethoxy at R4,5

2C-2
2C-MMDA-2
2-Methoxy-4,5-methylenedioxyphenethylamine

IUPAC: 2-(6-Methoxy-1,3-benzodioxol-5-yl)ethanamine

Formula: C10H13NO3 Molecular weight: 195.21512 g/mol InChI Key: VHBCQDKBQRHHPZ-UHFFFAOYSA-N

InChI=1S/C10H13NO3/c1-12-8-5-10-9(13-6-14-10)4-7(8)2-3-11/h4-5H,2-3,6,11H2,1H3

PubChem CID: 21831819; ChemSpider: 13802346

Shulgin Index: See #98 MMDA-2; Table: 5 Page: 339 Row: 24, See #98 MMDA-2; Table: 5 Page: 347 Row: 19

See also PiHKAL:	#133 MMDA-2

See also Pharmacology notes I:	p. 75, 2C-2: Subacute evaluation

Five skeleton analogues:

γ-Asarone

1061

Analogue 1: With Prop-2-en-1-ylbenzene skeleton

γ-Asarone
2,4,5-Trimethoxyphenylprop-2-ene

IUPAC: 1,2,4-Trimethoxy-5-(prop-2-en-1-yl)benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: AUNAUZZQBAIQFJ-UHFFFAOYSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3

PubChem CID: 636750; ChemSpider: 552473

See also PiHKAL:	#157 TMA	#158 TMA-2

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

β-Asarone

1062

Analogue 2: With (1Z)-Prop-1-en-1-ylbenzene skeleton

β-Asarone
cis-2,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,4-Trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RKFAZBXYICVSKP-WAYWQWQTSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

PubChem CID: 636822; ChemSpider: 4445072

See also PiHKAL:	#157 TMA	#158 TMA-2

See also Pharmacology notes I:	p. 154, β-Asarone

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. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

Zuba, D; Byrska, B. Alpha- and beta-asarone in herbal medicinal products. A case study. Forensic Sci. Int., . 229 kB. doi:10.1016/j.forsciint.2012.08.015

α-Asarone

1063

Analogue 3: With (1E)-Prop-1-en-1-ylbenzene skeleton

α-Asarone
Asarone
trans-2,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,4-Trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RKFAZBXYICVSKP-AATRIKPKSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

PubChem CID: 636822; ChemSpider: 552532; Wikipedia: Asarone

See also PiHKAL:	#157 TMA	#158 TMA-2

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

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

Zuba, D; Byrska, B. Alpha- and beta-asarone in herbal medicinal products. A case study. Forensic Sci. Int., . 229 kB. doi:10.1016/j.forsciint.2012.08.015

TMCPA

7326

Analogue 4: With 2-Phenylcyclopropan-1-amine skeleton

TMCPA

IUPAC: 2-(2,4,5-Trimethoxyphenyl)cyclopropanamine

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

InChI=1S/C12H17NO3/c1-14-10-6-12(16-3)11(15-2)5-8(10)7-4-9(7)13/h5-7,9H,4,13H2,1-3H3

PubChem CID: 21151752; ChemSpider: 27941063

Shulgin Index: See #41 DMCPA; Table: 5 Page: 344 Row: 26

TMCBA

522

Analogue 5: With 2-Phenylcyclobutan-1-amine skeleton

TMCBA

IUPAC: 2-(2,4,5-Trimethoxyphenyl)cyclobutanamine

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

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

PubChem CID: 146232; ChemSpider: 128991

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

35 isomers:

BOHD

Isomer 1

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

4-D

Isomer 2

4-D
4-Trideuteromethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-trideuteromethoxyphenethylamine

IUPAC: 2-{3,5-Dimethoxy-4-[(2H3)methyloxy]phenyl}ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-HPRDVNIFSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i3D3

ChemSpider: 23553050; Wikipedia: 4-D (psychedelic)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 35

See also PiHKAL:	#51 β-D

β-D

Isomer 3

β-D
β,β-Dideutero-3,4,5-trimethoxyphenethylamine
3,4,5-Trimethoxy-β,β-dideuterophenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(2,2-2H2)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-APZFVMQVSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i4D2

PubChem CID: 44719547; ChemSpider: 21106267; Wikipedia: Beta-D

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 19

See also PiHKAL:	#50 4-D	#96 M

Isomer 4

IM
Isomescaline
2,3,4-Trimethoxyphenethylamine

IUPAC: 2-(2,3,4-Trimethoxyphenyl)ethanamine

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

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

PubChem CID: 414332; ChemSpider: 366878; Wikipedia: Isomescaline

Shulgin Index: #72 IM; Table: 5 Page: 338 Row: 14

See also PiHKAL:	#92 IP	#153 3-TIM

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

Isomer 5

M
Mescaline
EA-1306
Mescaline
3,4,5-Trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 4076; ChemSpider: 3934; Drugs Forum: Mescaline; Erowid: Mescaline; Wikipedia: Mescaline

Shulgin Index: #91 Mescaline; Table: 5 Page: 349 Row: 26

See also PiHKAL:	#1 AEM #9 ASB #10 B #16 BOHD #17 BOM #25 3C-E #27 2C-G #37 CPM #41 2C-T-4 #43 2C-T-7 #44 2C-T-8 #50 4-D	#51 β-D #52 DESOXY #55 3,4-DMA #58 DMMDA #59 DMMDA-2 #68 DOM #72 E #91 IM #92 IP #93 IRIS #95 LOPHOPHINE #99 MAL	#100 MDA #115 MDPEA #119 ME #125 META-DOT #132 MMDA #135 MMDA-3b #142 PEA #144 SB #150 3-TE #151 4-TE #156 4-TM #157 TMA	#158 TMA-2 #159 TMA-3 #160 TMA-4 #161 TMA-5 #162 TMA-6 #163 3-TME #168 TMPEA #175 TRIS #178 3-T-TRIS
See also TiHKAL:	#8 α,N-DMT #9 DPT	#13 Harmaline #17 4-HO-DIPT	#45 5-MeO-TMT #48 α-MT	#53 T

See also Pharmacology notes I:	p. 1, Mescaline: Subjective response p. 2, Mescaline: Subjective response p. 3, Mescaline: Subjective response p. 4, Mescaline: Subjective response p. 5, Mescaline: Subjective response p. 6, Mescaline: Subjective response p. 7, Mescaline: Basis for M.U. calculation
See also Pharmacology notes II:	app. 5, Untitled p. 321, Mescaline

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

Desantis, F; Nieforth, KA. Synthesis of potential mescaline antagonists. J. Pharm. Sci., 1 Jan 1976, 65 (10), 1479–1484. 704 kB. doi:10.1002/jps.2600651016

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

Battersby, AR; Binks, R; Huxtable, R. Biosynthesis of cactus alkaloids. Tetrahedron Lett., 1 Jan 1967, 8 (6), 563–565. 134 kB. doi:10.1016/S0040-4039(00)90548-3

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

Ogunbodede, O; McCombs, D; Trout, K; Daley, P; Terry, M. New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) (“San Pedro”) and their relevance to shamanic practice. J. Ethnopharmacol., 15 Sep 2010, 131 (2), 356–362. 324 kB. doi:10.1016/j.jep.2010.07.021

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

Glennon, RA; 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

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

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

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

Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc., Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c

Smythies, JR. The mescaline phenomena. Br. J. Philos. Sci., 1 Feb 1953, 3 (12), 339–347. 72 kB. doi:10.1093/bjps/III.12.339

Friedhoff, AJ; Goldstein, M. New developments in metabolism of mescaline and related amines. Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 5–13. 506 kB. doi:10.1111/j.1749-6632.1962.tb50097.x

Daly, J; Axelrod, J; Witkop, B. Methylation and demethylation in relation to the in vitro metabolism of mescaline. Ann. N. Y. Acad. Sci., 1 Jan 1962, 96, 37–43. 397 kB. doi:10.1111/j.1749-6632.1962.tb50099.x

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.

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.

Shulgin, AT. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs, 1 Jan 1979, 11 (4), 355. 713 kB.

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB.

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

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

Fenderson5555. Two syntheses of mescaline. 21 Mar 2011.

TMPEA-5; 2C-TMA-5

307

Isomer 6

TMPEA-5
2C-TMA-5
2,3,6-Trimethoxyphenethylamine

IUPAC: 2-(2,3,6-Trimethoxyphenyl)ethanamine

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

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

PubChem CID: 414331; ChemSpider: 366877

Shulgin Index: See #121 TMA-5; Table: 5 Page: 353 Row: 1

See also PiHKAL:	#161 TMA-5

TMPEA-6; 2C-TMA-6

308

Isomer 7

TMPEA-6
2C-TMA-6
2,4,6-TMPEA
Ψ-2C-O
2,4,6-Trimethoxyphenethylamine

IUPAC: 2-(2,4,6-Trimethoxyphenyl)ethanamine

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

InChI=1S/C11H17NO3/c1-13-8-6-10(14-2)9(4-5-12)11(7-8)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 21679959; ChemSpider: 10296635

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 25

See also PiHKAL:	#162 TMA-6

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

3,5-D

3,5-D; 4-Methoxy-3,5-di(trideuteromethoxy)phenethylamine

2092

Isomer 8

3,5-D
4-Methoxy-3,5-di(trideuteromethoxy)phenethylamine

IUPAC: 2-{4-Methoxy-3,5-bis[(2H3)methyloxy]phenyl}ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-WFGJKAKNSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i1D3,2D3

ChemSpider: 23553050

See also PiHKAL:	#50 4-D	#51 β-D

2,6-D

2,6-D; 2,6-Dideutero-3,4,5-trimethoxyphenethylamine

2093

Isomer 9

2,6-D
2,6-Dideutero-3,4,5-trimethoxyphenethylamine

IUPAC: 2-[3,4,5-Trimethoxy(2H2)phenyl]ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-QFIQSOQBSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i6D,7D

ChemSpider: 23553050

See also PiHKAL:	#51 β-D

α-D

α-D; α,α-Dideutero-3,4,5-trimethoxyphenethylamine

2094

Isomer 10

α-D
α,α-Dideutero-3,4,5-trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(1,1-2H2)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-BFWBPSQCSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i5D2

ChemSpider: 23553050

See also PiHKAL:	#51 β-D

N-Me-3-DESMETHYL

2213

Isomer 11

N-Me-3-DESMETHYL
N-Methyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N-methylphenethylamine

IUPAC: 2,3-Dimethoxy-5-[2-(methylamino)ethyl]phenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: ZIXMCYWHHXSJOK-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO3/c1-12-5-4-8-6-9(13)11(15-3)10(7-8)14-2/h6-7,12-13H,4-5H2,1-3H3

PubChem CID: 57478610

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 6

2C-pEtOH

5396

Isomer 12

2C-pEtOH
4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 57474313

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

DOOH

2414

Isomer 13

DOOH
4-Hydroxy-2,5-dimethoxyamphetamine

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

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

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

PubChem CID: 44265202; ChemSpider: 23108622

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

β-HO-2,5-DMA

2394

Isomer 14

β-HO-2,5-DMA
2,5-Dimethoxynorephedrine

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

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

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

PubChem CID: 6082; ChemSpider: 5857

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 26

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

Rusterholz, DB; Dryer, SE; Long, JP; Barfknecht, CF; Mott, J. Sedative and analgesic actions of methoxylated 2-aminotetralins; involvement of α1- and α2-adrenoreceptors. Eur. J. Pharmacol., 25 Jul 1980, 65 (2–3), 201–211. 870 kB. doi:10.1016/0014-2999(80)90393-3

β,3,4-HO-N-iPr-DHPEA

6522

Isomer 15

β,3,4-HO-N-iPr-DHPEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol

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

InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3

PubChem CID: 3779; ChemSpider: 3647

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 22

MHMAOH

6565

Isomer 16

MHMAOH

IUPAC: 4-{2-[Hydroxy(methyl)amino]propyl}-2-methoxyphenol

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

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

Shulgin Index: See #33 DHA; Table: 4 Page: 329 Row: 15

N,N-Me-HME

6584

Isomer 17

N,N-Me-HME

IUPAC: 5-[2-(Dimethylamino)-1-hydroxyethyl]-2-methoxyphenol

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

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

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 34

N-Me-DME

6608

Isomer 18

N-Me-DME

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

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

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

PubChem CID: 3084840; ChemSpider: 2341843

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 8

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!.

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochem., 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

β,3,4-TMPEA

6611

Isomer 19

β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine

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

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

PubChem CID: 3014315; ChemSpider: 2282798

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 11

DMAOH

6619

Isomer 20

DMAOH

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

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

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

PubChem CID: 5190226; ChemSpider: 4361999

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 19

β-HO-DMA

6626

Isomer 21

β-HO-DMA

IUPAC: 2-Amino-1-(3,4-dimethoxyphenyl)propan-1-ol

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

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

PubChem CID: 13585934; ChemSpider: 12956236

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 26

β-HO-4,3-EMPEA

6634

Isomer 22

β-HO-4,3-EMPEA

IUPAC: 2-Amino-1-(4-ethoxy-3-methoxyphenyl)ethanol

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

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

PubChem CID: 16768023; ChemSpider: 11852804

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 34

β,2-HO-N-Me-5-MA

6856

Isomer 23

β,2-HO-N-Me-5-MA

IUPAC: 2-[1-Hydroxy-2-(methylamino)propyl]-4-methoxyphenol

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

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

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 6

β-HO-N-Me-2,5-DMPEA

6865

Isomer 24

β-HO-N-Me-2,5-DMPEA

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

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

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

PubChem CID: 46244; ChemSpider: 42102

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 15

BODM

6867

Isomer 25

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

β-HO,Me-2,5-DMPEA

6868

Isomer 26

β-HO,Me-2,5-DMPEA

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

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

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

PubChem CID: 46246; ChemSpider: 42104

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 18

β,2-HO-N-Me-5-EPEA

6906

Isomer 27

β,2-HO-N-Me-5-EPEA

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

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

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

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 6

β,2-HO-5-EA

6909

Isomer 28

β,2-HO-5-EA

IUPAC: 2-(2-Amino-1-hydroxypropyl)-4-ethoxyphenol

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

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

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 9

β-HO-N-Me-3,5-DMPEA

6926

Isomer 29

β-HO-N-Me-3,5-DMPEA

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

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

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

PubChem CID: 62774486

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 26

β-HO-N-Me-2,6-DMPEA

6972

Isomer 30

β-HO-N-Me-2,6-DMPEA

IUPAC: 1-(2,6-Dimethoxyphenyl)-2-(methylamino)ethanol

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

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

PubChem CID: 22574395; ChemSpider: 11474127

Shulgin Index: See #48 2,6-DMPEA; Table: 4 Page: 337 Row: 22

TMPEA-4

7071

Isomer 31

TMPEA-4

IUPAC: 2-(2,3,5-Trimethoxyphenyl)ethanamine

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

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)11(15-3)10(7-9)14-2/h6-7H,4-5,12H2,1-3H3

PubChem CID: 413872; ChemSpider: 366438

Shulgin Index: See #120 TMA-4; Table: 5 Page: 339 Row: 21

N-HO-2C-D

7210

Isomer 32

N-HO-2C-D

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxyethanamine

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

InChI=1S/C11H17NO3/c1-8-6-11(15-3)9(4-5-12-13)7-10(8)14-2/h6-7,12-13H,4-5H2,1-3H3

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 10

α-Me-3-DESMETHYL

7559

Isomer 33

α-Me-3-DESMETHYL

IUPAC: 5-(2-Aminopropyl)-2,3-dimethoxyphenol

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

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

ChemSpider: 26495745

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 9

DESMETHYL-M

7568

Isomer 34

DESMETHYL-M

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

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

InChI=1S/C11H17NO3/c1-12-5-4-8-6-9(14-2)11(13)10(7-8)15-3/h6-7,12-13H,4-5H2,1-3H3

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 18

α-Me-DESMETHYL

7572

Isomer 35

α-Me-DESMETHYL

IUPAC: 4-(2-Aminopropyl)-2,6-dimethoxyphenol

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

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

ChemSpider: 26495039

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 22