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PiHKAL#35 2C-O-4
35
Variant: α R4 isomers all
Analogues: 2 81 37 120

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethan-1-amine

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

Two α analogues:
302
Analogue 1: Adding Methyl at α

MIPM
2,5-Dimethoxy-4-isopropoxyamphetamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]propan-2-amine

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

InChI=1S/C14H23NO3/c1-9(2)18-14-8-12(16-4)11(6-10(3)15)7-13(14)17-5/h7-10H,6,15H2,1-5H3

ChemSpider: 23553121

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 6

See also PiHKAL: #35 2C-O-4 #138 MPM    
336
Analogue 2: Adding Ethyl at α

4C-iPrO
1-(4-Isopropoxy-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-isopropoxy-2,5-dimethoxyphenethylamine

IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]butan-2-amine

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: KKDGVJJZQGSVHK-LBPRGKRZSA-N

InChI=1S/C15H25NO3/c1-6-12(16)7-11-8-14(18-5)15(19-10(2)3)9-13(11)17-4/h8-10,12H,6-7,16H2,1-5H3/t12-/m0/s1

ChemSpider: 25040478

Shulgin Index: See #118 TMA-2; Table: 5 Page: 345 Row: 7

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1125 kB. doi:10.1021/jm00176a010

81 R4 analogues:
20
Analogue 1: Substituting Bromo for Isopropoxy at R4

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

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

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 Transcripts: 1.172, 2.204, 2.211, 2.279, 2.303, 2.305, 2.309, 2.323, 2.323.2, 3.342, 3.346, 3.368, 3.369, 3.370, 3.371, 3.445, 3.446, 4.447, 4.449_2, 4.450, 4.451, 4.452, 4.455, 4.459, 4.461, 4.484, 4.489, 4.491, 4.511, 4.512, 4.513, 4.514, 4.515, 4.516, 4.517, 4.521, 4.522, 4.523, 4.524, 4.525, 4.526, 4.527, 4.528, 4.529, 4.530, 4.531, 4.532, 4.533, 4.535, 4.536, 4.537, 4.538, 4.539, 4.541, 4.542, 4.543, 4.544, 4.545, 4.546, 4.547, 4.548, 4.549, 4.551, 4.552, 4.555, 4.557, 4.558

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

Páleníček, T; Fujáková, M; Brunovský, M; Horáček, J; Gorman, I; Balíková, M; Rambousek, L; Syslová, K; Kačer, P; Zach, P; Bubeníková-Valešová, V; Tylš, F; Kubešová, A; Puskarčíková, J; Höschl, C. Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats. Psychopharmacology, 1 Jan 2013, 225 (1), 75–93. 1079 kB. doi:10.1007/s00213-012-2797-7

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

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

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

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

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

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

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

Carmo, H; Hengstler, JG; Boer, D; Ringel, M; Remião, F; Carvalho, F; Fernandes, E; Reys, LA; Oesch, F; Bastos, ML. Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology, 5 Jan 2005, 206 (1), 75–89. 273 kB. doi:10.1016/j.tox.2004.07.004

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

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

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:10.1038/sj.bjp.0704747

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

Boer, D; Gijzels, MJ; Bosman, IJ; Maes, RAA. More data about the new psychoactive drug 2C-B. J. Anal. Toxicol., 1 Jul 1999, 23 (3), 227–228. 190 kB. doi:10.1093/jat/23.3.227

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

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

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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.

22
Analogue 2: Substituting Chloro for Isopropoxy at R4

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

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

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  

See also Transcripts: 4.462

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

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

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

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

23
Analogue 3: Substituting Methyl for Isopropoxy at R4

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

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

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

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

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

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

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

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

24
Analogue 4: Substituting Ethyl for Isopropoxy at R4

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

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

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 Transcripts: 2.236, 2.323.2, 3.329, 4.469

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

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

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

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

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

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

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

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

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

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

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

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

Kusin, S; Tesar, J; Hatten, B; Horowitz, BZ; Hendrickson, R; Leman, R; Buser, G. Severe methemoglobinemia and haemolytic anemia from aniline purchased as 2C-E (4-ethyl-2,5-dimethoxyphenethylamine), a recreational drug, on the internet – Oregon, 2011. Morbidity and Mortality Weekly Report, 10 Feb 2012, 61 (5), 85–88. 273 kB.

26
Analogue 5: Substituting Fluoro for Isopropoxy at R4

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

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

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.

32
Analogue 6: Removing Isopropoxy at R4

2C-H
25H
2,5-Dimethoxyphenethylamine

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

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
 

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

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. doi:10.1093/chromsci/bmr013

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

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

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

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

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

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.

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; 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

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

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

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

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

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

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

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

33
Analogue 7: Substituting Iodo for Isopropoxy at R4

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

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

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 Transcripts: 1.179, 3.335

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

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.

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

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

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

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

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

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, JL; 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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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

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

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

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

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

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

34
Analogue 8: Substituting Nitro for Isopropoxy at R4

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

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

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  

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

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

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

36
Analogue 9: Substituting Propyl for Isopropoxy at R4

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

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

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

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

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

Ger, A; Ger, D. Triple Goddess of the Night. British Neuroscience Association Bulletin, 1 Mar 2011, 63, 28–30. 234 kB. Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.

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

38
Analogue 10: Substituting Methylseleno for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(methylselanyl)phenyl]ethan-1-amine

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

39
Analogue 11: Substituting Methylthio for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]ethan-1-amine

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 Transcripts: 2.315, 4.465

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

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

Nichols, DE; 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.

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

Meyers-Riggs, B. 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.

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

40
Analogue 12: Substituting Ethylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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

See also Transcripts: 4.474, 4.499, 4.502, 4.509

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

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

Stolaroff, MJ. Letter to the editor (re: 2C-T-2 & 2C-T-7). J. Psychoactive Drugs, 1 Jan 1990, 22 (3), 379. 1090 kB. doi:10.1080/02791072.1990.10472568

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

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

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

41
Analogue 13: Substituting Isopropylthio for Isopropoxy 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]ethan-1-amine

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.

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

43
Analogue 14: Substituting Propylthio for Isopropoxy at R4

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

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

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
 

Curtis, BD. The forensic toxicology of 2,5-dimethoxy-4-N-propylthiophenethylamine (2C-T-7). Ph. D. Thesis, University of Oklahoma, Oklahoma City, OK, USA, 2005. 726 kB.

Stolaroff, MJ. Letter to the editor (re: 2C-T-2 & 2C-T-7). J. Psychoactive Drugs, 1 Jan 1990, 22 (3), 379. 1090 kB. doi:10.1080/02791072.1990.10472568

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

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

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 I. countyourculture: rational exploration of the underground, 15 Jan 2011.

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

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

44
Analogue 15: Substituting Cyclopropylmethylthio for Isopropoxy at R4

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

IUPAC: 2-{4-[(Cyclopropylmethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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.

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.

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.

45
Analogue 16: Substituting tert-Butylthio for Isopropoxy 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]ethan-1-amine

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.

46
Analogue 17: Substituting 2-Methoxyethylthio for Isopropoxy 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}ethan-1-amine

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. 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.

47
Analogue 18: Substituting Cyclopropylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Cyclopropylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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. 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.

48
Analogue 19: Substituting sec-Butylthio for Isopropoxy 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]ethan-1-amine

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.

49
Analogue 20: Substituting 2-Fluoroethylthio for Isopropoxy 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}ethan-1-amine

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. 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.

168
Analogue 21: Substituting Methoxy for Isopropoxy at R4

TMPEA
TMPEA-2
2C-O
2,4,5-Trimethoxyphenethylamine

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

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

InChI=1S/C11H17NO3/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: 151954; ChemSpider: 133931; Wikipedia: 2C-O

Shulgin Index: #124 TMPEA-2; Table: 5 Page: 344 Row: 21

See also PiHKAL: #35 2C-O-4 #157 TMA #158 TMA-2  
See also TiHKAL: #13 Harmaline      

Jansen, MPJM. β-2,4,5-Trimethoxyphenylethylamine, an isomer of mescaline. Recl. Trav. Chim. Pays-Bas, 1931, 50 (4), 291–312. 1227 kB. doi:10.1002/recl.19310500403

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

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

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

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

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

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

200
Analogue 22: Substituting Cyano for Isopropoxy 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      
201
Analogue 23: Substituting Carboxy for Isopropoxy 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      
2040
Analogue 24: Substituting Trifluoromethyl for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethan-1-amine

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, SP; 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; 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

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.

2068
Analogue 25: Substituting Ethoxy for Isopropoxy at R4

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

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

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

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

PubChem CID: 57474251

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

See also PiHKAL: #35 2C-O-4      
2069
Analogue 26: Substituting Propoxy for Isopropoxy at R4

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

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

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      
2070
Analogue 27: Substituting Butoxy for Isopropoxy at R4

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

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

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      
2072
Analogue 28: Substituting Ethylseleno for Isopropoxy at R4

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

IUPAC: 2-[4-(Ethylselanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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      
2073
Analogue 29: Substituting Isopropylseleno for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-ylselanyl)phenyl]ethan-1-amine

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      
2074
Analogue 30: Substituting Propylseleno for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(propylselanyl)phenyl]ethan-1-amine

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      
2075
Analogue 31: Substituting 2-Fluoroethylseleno for Isopropoxy at R4

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

IUPAC: 2-{4-[(2-Fluoroethyl)selanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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      
2076
Analogue 32: Substituting Methyltelluro for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(methyltellanyl)phenyl]ethan-1-amine

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      
2079
Analogue 33: Substituting 2-Pyridylthio for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(pyridin-2-ylsulfanyl)phenyl]ethan-1-amine

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 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.

2080
Analogue 34: Substituting 4-Bromophenylthio for Isopropoxy at R4

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

IUPAC: 2-{4-[(4-Bromophenyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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.

2081
Analogue 35: Substituting 1-Morpholinothio for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(morpholin-4-ylsulfanyl)phenyl]ethan-1-amine

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.

2082
Analogue 36: Substituting 2-Methylthioethylthio for Isopropoxy at R4

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

IUPAC: 2-(2,5-Dimethoxy-4-{[2-(methylsulfanyl)ethyl]sulfanyl}phenyl)ethan-1-amine

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.

2083
Analogue 37: Substituting Cyclohexylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Cyclohexylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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.

2086
Analogue 38: Substituting Allylthio for Isopropoxy at R4

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

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

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 In German.

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

2087
Analogue 39: Substituting Phenylthio for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(phenylsulfanyl)phenyl]ethan-1-amine

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.

2089
Analogue 40: Substituting Butylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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

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 In German.

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

2090
Analogue 41: Substituting 2,2-Difluouroethylthio for Isopropoxy at R4

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

IUPAC: 2-{4-[(2,2-Difluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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

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 In German.

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

2091
Analogue 42: Substituting 2,2,2-Trifluoroethylthio for Isopropoxy 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}ethan-1-amine

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

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 In German.

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

2108
Analogue 43: Substituting Cyclobutylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Cyclobutylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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      
2109
Analogue 44: Substituting Cyclopentylthio for Isopropoxy at R4

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

IUPAC: 2-[4-(Cyclopentylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

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.

5378
Analogue 45: Substituting Ethynyl for Isopropoxy at R4

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

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

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

5396
Analogue 46: Substituting 2-Hydroxyethyl for Isopropoxy 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.

5397
Analogue 47: Substituting Acetoxy for Isopropoxy 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.

2177
Analogue 48: Substituting Methallylthio for Isopropoxy at R4

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

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

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      

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 In German.

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.

2178
Analogue 49: Substituting Isobutylthio for Isopropoxy at R4

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

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethan-1-amine

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

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 In German.

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

2179
Analogue 50: Substituting Benzylthio for Isopropoxy at R4

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

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

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

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 In German.

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

2180
Analogue 51: Substituting 3-Fluoropropylthio for Isopropoxy at R4

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

IUPAC: 2-{4-[(3-Fluoropropyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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. 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 In German.

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.

2181
Analogue 52: Substituting 4-Fluorobutylthio for Isopropoxy at R4

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

IUPAC: 2-{4-[(4-Fluorobutyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine

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. 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 In German.

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.

2182
Analogue 53: Substituting 4-(Trifluoromethyl)benzylthio for Isopropoxy at R4

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

IUPAC: 2-(2,5-Dimethoxy-4-{[4-(trifluoromethyl)benzyl]sulfanyl}phenyl)ethan-1-amine

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

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 In German.

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

2183
Analogue 54: Substituting 2,3,4,5,6-Pentafluorobenzylthio for Isopropoxy 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}ethan-1-amine

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

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 In German.

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

2184
Analogue 55: Substituting 3-Methoxybenzylthio for Isopropoxy at R4

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

IUPAC: 2-{2,5-Dimethoxy-4-[(3-methoxybenzyl)sulfanyl]phenyl}ethan-1-amine

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

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 In German.

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

2198
Analogue 56: Substituting Ethenyl for Isopropoxy at R4

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

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

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

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

2300
Analogue 57: Substituting Phenyl for Isopropoxy at R4

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

IUPAC: 2-(2,5-Dimethoxybiphenyl-4-yl)ethan-1-amine

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

2301
Analogue 58: Substituting 2-Methoxyphenyl for Isopropoxy at R4

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

IUPAC: 2-(2,2′,5-Trimethoxybiphenyl-4-yl)ethan-1-amine

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

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

2302
Analogue 59: Substituting 2-Methylphenyl for Isopropoxy at R4

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

IUPAC: 2-(2,5-Dimethoxy-2′-methylbiphenyl-4-yl)ethan-1-amine

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

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

2303
Analogue 60: Substituting 2-(Trifluoromethyl)phenyl for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-2′-(trifluoromethyl)biphenyl-4-yl]ethan-1-amine

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

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

2304
Analogue 61: Substituting Naphthalen-2-yl for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(naphthalen-2-yl)phenyl]ethan-1-amine

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

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

2305
Analogue 62: Substituting 3-Methoxyphenyl for Isopropoxy at R4

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

IUPAC: 2-(2,3′,5-Trimethoxybiphenyl-4-yl)ethan-1-amine

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

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

2306
Analogue 63: Substituting 3-Nitrophenyl for Isopropoxy at R4

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

IUPAC: 2-(2,5-Dimethoxy-3′-nitrobiphenyl-4-yl)ethan-1-amine

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

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

2307
Analogue 64: Substituting 4-Methoxyphenyl for Isopropoxy at R4

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

IUPAC: 2-(2,4′,5-Trimethoxybiphenyl-4-yl)ethan-1-amine

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

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

2308
Analogue 65: Substituting 4-Butylphenyl for Isopropoxy at R4

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

IUPAC: 2-(4′-Butyl-2,5-dimethoxybiphenyl-4-yl)ethan-1-amine

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

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

2309
Analogue 66: Substituting 4-(Trifluoromethyl)phenyl for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4′-(trifluoromethyl)biphenyl-4-yl]ethan-1-amine

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

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

2310
Analogue 67: Substituting 4-Phenylphenyl for Isopropoxy at R4

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

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

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

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

2311
Analogue 68: Substituting 1,3-Benzodioxol-5-yl for Isopropoxy at R4

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

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

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

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

2326
Analogue 69: Substituting Phenylpropyl for Isopropoxy at R4

2,5-Dimethoxy-4-phenylpropylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(3-phenylpropyl)phenyl]ethan-1-amine

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
Analogue 70: Substituting 2-Phenylethyl for Isopropoxy at R4

2,5-Dimethoxy-4-phenethylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(2-phenylethyl)phenyl]ethan-1-amine

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

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

2327
Analogue 71: Substituting Phenylbutyl for Isopropoxy at R4

2,5-Dimethoxy-4-phenylbutylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(4-phenylbutyl)phenyl]ethan-1-amine

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

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

2361
Analogue 72: Substituting Isopropyl for Isopropoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yl)phenyl]ethan-1-amine

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

Ger, A; Ger, D. Triple Goddess of the Night. British Neuroscience Association Bulletin, 1 Mar 2011, 63, 28–30. 234 kB. Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.

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

370
Analogue 73: Substituting 2-Fluoroethyl for Isopropoxy at R4

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

IUPAC: 2-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]ethan-1-amine

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: 23206505

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

See also PiHKAL: #65 DOEF      
7179
Analogue 74: Substituting Amino for Isopropoxy 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

7253
Analogue 75: Substituting Hydroxymethyl for Isopropoxy 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

7302
Analogue 76: Substituting Isobutyl for Isopropoxy at R4

2C-IB

IUPAC: 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethan-1-amine

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

472
Analogue 77: Substituting 2,2,2-Trifluoroethyl for Isopropoxy at R4

2C-TFE

IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethan-1-amine

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

466
Analogue 78: Substituting 2,2,2-Trifluoroethoxy for Isopropoxy at R4

2C-O-22

IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethan-1-amine

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

465
Analogue 79: Substituting 2,2-Difluoroethoxy for Isopropoxy at R4

2C-O-21.5

IUPAC: 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethan-1-amine

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

464
Analogue 80: Substituting 2-Fluoroethyoxy for Isopropoxy at R4

2C-O-21

IUPAC: 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethan-1-amine

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

2474
Analogue 81: Substituting Astato for Isopropoxy 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.

37 isomers:
1
Isomer 1

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

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

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

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

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

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

See also PiHKAL: #157 TMA      

See also Transcripts: 1.20

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

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

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

Daley, PF; Morris, H. Pages from the lab notebook of Alexander Shulgin: A glance through the history of psychedelic chemistry. Vice, 1 Oct 2012.

9
Isomer 2

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

IUPAC: 2-(3,4-Diethoxy-5-methoxyphenyl)ethan-1-amine

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

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

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

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

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

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

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

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

25
Isomer 3

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

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

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

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

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

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

See also PiHKAL: #72 E      

See also Transcripts: 2.222

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

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

76
Isomer 4

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

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

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

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

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

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

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

See also Transcripts: 1.60

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

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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

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

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

92
Isomer 5

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethan-1-amine

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

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

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

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

See also Transcripts: 3.389, 3.418

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

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

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

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

122
Isomer 6

MEM
2,5-Dimethoxy-4-ethoxyamphetamine

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

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

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

PubChem CID: 542053; ChemSpider: 472023; Wikipedia: 2,5-Dimethoxy-4-ethoxyamphetamine

Shulgin Index: #87 MEM; Table: 5 Page: 344 Row: 32

See also PiHKAL: #35 2C-O-4
#72 E
#73 EEE
#74 EEM
#76 EMM
#93 IRIS
#121 MEE
#136 MME
#138 MPM
 
See also TiHKAL: #19 5-HO-DMT #46 5-MeS-DMT    

See also Transcripts: 1.78, 1.78.2, 1.80, 1.112, 1.151, 2.229, 2.260, 2.270, 2.323.2, 2.323.4, 2.380, 3.380

See also Pharmacology notes I: p. 78.1, Subacute effects of MEM (XV-136)
p. 80, MEM: Marginal effects
p. 112, MEM: Subjective response
p. 151, MEM
See also Pharmacology notes II: app. 2, Abuse week
p. 229, MEM
p. 260, MEM
p. 270, MEM
p. 380, MEM

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

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

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

By, AW; Dawson, BA; Lodge, BA; Neville, GA; Sy, W; Zamecnik, J. Synthesis and spectral properties of 2,5-dimethoxy-4-ethoxyamphetamine and its precursors. J. Forensic Sci., 1 Mar 1990, 35 (2), 316–335. 538 kB. doi:10.1520/JFS12833J

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

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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; 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

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

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

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

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

Glennon, RA; 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

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

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

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

136
Isomer 7

MME
2,4-Dimethoxy-5-ethoxyamphetamine

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

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

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

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

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

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

See also Transcripts: 1.77

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

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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

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

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

137
Isomer 8

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

IUPAC: 2-(3,4-Dimethoxy-5-propoxyphenyl)ethan-1-amine

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

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

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

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

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

See also Transcripts: 3.430

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

140
Isomer 9

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

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethan-1-amine

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

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

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

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

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

See also Transcripts: 2.209, 4.560

See also Pharmacology notes II: p. 209, Proscaline

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

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

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

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

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

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

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

144
Isomer 10

SB
Symbescaline
3,5-Diethoxy-4-methoxyphenethylamine

IUPAC: 2-(3,5-Diethoxy-4-methoxyphenyl)ethan-1-amine

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

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

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

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

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

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

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

189
Isomer 11

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

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

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

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

See also PiHKAL: #8 ARIADNE      
190
Isomer 12

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

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

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

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

PubChem CID: 43565966

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

See also PiHKAL: #8 ARIADNE      
194
Isomer 13

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

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

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

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

See also PiHKAL: #14 BOD      

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

244
Isomer 14

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

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

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

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

See also PiHKAL: #69 Ψ-DOM      
263
Isomer 15

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

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

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

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

PubChem CID: 420418; ChemSpider: 372161

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

See also PiHKAL: #96 M      

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

288
Isomer 16

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

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

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

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

PubChem CID: 24257271; ChemSpider: 23900079

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

See also PiHKAL: #126 METHYL-DMA      

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

289
Isomer 17

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

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

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

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

PubChem CID: 69454104

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

See also PiHKAL: #126 METHYL-DMA      

See also Transcripts: 1.59

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

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

290
Isomer 18

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

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

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

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

PubChem CID: 69393054

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

See also PiHKAL: #126 METHYL-DMA      

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

2069
Isomer 19

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

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

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      
5549
Isomer 20

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

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

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

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

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

620
Isomer 21

homo-TMA-2

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

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

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

PubChem CID: 3839009; ChemSpider: 3064644

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

622
Isomer 22

homo-TMA-3

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

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

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

PubChem CID: 3041182; ChemSpider: 2304487

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

623
Isomer 23

homo-TMA-6

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

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

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

PubChem CID: 3041180; ChemSpider: 2304485

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

6613
Isomer 24

N,N-Me-β,3,4-TMPEA

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

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

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

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

6870
Isomer 25

β-HO-β,N,N-Me-2,5-DMPEA

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

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

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

PubChem CID: 50632; ChemSpider: 45892

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

6878
Isomer 26

β-HO-N,N-Me-2,5-DMA

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

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

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

PubChem CID: 46240; ChemSpider: 42098

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

6913
Isomer 27

β-HO-N-Me-2,5-DEPEA

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

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

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

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

6915
Isomer 28

β-HO-2,5-DEA

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

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

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

PubChem CID: 11253430; ChemSpider: 9428457

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

7016
Isomer 29

N-Me-TMA-3

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

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

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

ChemSpider: 21476716

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

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

7017
Isomer 30

4C-TMPEA-3

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

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

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

PubChem CID: 43566032

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

7255
Isomer 31

4C-HM

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

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

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

PubChem CID: 20315288

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

7262
Isomer 32

BOE

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

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

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

PubChem CID: 10331826; ChemSpider: 8507286

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

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

7275
Isomer 33

DOEH

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

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

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

PubChem CID: 14201978; ChemSpider: 21415075

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 25

7327
Isomer 34

4C-MeO

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

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

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

PubChem CID: 43566022

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

7570
Isomer 35

DESMETHYL-iPr

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

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

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

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

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

7609
Isomer 36

α-MM-M

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

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

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

PubChem CID: 3029803; ChemSpider: 2295076

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

1520
Isomer 37

DOMOM

IUPAC: 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine

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

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

PubChem CID: 10934687; ChemSpider: 9109923

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

Harms, A; Ulmer, E; Kovar, K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm. Pharm. Med. Chem., 16 Jun 2003, 336 (3), 155–158. 69 kB. doi:10.1002/ardp.200390014

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