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2C-SE-2; 2,5-Dimethoxy-4-ethylselenophenethylamine
2072
Variant: R4 all
Analogues: 81 81

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      
81 R4 analogues:
20
Analogue 1: Substituting Bromo for Ethylseleno 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, 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, 5.563, 5.564, 5.565, 5.574, 5.575, 5.577, 5.578, 5.579, 5.580, 5.581, 5.614, 5.615, 5.616, 5.617, 5.618, 5.619, 5.620, 5.632, 5.647

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 Ethylseleno 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, 5.589

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 Ethylseleno 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, 5.628, 5.628.2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

24
Analogue 4: Substituting Ethyl for Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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  

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

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

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

35
Analogue 9: Substituting Isopropoxy for Ethylseleno at R4

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

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

36
Analogue 10: Substituting Propyl for Ethylseleno 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.

Fenderson5555. Mechanisms and named reactions in 2C-P synthesis. 7 Jan 2011. Wanted! Please contact me if you find this video.

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 11: Substituting Methylseleno for Ethylseleno 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

See also Transcripts: 5.681

39
Analogue 12: Substituting Methylthio for Ethylseleno 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 13: Substituting Ethylthio for Ethylseleno 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, 5.673, 5.674, 5.675, 5.676, 5.677

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.

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.

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

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

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

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.

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

41
Analogue 14: Substituting Isopropylthio for Ethylseleno 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  

See also Transcripts: 5.661

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 15: Substituting Propylthio for Ethylseleno 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 16: Substituting Cyclopropylmethylthio for Ethylseleno 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 17: Substituting tert-Butylthio for Ethylseleno 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 18: Substituting 2-Methoxyethylthio for Ethylseleno 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 19: Substituting Cyclopropylthio for Ethylseleno 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 20: Substituting sec-Butylthio for Ethylseleno 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 21: Substituting 2-Fluoroethylthio for Ethylseleno 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 22: Substituting Methoxy for Ethylseleno 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 23: Substituting Cyano for Ethylseleno 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 24: Substituting Carboxy for Ethylseleno 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 25: Substituting Trifluoromethyl for Ethylseleno 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 26: Substituting Ethoxy for Ethylseleno 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 27: Substituting Propoxy for Ethylseleno 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 28: Substituting Butoxy for Ethylseleno 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      
2073
Analogue 29: Substituting Isopropylseleno for Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 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.

2080
Analogue 34: Substituting 4-Bromophenylthio for Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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. 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.

2090
Analogue 41: Substituting 2,2-Difluouroethylthio for Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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

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.

370
Analogue 73: Substituting 2-Fluoroethyl for Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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 Ethylseleno 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.

Show all 81 analogues and isomers Show only the 81 R4 analogues
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