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You are currently exploring PiHKAL#45 2C-T-9.
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IUPAC: 2-[4-(tert-Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: PSVDMTZXLJTPNX-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-14(2,3)18-13-9-11(16-4)10(6-7-15)8-12(13)17-5/h8-9H,6-7,15H2,1-5H3 PubChem CID: 44349799; ChemSpider: 23206245; Wikipedia: 2C-T-9 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 8 Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. |
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Analogue 1: Substituting Bromo for tert-Butylthio at R4
2C-B IUPAC: 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: YMHOBZXQZVXHBM-UHFFFAOYSA-N InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 PubChem CID: 98527; ChemSpider: 88978; Drugs Forum: 2C-B; Erowid: 2C-B; Wikipedia: 2C-B Shulgin Index: #18 2C-B; Table: 5 Page: 340 Row: 23
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 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 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 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 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:10.1039/sj.bjp.0704747 Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507 Caudevilla-Gálligo, F; Riba, J; Ventura, M; González, D; Farré, M; Barbanoj, MJ; Bouso, JC. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. J. Psychopharmacol., 1 Jul 2012, 26 (7), 1026–1035. 586 kB. doi:10.1177/0269881111431752 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 Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB. Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB. Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium. Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB. Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010. Shulgin, AT. 2,5-Dimethoxy-4-bromophenethylamine (2C-B). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 7 Feb 2003. |
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Analogue 2: Substituting Chloro for tert-Butylthio at R4
2C-C IUPAC: 2-(4-Chloro-2,5-dimethoxyphenyl)ethanamine Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: CGKQFIWIPSIVAS-UHFFFAOYSA-N InChI=1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 PubChem CID: 29979100; ChemSpider: 21106221; Drugs Forum: 2C-C; Erowid: 2C-C; Wikipedia: 2C-C Shulgin Index: #19 2C-C; Table: 5 Page: 340 Row: 19
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 Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010. |
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Analogue 3: Substituting Methyl for tert-Butylthio at R4
2C-D IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)ethanamine Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UNQQFDCVEMVQHM-UHFFFAOYSA-N InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3 PubChem CID: 135740; ChemSpider: 119559; Drugs Forum: 2C-D; Erowid: 2C-D; Wikipedia: 2C-D Shulgin Index: #20 2C-D; Table: 5 Page: 342 Row: 9
Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133 Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733 Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of &alpha-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2 White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034 Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1039/sj.bjp.0704747 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 Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium. Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. Meyers-Riggs, B. The alkylated 2Cs . countyourculture: rational exploration of the underground, 4 Oct 2010. |
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Analogue 4: Substituting Ethyl for tert-Butylthio at R4
2C-E IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)ethanamine Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: VDRGNAMREYBIHA-UHFFFAOYSA-N InChI=1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3 PubChem CID: 24729233; ChemSpider: 21106222; Drugs Forum: 2C-E; Erowid: 2C-E; Wikipedia: 2C-E Shulgin Index: #21 2C-E; Table: 5 Page: 343 Row: 11
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 Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019 Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB. Shulgin, AT. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB. Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. Meyers-Riggs, B. The alkylated 2Cs . countyourculture: rational exploration of the underground, 4 Oct 2010. |
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Analogue 5: Substituting Fluoro for tert-Butylthio at R4
2C-F IUPAC: 2-(4-Fluoro-2,5-dimethoxyphenyl)ethanamine Formula: C10H14FNO2 Molecular weight: 199.2220632 g/mol InChI Key: QAVFEDRVOUKIPM-UHFFFAOYSA-N InChI=1S/C10H14FNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 PubChem CID: 44719499; ChemSpider: 21106223; Wikipedia: 2C-F Shulgin Index: See #20 2C-D; Table: 5 Page: 340 Row: 17
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. |
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Analogue 6: Removing tert-Butylthio at R4
2C-H IUPAC: 2-(2,5-Dimethoxyphenyl)ethanamine Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: WNCUVUUEJZEATP-UHFFFAOYSA-N InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3 PubChem CID: 76632; ChemSpider: 69096; Wikipedia: 2C-H Shulgin Index: #22 2C-H; Table: 4 Page: 335 Row: 7
Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB. Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 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 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 Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1039/sj.bjp.0704747 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 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 Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB. Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017 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 |
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Analogue 7: Substituting Iodo for tert-Butylthio at R4
2C-I IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)ethanamine Formula: C10H14INO2 Molecular weight: 307.12813 g/mol InChI Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 PubChem CID: 10267191; ChemSpider: 8442670; Drugs Forum: 2C-I; Erowid: 2C-I; Wikipedia: 2C-I Shulgin Index: #23 2C-I; Table: 5 Page: 341 Row: 8
Braun, U; Shulgin, AT; Braun, G; Sargent, T. Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs. J. Med. Chem., 1 Jan 1977, 20 (12), 1543–1546. 1124 kB. doi:10.1021/jm00222a001 Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB. Ettrup, A; Hansen, M; Santini, MA; Paine, J; Gillings, N; Palner, M; Lehel, S; Herth, MM; Madsen, J; Kristensen, J; Begtrup, M; Knudsen, GM. Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers. Eur. J. Nucl. Med. Mol. Imaging, 21 Nov 2010. 752 kB. doi:10.1007/s00259-010-1686-8 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:10.1039/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 Johnson, MP; Mathis, CA; Shulgin, AT; Hoffman, AJ; Nichols, DE. [125I]-2-(2,5-Dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex. Pharmacol. Biochem. Behav., 1 Jan 1990, 35 (1), 211–217. 724 kB. doi:10.1016/0091-3057(90)90228-A Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB. Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB. Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. 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 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004. 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 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 |
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Analogue 8: Substituting Nitro for tert-Butylthio at R4
2C-N IUPAC: 2-(2,5-Dimethoxy-4-nitrophenyl)ethanamine Formula: C10H14N2O4 Molecular weight: 226.22916 g/mol InChI Key: ZMUSDZGRRJGRAO-UHFFFAOYSA-N InChI=1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3 PubChem CID: 10036637; ChemSpider: 8212202; Wikipedia: 2C-N Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 1
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:10.1039/sj.bjp.0704747 Zuba, D; Sekuła, K; Buczek, A. Identification and characterization of 2,5-dimethoxy-4-nitro-β-phenethylamine (2C-N)–A new member of 2C-series of designer drug. Forensic Sci. Int., 10 Oct 2012, 222 (1–3), 298–305. 588 kB. doi:10.1016/j.forsciint.2012.07.006 |
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Analogue 9: Substituting Isopropoxy for tert-Butylthio at R4
2C-O-4 IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethanamine Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: KAKXJLWAEMHHTL-UHFFFAOYSA-N InChI=1S/C13H21NO3/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 PubChem CID: 44719510; ChemSpider: 21106225; Wikipedia: 2C-O-4 Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 5 |
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Analogue 10: Substituting n-Propyl for tert-Butylthio at R4
2C-P IUPAC: 2-(2,5-Dimethoxy-4-propylphenyl)ethanamine Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: PZJOKFZGPTVNBF-UHFFFAOYSA-N InChI=1S/C13H21NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h8-9H,4-7,14H2,1-3H3 PubChem CID: 44350080; ChemSpider: 21106226; Drugs Forum: 2C-P; Erowid: 2C-P; Wikipedia: 2C-P Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 31 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. |
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Analogue 11: Substituting Methylseleno for tert-Butylthio at R4
2C-SE IUPAC: 2-[2,5-Dimethoxy-4-(methylselanyl)phenyl]ethanamine Formula: C11H17NO2Se Molecular weight: 274.21818 g/mol InChI Key: CXQUHXATPUFGMC-UHFFFAOYSA-N InChI=1S/C11H17NO2Se/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 PubChem CID: 44719515; ChemSpider: 21106227; Wikipedia: 2C-SE Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 346 Row: 17 |
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Analogue 12: Substituting Methylthio for tert-Butylthio at R4
2C-T IUPAC: 2-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]ethanamine Formula: C11H17NO2S Molecular weight: 227.32318 g/mol InChI Key: UPZMYCMLLQTYEM-UHFFFAOYSA-N InChI=1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 PubChem CID: 12315927; ChemSpider: 10438674; Wikipedia: 2C-T Shulgin Index: #25 2C-T; Table: 5 Page: 345 Row: 12
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. 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. |
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Analogue 13: Substituting Ethylthio for tert-Butylthio at R4
2C-T-2 IUPAC: 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C12H19NO2S Molecular weight: 241.34976 g/mol InChI Key: HCWQGDLBIKOJPM-UHFFFAOYSA-N InChI=1S/C12H19NO2S/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3 PubChem CID: 12074193; ChemSpider: 16787961; Drugs Forum: 2C-T-2; Erowid: 2C-T-2; Wikipedia: 2C-T-2 Shulgin Index: #26 2C-T-2; Table: 5 Page: 345 Row: 17
Shulgin, AT. 2C-T-7. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jun 2001. Stolaroff, MJ; Wells, CW. Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7. In Jahrbuch für Ethnomedizin und Bewußtseinsforschung (Yearbook of Ethnomedicine and the Study of Consciousness); Rätsch, C; Baker, J, Eds., 1 Jan 1993; Vol. 2, pp 99–117. 185 kB. Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB. Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB. Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36 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 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004. 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 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 |
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Analogue 14: Substituting Isopropylthio for tert-Butylthio at R4
2C-T-4 IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-ylsulfanyl)phenyl]ethanamine Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: HDYZSVKZKDPLDT-UHFFFAOYSA-N InChI=1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 PubChem CID: 44350070; ChemSpider: 21106232; Erowid: 2C-T-4; Wikipedia: 2C-T-4 Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 33
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 |
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Analogue 15: Substituting n-Propylthio for tert-Butylthio at R4
2C-T-7 IUPAC: 2-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]ethanamine Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: OLEVEPDJOFPJTF-UHFFFAOYSA-N InChI=1S/C13H21NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3 PubChem CID: 24728635; ChemSpider: 21106233; Drugs Forum: 2C-T-7; Erowid: 2C-T-7; Wikipedia: 2C-T-7 Shulgin Index: #27 2C-T-7; Table: 5 Page: 345 Row: 26
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 Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. Fantegrossi, WE; Harrington, AW; Eckler, JR; Arshad, S; Rabin, RA; Winter, JC; Coop, A; Rice, KC; Woods, JH. Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats. Psychopharmacology, 1 Sep 2005, 181 (3), 496–503. 182 kB. doi:10.1007/s00213-005-0009-4 Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB. Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36 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 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004. 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 |
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Analogue 16: Substituting Cyclopropylmethylthio for tert-Butylthio at R4
2C-T-8 IUPAC: 2-{4-[(Cyclopropylmethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: AHMSSHCYIDBVQB-UHFFFAOYSA-N InChI=1S/C14H21NO2S/c1-16-12-8-14(18-9-10-3-4-10)13(17-2)7-11(12)5-6-15/h7-8,10H,3-6,9,15H2,1-2H3 PubChem CID: 44350055; ChemSpider: 21106234; Wikipedia: 2C-T-8 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 10
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. |
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Analogue 17: Substituting 2-Methoxyethylthio for tert-Butylthio at R4
2C-T-13 IUPAC: 2-{2,5-Dimethoxy-4-[(2-methoxyethyl)sulfanyl]phenyl}ethanamine Formula: C13H21NO3S Molecular weight: 271.37574 g/mol InChI Key: PYJLRNOGMKMRTK-UHFFFAOYSA-N InChI=1S/C13H21NO3S/c1-15-6-7-18-13-9-11(16-2)10(4-5-14)8-12(13)17-3/h8-9H,4-7,14H2,1-3H3 PubChem CID: 44350108; ChemSpider: 21106228; Wikipedia: 2C-T-13 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 11
Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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Analogue 18: Substituting Cyclopropylthio for tert-Butylthio at R4
2C-T-15 IUPAC: 2-[4-(Cyclopropylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: HHAPMOUVSYQKLK-UHFFFAOYSA-N InChI=1S/C13H19NO2S/c1-15-11-8-13(17-10-3-4-10)12(16-2)7-9(11)5-6-14/h7-8,10H,3-6,14H2,1-2H3 PubChem CID: 44719534; ChemSpider: 21106229; Wikipedia: 2C-T-15 Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 35
Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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Analogue 19: Substituting sec-Butylthio for tert-Butylthio at R4
2C-T-17 IUPAC: 2-[4-(Butan-2-ylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: KSZHVRPGICAZOA-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-10(2)18-14-9-12(16-3)11(6-7-15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3 PubChem CID: 44349798; ChemSpider: 21106230; Wikipedia: 2C-T-17 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 6
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. |
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Analogue 20: Substituting 2-Fluoroethylthio for tert-Butylthio at R4
2C-T-21 IUPAC: 2-{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C12H18FNO2S Molecular weight: 259.3402232 g/mol InChI Key: ZBUUUKBTOCTOPW-UHFFFAOYSA-N InChI=1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3 PubChem CID: 44349972; ChemSpider: 21106231; Drugs Forum: 2C-T-21; Erowid: 2C-T-21; Wikipedia: 2C-T-21 Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 23
Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011. Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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Analogue 21: Substituting Methoxy for tert-Butylthio at R4
TMPEA IUPAC: 2-(2,4,5-Trimethoxyphenyl)ethanamine 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
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 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 Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1 Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009 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 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. |
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200
|
Analogue 22: Substituting Cyano for tert-Butylthio at R4
2C-CN 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
|
||||||||||||||
201
|
Analogue 23: Substituting Carboxy for tert-Butylthio at R4
2C-CA 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
|
||||||||||||||
2040
|
Analogue 24: Substituting Trifluoromethyl for tert-Butylthio at R4
2C-TFM IUPAC: 2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethanamine Formula: C11H14F3NO2 Molecular weight: 249.2295696 g/mol InChI Key: LYXGNMLWYONZID-UHFFFAOYSA-N InChI=1S/C11H14F3NO2/c1-16-9-6-8(11(12,13)14)10(17-2)5-7(9)3-4-15/h5-6H,3-4,15H2,1-2H3 PubChem CID: 10399795; ChemSpider: 8575233; Drugs Forum: 2C-TFM; Wikipedia: 2C-TFM Shulgin Index: #28 2C-TFM; Table: 5 Page: 343 Row: 1 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 Nichols, DE; Frescas, S; Marona-Lewicka, D; Huang, X; Roth, BL; Gudelsky, GA; Nash, JF. 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: A potent serotonin 5-HT2A/2C agonist. J. Med. Chem., 1 Jan 1994, 37 (25), 4346–4351. 873 kB. doi:10.1021/jm00051a011 Parrish, JC; 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. |
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2068
|
Analogue 25: Substituting Ethoxy for tert-Butylthio at R4
2C-O-2 IUPAC: 2-(4-Ethoxy-2,5-dimethoxyphenyl)ethanamine Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: JFXGDWIZRPHJKN-UHFFFAOYSA-N InChI=1S/C12H19NO3/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3 PubChem CID: 57474251 Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 31
|
||||||||||||||
2069
|
Analogue 26: Substituting n-Propoxy for tert-Butylthio at R4
2C-O-7 IUPAC: 2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RRKXVAQJHSSQHK-UHFFFAOYSA-N InChI=1S/C13H21NO3/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3 PubChem CID: 57474252 Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 35
|
||||||||||||||
2070
|
Analogue 27: Substituting n-Butoxy for tert-Butylthio at R4
2C-O-19 IUPAC: 2-(4-Butoxy-2,5-dimethoxyphenyl)ethanamine Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: XPEDBJCAOYNBMP-UHFFFAOYSA-N InChI=1S/C14H23NO3/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3 PubChem CID: 57474253 Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 8
|
||||||||||||||
2072
|
Analogue 28: Substituting Ethylseleno for tert-Butylthio at R4
2C-SE-2 IUPAC: 2-[4-(Ethylselanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C12H19NO2Se Molecular weight: 288.24476 g/mol InChI Key: HUFWOPLGIJKCJU-UHFFFAOYSA-N InChI=1S/C12H19NO2Se/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3 PubChem CID: 57474255
|
||||||||||||||
2073
|
Analogue 29: Substituting Isopropylseleno for tert-Butylthio at R4
2C-SE-4 IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-ylselanyl)phenyl]ethanamine Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: UUGAXTBZOCLVOE-UHFFFAOYSA-N InChI=1S/C13H21NO2Se/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 PubChem CID: 57474257
|
||||||||||||||
2074
|
Analogue 30: Substituting n-Propylseleno for tert-Butylthio at R4
2C-SE-7 IUPAC: 2-[2,5-Dimethoxy-4-(propylselanyl)phenyl]ethanamine Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: XMFDSLMFVAJUSR-UHFFFAOYSA-N InChI=1S/C13H21NO2Se/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3 PubChem CID: 57474258
|
||||||||||||||
2075
|
Analogue 31: Substituting 2-Fluoroethylseleno for tert-Butylthio at R4
2C-SE-21 IUPAC: 2-{4-[(2-Fluoroethyl)selanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C12H18FNO2Se Molecular weight: 306.2352232 g/mol InChI Key: XSVWIVWPLWEQOK-UHFFFAOYSA-N InChI=1S/C12H18FNO2Se/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3 PubChem CID: 57474261
|
||||||||||||||
2076
|
Analogue 32: Substituting Methyltelluro for tert-Butylthio at R4
2C-TE IUPAC: 2-[2,5-Dimethoxy-4-(methyltellanyl)phenyl]ethanamine Formula: C11H17NO2Te Molecular weight: 322.85818 g/mol InChI Key: OLHAAXPQNWOKOE-UHFFFAOYSA-N InChI=1S/C11H17NO2Te/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 PubChem CID: 57474263
|
||||||||||||||
2079
|
Analogue 33: Substituting 2-Pyridylthio for tert-Butylthio at R4
2C-T-10 IUPAC: 2-[2,5-Dimethoxy-4-(pyridin-2-ylsulfanyl)phenyl]ethanamine Formula: C15H18N2O2S Molecular weight: 290.38062 g/mol InChI Key: QGMVABLWTNWDAY-UHFFFAOYSA-N InChI=1S/C15H18N2O2S/c1-18-12-10-14(20-15-5-3-4-8-17-15)13(19-2)9-11(12)6-7-16/h3-5,8-10H,6-7,16H2,1-2H3 PubChem CID: 57474265
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 tert-Butylthio at R4
2C-T-11 IUPAC: 2-{4-[(4-Bromophenyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C16H18BrNO2S Molecular weight: 368.28862 g/mol InChI Key: YSYFWLXCMAVLOQ-UHFFFAOYSA-N InChI=1S/C16H18BrNO2S/c1-19-14-10-16(15(20-2)9-11(14)7-8-18)21-13-5-3-12(17)4-6-13/h3-6,9-10H,7-8,18H2,1-2H3 PubChem CID: 57474267
Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. |
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2081
|
Analogue 35: Substituting 1-Morpholinothio for tert-Butylthio at R4
2C-T-12 IUPAC: 2-[2,5-Dimethoxy-4-(morpholin-4-ylsulfanyl)phenyl]ethanamine Formula: C14H22N2O3S Molecular weight: 298.40108 g/mol InChI Key: PHXFPOFFCCVTDK-UHFFFAOYSA-N InChI=1S/C14H22N2O3S/c1-17-12-10-14(20-16-5-7-19-8-6-16)13(18-2)9-11(12)3-4-15/h9-10H,3-8,15H2,1-2H3 PubChem CID: 57474268
Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. |
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2082
|
Analogue 36: Substituting 2-Methylthioethylthio for tert-Butylthio at R4
2C-T-14 IUPAC: 2-(2,5-Dimethoxy-4-{[2-(methylsulfanyl)ethyl]sulfanyl}phenyl)ethanamine Formula: C13H21NO2S2 Molecular weight: 287.44134 g/mol InChI Key: YFENVCWPZGGJQO-UHFFFAOYSA-N InChI=1S/C13H21NO2S2/c1-15-11-9-13(18-7-6-17-3)12(16-2)8-10(11)4-5-14/h8-9H,4-7,14H2,1-3H3 PubChem CID: 57474270
Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
||||||||||||||
2083
|
Analogue 37: Substituting Cyclohexylthio for tert-Butylthio at R4
2C-T-5 IUPAC: 2-[4-(Cyclohexylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C16H25NO2S Molecular weight: 295.4402 g/mol InChI Key: OABFYEYTJSTAMV-UHFFFAOYSA-N InChI=1S/C16H25NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h10-11,13H,3-9,17H2,1-2H3 PubChem CID: 57474272; ChemSpider: 21375815
Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. |
||||||||||||||
2086
|
Analogue 38: Substituting Allylthio for tert-Butylthio at R4
2C-T-16 IUPAC: 2-[2,5-Dimethoxy-4-(prop-2-en-1-ylsulfanyl)phenyl]ethanamine Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: BXCMEIZBXNLJKM-UHFFFAOYSA-N InChI=1S/C13H19NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 PubChem CID: 12063256 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 1
Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
||||||||||||||
2087
|
Analogue 39: Substituting Phenylthio for tert-Butylthio at R4
2C-T-6 IUPAC: 2-[2,5-Dimethoxy-4-(phenylsulfanyl)phenyl]ethanamine Formula: C16H19NO2S Molecular weight: 289.39256 g/mol InChI Key: JRDQLJCYERGHDJ-UHFFFAOYSA-N InChI=1S/C16H19NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3 PubChem CID: 57474275
Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011. |
||||||||||||||
2089
|
Analogue 40: Substituting n-Butylthio for tert-Butylthio at R4
2C-T-19 IUPAC: 2-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: LGUVDOBGXUFUAJ-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3 PubChem CID: 12063257; ChemSpider: 21106235 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 3
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 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. |
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2090
|
Analogue 41: Substituting 2,2-Difluouroethylthio for tert-Butylthio at R4
2C-T-21.5 IUPAC: 2-{4-[(2,2-Difluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C12H17F2NO2S Molecular weight: 277.3306864 g/mol InChI Key: LVCSIKISADNGMR-UHFFFAOYSA-N InChI=1S/C12H17F2NO2S/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3 PubChem CID: 12063258 Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 24
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 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. |
||||||||||||||
2091
|
Analogue 42: Substituting 2,2,2-Trifluoroethylthio for tert-Butylthio at R4
2C-T-22 IUPAC: 2-{2,5-Dimethoxy-4-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanamine Formula: C12H16F3NO2S Molecular weight: 295.3211496 g/mol InChI Key: LDOOFVKAIHFXAR-UHFFFAOYSA-N InChI=1S/C12H16F3NO2S/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3 PubChem CID: 12063259 Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 25
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 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. |
||||||||||||||
2108
|
Analogue 43: Substituting Cyclobutylthio for tert-Butylthio at R4
2C-T-18 IUPAC: 2-[4-(Cyclobutylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: CSLQQULZSBSZTM-UHFFFAOYSA-N InChI=1S/C14H21NO2S/c1-16-12-9-14(18-11-4-3-5-11)13(17-2)8-10(12)6-7-15/h8-9,11H,3-7,15H2,1-2H3
|
||||||||||||||
2109
|
Analogue 44: Substituting Cyclopentylthio for tert-Butylthio at R4
2C-T-23 IUPAC: 2-[4-(Cyclopentylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C15H23NO2S Molecular weight: 281.41362 g/mol InChI Key: OVWHCXSUEIYTRY-UHFFFAOYSA-N InChI=1S/C15H23NO2S/c1-17-13-10-15(19-12-5-3-4-6-12)14(18-2)9-11(13)7-8-16/h9-10,12H,3-8,16H2,1-2H3 PubChem CID: 57478605
Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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5378
|
Analogue 45: Substituting Ethynyl for tert-Butylthio at R4
2C-YN IUPAC: 2-(4-Ethynyl-2,5-dimethoxyphenyl)ethanamine Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: MLJHHYIJBZVUEA-UHFFFAOYSA-N InChI=1S/C12H15NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h1,7-8H,5-6,13H2,2-3H3 PubChem CID: 12063400; ChemSpider: 26234934; Wikipedia: 2C-YN Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 21 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224 |
||||||||||||||
5396
|
Analogue 46: Substituting 2-Hydroxyethyl for tert-Butylthio at R4
2C-pEtOH 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 tert-Butylthio at R4
2C-pKet 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 tert-Butylthio at R4
2C-T-3 IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)sulfanyl]phenyl}ethanamine Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: JCDUUDQZKIXJJP-UHFFFAOYSA-N InChI=1S/C14H21NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3 PubChem CID: 12063255 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 9
Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part 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. |
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2178
|
Analogue 49: Substituting Isobutylthio for tert-Butylthio at R4
2C-T-25 IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: OEPKQBQEDYEXMC-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8,10H,5-6,9,15H2,1-4H3 PubChem CID: 12063260 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 5 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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2179
|
Analogue 50: Substituting Benzylthio for tert-Butylthio at R4
2C-T-27 IUPAC: 2-[4-(Benzylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C17H21NO2S Molecular weight: 303.41914 g/mol InChI Key: GRZVJRPTNCONNT-UHFFFAOYSA-N InChI=1S/C17H21NO2S/c1-19-15-11-17(16(20-2)10-14(15)8-9-18)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3 PubChem CID: 12063261 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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2180
|
Analogue 51: Substituting 3-Fluoropropylthio for tert-Butylthio at R4
2C-T-28 IUPAC: 2-{4-[(3-Fluoropropyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C13H20FNO2S Molecular weight: 273.3668032 g/mol InChI Key: XAFVGDRNPGLCMI-UHFFFAOYSA-N InChI=1S/C13H20FNO2S/c1-16-11-9-13(18-7-3-5-14)12(17-2)8-10(11)4-6-15/h8-9H,3-7,15H2,1-2H3 PubChem CID: 12063262 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 2 Trachsel, D. 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 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. |
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2181
|
Analogue 52: Substituting 4-Fluorobutylthio for tert-Butylthio at R4
2C-T-30 IUPAC: 2-{4-[(4-Fluorobutyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine Formula: C14H22FNO2S Molecular weight: 287.3933832 g/mol InChI Key: BILSBDMCLLFSAV-UHFFFAOYSA-N InChI=1S/C14H22FNO2S/c1-17-12-10-14(19-8-4-3-6-15)13(18-2)9-11(12)5-7-16/h9-10H,3-8,16H2,1-2H3 PubChem CID: 12063263 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 12 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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![2C-T-31; 2,5-Dimethoxy-4-[4-(trifluoromethyl)benzylthio]phenethylamine](C/pk2182.png "Explore the structure and analogues of 2C-T-31; 2,5-Dimethoxy-4-[4-(trifluoromethyl)benzylthio]phenethylamine")
2182
|
Analogue 53: Substituting 4-(Trifluoromethyl)benzylthio for tert-Butylthio at R4
2C-T-31 IUPAC: 2-(2,5-Dimethoxy-4-{[4-(trifluoromethyl)benzyl]sulfanyl}phenyl)ethanamine Formula: C18H20F3NO2S Molecular weight: 371.4171096 g/mol InChI Key: BDOJPUSYOLIGBS-UHFFFAOYSA-N InChI=1S/C18H20F3NO2S/c1-23-15-10-17(16(24-2)9-13(15)7-8-22)25-11-12-3-5-14(6-4-12)18(19,20)21/h3-6,9-10H,7-8,11,22H2,1-2H3 PubChem CID: 12063264 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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2183
|
Analogue 54: Substituting 2,3,4,5,6-Pentafluorobenzylthio for tert-Butylthio at R4
2C-T-32 IUPAC: 2-{2,5-Dimethoxy-4-[(pentafluorobenzyl)sulfanyl]phenyl}ethanamine Formula: C17H16F5NO2S Molecular weight: 393.371456 g/mol InChI Key: SCZNXZRFVLLJGV-UHFFFAOYSA-N InChI=1S/C17H16F5NO2S/c1-24-10-6-12(11(25-2)5-8(10)3-4-23)26-7-9-13(18)15(20)17(22)16(21)14(9)19/h5-6H,3-4,7,23H2,1-2H3 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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2184
|
Analogue 55: Substituting 3-Methoxybenzylthio for tert-Butylthio at R4
2C-T-33 IUPAC: 2-{2,5-Dimethoxy-4-[(3-methoxybenzyl)sulfanyl]phenyl}ethanamine Formula: C18H23NO3S Molecular weight: 333.44512 g/mol InChI Key: ADENDGINQJWQOK-UHFFFAOYSA-N InChI=1S/C18H23NO3S/c1-20-15-6-4-5-13(9-15)12-23-18-11-16(21-2)14(7-8-19)10-17(18)22-3/h4-6,9-11H,7-8,12,19H2,1-3H3 PubChem CID: 12063266 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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2198
|
Analogue 56: Substituting Ethenyl for tert-Butylthio at R4
2C-VI IUPAC: 2-(4-Ethenyl-2,5-dimethoxyphenyl)ethanamine Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: LGLJOVNOGICITR-UHFFFAOYSA-N InChI=1S/C12H17NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h4,7-8H,1,5-6,13H2,2-3H3 PubChem CID: 57474284 Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 19 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 |
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2300
|
Analogue 57: Substituting Phenyl for tert-Butylthio at R4
2C-BI-1 IUPAC: 2-(2,5-Dimethoxybiphenyl-4-yl)ethanamine Formula: C16H19NO2 Molecular weight: 257.32756 g/mol InChI Key: RMMCNNHGPNUXOX-UHFFFAOYSA-N InChI=1S/C16H19NO2/c1-18-15-11-14(12-6-4-3-5-7-12)16(19-2)10-13(15)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3 PubChem CID: 57474287 Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235 |
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2301
|
Analogue 58: Substituting 2-Methoxyphenyl for tert-Butylthio at R4
2C-BI-2 IUPAC: 2-(2,2′,5-Trimethoxybiphenyl-4-yl)ethanamine Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WEQGJWJNANPJNP-UHFFFAOYSA-N InChI=1S/C17H21NO3/c1-19-15-7-5-4-6-13(15)14-11-16(20-2)12(8-9-18)10-17(14)21-3/h4-7,10-11H,8-9,18H2,1-3H3 PubChem CID: 44219736 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 |
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2302
|
Analogue 59: Substituting 2-Methylphenyl for tert-Butylthio at R4
2C-BI-3 IUPAC: 2-(2,5-Dimethoxy-2′-methylbiphenyl-4-yl)ethanamine Formula: C17H21NO2 Molecular weight: 271.35414 g/mol InChI Key: INAUMGJNDBATML-UHFFFAOYSA-N InChI=1S/C17H21NO2/c1-12-6-4-5-7-14(12)15-11-16(19-2)13(8-9-18)10-17(15)20-3/h4-7,10-11H,8-9,18H2,1-3H3 PubChem CID: 57474290 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 |
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![2C-BI-4; 2,5-Dimethoxy-4-[2-(trifluoromethyl)phenyl]phenethylamine](C/pk2303.png "Explore the structure and analogues of 2C-BI-4; 2,5-Dimethoxy-4-[2-(trifluoromethyl)phenyl]phenethylamine")
2303
|
Analogue 60: Substituting 2-(Trifluoromethyl)phenyl for tert-Butylthio at R4
2C-BI-4 IUPAC: 2-[2,5-Dimethoxy-2′-(trifluoromethyl)biphenyl-4-yl]ethanamine Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: XCNBZPCBVPDJFY-UHFFFAOYSA-N InChI=1S/C17H18F3NO2/c1-22-15-10-13(16(23-2)9-11(15)7-8-21)12-5-3-4-6-14(12)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3 PubChem CID: 57474292 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 |
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2304
|
Analogue 61: Substituting Naphthalen-2-yl for tert-Butylthio at R4
2C-BI-5 IUPAC: 2-[2,5-Dimethoxy-4-(naphthalen-2-yl)phenyl]ethanamine Formula: C20H21NO2 Molecular weight: 307.38624 g/mol InChI Key: KQKCTYPWGSPYLP-UHFFFAOYSA-N InChI=1S/C20H21NO2/c1-22-19-13-18(20(23-2)12-17(19)9-10-21)16-8-7-14-5-3-4-6-15(14)11-16/h3-8,11-13H,9-10,21H2,1-2H3 PubChem CID: 57474294 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 |
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2305
|
Analogue 62: Substituting 3-Methoxyphenyl for tert-Butylthio at R4
2C-BI-6 IUPAC: 2-(2,3′,5-Trimethoxybiphenyl-4-yl)ethanamine Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WMTQTFIOUBEGJW-UHFFFAOYSA-N InChI=1S/C17H21NO3/c1-19-14-6-4-5-12(9-14)15-11-16(20-2)13(7-8-18)10-17(15)21-3/h4-6,9-11H,7-8,18H2,1-3H3 PubChem CID: 57474296 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 |
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2306
|
Analogue 63: Substituting 3-Nitrophenyl for tert-Butylthio at R4
2C-BI-7 IUPAC: 2-(2,5-Dimethoxy-3′-nitrobiphenyl-4-yl)ethanamine Formula: C16H18N2O4 Molecular weight: 302.32512 g/mol InChI Key: YNWQIUDDSDYOFB-UHFFFAOYSA-N InChI=1S/C16H18N2O4/c1-21-15-10-14(16(22-2)9-12(15)6-7-17)11-4-3-5-13(8-11)18(19)20/h3-5,8-10H,6-7,17H2,1-2H3 PubChem CID: 57474298 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 |
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2307
|
Analogue 64: Substituting 4-Methoxyphenyl for tert-Butylthio at R4
2C-BI-8 IUPAC: 2-(2,4′,5-Trimethoxybiphenyl-4-yl)ethanamine Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: ZALWHJKGZWNFNR-UHFFFAOYSA-N InChI=1S/C17H21NO3/c1-19-14-6-4-12(5-7-14)15-11-16(20-2)13(8-9-18)10-17(15)21-3/h4-7,10-11H,8-9,18H2,1-3H3 PubChem CID: 57474300 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 |
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2308
|
Analogue 65: Substituting 4-Butylphenyl for tert-Butylthio at R4
2C-BI-9 IUPAC: 2-(4′-Butyl-2,5-dimethoxybiphenyl-4-yl)ethanamine Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: NDHZIVILVFWOSE-UHFFFAOYSA-N InChI=1S/C20H27NO2/c1-4-5-6-15-7-9-16(10-8-15)18-14-19(22-2)17(11-12-21)13-20(18)23-3/h7-10,13-14H,4-6,11-12,21H2,1-3H3 PubChem CID: 57474302 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 |
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![2C-BI-10; 2,5-Dimethoxy-4-[4-(trifluoromethyl)phenyl]phenethylamine](C/pk2309.png "Explore the structure and analogues of 2C-BI-10; 2,5-Dimethoxy-4-[4-(trifluoromethyl)phenyl]phenethylamine")
2309
|
Analogue 66: Substituting 4-(Trifluoromethyl)phenyl for tert-Butylthio at R4
2C-BI-10 IUPAC: 2-[2,5-Dimethoxy-4′-(trifluoromethyl)biphenyl-4-yl]ethanamine Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: BFFLBYIGPNMJQH-UHFFFAOYSA-N InChI=1S/C17H18F3NO2/c1-22-15-10-14(16(23-2)9-12(15)7-8-21)11-3-5-13(6-4-11)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3 PubChem CID: 57474304 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 |
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2310
|
Analogue 67: Substituting 4-Phenylphenyl for tert-Butylthio at R4
2C-BI-11 IUPAC: 2-(2,5-Dimethoxy-1,1′:4′,1′′-terphenyl-4-yl)ethanamine Formula: C22H23NO2 Molecular weight: 333.42352 g/mol InChI Key: ZQEKXNJKMUWVBC-UHFFFAOYSA-N InChI=1S/C22H23NO2/c1-24-21-15-20(22(25-2)14-19(21)12-13-23)18-10-8-17(9-11-18)16-6-4-3-5-7-16/h3-11,14-15H,12-13,23H2,1-2H3 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 |
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2311
|
Analogue 68: Substituting 1,3-Benzodioxol-5-yl for tert-Butylthio at R4
2C-BI-12 IUPAC: 2-[4-(1,3-Benzodioxol-5-yl)-2,5-dimethoxyphenyl]ethanamine Formula: C17H19NO4 Molecular weight: 301.33706 g/mol InChI Key: QNWIOBZDXFFFLT-UHFFFAOYSA-N InChI=1S/C17H19NO4/c1-19-15-9-13(16(20-2)8-12(15)5-6-18)11-3-4-14-17(7-11)22-10-21-14/h3-4,7-9H,5-6,10,18H2,1-2H3 PubChem CID: 57474306 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 |
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2326
|
Analogue 69: Substituting Phenylpropyl for tert-Butylthio at R4
2,5-Dimethoxy-4-phenylpropylphenethylamine IUPAC: 2-[2,5-Dimethoxy-4-(3-phenylpropyl)phenyl]ethanamine Formula: C19H25NO2 Molecular weight: 299.4073 g/mol InChI Key: UCMBNCAZQUWZLT-UHFFFAOYSA-N InChI=1S/C19H25NO2/c1-21-18-14-17(11-12-20)19(22-2)13-16(18)10-6-9-15-7-4-3-5-8-15/h3-5,7-8,13-14H,6,9-12,20H2,1-2H3 PubChem CID: 10542173; ChemSpider: 8717564 Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062 |
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2324
|
Analogue 70: Substituting Phenethyl for tert-Butylthio at R4
2,5-Dimethoxy-4-phenethylphenethylamine IUPAC: 2-[2,5-Dimethoxy-4-(2-phenylethyl)phenyl]ethanamine Formula: C18H23NO2 Molecular weight: 285.38072 g/mol InChI Key: YIMMOGDNQSRZTF-UHFFFAOYSA-N InChI=1S/C18H23NO2/c1-20-17-13-16(10-11-19)18(21-2)12-15(17)9-8-14-6-4-3-5-7-14/h3-7,12-13H,8-11,19H2,1-2H3 PubChem CID: 10827012; ChemSpider: 9002312 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 |
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2327
|
Analogue 71: Substituting Phenylbutyl for tert-Butylthio at R4
2,5-Dimethoxy-4-phenylbutylphenethylamine IUPAC: 2-[2,5-Dimethoxy-4-(4-phenylbutyl)phenyl]ethanamine Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: SUAFIELOZLKXOQ-UHFFFAOYSA-N InChI=1S/C20H27NO2/c1-22-19-15-18(12-13-21)20(23-2)14-17(19)11-7-6-10-16-8-4-3-5-9-16/h3-5,8-9,14-15H,6-7,10-13,21H2,1-2H3 PubChem CID: 10805159; ChemSpider: 8980464 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 |
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2361
|
Analogue 72: Substituting Isopropyl for tert-Butylthio at R4
2C-IP IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yl)phenyl]ethanamine Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: XUGPCRRUMVWELT-UHFFFAOYSA-N InChI=1S/C13H21NO2/c1-9(2)11-8-12(15-3)10(5-6-14)7-13(11)16-4/h7-9H,5-6,14H2,1-4H3 PubChem CID: 57474311; ChemSpider: 27750188 Meyers-Riggs, B. The alkylated 2Cs . countyourculture: rational exploration of the underground, 4 Oct 2010. |
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370
|
Analogue 73: Substituting 2-Fluoroethyl for tert-Butylthio at R4
2C-EF IUPAC: 2-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]ethanamine Formula: C12H18FNO2 Molecular weight: 227.2752232 g/mol InChI Key: KXPMRPNOYIOXFY-UHFFFAOYSA-N InChI=1S/C12H18FNO2/c1-15-11-8-10(4-6-14)12(16-2)7-9(11)3-5-13/h7-8H,3-6,14H2,1-2H3 PubChem CID: 44350106; ChemSpider: 21106293 Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 23
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7179
|
Analogue 74: Substituting Amino for tert-Butylthio 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 |
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7253
|
Analogue 75: Substituting Hydroxymethyl for tert-Butylthio 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 |
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![2C-IB; 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethanamine](C/pk7302.png "Explore the structure and analogues of 2C-IB; 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethanamine")
7302
|
Analogue 76: Substituting Isobutyl for tert-Butylthio at R4
2C-IB IUPAC: 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethanamine Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: FLBABUVVTQBINW-UHFFFAOYSA-N InChI=1S/C14H23NO2/c1-10(2)7-12-9-13(16-3)11(5-6-15)8-14(12)17-4/h8-10H,5-7,15H2,1-4H3 PubChem CID: 57486931 Shulgin Index: See #20 2C-D; Table: 5 Page: 344 Row: 2 |
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![2C-TFE; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethanamine](C/pk472.png "Explore the structure and analogues of 2C-TFE; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethanamine")
472
|
Analogue 77: Substituting 2,2,2-Trifluoroethyl for tert-Butylthio at R4
2C-TFE IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethanamine Formula: C12H16F3NO2 Molecular weight: 263.2561496 g/mol InChI Key: DVENUPQPPXYSLN-UHFFFAOYSA-N InChI=1S/C12H16F3NO2/c1-17-10-6-9(7-12(13,14)15)11(18-2)5-8(10)3-4-16/h5-6H,3-4,7,16H2,1-2H3 PubChem CID: 57498513 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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![2C-O-22; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine](C/pk466.png "Explore the structure and analogues of 2C-O-22; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine")
466
|
Analogue 78: Substituting 2,2,2-Trifluoroethoxy for tert-Butylthio at R4
2C-O-22 IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine Formula: C12H16F3NO3 Molecular weight: 279.2555496 g/mol InChI Key: WXMPTDDEIHHBRM-UHFFFAOYSA-N InChI=1S/C12H16F3NO3/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3 PubChem CID: 57498514 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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![2C-O-21.5; 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethanamine](C/pk465.png "Explore the structure and analogues of 2C-O-21.5; 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethanamine")
465
|
Analogue 79: Substituting 2,2-Difluoroethoxy for tert-Butylthio at R4
2C-O-21.5 IUPAC: 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethanamine Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: USTOBZVLZKAMKI-UHFFFAOYSA-N InChI=1S/C12H17F2NO3/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3 PubChem CID: 57498515 Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413 |
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![2C-O-21; 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethanamine](C/pk464.png "Explore the structure and analogues of 2C-O-21; 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethanamine")
464
|
Analogue 80: Substituting 2-Fluoroethyoxy for tert-Butylthio at R4
2C-O-21 IUPAC: 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethanamine Formula: C12H18FNO3 Molecular weight: 243.2746232 g/mol InChI Key: QFEAVTWEYZNLIS-UHFFFAOYSA-N InChI=1S/C12H18FNO3/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3 PubChem CID: 57498516 |
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2474
|
Analogue 81: Substituting Astato for tert-Butylthio at R4
2C-A 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
Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010. |
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17 isomers:
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5
|
Isomer 1
ALEPH-4 IUPAC: 1-[2,5-Dimethoxy-4-(propan-2-ylsulfanyl)phenyl]propan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: BCWCXWKCQMBFBQ-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-9(2)18-14-8-12(16-4)11(6-10(3)15)7-13(14)17-5/h7-10H,6,15H2,1-5H3 PubChem CID: 44350301; ChemSpider: 21500994; Wikipedia: Aleph (psychedelic) Shulgin Index: #5 ALEPH-4; Table: 5 Page: 345 Row: 34
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 Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109 |
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7
|
Isomer 2
ALEPH-7 IUPAC: 1-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]propan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: XHWDHFUBCVWXDZ-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3 PubChem CID: 11197521; ChemSpider: 9372590; Wikipedia: Aleph (psychedelic) Shulgin Index: #6 ALEPH-7; Table: 5 Page: 345 Row: 29
Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109 |
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|
48
|
Isomer 3
2C-T-17 IUPAC: 2-[4-(Butan-2-ylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: KSZHVRPGICAZOA-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-10(2)18-14-9-12(16-3)11(6-7-15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3 PubChem CID: 44349798; ChemSpider: 21106230; Wikipedia: 2C-T-17 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 6
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. |
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149
|
Isomer 4
TB IUPAC: 2-[4-(Butylsulfanyl)-3,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: CPNWMHCBHUXITO-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-5-8-18-14-12(16-2)9-11(6-7-15)10-13(14)17-3/h9-10H,4-8,15H2,1-3H3 PubChem CID: 44349865; ChemSpider: 21106390; Wikipedia: Thiobuscaline Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 31
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 Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013 |
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178
|
Isomer 5
3-T-TRIS IUPAC: 2-[3,4-Diethoxy-5-(ethylsulfanyl)phenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: JSWFZFXPKROBKR-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-16-12-9-11(7-8-15)10-13(18-6-3)14(12)17-5-2/h9-10H,4-8,15H2,1-3H3 PubChem CID: 44374795; ChemSpider: 21106413; Wikipedia: Thiotrisescaline Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 2
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 Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013 |
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179
|
Isomer 6
4-T-TRIS IUPAC: 2-[3,5-Diethoxy-4-(ethylsulfanyl)phenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: VFCYKJRATPCSED-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-16-12-9-11(7-8-15)10-13(17-5-2)14(12)18-6-3/h9-10H,4-8,15H2,1-3H3 PubChem CID: 44374794; ChemSpider: 21106395; Wikipedia: Thiotrisescaline Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 4
Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013 Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1 |
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214
|
Isomer 7
2CT2-2,5DIETO IUPAC: 2-[2,5-Diethoxy-4-(ethylsulfanyl)phenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: HDKGMXYAXURMGE-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-16-12-10-14(18-6-3)13(17-5-2)9-11(12)7-8-15/h9-10H,4-8,15H2,1-3H3
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215
|
Isomer 8
2CT4-2ETO IUPAC: 2-[2-Ethoxy-5-methoxy-4-(propan-2-ylsulfanyl)phenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: BASFTYSLRQAKTB-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-17-12-9-14(18-10(2)3)13(16-4)8-11(12)6-7-15/h8-10H,5-7,15H2,1-4H3
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216
|
Isomer 9
2CT7-2ETO IUPAC: 2-[2-Ethoxy-5-methoxy-4-(propylsulfanyl)phenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: MSZZWXMFLAAWIT-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-8-18-14-10-12(17-5-2)11(6-7-15)9-13(14)16-3/h9-10H,4-8,15H2,1-3H3
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2077
|
Isomer 10
METHYL-2C-T-7 IUPAC: 2-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]-N-methylethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: PKGJTUGRJVOEBF-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-8-18-14-10-12(16-3)11(6-7-15-2)9-13(14)17-4/h9-10,15H,5-8H2,1-4H3
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2089
|
Isomer 11
2C-T-19 IUPAC: 2-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: LGUVDOBGXUFUAJ-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3 PubChem CID: 12063257; ChemSpider: 21106235 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 3
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 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. |
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2178
|
Isomer 12
2C-T-25 IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethanamine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: OEPKQBQEDYEXMC-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8,10H,5-6,9,15H2,1-4H3 PubChem CID: 12063260 Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 5 Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011. |
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![2,5,3-2C-T-7; 1-[2,5-Dimethoxy-3-(propylsulfanyl)phenyl]propan-2-amine](C/pk7064.png "Explore the structure and analogues of 2,5,3-2C-T-7; 1-[2,5-Dimethoxy-3-(propylsulfanyl)phenyl]propan-2-amine")
7064
|
Isomer 13
2,5,3-2C-T-7 IUPAC: 1-[2,5-Dimethoxy-3-(propylsulfanyl)phenyl]propan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: JZHNOQQFNYDATF-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-6-18-13-9-12(16-3)8-11(7-10(2)15)14(13)17-4/h8-10H,5-7,15H2,1-4H3 Shulgin Index: See #27 2C-T-7; Table: 5 Page: 339 Row: 14 |
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![N-Me-4C-T; 1-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]-N-methylbutan-2-amine](C/pk7366.png "Explore the structure and analogues of N-Me-4C-T; 1-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]-N-methylbutan-2-amine")
7366
|
Isomer 14
N-Me-4C-T IUPAC: 1-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]-N-methylbutan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: VDSMOAJRXWDJOF-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-6-11(15-2)7-10-8-13(17-4)14(18-5)9-12(10)16-3/h8-9,11,15H,6-7H2,1-5H3 PubChem CID: 11301205; ChemSpider: 9476182 Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 16 Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109 |
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![N-Me-ALEPH-2; 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]-N-methylpropan-2-amine](C/pk7370.png "Explore the structure and analogues of N-Me-ALEPH-2; 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]-N-methylpropan-2-amine")
7370
|
Isomer 15
N-Me-ALEPH-2 IUPAC: 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]-N-methylpropan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: RXMRQMALCRZCOI-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-6-18-14-9-12(16-4)11(7-10(2)15-3)8-13(14)17-5/h8-10,15H,6-7H2,1-5H3 PubChem CID: 11460934; ChemSpider: 9635774 Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 20 Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109 |
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![4C-T-2; 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]butan-2-amine](C/pk7371.png "Explore the structure and analogues of 4C-T-2; 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]butan-2-amine")
7371
|
Isomer 16
4C-T-2 IUPAC: 1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]butan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: KLAWPCIXPDTGCZ-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-11(15)7-10-8-13(17-4)14(18-6-2)9-12(10)16-3/h8-9,11H,5-7,15H2,1-4H3 PubChem CID: 11197523; ChemSpider: 9372592 Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 21 Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109 |
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![2,4,5-2C-T-7; 1-[2,4-Dimethoxy-5-(propylsulfanyl)phenyl]propan-2-amine](C/pk7504.png "Explore the structure and analogues of 2,4,5-2C-T-7; 1-[2,4-Dimethoxy-5-(propylsulfanyl)phenyl]propan-2-amine")
7504
|
Isomer 17
2,4,5-2C-T-7 IUPAC: 1-[2,4-Dimethoxy-5-(propylsulfanyl)phenyl]propan-2-amine Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: WPEOSQBUHPSLAM-UHFFFAOYSA-N InChI=1S/C14H23NO2S/c1-5-6-18-14-8-11(7-10(2)15)12(16-3)9-13(14)17-4/h8-10H,5-7,15H2,1-4H3 Shulgin Index: See #27 2C-T-7; Table: 5 Page: 348 Row: 4 |
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