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4C-T; 1-(2,5-Dimethoxyphenyl-4-methylthio)-2-aminobutane
330
Variant: N α R4 isomers all
Analogues: 1 2 20 27 50

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

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: QHDXWWJHBCJTDG-JTQLQIEISA-N

InChI=1S/C13H21NO2S/c1-5-10(14)6-9-7-12(16-3)13(17-4)8-11(9)15-2/h7-8,10H,5-6,14H2,1-4H3/t10-/m0/s1

PubChem CID: 25832260

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 15

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

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

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

One N analogue:
7366
Analogue 1: Adding Methyl at N

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

Two α analogues:
3
Analogue 1: Substituting Methyl for Ethyl at α

ALEPH
DOT
PARA-DOT
4-Methylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-methylthioamphetamine

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

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

InChI=1S/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

PubChem CID: 143828; ChemSpider: 126887; Wikipedia: Aleph (psychedelic)

Shulgin Index: #3 ALEPH; Table: 5 Page: 345 Row: 13

See also PiHKAL: #4 ALEPH-2
#39 2C-T
#44 2C-T-8
#45 2C-T-9
#125 META-DOT
#139 ORTHO-DOT
#167 4T-MMDA-2
See also TiHKAL: #2 DBT #46 5-MeS-DMT    

See also Transcripts: 1.178, 1.200

See also Pharmacology notes I: p. 178, ALEPH: Trials
p. 200, Additional detail on PARADOT; additional trials

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

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

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

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

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

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

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

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

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

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

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

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.

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon Press, New York, 1 Jan 1978; pp 74–84. 547 kB.

Jacob, P; Anderson, G; Meshul, CK; Shulgin, AT; Castagnoli, N. Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 1977, 20 (10), 1235–1239. 717 kB. doi:10.1021/jm00220a001

39
Analogue 2: Removing Ethyl at α

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

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

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

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

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

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

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

See also Transcripts: 2.315, 4.465

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

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

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

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

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

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

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

20 R4 analogues:
8
Analogue 1: Substituting Methyl for Methylthio at R4

ARIADNE
4C-DOM
BL-3912
Dimoxamine
1-(2,5-Dimethoxy-4-methylphenyl)-2-aminobutane
2,5-Dimethoxy-α-ethyl-4-methylphenethylamine

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

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

InChI=1S/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3

PubChem CID: 169886; ChemSpider: 148565; Wikipedia: Ariadne (psychedelic)

Shulgin Index: #7 ARIADNE; Table: 5 Page: 342 Row: 26

See also PiHKAL: #55 3,4-DMA
#61 DOAM
#62 DOB
#67 DOI
#80 F-22
#85 GANESHA
#93 IRIS
#149 TB
See also TiHKAL: #5 α,O-DMS      

See also Transcripts: 1.159

See also Pharmacology notes I: p. 159, ARIADNE

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

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

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.

Glennon, RA. MDMA-like stimulus effects of α-ethyltryptamine and the α-ethyl homolog of DOM. Pharmacol. Biochem. Behav., 1 Oct 1993, 46 (2), 459–462. 396 kB. doi:10.1016/0091-3057(93)90379-8

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

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

Barfknecht, CF; Caputo, JF; Tobin, MB; Dyer, DC; Standridge, RT; Howell, HG; Goodwin, WR; Partyka, RA; Gylys, JA; Cavanagh, RL. Congeners of DOM: Effect of distribution on the evaluation of pharmacologic data. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 16–26. 502 kB.

Standridge, RT; Howell, HG; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane. J. Med. Chem., 1 Jan 1976, 19 (12), 1400 –1404. 730 kB. doi:10.1021/jm00234a010

183
Analogue 2: Removing Methylthio at R4

4C-H
1-(2,5-Dimethoxyphenyl)-2-aminobutane

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

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

InChI=1S/C12H19NO2/c1-4-10(13)7-9-8-11(14-2)5-6-12(9)15-3/h5-6,8,10H,4,7,13H2,1-3H3

PubChem CID: 20315283; ChemSpider: 15384808

Shulgin Index: See #7 ARIADNE; Table: 4 Page: 336 Row: 4

See also PiHKAL: #8 ARIADNE #67 DOI    

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

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

185
Analogue 3: Substituting Bromo for Methylthio at R4

4C-DOB
1-(2,5-Dimethoxy-4-bromophenyl)-2-aminobutane

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

Formula: C12H18BrNO2 Molecular weight: 288.18082 g/mol InChI Key: QQPRORAZQWLMTQ-UHFFFAOYSA-N

InChI=1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3

PubChem CID: 12140147; ChemSpider: 23256805

Shulgin Index: See #52 DOB; Table: 5 Page: 341 Row: 7

See also PiHKAL: #8 ARIADNE      

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

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

240
Analogue 4: Substituting Iodo for Methylthio at R4

4C-I
1-(2,5-Dimethoxy-4-iodophenyl)-2-aminobutane

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

Formula: C12H18INO2 Molecular weight: 335.18129 g/mol InChI Key: KQTCNDCMXMIDEQ-UHFFFAOYSA-N

InChI=1S/C12H18INO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3

PubChem CID: 44288588; ChemSpider: 25047981

Shulgin Index: See #58 DOI; Table: 5 Page: 341 Row: 28

See also PiHKAL: #8 ARIADNE #67 DOI    

See also Transcripts: 1.174

See also Pharmacology notes I: p. 174, 4C-I: Acute trials

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

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

328
Analogue 5: Substituting Ethyl for Methylthio at R4

4C-E
1-(4-Ethyl-2,5-dimethoxyphenyl)-2-aminobutane
4,α-Diethyl-2,5-dimethoxyphenethylamine

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

Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: XJSXHKNUJUKEOV-LBPRGKRZSA-N

InChI=1S/C14H23NO2/c1-5-10-8-14(17-4)11(7-12(15)6-2)9-13(10)16-3/h8-9,12H,5-7,15H2,1-4H3/t12-/m0/s1

PubChem CID: 54473229

Shulgin Index: See #7 ARIADNE; Table: 5 Page: 343 Row: 14

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

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

329
Analogue 6: Substituting Isopropyl for Methylthio at R4

4C-IP
1-(4-Isopropyl-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-isopropyl-2,5-dimethoxyphenethylamine

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

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: VKDJBDSWDPWPQW-LBPRGKRZSA-N

InChI=1S/C15H25NO2/c1-6-12(16)7-11-8-15(18-5)13(10(2)3)9-14(11)17-4/h8-10,12H,6-7,16H2,1-5H3/t12-/m0/s1

Shulgin Index: See #7 ARIADNE; Table: 5 Page: 343 Row: 35

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

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

331
Analogue 7: Substituting Propyl for Methylthio at R4

4C-P
1-(2,5-Dimethoxyphenyl-4-propyl)-2-aminobutane
α-Ethyl-2,5-dimethoxy-4-propylphenethylamine

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

Formula: C15H25NO2 Molecular weight: 251.3645 g/mol InChI Key: JQUVOKBZTCXBPH-ZDUSSCGKSA-N

InChI=1S/C15H25NO2/c1-5-7-11-9-15(18-4)12(8-13(16)6-2)10-14(11)17-3/h9-10,13H,5-8,16H2,1-4H3/t13-/m0/s1

Shulgin Index: See #7 ARIADNE; Table: 5 Page: 343 Row: 33

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

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

332
Analogue 8: Substituting Butyl for Methylthio at R4

4C-BU
1-(4-Butyl-2,5-dimethoxyphenyl)-2-aminobutane
4-Butyl-α-ethyl-2,5-dimethoxyphenethylamine

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

Formula: C16H27NO2 Molecular weight: 265.39108 g/mol InChI Key: CSLQMMHMEWQUDC-AWEZNQCLSA-N

InChI=1S/C16H27NO2/c1-5-7-8-12-10-16(19-4)13(9-14(17)6-2)11-15(12)18-3/h10-11,14H,5-9,17H2,1-4H3/t14-/m0/s1

Shulgin Index: See #7 ARIADNE; Table: 5 Page: 344 Row: 1

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

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

333
Analogue 9: Substituting Hydroxy for Methylthio at R4

4C-HO
1-(4-Hydroxy-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-hydroxy-2,5-dimethoxyphenethylamine

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

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: ASFOLEVMZYIHRE-VIFPVBQESA-N

InChI=1S/C12H19NO3/c1-4-9(13)5-8-6-12(16-3)10(14)7-11(8)15-2/h6-7,9,14H,4-5,13H2,1-3H3/t9-/m0/s1

ChemSpider: 25045865

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 12

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

334
Analogue 10: Substituting Ethoxy for Methylthio at R4

4C-EtO
1-(4-Ethoxy-2,5-dimethoxyphenyl)-2-aminobutane
4-Ethoxy-α-ethyl-2,5-dimethoxyphenethylamine

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

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: IFHFZYCBFHDQCO-NSHDSACASA-N

InChI=1S/C14H23NO3/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/t11-/m0/s1

ChemSpider: 25042426

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 33

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

335
Analogue 11: Substituting Propoxy for Methylthio at R4

4C-PrO
1-(2,5-Dimethoxyphenyl-4-propoxy)-2-aminobutane
α-Ethyl-2,5-dimethoxy-4-propoxyphenethylamine

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

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

InChI=1S/C15H25NO3/c1-5-7-19-15-10-13(17-3)11(8-12(16)6-2)9-14(15)18-4/h9-10,12H,5-8,16H2,1-4H3/t12-/m0/s1

ChemSpider: 25051967

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

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

336
Analogue 12: Substituting Isopropoxy for Methylthio at R4

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

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

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

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

ChemSpider: 25040478

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

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

337
Analogue 13: Substituting Nitro for Methylthio at R4

4C-NO
1-(2,5-Dimethoxyphenyl-4-nitro)-2-aminobutane
α-Ethyl-2,5-dimethoxy-4-nitrophenethylamine

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

Formula: C12H18N2O4 Molecular weight: 254.28232 g/mol InChI Key: MBSMTOOGSMCQBM-VIFPVBQESA-N

InChI=1S/C12H18N2O4/c1-4-9(13)5-8-6-12(18-3)10(14(15)16)7-11(8)17-2/h6-7,9H,4-5,13H2,1-3H3/t9-/m0/s1

ChemSpider: 25042787

Shulgin Index: See #61 DON; Table: 5 Page: 342 Row: 5

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

338
Analogue 14: Substituting Amino for Methylthio at R4

4C-NH
1-(4-Amino-2,5-dimethoxyphenyl)-2-aminobutane
4-Amino-α-ethyl-2,5-dimethoxyphenethylamine

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

Formula: C12H20N2O2 Molecular weight: 224.2994 g/mol InChI Key: RSHZRAACDMYHMP-UHFFFAOYSA-N

InChI=1S/C12H20N2O2/c1-4-9(13)5-8-6-12(16-3)10(14)7-11(8)15-2/h6-7,9H,4-5,13-14H2,1-3H3

PubChem CID: 44288564; ChemSpider: 25048621

Shulgin Index: See #61 DON; Table: 5 Page: 341 Row: 32

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

339
Analogue 15: Substituting Chloro for Methylthio at R4

4C-Cl
1-(4-Chloro-2,5-dimethoxyphenyl)-2-aminobutane
4-Chloro-α-ethyl-2,5-dimethoxyphenethylamine

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

Formula: C12H18ClNO2 Molecular weight: 243.72982 g/mol InChI Key: DIVLTSLMCQXQCK-VIFPVBQESA-N

InChI=1S/C12H18ClNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3/t9-/m0/s1

ChemSpider: 25041952

Shulgin Index: See #54 DOC; Table: 5 Page: 340 Row: 22

See also PiHKAL: #8 ARIADNE      

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

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

7255
Analogue 16: Substituting Hydroxymethyl for Methylthio at R4

4C-HM

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

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

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

PubChem CID: 20315288

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

7256
Analogue 17: Substituting 1-Hydroxyethyl for Methylthio at R4

4C-HE

IUPAC: 1-[4-(2-Aminobutyl)-2,5-dimethoxyphenyl]ethanone

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

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

Shulgin Index: See #118 TMA-2; Table: 5 Page: 343 Row: 6

7327
Analogue 18: Substituting Methoxy for Methylthio at R4

4C-MeO

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

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

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

PubChem CID: 43566022

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

7371
Analogue 19: Substituting Ethylthio for Methylthio at R4

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

7381
Analogue 20: Substituting Propylthio for Methylthio at R4

4C-T-7

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

Formula: C15H25NO2S Molecular weight: 283.4295 g/mol InChI Key: RGZBRSAMNZVOHP-UHFFFAOYSA-N

InChI=1S/C15H25NO2S/c1-5-7-19-15-10-13(17-3)11(8-12(16)6-2)9-14(15)18-4/h9-10,12H,5-8,16H2,1-4H3

PubChem CID: 11450020; ChemSpider: 9624872

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 31

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

27 isomers:
4
Isomer 1

ALEPH-2
4-Ethylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-ethylthioamphetamine

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

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

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

PubChem CID: 10264356; ChemSpider: 8439835; Wikipedia: Aleph (psychedelic)

Shulgin Index: #4 ALEPH-2; Table: 5 Page: 345 Row: 19

See also PiHKAL: #47 2C-T-15      
See also TiHKAL: #46 5-MeS-DMT      

See also Transcripts: 1.194, 2.205, 2.220, 2.318

See also Pharmacology notes I: p. 194, ALEPH-2: Trials
See also Pharmacology notes II: p. 205, ALEPH-2
p. 220, ALEPH-2
p. 318, ALEPH-2

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

Scorza, MC; Reyes-Parada, M; Silveira, R; Viola, H; Medina, JH; Viana, MB; Zangrossi, H; Graeff, FG. Behavioral effects of the putative anxiolytic (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice. Pharmacol. Biochem. Behav., 1 May 1996, 54 (2), 355–361. 504 kB. doi:10.1016/0091-3057(95)02149-3

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

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

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

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

Rezende, MC; Núñez, C; Sepúlveda-Boza, S; Cassels, BK; Hurtado-Guzmán, C. S-Oxidation products of alkylthioamphetamines. Synth. Commun., 1 Jan 2002, 32 (17), 2741–2750. 225 kB. doi:10.1081/SCC-120006041

Acuña-Castillo, C; Scorza, C; Reyes-Parada, M; Cassels, BK; Huidobro-Toro, JP. ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2A and 5-HT2C receptor agonist. Life Sci., 17 Nov 2000, 67 (26), 3241–3247. 89 kB. doi:10.1016/S0024-3205(00)00906-1

Reyes-Parada, M; Scorza, C; Romero, V; Silveira, R; Medina, JH; Andrus, D; Nichols, DE; Cassels, BK. (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors. N-S. Arch. Pharmacol., 1 Nov 1996, 354 (5), 579–585. 1417 kB. doi:10.1007/BF00170831

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

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.

41
Isomer 2

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

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

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

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

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

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

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

See also Transcripts: 5.661

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

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

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

42
Isomer 3

Ψ-2C-T-4
4-Isopropylthio-2,6-dimethoxyphenethylamine
2,6-Dimethoxy-4-isopropylthiophenethylamine

IUPAC: 2-[2,6-Dimethoxy-4-(propan-2-ylsulfanyl)phenyl]ethan-1-amine

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

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

ChemSpider: 23553027; Wikipedia: psi-2C-T-4

Shulgin Index: See #25 2C-T; Table: 5 Page: 354 Row: 2

See also PiHKAL: #162 TMA-6      
43
Isomer 4

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

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

146
Isomer 5

3-TASB
3-Thioasymbescaline
4-Ethoxy-3-ethylthio-5-methoxyphenethylamine

IUPAC: 2-[4-Ethoxy-3-(ethylsulfanyl)-5-methoxyphenyl]ethan-1-amine

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

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

PubChem CID: 44349933; ChemSpider: 23206361; Wikipedia: TASB (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 4

See also PiHKAL: #148 5-TASB #150 3-TE #163 3-TME #176 3-TSB

See also Transcripts: 5.669

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

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

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

147
Isomer 6

4-TASB
4-Thioasymbescaline
3-Ethoxy-4-ethylthio-5-methoxyphenethylamine

IUPAC: 2-[3-Ethoxy-4-(ethylsulfanyl)-5-methoxyphenyl]ethan-1-amine

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

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

PubChem CID: 44349945; ChemSpider: 23206368; Wikipedia: TASB (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 29

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

See also Transcripts: 5.646

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

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

148
Isomer 7

5-TASB
5-Thioasymbescaline
3,4-Diethoxy-5-methylthiophenethylamine

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

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

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

PubChem CID: 44349932; ChemSpider: 23206360; Wikipedia: TASB (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 1

See also PiHKAL: #9 ASB #163 3-TME #176 3-TSB  

See also Transcripts: 5.670

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

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

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

174
Isomer 8

TP
Thioproscaline
4-Propylthio-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-n-propylthiophenethylamine

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

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

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

PubChem CID: 44349931; ChemSpider: 21106393; Wikipedia: Thioproscaline

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 351 Row: 30

See also PiHKAL: #151 4-TE      

See also Transcripts: 5.648

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

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

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

176
Isomer 9

3-TSB
3-Thiosymbescaline
3-Ethoxy-5-ethylthio-4-methoxyphenethylamine

IUPAC: 2-[3-Ethoxy-5-(ethylsulfanyl)-4-methoxyphenyl]ethan-1-amine

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

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

PubChem CID: 44374939; ChemSpider: 21106412; Wikipedia: Thiosymbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 35

See also PiHKAL: #146 3-TASB #150 3-TE #163 3-TME  

See also Transcripts: 5.639

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

177
Isomer 10

4-TSB
4-Thiosymbescaline
3,5-Diethoxy-4-methylthiophenethylamine

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

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

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

PubChem CID: 44375085; ChemSpider: 21106394; Wikipedia: Thiosymbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 3

See also PiHKAL: #163 3-TME      

See also Transcripts: 5.672

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

212
Isomer 11

2CT2-2ETO
2-Ethoxy-4-ethylthio-5-methoxyphenethylamine

IUPAC: 2-[2-Ethoxy-4-(ethylsulfanyl)-5-methoxyphenyl]ethan-1-amine

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

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

PubChem CID: 57498520

See also PiHKAL: #40 2C-T-2      
213
Isomer 12

2CT2-5ETO
5-Ethoxy-4-ethylthio-2-methoxyphenethylamine

IUPAC: 2-[5-Ethoxy-4-(ethylsulfanyl)-2-methoxyphenyl]ethan-1-amine

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

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

PubChem CID: 57498522

See also PiHKAL: #40 2C-T-2      
7008
Isomer 13

2,4,3-2C-T-7

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

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

InChI=1S/C13H21NO2S/c1-4-9-17-13-11(15-2)6-5-10(7-8-14)12(13)16-3/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 338 Row: 8

7021
Isomer 14

3,4,2-2C-T-7

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

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

InChI=1S/C13H21NO2S/c1-4-9-17-13-10(7-8-14)5-6-11(15-2)12(13)16-3/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 338 Row: 21

7052
Isomer 15

2,3,4-2C-T-7

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

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

InChI=1S/C13H21NO2S/c1-4-9-17-11-6-5-10(7-8-14)12(15-2)13(11)16-3/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 339 Row: 2

7073
Isomer 16

3,5,2-2C-T-7

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

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 339 Row: 23

7076
Isomer 17

2,3,5-2C-T-7

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

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 339 Row: 26

7330
Isomer 18

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

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

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

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

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

7364
Isomer 19

N-Me-ALEPH

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

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

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

PubChem CID: 11392188; ChemSpider: 9567090

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 14

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

7634
Isomer 20

3,4,5-2C-T-7

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

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 350 Row: 34

7728
Isomer 21

2,6,3-2C-T-7

IUPAC: 2-[2,6-Dimethoxy-3-(propylsulfanyl)phenyl]ethan-1-amine

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

InChI=1S/C13H21NO2S/c1-4-9-17-12-6-5-11(15-2)10(7-8-14)13(12)16-3/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 352 Row: 28

7753
Isomer 22

3,6,2-2C-T-7

IUPAC: 2-[3,6-Dimethoxy-2-(propylsulfanyl)phenyl]ethan-1-amine

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

InChI=1S/C13H21NO2S/c1-4-9-17-13-10(7-8-14)11(15-2)5-6-12(13)16-3/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 353 Row: 3

7756
Isomer 23

2,3,6-2C-T-7

IUPAC: 2-[2,3-Dimethoxy-6-(propylsulfanyl)phenyl]ethan-1-amine

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

InChI=1S/C13H21NO2S/c1-4-9-17-12-6-5-11(15-2)13(16-3)10(12)7-8-14/h5-6H,4,7-9,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 353 Row: 6

7779
Isomer 24

4,6,2-2C-T-7

IUPAC: 2-[2,4-Dimethoxy-6-(propylsulfanyl)phenyl]ethan-1-amine

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 353 Row: 29

7782
Isomer 25

Ψ-ALEPH-2

IUPAC: 1-[4-(Ethylsulfanyl)-2,6-dimethoxyphenyl]propan-2-amine

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

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

PubChem CID: 11335306; ChemSpider: 9510252

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 32

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

7801
Isomer 26

Ψ-2C-T-7

IUPAC: 2-[2,6-Dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 354 Row: 1

1519
Isomer 27

DOMSM

IUPAC: 1-{2,5-Dimethoxy-4-[(methylsulfanyl)methyl]phenyl}propan-2-amine

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

InChI=1S/C13H21NO2S/c1-9(14)5-10-6-13(16-3)11(8-17-4)7-12(10)15-2/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 69399016

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

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