TiHKAL • info | explore | 2CT-2ETO; 2-Ethoxy-5-methoxy-4-methylthiophenethylamine

One R2 analogue:

2C-T

Analogue 1: Substituting Methoxy for Ethoxy at R2

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

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

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

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

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

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

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

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

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

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.

Six R4 analogues:

2C-B-2-EtO; 2CB-2ETO

2C-B-2-EtO; 4-Bromo-2-ethoxy-5-methoxyphenethylamine

195

Analogue 1: Substituting Bromo for Methylthio at R4

2C-B-2-EtO
2CB-2ETO
4-Bromo-2-ethoxy-5-methoxyphenethylamine

IUPAC: 2-(4-Bromo-2-ethoxy-5-methoxyphenyl)ethanamine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: FLMAKYQLBBLIAH-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-3-15-10-7-9(12)11(14-2)6-8(10)4-5-13/h6-7H,3-5,13H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 346 Row: 21

See also PiHKAL:	#20 2C-B

2C-D-2-EtO; 2CD-2ETO

2C-D-2-EtO; 2-Ethoxy-5-methoxy-4-methylphenethylamine

204

Analogue 2: Substituting Methyl for Methylthio at R4

2C-D-2-EtO
2CD-2ETO
2-Ethoxy-5-methoxy-4-methylphenethylamine

IUPAC: 2-(2-Ethoxy-5-methoxy-4-methylphenyl)ethanamine

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

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

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 30

See also PiHKAL:	#8 ARIADNE	#23 2C-D

2CI-2ETO

209

Analogue 3: Substituting Iodo for Methylthio at R4

2CI-2ETO
2-Ethoxy-4-iodo-5-methoxyphenethylamine

IUPAC: 2-(2-Ethoxy-4-iodo-5-methoxyphenyl)ethanamine

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: KGZIRCONPUCBOO-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-3-15-10-7-9(12)11(14-2)6-8(10)4-5-13/h6-7H,3-5,13H2,1-2H3

See also PiHKAL:	#33 2C-I

2CT2-2ETO

212

Analogue 4: Substituting Ethylthio for Methylthio at R4

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

IUPAC: 2-[2-Ethoxy-4-(ethylsulfanyl)-5-methoxyphenyl]ethanamine

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

2CT4-2ETO

215

Analogue 5: Substituting Isopropylthio for Methylthio at R4

2CT4-2ETO
2-Ethoxy-5-methoxy-4-isopropylthiophenethylamine

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

See also PiHKAL:	#41 2C-T-4

2CT7-2ETO

216

Analogue 6: Substituting n-Propylthio for Methylthio at R4

2CT7-2ETO
2-Ethoxy-5-methoxy-4-n-propylthiophenethylamine

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

See also PiHKAL:	#43 2C-T-7

13 isomers:

ALEPH

Isomer 1

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

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.

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

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

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

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

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

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.

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

2C-T-2

Isomer 2

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

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

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

InChI=1S/C12H19NO2S/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 12074193; ChemSpider: 16787961; Drugs Forum: 2C-T-2; Erowid: 2C-T-2; Wikipedia: 2C-T-2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

META-DOT

125

Isomer 3

META-DOT
m-DOT
5-Methylthio-2,4-dimethoxyamphetamine
2,4-Dimethoxy-5-methylthioamphetamine

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

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

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

PubChem CID: 144891; ChemSpider: 127832; Wikipedia: Meta-DOT

Shulgin Index: See #3 ALEPH; Table: 5 Page: 348 Row: 3

See also PiHKAL:	#3 ALEPH

See also Pharmacology notes I:	p. 182, META-DOT: Trials

ORTHO-DOT

139

Isomer 4

ORTHO-DOT
o-DOT
2-Methylthio-4,5-dimethoxyamphetamine
4,5-Dimethoxy-2-methylthioamphetamine

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

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

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

PubChem CID: 144890; ChemSpider: 127831; Wikipedia: Ortho-DOT

Shulgin Index: See #3 ALEPH; Table: 5 Page: 344 Row: 29

See also PiHKAL:	#3 ALEPH	#125 META-DOT

See also Pharmacology notes I:	p. 181, ORTHO-DOT: Trials

3-TE

150

Isomer 5

3-TE
3-Thioescaline
4-Ethoxy-5-methoxy-3-methylthiophenethylamine
4-Ethoxy-3-methoxy-5-methylthiophenethylamine

IUPAC: 2-[4-Ethoxy-3-methoxy-5-(methylsulfanyl)phenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-15-12-10(14-2)7-9(5-6-13)8-11(12)16-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44350018; ChemSpider: 21106410; Wikipedia: Thioescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 3

See also PiHKAL:	#163 3-TME

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

4-TE

151

Isomer 6

4-TE
TE
4-Thioescaline
3,5-Dimethoxy-4-ethylthiophenethylamine

IUPAC: 2-[4-(Ethylsulfanyl)-3,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44349999; ChemSpider: 21106391; Wikipedia: Thioescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 28

See also PiHKAL:	#150 3-TE	#163 3-TME	#174 TP

3-TME

163

Isomer 7

3-TME
3-Thiometaescaline
4,5-Dimethoxy-3-ethylthiophenethylamine

IUPAC: 2-[3-(Ethylsulfanyl)-4,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44350009; ChemSpider: 21106407; Wikipedia: TME (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 33

4-TME

164

Isomer 8

4-TME
4-Thiometaescaline
3-Ethoxy-5-methoxy-4-methylthiophenethylamine

IUPAC: 2-[3-Ethoxy-5-methoxy-4-(methylsulfanyl)phenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-15-11-8-9(5-6-13)7-10(14-2)12(11)16-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44350008; ChemSpider: 21106406; Wikipedia: TME (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 27

See also PiHKAL:	#163 3-TME

5-TME

165

Isomer 9

5-TME
5-Thiometaescaline
3-Ethoxy-4-methoxy-5-methylthiophenethylamine

IUPAC: 2-[3-Ethoxy-4-methoxy-5-(methylsulfanyl)phenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-15-10-7-9(5-6-13)8-11(16-3)12(10)14-2/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44374913; ChemSpider: 21106385; Wikipedia: TME (psychedelics)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 34

See also PiHKAL:	#163 3-TME

TOMSO

173

Isomer 10

TOMSO
5-TOMSO
2-Methoxy-4-methyl-5-methylsulfinylamphetamine

IUPAC: 1-[2-Methoxy-4-methyl-5-(methylsulfinyl)phenyl]propan-2-amine

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

InChI=1S/C12H19NO2S/c1-8-5-11(15-3)10(6-9(2)13)7-12(8)16(4)14/h5,7,9H,6,13H2,1-4H3

PubChem CID: 15915372; ChemSpider: 21106387; Wikipedia: TOMSO

Shulgin Index: See #60 DOM; Table: 5 Page: 348 Row: 5

See also PiHKAL:	#119 ME #127 METHYL-DOB	#149 TB #170 5-TOET	#172 5-TOM

2CT-5ETO

211

Isomer 11

2CT-5ETO
5-Ethoxy-2-methoxy-4-methylthiophenethylamine

IUPAC: 2-[5-Ethoxy-2-methoxy-4-(methylsulfanyl)phenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-15-11-7-9(5-6-13)10(14-2)8-12(11)16-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 57498529

See also PiHKAL:	#39 2C-T

Ψ-ALEPH

371

Isomer 12

Ψ-ALEPH
2,6-Dimethoxy-4-methylthioamphetamine

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

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

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

PubChem CID: 11300389; ChemSpider: 9475366

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 31

See also PiHKAL:	#162 TMA-6

DOHSM

1518

Isomer 13

DOHSM

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

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

InChI=1S/C12H19NO2S/c1-8(13)4-9-5-12(15-3)10(7-16)6-11(9)14-2/h5-6,8,16H,4,7,13H2,1-3H3

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