Go to TiHKAL • info home
Browse the short index of TiHKAL tryptamines. Read book II of TiHKAL
Search for tryptamines and related structures Beyond TiHKAL—Selected writings by Sasha and others. Explore tryptamine structures and analogues
The alkaloids of the peyote cactus. How TiHKAL • info differs from the printed version
Go to PiHKAL • info home
You are currently exploring 2CT-2ETO.
To explore a different substance, type its name: Help
2CT-2ETO; 2-Ethoxy-5-methoxy-4-methylthiophenethylamine
210
Variant: R2 R4 isomers all
Analogues: 1 6 13 20

IUPAC: 2-[2-Ethoxy-5-methoxy-4-(methylsulfanyl)phenyl]ethan-1-amine

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

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

PubChem CID: 57498527

See also PiHKAL: #39 2C-T      
One R2 analogue:
39
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]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

Six R4 analogues:
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)ethan-1-amine

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      
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)ethan-1-amine

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    
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)ethan-1-amine

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      
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]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      
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]ethan-1-amine

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      
216
Analogue 6: Substituting Propylthio for Methylthio at R4

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

IUPAC: 2-[2-Ethoxy-5-methoxy-4-(propylsulfanyl)phenyl]ethan-1-amine

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:
3
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 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

40
Isomer 2

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

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

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

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

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

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

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

See also Transcripts: 4.474, 4.499, 4.502, 4.509, 5.673, 5.674, 5.675, 5.676, 5.677

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

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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 Transcripts: 1.182, 4.481

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

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

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

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 Transcripts: 1.181, 4.480

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

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

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

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]ethan-1-amine

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      

See also Transcripts: 4.498, 5.573

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

151
Isomer 6

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

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

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  

See also Transcripts: 4.464, 5.644, 5.649, 5.650

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

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

163
Isomer 7

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

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

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

See also Transcripts: 4.448, 4.476, 4.477, 4.478, 4.479, 4.485

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

164
Isomer 8

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

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

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      

See also Transcripts: 5.571

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

165
Isomer 9

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

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

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      

See also Transcripts: 4.500

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

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  

See also Transcripts: 5.585

211
Isomer 11

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

IUPAC: 2-[5-Ethoxy-2-methoxy-4-(methylsulfanyl)phenyl]ethan-1-amine

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      
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      

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

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

Show all 20 analogues and isomers Show only the one R2 analogues Show only the six R4 analogues
Page updated 1 November 2014 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·