PiHKAL • info | explore | 2CT7-2ETO; 2-Ethoxy-5-methoxy-4-n-propylthiophenethylamine

One R2 analogue:

2C-T-7

Analogue 1: Substituting Methoxy for Ethoxy at R2

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

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

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

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

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

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 n-Propylthio 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 n-Propylthio 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 n-Propylthio 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

2CT-2ETO

210

Analogue 4: Substituting Methylthio for n-Propylthio at R4

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

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

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

2CT2-2ETO

212

Analogue 5: Substituting Ethylthio for n-Propylthio 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 6: Substituting Isopropylthio for n-Propylthio 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

17 isomers:

ALEPH-4

Isomer 1

ALEPH-4
4-Isopropylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-isopropylthioamphetamine

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

See also PiHKAL:	#4 ALEPH-2	#7 ALEPH-7

See also Pharmacology notes II:	app. 5, Untitled p. 219, ALEPH-4 p. 265, ALEPH-4 p. 266, ALEPH-4 p. 268, ALEPH-4 p. 282, ALEPH-4: Report of experience p. 294, ALEPH-4 p. 296, ALEPH-4: Report of experience p. 297, ALEPH-4: Report of experience p. 300, ALEPH-4 p. 301, ALEPH-4 p. 302, ALEPH-4

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

ALEPH-7

Isomer 2

ALEPH-7
4-Propylthio-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-n-propylthioamphetamine

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

See also PiHKAL:	#4 ALEPH-2
See also TiHKAL:	#17 4-HO-DIPT

See also Pharmacology notes II:	p. 223, ALEPH-7

2C-T-9

Isomer 3

2C-T-9
4-tert-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-tert-butylthiophenethylamine

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.

2C-T-17

Isomer 4

2C-T-17
NIMITZ
4-sec-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-sec-butylthiophenethylamine

IUPAC: 2-[4-(Butan-2-ylsulfanyl)-2,5-dimethoxyphenyl]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

See also PiHKAL:	#81 FLEA	#89 HOT-17

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

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

149

Isomer 5

TB
4-Thiobuscaline
4-Thiobutoxy-3,5-dimethoxyphenethylamine
4-Butylthio-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-n-butylthiophenethylamine

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

See also PiHKAL:	#151 4-TE	#174 TP

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

3-T-TRIS

178

Isomer 6

3-T-TRIS
3-Thiotrescaline
3-Thiotrisescaline
4,5-Diethoxy-3-ethylthiophenethylamine
3,4-Diethoxy-5-ethylthiophenethylamine
3,4-Diethoxy-5-ethylthiophenethylamine

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

See also PiHKAL:	#9 ASB	#163 3-TME	#176 3-TSB	#179 4-T-TRIS

4-T-TRIS

179

Isomer 7

4-T-TRIS
4-Thiotrescaline
4-Thiotrisescaline
3,5-Diethoxy-4-ethylthiophenethylamine

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

See also PiHKAL:	#163 3-TME

2CT2-2,5DIETO

214

Isomer 8

2CT2-2,5DIETO
2,5-Diethoxy-4-ethylthiophenethylamine

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

See also PiHKAL:	#40 2C-T-2

2CT4-2ETO

215

Isomer 9

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

METHYL-2C-T-7

2077

Isomer 10

METHYL-2C-T-7
2,5-Dimethoxy-N-methyl-4-n-propylthiophenethylamine

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

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

2C-T-19

2089

Isomer 11

2C-T-19
4-n-Butylthio-2,5-dimethoxyphenethylamine

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

See also PiHKAL:	#35 2C-O-4	#49 2C-T-21

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210

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.

2C-T-25

2178

Isomer 12

2C-T-25
4-Isobutylthio-2,5-dimethoxyphenethylamine

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

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

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

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

N-Me-4C-T

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

N-Me-ALEPH-2

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

4C-T-2

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

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

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