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PiHKAL#149 TB
149
Variant: R4 isomers all
Analogues: 33 17 50

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

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

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

33 R4 analogues:
2
Analogue 1: Substituting Allyloxy for Butylthio at R4

AL
Allylescaline
4-Allyloxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-allyloxyphenethylamine

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

Formula: C13H19NO3 Molecular weight: 237.29486 g/mol InChI Key: JNUAYHHGCXYBHX-UHFFFAOYSA-N

InChI=1S/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3

PubChem CID: 44719469; ChemSpider: 21106254; Wikipedia: Allylescaline

Shulgin Index: #2 AL; Table: 5 Page: 351 Row: 15

See also PiHKAL: #99 MAL #123 MEPEA    

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

10
Analogue 2: Substituting Butoxy for Butylthio at R4

B
Buscaline
4-Butoxy-3,5-dimethoxyphenethylamine
4-n-Butoxy-3,5-dimethoxyphenethylamine

IUPAC: 2-(4-Butoxy-3,5-dimethoxyphenyl)ethan-1-amine

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

InChI=1S/C14H23NO3/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: 15102780; ChemSpider: 10440102; Wikipedia: Buscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 19

See also PiHKAL: #141 PE      

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

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

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

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

37
Analogue 3: Substituting Cyclopropylmethoxy for Butylthio at R4

CPM
Cyclopropylmescaline
4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine

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

Formula: C14H21NO3 Molecular weight: 251.32144 g/mol InChI Key: LNTBHKZMYJTHTH-UHFFFAOYSA-N

InChI=1S/C14H21NO3/c1-16-12-7-11(5-6-15)8-13(17-2)14(12)18-9-10-3-4-10/h7-8,10H,3-6,9,15H2,1-2H3

PubChem CID: 44350143; ChemSpider: 21106288; Wikipedia: Cyclopropylmescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 18

See also PiHKAL: #72 E #99 MAL #104 MDCPM  
See also Pharmacology notes II: p. 218, 5-MeO-DIPT
50
Analogue 4: Substituting Trideuteromethoxy for Butylthio at R4

4-D
4-Trideuteromethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-trideuteromethoxyphenethylamine

IUPAC: 2-{3,5-Dimethoxy-4-[(2H3)methyloxy]phenyl}ethan-1-amine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-HPRDVNIFSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i3D3

ChemSpider: 23553050; Wikipedia: 4-D (psychedelic)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 35

See also PiHKAL: #51 β-D      
52
Analogue 5: Substituting Methyl for Butylthio at R4

DESOXY
4-Methyl-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-methylphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: LLHRMWHYJGLIEV-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-10(13-2)6-9(4-5-12)7-11(8)14-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 44350128; ChemSpider: 21106289; Wikipedia: DESOXY

Shulgin Index: #31 DESOXY; Table: 5 Page: 349 Row: 13

Benington, F; Morin, R; Clark, LC. Mescaline analogs. X. 3,4-Dimethyl-, 3,4-dichloro- and 3,5-dimethoxy-4-methyl-β-phenethylamines. J. Org. Chem., 1 Nov 1960, 25 (11), 2066–2067. 286 kB. doi:10.1021/jo01081a626

72
Analogue 6: Substituting Ethoxy for Butylthio at R4

E
Escaline
Escaline
4-Ethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-ethoxyphenethylamine

IUPAC: 2-(4-Ethoxy-3,5-dimethoxyphenyl)ethan-1-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: RHOGRSKNWDNCDN-UHFFFAOYSA-N

InChI=1S/C12H19NO3/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: 38240; ChemSpider: 35053; Wikipedia: Escaline

Shulgin Index: #64 Escaline; Table: 5 Page: 350 Row: 36

See also PiHKAL: #2 AL
#10 B
#25 3C-E
#50 4-D
#51 β-D
#92 IP
#93 IRIS
#99 MAL
#119 ME
#123 MEPEA
#140 P
#141 PE
#143 PROPYNYL
#150 3-TE
#163 3-TME
See also Pharmacology notes II: p. 217, Escaline

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. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

Benington, F; Morin, RD; Clarke, LC. Synthesis of 4-hydroxy- and 4-ethoxy-3,5-dimethoxy-β-phenethylamines. J. Am. Chem. Soc., 1 Nov 1954, 76 (21), 5555–5556. 307 kB. doi:10.1021/ja01650a084

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

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

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

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

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.

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

92
Analogue 7: Substituting Isopropoxy for Butylthio at R4

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

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

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

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

PubChem CID: 15102787; ChemSpider: 10439597; Wikipedia: Isoproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 13

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

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

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

96
Analogue 8: Substituting Methoxy for Butylthio at R4

M
Mescaline
EA-1306
Mescaline
3,4,5-Trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)ethan-1-amine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 4076; ChemSpider: 3934; Drugs Forum: Mescaline; Erowid: Mescaline; Wikipedia: Mescaline

Shulgin Index: #91 Mescaline; Table: 5 Page: 349 Row: 26

See also PiHKAL: #1 AEM
#9 ASB
#10 B
#16 BOHD
#17 BOM
#25 3C-E
#27 2C-G
#37 CPM
#41 2C-T-4
#43 2C-T-7
#44 2C-T-8
#50 4-D
#51 β-D
#52 DESOXY
#55 3,4-DMA
#58 DMMDA
#59 DMMDA-2
#68 DOM
#72 E
#91 IM
#92 IP
#93 IRIS
#95 LOPHOPHINE
#99 MAL
#100 MDA
#115 MDPEA
#119 ME
#125 META-DOT
#132 MMDA
#135 MMDA-3b
#142 PEA
#144 SB
#150 3-TE
#151 4-TE
#156 4-TM
#157 TMA
#158 TMA-2
#159 TMA-3
#160 TMA-4
#161 TMA-5
#162 TMA-6
#163 3-TME
#168 TMPEA
#175 TRIS
#178 3-T-TRIS
See also TiHKAL: #8 α,N-DMT
#9 DPT
#13 Harmaline
#17 4-HO-DIPT
#45 5-MeO-TMT
#48 α-MT
#53 T
See also Pharmacology notes I: p. 1, Mescaline: Subjective response
p. 2, Mescaline: Subjective response
p. 3, Mescaline: Subjective response
p. 4, Mescaline: Subjective response
p. 5, Mescaline: Subjective response
p. 6, Mescaline: Subjective response
p. 7, Mescaline: Basis for M.U. calculation
See also Pharmacology notes II: app. 5, Untitled
p. 321, Mescaline

Friedhoff, AJ; Goldstein, M. New developments in metabolism of mescaline and related amines. Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 5–13. 506 kB. doi:10.1111/j.1749-6632.1962.tb50097.x

Smythies, JR. The mescaline phenomena. Br. J. Philos. Sci., 1 Feb 1953, 3 (12), 339–347. 72 kB. doi:10.1093/bjps/III.12.339

Shulgin, AT. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs, 1 Jan 1979, 11 (4), 355. 713 kB. doi:10.1080/02791072.1979.10471421

Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc. Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Daly, J; Axelrod, J; Witkop, B. Methylation and demethylation in relation to the in vitro metabolism of mescaline. Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 37–43. 397 kB. doi:10.1111/j.1749-6632.1962.tb50099.x

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

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

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

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

Fenderson5555. Two syntheses of mescaline. 21 Mar 2011.

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

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.

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

Desantis, F; Nieforth, KA. Synthesis of potential mescaline antagonists. J. Pharm. Sci., 1 Jan 1976, 65 (10), 1479–1484. 704 kB. doi:10.1002/jps.2600651016

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

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

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

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

Battersby, AR; Binks, R; Huxtable, R. Biosynthesis of cactus alkaloids. Tetrahedron Lett., 1 Jan 1967, 8 (6), 563–565. 134 kB. doi:10.1016/S0040-4039(00)90548-3

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

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

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

Ogunbodede, O; McCombs, D; Trout, K; Daley, PF; Terry, M. New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) (“San Pedro”) and their relevance to shamanic practice. J. Ethnopharmacol., 15 Sep 2010, 131 (2), 356–362. 324 kB. doi:10.1016/j.jep.2010.07.021

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

99
Analogue 9: Substituting Methallyloxy for Butylthio at R4

MAL
Methallylescaline
3,5-Dimethoxy-4-methallyloxyphenethylamine

IUPAC: 2-{3,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl}ethan-1-amine

Formula: C14H21NO3 Molecular weight: 251.32144 g/mol InChI Key: FOXJFBFFGULACD-UHFFFAOYSA-N

InChI=1S/C14H21NO3/c1-10(2)9-18-14-12(16-3)7-11(5-6-15)8-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3

PubChem CID: 44350127; ChemSpider: 21106346; Wikipedia: Methallylescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 22

140
Analogue 10: Substituting Propoxy for Butylthio at R4

P
Proscaline
Proscaline
3,5-Dimethoxy-4-propoxyphenethylamine
3,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethan-1-amine

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

InChI=1S/C13H21NO3/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: 15102790; ChemSpider: 10439596; Wikipedia: Proscaline

Shulgin Index: #104 Proscaline; Table: 5 Page: 351 Row: 11

See also PiHKAL: #72 E
#80 F-22
#123 MEPEA
#141 PE
#163 3-TME  
See also Pharmacology notes II: p. 209, Proscaline

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

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.

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

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

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

141
Analogue 11: Substituting Phenethyloxy for Butylthio at R4

PE
Phenescaline
3,5-Dimethoxy-4-phenethyloxyphenethylamine

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

Formula: C18H23NO3 Molecular weight: 301.38012 g/mol InChI Key: FKXBCTFKCKEDNI-UHFFFAOYSA-N

InChI=1S/C18H23NO3/c1-20-16-12-15(8-10-19)13-17(21-2)18(16)22-11-9-14-6-4-3-5-7-14/h3-7,12-13H,8-11,19H2,1-2H3

PubChem CID: 44567543; ChemSpider: 21106364; Wikipedia: Phenescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 25

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

143
Analogue 12: Substituting Prop-2-ynyloxy for Butylthio at R4

PROPYNYL
4-Propynyloxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-(2-propynyloxy)phenethylamine

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

Formula: C13H17NO3 Molecular weight: 235.27898 g/mol InChI Key: KNIWBMMJSJHUJB-UHFFFAOYSA-N

InChI=1S/C13H17NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h1,8-9H,5-7,14H2,2-3H3

PubChem CID: 44719613; ChemSpider: 21106371; Wikipedia: Propynyl (psychedelic)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 17

See also PiHKAL: #99 MAL      
151
Analogue 13: Substituting Ethylthio for Butylthio at R4

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  

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

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

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

156
Analogue 14: Substituting Methylthio for Butylthio at R4

4-TM
TM
4-Thiomescaline
4-Methylthio-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-methylthiophenethylamine

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

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

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

PubChem CID: 44276771; ChemSpider: 21106392; Wikipedia: Thiomescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 26

See also PiHKAL: #150 3-TE #151 4-TE #153 3-TIM #163 3-TME
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 239, 4-TM

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

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.

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

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline. J. Med. Chem., 1 Jan 1981, 24 (11), 1348–1353. 953 kB. doi:10.1021/jm00143a017

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

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

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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

174
Analogue 15: Substituting Propylthio for Butylthio at R4

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      

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

318
Analogue 16: Substituting Benzyloxy for Butylthio at R4

BZ
4-Benzyloxy-3,5-dimethoxyphenethylamine

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

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: BUJBXOZJFOWVCR-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-15-10-14(8-9-18)11-16(20-2)17(15)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3

PubChem CID: 10613284; ChemSpider: 8788650

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 23

See also PiHKAL: #141 PE      

Smythies, JR; Levy, CK. The comparative psychopharmacology of some mescaline analogues. J. Mental Sci., 1 Jan 1960, 106 (443), 531–536. 637 kB. doi:10.1192/bjp.106.443.531

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

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

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

319
Analogue 17: Substituting Pentyloxy for Butylthio at R4

A
4-n-Amyloxy-3,5-dimethoxyphenethylamine

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

Formula: C15H25NO3 Molecular weight: 267.3639 g/mol InChI Key: XXJMQLZVSYOWQC-UHFFFAOYSA-N

InChI=1S/C15H25NO3/c1-4-5-6-9-19-15-13(17-2)10-12(7-8-16)11-14(15)18-3/h10-11H,4-9,16H2,1-3H3

PubChem CID: 54930597

Shulgin Index: Table: 2 Page: 318 Row: 15

See also PiHKAL: #10 B      

Galloway, G; Shulgin, AT; Kornfeld, H; Frederick, SL. Amphetamine, not MDMA, is associated with intracranial hemorrhage. J. Accid Emerg Med., 1 Jan 1995, 12 (3), 231–2. 428 kB. doi:10.1136/emj.12.3.231 The target of Sasha’s critique: Intracranial haemorrhage associated with ingestion of ‘Ecstasy’.

320
Analogue 18: Substituting Hexyloxy for Butylthio at R4

H
4-n-Hexyloxy-3,5-dimethoxyphenethylamine

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

Formula: C16H27NO3 Molecular weight: 281.39048 g/mol InChI Key: VISZDYZGSWOKMZ-UHFFFAOYSA-N

InChI=1S/C16H27NO3/c1-4-5-6-7-10-20-16-14(18-2)11-13(8-9-17)12-15(16)19-3/h11-12H,4-10,17H2,1-3H3

PubChem CID: 57478624

See also PiHKAL: #10 B      
321
Analogue 19: Substituting Heptyloxy for Butylthio at R4

S
4-n-Heptyloxy-3,5-dimethoxyphenethylamine

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

Formula: C17H29NO3 Molecular weight: 295.41706 g/mol InChI Key: XUJUYQSTWQJFMQ-UHFFFAOYSA-N

InChI=1S/C17H29NO3/c1-4-5-6-7-8-11-21-17-15(19-2)12-14(9-10-18)13-16(17)20-3/h12-13H,4-11,18H2,1-3H3

PubChem CID: 57478625

See also PiHKAL: #10 B      
2185
Analogue 20: Substituting 2-Fluoroethyoxy for Butylthio at R4

FE
Fluoroescaline
4-(2-Fluoroethyloxy)-3,5-dimethoxyphenethylamine

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

Formula: C12H18FNO3 Molecular weight: 243.2746232 g/mol InChI Key: RODJFRFKJSPAGG-UHFFFAOYSA-N

InChI=1S/C12H18FNO3/c1-15-10-7-9(3-5-14)8-11(16-2)12(10)17-6-4-13/h7-8H,3-6,14H2,1-2H3

PubChem CID: 12970140

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

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

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

2186
Analogue 21: Substituting 2,2-Difluoroethoxy for Butylthio at R4

DFE
4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine

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

Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: PCAYHBWBNGPKII-UHFFFAOYSA-N

InChI=1S/C12H17F2NO3/c1-16-9-5-8(3-4-15)6-10(17-2)12(9)18-7-11(13)14/h5-6,11H,3-4,7,15H2,1-2H3

PubChem CID: 54939674

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 351 Row: 7

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

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

2187
Analogue 22: Substituting 2,2,2-Trifluoroethoxy for Butylthio at R4

TFE
3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenethylamine

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

Formula: C12H16F3NO3 Molecular weight: 279.2555496 g/mol InChI Key: LMULYKOEWFMASK-UHFFFAOYSA-N

InChI=1S/C12H16F3NO3/c1-17-9-5-8(3-4-16)6-10(18-2)11(9)19-7-12(13,14)15/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 54930645

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 351 Row: 9

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

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

2188
Analogue 23: Substituting 3-Fluoropropoxy for Butylthio at R4

FP
Fluoroproscaline
4-(3-Fluoropropoxy)-3,5-dimethoxyphenethylamine

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

Formula: C13H20FNO3 Molecular weight: 257.3012032 g/mol InChI Key: FMAGEKSBHIYXPF-UHFFFAOYSA-N

InChI=1S/C13H20FNO3/c1-16-11-8-10(4-6-15)9-12(17-2)13(11)18-7-3-5-14/h8-9H,3-7,15H2,1-2H3

PubChem CID: 57478627

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

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

2189
Analogue 24: Substituting Isobutoxy for Butylthio at R4

IB
4-Isobutoxy-3,5-dimethoxyphenethylamine

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

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

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

PubChem CID: 57478628

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 20

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives. Helv. Chim. Acta, 21 Jun 2002, 85 (9), 3019–3026. 98 kB. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 In German.

341
Analogue 25: Substituting 2-Methoxyethoxy for Butylthio at R4

3,5-Dimethoxy-4-(2-methoxyethoxy)phenethylamine

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

Formula: C13H21NO4 Molecular weight: 255.31014 g/mol InChI Key: QTFSKSJBDMDYDO-UHFFFAOYSA-N

InChI=1S/C13H21NO4/c1-15-6-7-18-13-11(16-2)8-10(4-5-14)9-12(13)17-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57478626

See also PiHKAL: #99 MAL      
340
Analogue 26: Substituting Bromo for Butylthio at R4

3,4,5-MBM
4-Br-3,5-DMPEA
4-Bromo-3,5-dimethoxyphenethylamine

IUPAC: 2-(4-Bromo-3,5-dimethoxyphenyl)ethan-1-amine

Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: DQTTUBZTFBEBCK-UHFFFAOYSA-N

InChI=1S/C10H14BrNO2/c1-13-8-5-7(3-4-12)6-9(14-2)10(8)11/h5-6H,3-4,12H2,1-2H3

PubChem CID: 15102778; ChemSpider: 10438341

Shulgin Index: See #18 2C-B; Table: 5 Page: 349 Row: 10

See also PiHKAL: #52 DESOXY      

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

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

446
Analogue 27: Substituting Hydroxy for Butylthio at R4

DESMETHYL

IUPAC: 4-(2-Aminoethyl)-2,6-dimethoxyphenol

Formula: C10H15NO3 Molecular weight: 197.231 g/mol InChI Key: ISVPPMXWQFCRSS-UHFFFAOYSA-N

InChI=1S/C10H15NO3/c1-13-8-5-7(3-4-11)6-9(14-2)10(8)12/h5-6,12H,3-4,11H2,1-2H3

PubChem CID: 533955; ChemSpider: 465214

Shulgin Index: #29 DESMETHYL; Table: 5 Page: 349 Row: 17

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

Benington, F; Morin, RD; Clarke, LC. Synthesis of 4-hydroxy- and 4-ethoxy-3,5-dimethoxy-β-phenethylamines. J. Am. Chem. Soc., 1 Nov 1954, 76 (21), 5555–5556. 307 kB. doi:10.1021/ja01650a084

450
Analogue 28: Removing Butylthio at R4

3,5-DMPEA

IUPAC: 2-(3,5-Dimethoxyphenyl)ethan-1-amine

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: ZHSFEDDRTVLPHH-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-12-9-5-8(3-4-11)6-10(7-9)13-2/h5-7H,3-4,11H2,1-2H3

PubChem CID: 137857; ChemSpider: 121506

Shulgin Index: #50 3,5-DMPEA; Table: 4 Page: 336 Row: 22

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. doi:10.1093/chromsci/bmr013

487
Analogue 29: Substituting Difluoromethoxy for Butylthio at R4

3C-DFM

IUPAC: 1-[4-(Difluoromethoxy)-3,5-dimethoxyphenyl]propan-2-amine

Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: BQVYKMZBEBFRIG-UHFFFAOYSA-N

InChI=1S/C12H17F2NO3/c1-7(15)4-8-5-9(16-2)11(18-12(13)14)10(6-8)17-3/h5-7,12H,4,15H2,1-3H3

PubChem CID: 54929188

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

486
Analogue 30: Substituting 1,3-Difluoroprop-2-yloxy for Butylthio at R4

DFIP
Difluoroisoproscaline

IUPAC: 2-{4-[(1,3-Difluoropropan-2-yl)oxy]-3,5-dimethoxyphenyl}ethan-1-amine

Formula: C13H19F2NO3 Molecular weight: 275.2916664 g/mol InChI Key: ZLDOCTQJEGDYQU-UHFFFAOYSA-N

InChI=1S/C13H19F2NO3/c1-17-11-5-9(3-4-16)6-12(18-2)13(11)19-10(7-14)8-15/h5-6,10H,3-4,7-8,16H2,1-2H3

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

485
Analogue 31: Substituting 3,3,3-Trifluoropropoxy for Butylthio at R4

TFP
Trifluoroproscaline

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

Formula: C13H18F3NO3 Molecular weight: 293.2821296 g/mol InChI Key: SANRTCNYSAUXOQ-UHFFFAOYSA-N

InChI=1S/C13H18F3NO3/c1-18-10-7-9(3-5-17)8-11(19-2)12(10)20-6-4-13(14,15)16/h7-8H,3-6,17H2,1-2H3

PubChem CID: 64565107

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

483
Analogue 32: Substituting Trifluoromethoxy for Butylthio at R4

TFM
Trifluoromescaline

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

Formula: C11H14F3NO3 Molecular weight: 265.2289696 g/mol InChI Key: AVPVNYDXWCNFJD-UHFFFAOYSA-N

InChI=1S/C11H14F3NO3/c1-16-8-5-7(3-4-15)6-9(17-2)10(8)18-11(12,13)14/h5-6H,3-4,15H2,1-2H3

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

482
Analogue 33: Substituting Difluoromethoxy for Butylthio at R4

DFM
Difluoromescaline

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

Formula: C11H15F2NO3 Molecular weight: 247.2385064 g/mol InChI Key: MMARNDCKXDBJES-UHFFFAOYSA-N

InChI=1S/C11H15F2NO3/c1-15-8-5-7(3-4-14)6-9(16-2)10(8)17-11(12)13/h5-6,11H,3-4,14H2,1-2H3

PubChem CID: 54930734

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

17 isomers:
5
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

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

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

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

45
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]ethan-1-amine

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.

48
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]ethan-1-amine

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

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

178
Isomer 5

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]ethan-1-amine

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

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

179
Isomer 6

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

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

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      

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

214
Isomer 7

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

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

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      
215
Isomer 8

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
Isomer 9

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      
2077
Isomer 10

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

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

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      
2089
Isomer 11

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

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

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

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

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

2178
Isomer 12

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

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethan-1-amine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: OEPKQBQEDYEXMC-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8,10H,5-6,9,15H2,1-4H3

PubChem CID: 12063260

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 5

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

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

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

7366
Isomer 14

N-Me-4C-T

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

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: VDSMOAJRXWDJOF-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-6-11(15-2)7-10-8-13(17-4)14(18-5)9-12(10)16-3/h8-9,11,15H,6-7H2,1-5H3

PubChem CID: 11301205; ChemSpider: 9476182

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 16

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

7370
Isomer 15

N-Me-ALEPH-2

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

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: RXMRQMALCRZCOI-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-6-18-14-9-12(16-4)11(7-10(2)15-3)8-13(14)17-5/h8-10,15H,6-7H2,1-5H3

PubChem CID: 11460934; ChemSpider: 9635774

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 20

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

7371
Isomer 16

4C-T-2

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

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: KLAWPCIXPDTGCZ-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-5-11(15)7-10-8-13(17-4)14(18-6-2)9-12(10)16-3/h8-9,11H,5-7,15H2,1-4H3

PubChem CID: 11197523; ChemSpider: 9372592

Shulgin Index: See #3 ALEPH; Table: 5 Page: 345 Row: 21

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

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

Show all 50 analogues and isomers Show only the 33 R4 analogues
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