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PiHKAL#72 E; SI#64 Escaline
72
Variant: N α R3 R4 R5 isomers all
Analogues: 1 1 2 33 2 29 68

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 Transcripts: 2.217, 3.365, 3.397

See also Pharmacology notes II: p. 217, Escaline

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

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

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

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

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

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

One N analogue:
2419
Analogue 1: Adding 2-Methoxybenzyl at N

Escaline-NBOMe
NBOMe-escaline

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

Formula: C20H27NO4 Molecular weight: 345.43268 g/mol InChI Key: VIFKVOUQWKUXLL-UHFFFAOYSA-N

InChI=1S/C20H27NO4/c1-5-25-20-18(23-3)12-15(13-19(20)24-4)10-11-21-14-16-8-6-7-9-17(16)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3

PubChem CID: 10405293; ChemSpider: 8580731

Anon. Personal communication of unpublished research. 1 Dec 2011.

Pertz, HH; Rheineck, A; Elz, S. N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors. N-S. Arch. Pharmacol., 1999, 359 (Suppl. 3), R29. 104 kB.

One α analogue:
25
Analogue 1: Adding Methyl at α

3C-E
4-Ethoxy-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-ethoxyamphetamine

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

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

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

PubChem CID: 44350137; ChemSpider: 21106237; Wikipedia: 3C-E

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 1

See also PiHKAL: #72 E    

See also Transcripts: 2.222

See also Pharmacology notes II: p. 222, 3C-E

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

Two R3 analogues:
9
Analogue 1: Substituting Ethoxy for Methoxy at R3

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

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

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

InChI=1S/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 45367; ChemSpider: 41279; Wikipedia: Asymbescaline

Shulgin Index: #8 ASB; Table: 5 Page: 351 Row: 2, #8 ASB; Table: 5 Page: 351 Row: 36

See also PiHKAL: #148 5-TASB #163 3-TME #178 3-T-TRIS

See also Transcripts: 5.587

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

146
Analogue 2: Substituting Ethylthio for Methoxy at R3

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

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

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

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

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

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

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

See also Transcripts: 5.669

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

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

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

33 R4 analogues:
2
Analogue 1: Substituting Allyloxy for Ethoxy 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  

See also Transcripts: 5.582, 5.598, 5.599

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

10
Analogue 2: Substituting Butoxy for Ethoxy 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    

See also Transcripts: 3.419

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

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

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

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

37
Analogue 3: Substituting Cyclopropylmethoxy for Ethoxy 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 Transcripts: 2.218, 4.470

See also Pharmacology notes II: p. 218, 5-MeO-DIPT
50
Analogue 4: Substituting Trideuteromethoxy for Ethoxy 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 Ethoxy 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

92
Analogue 6: Substituting Isopropoxy for Ethoxy 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

See also Transcripts: 3.389, 3.418

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

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

96
Analogue 7: Substituting Methoxy for Ethoxy 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 Transcripts: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 2.321, 2.323.4, 2.323.5, 3.353, 4.471, 4.472

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

Fenderson5555. Two syntheses of mescaline. 21 Mar 2011. 2247 kB.

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

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

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

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

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

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

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

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

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

Walters, GC; Cooper, PD. Alicyclic analogue of mescaline. Nature, 20 Apr 1968, 218 (5138), 298–300. 3141 kB. doi:10.1038/218298a0

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

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 α-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.

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

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

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

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

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

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.

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

Shulgin, AT. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs, 1 Jan 1979, 11 (4), 355. 1336 kB. doi:10.1080/02791072.1979.10471421

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

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

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. 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.

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

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

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

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

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

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

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

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

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

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

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

99
Analogue 8: Substituting Methallyloxy for Ethoxy 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

See also Transcripts: 4.483, 5.586

140
Analogue 9: Substituting Propoxy for Ethoxy 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 Transcripts: 2.209, 4.560, 5.567, 5.569, 5.595, 5.665, 5.667

See also Pharmacology notes II: p. 209, Proscaline

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

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

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.

141
Analogue 10: Substituting Phenethyloxy for Ethoxy 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

See also Transcripts: 5.602

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 11: Substituting Prop-2-ynyloxy for Ethoxy 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    

See also Transcripts: 5.627

149
Analogue 12: Substituting Butylthio for Ethoxy at R4

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]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  

See also Transcripts: 5.668, 5.678

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
Analogue 13: Substituting Ethylthio for Ethoxy 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

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

156
Analogue 14: Substituting Methylthio for Ethoxy 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 Transcripts: 2.239, 2.323.4, 3.345, 3.351

See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 239, 4-TM

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. Monothio analogues of mescaline and isomescaline. J. Med. Chem., 1 Jan 1981, 24 (11), 1348–1353. 953 kB. doi:10.1021/jm00143a017

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

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

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

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

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

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

174
Analogue 15: Substituting Propylthio for Ethoxy 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    

See also Transcripts: 5.648

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

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

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

318
Analogue 16: Substituting Benzyloxy for Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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 Ethoxy 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

Two R5 analogues:
123
Analogue 1: Removing Methoxy at R5

MEPEA
3-Methoxy-4-ethoxyphenethylamine

IUPAC: 2-(4-Ethoxy-3-methoxyphenyl)ethan-1-amine

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

InChI=1S/C11H17NO2/c1-3-14-10-5-4-9(6-7-12)8-11(10)13-2/h4-5,8H,3,6-7,12H2,1-2H3

PubChem CID: 142076; ChemSpider: 125332; Wikipedia: 3-Methoxy-4-ethoxyphenethylamine

Shulgin Index: #90 MEPEA; Table: 4 Page: 330 Row: 32

See also PiHKAL: #55 3,4-DMA    

See also Transcripts: 3.431

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

150
Analogue 2: Substituting Methylthio for Methoxy at R5

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

29 isomers:
14
Isomer 1

BOD
β-Methoxy-2C-D
2,5,β-Trimethoxy-4-methylphenethylamine
4-Methyl-2,5,β-trimethoxyphenethylamine

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

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

InChI=1S/C12H19NO3/c1-8-5-11(15-3)9(6-10(8)14-2)12(7-13)16-4/h5-6,12H,7,13H2,1-4H3

PubChem CID: 44719486; ChemSpider: 21106262; Wikipedia: BOD (psychedelic)

Shulgin Index: #14 BOB; Table: 5 Page: 342 Row: 29

See also PiHKAL: #13 BOB
#15 BOH
#16 BOHD
#17 BOM
 

See also Transcripts: 4.462, 5.628, 5.628.2

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

Torres, MA; Cassels, BK; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

119
Isomer 2

ME
Metaescaline
3,4-Dimethoxy-5-ethoxyphenethylamine
3-Ethoxy-4,5-dimethoxyphenethylamine

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

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

InChI=1S/C12H19NO3/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: 44350068; ChemSpider: 21106344; Wikipedia: Metaescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 32

See also PiHKAL: #9 ASB
#137 MP
#163 3-TME
#165 5-TME
#176 3-TSB

See also Transcripts: 3.409

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

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

157
Isomer 3

TMA
AMM
EA-1319
3,4,5-Trimethoxyamphetamine

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

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: WGTASENVNYJZBK-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 31016; ChemSpider: 28775; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #117 TMA; Table: 5 Page: 349 Row: 27

See also PiHKAL: #1 AEM
#14 BOD
#21 3C-BZ
#27 2C-G
#42 Ψ-2C-T-4
#50 4-D
#72 E
#97 4-MA
#100 MDA
#120 MEDA
#132 MMDA
#145 TA
#158 TMA-2
#160 TMA-4
#166 2T-MMDA-3a
See also TiHKAL: #13 Harmaline    

See also Transcripts: 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.72, 1.139, 2.227

See also Pharmacology notes I: p. 8, TMA: Subacute human in vivo tests
p. 9, TMA: Objective response
p. 10, TMA: Objective response
p. 11, TMA: Objective response
p. 12, TMA: Objective response
p. 13, TMA: Subjective response
p. 14, TMA: Subjective response
p. 15, TMA: Subjective response
p. 16, TMA: Subjective response
p. 17, TMA: Subjective response
p. 18, TMA: Subjective response
p. 19, TMA: Subjective response
p. 72, SARs
p. 139, The Pseunut Cocktail
See also Pharmacology notes II: p. 227, TMA: Subjective response

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

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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

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 α-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.

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

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

Tsujikawa, K; Kanamori, T; Kuwayama, K; Miyaguchi, H; Iwata, YT; Inoue, H. Analytical profiles for 3,4,5-, 2,4,5-, and 2,4,6-trimethoxyamphetamine. Microgram J., 1 Jan 2006, 4 (1–4), 12–23. 162 kB.

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

Weil, AT. The use of nutmeg as a psychotropic agent. Bull. Narc., United Nations Office on Drugs and Crime, 1 Jan 1966.

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

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

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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

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

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

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Peretz, DI; Smythies, JR; Gibson, WC. A new hallucinogen: 3,4,5-Trimethoxyphenyl-β-aminopropane. With notes on the stroboscopic phenomenon. J. Mental Sci., 1 Jan 1955, 101 (423), 317–329. 1559 kB. doi:10.1192/bjp.101.423.317

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. doi:10.1038/210380a0

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Shulgin, AT; Bunnell, S; Sargent, T. The psychotomimetic properties of 3,4,5-trimethoxyamphetamine. Nature, 1 Jan 1961, 189, 1011–1012. 306 kB. doi:10.1038/1891011a0 Rhodium.

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

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

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

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

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

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

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.

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

158
Isomer 4

TMA-2
2,4,5-Trimethoxyamphetamine

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

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: TVSIMAWGATVNGK-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C12H19NO3/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: 31014; ChemSpider: 28773; Drugs Forum: TMA-2; Erowid: TMA-2; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #118 TMA-2; Table: 5 Page: 344 Row: 23

See also PiHKAL: #35 2C-O-4
#42 Ψ-2C-T-4
#52 DESOXY
#69 Ψ-DOM
#73 EEE
#75 EME
#76 EMM
#93 IRIS
#120 MEDA
#121 MEE
#122 MEM
#136 MME
#138 MPM
#139 ORTHO-DOT
#145 TA
#157 TMA
#162 TMA-6
#167 4T-MMDA-2
#168 TMPEA
See also TiHKAL: #13 Harmaline #19 5-HO-DMT #46 5-MeS-DMT

See also Transcripts: 1.54, 1.55, 1.55.2, 1.56, 1.64, 1.65, 1.72, 1.108, 1.151, 1.160, 1.161, 1.185, 2.224

See also Pharmacology notes I: p. 54, TMA-2: Subacute evaluation
p. 55.1, TMA-2: Subjective response
p. 56, TMA-2: Subjective response
p. 64, TMA-2: Subjective response
p. 65, TMA-2: Subjective response
p. 72, SARs
p. 108, TMA-2: Subjective response
p. 151, TMA-2
p. 160, TMA-2
p. 161, TMA-2
p. 185, TMA-2: Qualitative description
See also Pharmacology notes II: p. 224, TMA-2

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

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

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

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.

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

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

Tsujikawa, K; Kanamori, T; Kuwayama, K; Miyaguchi, H; Iwata, YT; Inoue, H. Analytical profiles for 3,4,5-, 2,4,5-, and 2,4,6-trimethoxyamphetamine. Microgram J., 1 Jan 2006, 4 (1–4), 12–23. 162 kB.

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

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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 TMA-2, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

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

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

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

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Sargent, T; Shulgin, AT; Kusubov, N. Quantitative measurement of demethylation of [14]C-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharmacol. Commun., 1 Jan 1976, 2 (3), 199–206. 8643 kB.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

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

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

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

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

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

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

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.

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. doi:10.1080/02791072.1976.10471846

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

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

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

159
Isomer 5

TMA-3
2,3,4-Trimethoxyamphetamine

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

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

InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31012; ChemSpider: 28771; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #119 TMA-3; Table: 5 Page: 338 Row: 15

See also PiHKAL: #42 Ψ-2C-T-4 #152 2-TIM #158 TMA-2

See also Transcripts: 1.72, 1.85, 1.85.2

See also Pharmacology notes I: p. 72, SARs
p. 85, TMA-3: Subacute evaluation

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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

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

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

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.

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

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.

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

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

160
Isomer 6

TMA-4
2,3,5-Trimethoxyamphetamine

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

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

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

PubChem CID: 602804; ChemSpider: 523988; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #120 TMA-4; Table: 5 Page: 339 Row: 22

See also PiHKAL: #42 Ψ-2C-T-4
#135 MMDA-3b
#136 MME
#158 TMA-2
#161 TMA-5

See also Transcripts: 1.61, 1.72

See also Pharmacology notes I: p. 61, TMA-4: Subacute evaluation
p. 72, SARs

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; 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

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

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

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.

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.

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

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

161
Isomer 7

TMA-5
2,3,6-Trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxyphenyl)propan-2-amine

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

InChI=1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31013; ChemSpider: 28772; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #121 TMA-5; Table: 5 Page: 353 Row: 2

See also PiHKAL: #8 ARIADNE #42 Ψ-2C-T-4 #158 TMA-2

See also Transcripts: 1.72, 1.97

See also Pharmacology notes I: p. 72, SARs
p. 97, TMA-5: Subacute evaluation

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. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

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

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.

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.

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

162
Isomer 8

TMA-6
2,4,6-Trimethoxyamphetamine

IUPAC: 1-(2,4,6-Trimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 31015; ChemSpider: 28774; Drugs Forum: TMA-6; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #122 TMA-6; Table: 5 Page: 353 Row: 26

See also PiHKAL: #8 ARIADNE
#42 Ψ-2C-T-4
#69 Ψ-DOM
#122 MEM
#134 MMDA-3a
#158 TMA-2

See also Transcripts: 1.72, 1.93, 1.93.2, 1.98, 1.99, 1.150, 1.188, 1.189, 2.253, 5.633, 5.634, 5.679, 5.682

See also Pharmacology notes I: p. 72, SARs
p. 93.1, Subacute evaluation TMA-6 (XVI-21)
p. 98, TMA-6: Subjective response
p. 99, TMA-6: Subjective response
p. 150, TMA-6
p. 188, TMA-6: Qualitative effects
p. 189, TMA-6: Qualitative effects
See also Pharmacology notes II: p. 253, TMA-6

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

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; 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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

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

Chambers, JJ. Use of conformationally-restricted analogues and homology modeling to provide insight into the nature of the 5-HT2A receptor agonist binding site. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2002. 8389 kB.

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

Tsujikawa, K; Kanamori, T; Kuwayama, K; Miyaguchi, H; Iwata, YT; Inoue, H. Analytical profiles for 3,4,5-, 2,4,5-, and 2,4,6-trimethoxyamphetamine. Microgram J., 1 Jan 2006, 4 (1–4), 12–23. 162 kB.

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. I. 2,4,6-Trialkoxy-β-phenethylamines. J. Org. Chem., 1 Jan 1954, 19 (1), 11–16. 436 kB. doi:10.1021/jo01366a003

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

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.

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

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

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

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

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

Shulgin, AT. Trimethoxylated amphetamine derivatives. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 14 Mar 2002.

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. 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.

262
Isomer 9

METHYL-MESCALINE
M-M
N-Methyl-3,4,5-trimethoxyphenethylamine
N-Methylmescaline

IUPAC: N-Methyl-2-(3,4,5-trimethoxyphenyl)ethan-1-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: OTXANOLOOUNVSR-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C12H19NO3/c1-13-6-5-9-7-10(14-2)12(16-4)11(8-9)15-3/h7-8,13H,5-6H2,1-4H3

PubChem CID: 138365; ChemSpider: 121990

Shulgin Index: #97 MMDA; Table: 5 Page: 350 Row: 24

See also PiHKAL: #96 M    

See also Transcripts: 1.142

See also Pharmacology notes I: p. 142, Methyl-mescaline

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; 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

2068
Isomer 10

2C-O-2
2C-O-2
2,5-Dimethoxy-4-ethoxyphenethylamine

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

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

InChI=1S/C12H19NO3/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: 57474251

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 31

See also PiHKAL: #35 2C-O-4    
2214
Isomer 11

N,N-Me-3-DESMETHYL
N,N-Dimethyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 5-[2-(Dimethylamino)ethyl]-2,3-dimethoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: INYMWXUUZSMPQM-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C12H19NO3/c1-13(2)6-5-9-7-10(14)12(16-4)11(8-9)15-3/h7-8,14H,5-6H2,1-4H3

PubChem CID: 57478611

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 7

5383
Isomer 12

N,N-Me-DME
Macromerine
β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3

PubChem CID: 165055; ChemSpider: 144706; Wikipedia: Macromerine

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 10

Hodgkins, JE; Brown, SD; Massingill, JL. Two new alkaloids in cacti. Tetrahedron Lett., 1 Jan 1967, 8 (14), 1321–1324. 202 kB. doi:10.1016/S0040-4039(00)90694-4

333
Isomer 13

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

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

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

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

ChemSpider: 25045865

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

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

619
Isomer 14

homo-Mescaline

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

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

InChI=1S/C12H19NO3/c1-14-10-7-9(5-4-6-13)8-11(15-2)12(10)16-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 614460; ChemSpider: 534098

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 26

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. VI. Mescaline homologs. J. Org. Chem., 1 Dec 1956, 21 (12), 1545–1546. 282 kB. doi:10.1021/jo01118a635

6559
Isomer 15

β-HO-N-iPr-GEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]-2-methoxyphenol

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

InChI=1S/C12H19NO3/c1-8(2)13-7-11(15)9-4-5-10(14)12(6-9)16-3/h4-6,8,11,13-15H,7H2,1-3H3

PubChem CID: 68951; ChemSpider: 62174

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 9

6612
Isomer 16

N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethan-1-amine

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

InChI=1S/C12H19NO3/c1-13-8-12(16-4)9-5-6-10(14-2)11(7-9)15-3/h5-7,12-13H,8H2,1-4H3

PubChem CID: 15612893; ChemSpider: 26711698

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 12

6625
Isomer 17

DMMAOH

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-hydroxy-N-methylpropan-2-amine

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

InChI=1S/C12H19NO3/c1-9(13(2)14)7-10-5-6-11(15-3)12(8-10)16-4/h5-6,8-9,14H,7H2,1-4H3

PubChem CID: 11368108; ChemSpider: 9543025

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 25

6655
Isomer 18

DEE

IUPAC: 2-Amino-1-(3,4-diethoxyphenyl)ethanol

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

InChI=1S/C12H19NO3/c1-3-15-11-6-5-9(10(14)8-13)7-12(11)16-4-2/h5-7,10,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627975

Shulgin Index: See #49 DMPEA; Table: 4 Page: 331 Row: 5

6866
Isomer 19

β-HO-N,N-Me-2,5-DMPEA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-11(14)10-7-9(15-3)5-6-12(10)16-4/h5-7,11,14H,8H2,1-4H3

PubChem CID: 46242; ChemSpider: 42100

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 16

6869
Isomer 20

β-HO-β,N-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)-1-(methylamino)propan-2-ol

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

InChI=1S/C12H19NO3/c1-12(14,8-13-2)10-7-9(15-3)5-6-11(10)16-4/h5-7,13-14H,8H2,1-4H3

PubChem CID: 50630; ChemSpider: 45890

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 19

6877
Isomer 21

β-HO-N-Me-2,5-DMA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(methylamino)propan-1-ol

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

InChI=1S/C12H19NO3/c1-8(13-2)12(14)10-7-9(15-3)5-6-11(10)16-4/h5-8,12-14H,1-4H3

PubChem CID: 3027653; ChemSpider: 2293151

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 27

6910
Isomer 22

β,2-HO-N-Me-5-EA

IUPAC: 4-Ethoxy-2-[1-hydroxy-2-(methylamino)propyl]phenol

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

InChI=1S/C12H19NO3/c1-4-16-9-5-6-11(14)10(7-9)12(15)8(2)13-3/h5-8,12-15H,4H2,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 10

6912
Isomer 23

β-HO-2,5-DEPEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)ethanol

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

InChI=1S/C12H19NO3/c1-3-15-9-5-6-12(16-4-2)10(7-9)11(14)8-13/h5-7,11,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627950

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 12

6927
Isomer 24

β-HO-N,N-Me-3,5-DMPEA

IUPAC: 1-(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

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

InChI=1S/C12H19NO3/c1-13(2)8-12(14)9-5-10(15-3)7-11(6-9)16-4/h5-7,12,14H,8H2,1-4H3

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 27

7217
Isomer 25

N-HO-DOM

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

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

InChI=1S/C12H19NO3/c1-8-5-12(16-4)10(6-9(2)13-14)7-11(8)15-3/h5,7,9,13-14H,6H2,1-4H3

PubChem CID: 597107; ChemSpider: 519067

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 17

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

7569
Isomer 26

DESMETHYL-MM

IUPAC: 4-[2-(Dimethylamino)ethyl]-2,6-dimethoxyphenol

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

InChI=1S/C12H19NO3/c1-13(2)6-5-9-7-10(15-3)12(14)11(8-9)16-4/h7-8,14H,5-6H2,1-4H3

PubChem CID: 24971842; ChemSpider: 21404060

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 19

1019
Isomer 27

β-HO-DOM

IUPAC: 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)propan-1-ol

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

InChI=1S/C12H19NO3/c1-7-5-11(16-4)9(6-10(7)15-3)12(14)8(2)13/h5-6,8,12,14H,13H2,1-4H3

ChemSpider: 26711720

Ho, B; Tansey, LW; McIsaac, WM. Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM). J. Med. Chem., 1 Sep 1970, 13 (5), 1022. 99 kB. doi:10.1021/jm00299a071

1016
Isomer 28

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

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

InChI=1S/C12H19NO3/c1-8(13)4-9-5-12(16-3)10(7-14)6-11(9)15-2/h5-6,8,14H,4,7,13H2,1-3H3

Ho, B; Estevez, V; Tansey, LW; Englert, LF; Creaven, PJ; McIsaac, WM. Analogs of amphetamine. 5. Excretory metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) in rats. J. Med. Chem., 1 Feb 1971, 14 (2), 158–160. 371 kB. doi:10.1021/jm00284a019

Ho, B; Tansey, LW. Analogs of amphetamine. 4. Synthesis of metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). J. Med. Chem., 1 Feb 1971, 14 (2), 156–157. 316 kB. doi:10.1021/jm00284a018

701
Isomer 29

N-MeO-3,4-DMA
N,3,4-Trimethoxyamphetamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-methoxypropan-2-amine

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

InChI=1S/C12H19NO3/c1-9(13-16-4)7-10-5-6-11(14-2)12(8-10)15-3/h5-6,8-9,13H,7H2,1-4H3

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Show all 68 analogues and isomers Show only the one N analogues Show only the one α analogues Show only the two R3 analogues Show only the 33 R4 analogues Show only the two R5 analogues
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