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PiHKAL#96 M; SI#91 Mescaline
96
Variant: N α β R2 R3 R4 R5 R4,5 skeleton isomers all
Analogues: 12 16 3 3 5 33 4 1 27 31 135

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. 4, Experiment for Death Valley
p. 321, Mescaline

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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

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

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

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

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.

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

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

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

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

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

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

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

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

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

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

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

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

12 N analogues:
261
Analogue 1: Adding Acetyl at N

N-Acetylmescaline
N-Acetyl-3,4,5-trimethoxyphenethylamine

IUPAC: N-[2-(3,4,5-Trimethoxyphenyl)ethyl]acetamide

Formula: C13H19NO4 Molecular weight: 253.29426 g/mol InChI Key: SNMFNOQKGANWHD-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C13H19NO4/c1-9(15)14-6-5-10-7-11(16-2)13(18-4)12(8-10)17-3/h7-8H,5-6H2,1-4H3,(H,14,15)

PubChem CID: 100597; ChemSpider: 90893

See also PiHKAL: #96 M    

See also Transcripts: 1.38

See also Pharmacology notes I: p. 38, N-Acetylmescaline: Subacute evaluation

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.

262
Analogue 2: Adding Methyl at N

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

263
Analogue 3: Adding Dimethyl at N

Trichocerine
Trichocereine
N,N-Dimethylmescaline
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine

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

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

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

PubChem CID: 420418; ChemSpider: 372161

Shulgin Index: #125 Trichocereine; Table: 5 Page: 350 Row: 25

See also PiHKAL: #96 M    

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.

2219
Analogue 4: Adding Formyl at N

N-Formylmescaline
N-Formyl-3,4,5-trimethoxyphenethylamine

IUPAC: N-[2-(3,4,5-Trimethoxyphenyl)ethyl]formamide

Formula: C12H17NO4 Molecular weight: 239.26768 g/mol InChI Key: BESRMWQCUXKEMP-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C12H17NO4/c1-15-10-6-9(4-5-13-8-14)7-11(16-2)12(10)17-3/h6-8H,4-5H2,1-3H3,(H,13,14)

PubChem CID: 20156351

See also PiHKAL: #96 M    
2252
Analogue 5: Adding Carboxymethyl at N

Mescaloxylic acid
N-[2-(3,4,5-Trimethoxyphenyl)ethyl]glycine
N-Carboxymethyl-3,4,5-trimethoxyphenethylamine

IUPAC: {[2-(3,4,5-Trimethoxyphenyl)ethyl]amino}acetic acid

Formula: C13H19NO5 Molecular weight: 269.29366 g/mol InChI Key: OUKOSEIHBSLNGJ-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C13H19NO5/c1-17-10-6-9(4-5-14-8-12(15)16)7-11(18-2)13(10)19-3/h6-7,14H,4-5,8H2,1-3H3,(H,15,16)

PubChem CID: 57478618

2253
Analogue 6: Adding 1-Carboxyethyl at N

Mescaloruvic acid
N-[2-(3,4,5-Trimethoxyphenyl)ethyl]alanine
N-(1-Carboxyethyl)-3,4,5-trimethoxyphenethylamine

IUPAC: 2-{[2-(3,4,5-Trimethoxyphenyl)ethyl]amino}propanoic acid

Formula: C14H21NO5 Molecular weight: 283.32024 g/mol InChI Key: FNJLIRQMUUTSGR-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C14H21NO5/c1-9(14(16)17)15-6-5-10-7-11(18-2)13(20-4)12(8-10)19-3/h7-9,15H,5-6H2,1-4H3,(H,16,17)

PubChem CID: 57478619

403
Analogue 7: Adding 2-Methoxybenzyl at N

Mescaline-NBOMe
NBOMe-mescaline
3,4,5-Trimethoxy-N-(2-methoxybenzyl)phenethylamine
N-(2-Methoxybenzyl)-3,4,5-trimethoxyphenethylamine

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

Formula: C19H25NO4 Molecular weight: 331.4061 g/mol InChI Key: USPSMWCGHVXKMN-UHFFFAOYSA-N

InChI=1S/C19H25NO4/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-17(22-2)19(24-4)18(12-14)23-3/h5-8,11-12,20H,9-10,13H2,1-4H3

PubChem CID: 57501069; ChemSpider: 25949200; Erowid: NBOMe Series

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.

7627
Analogue 8: Adding Allyl at N

N-AL-M

IUPAC: N-[2-(3,4,5-Trimethoxyphenyl)ethyl]prop-2-en-1-amine

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

InChI=1S/C14H21NO3/c1-5-7-15-8-6-11-9-12(16-2)14(18-4)13(10-11)17-3/h5,9-10,15H,1,6-8H2,2-4H3

PubChem CID: 3046363; ChemSpider: 2308985

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 27

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

7628
Analogue 9: Adding 2-Chloroethyl at N

N-CCCI-M

IUPAC: 2-Chloro-N-[2-(3,4,5-trimethoxyphenyl)ethyl]ethan-1-amine

Formula: C13H20ClNO3 Molecular weight: 273.7558 g/mol InChI Key: OMAIONYQWKOIEJ-UHFFFAOYSA-N

InChI=1S/C13H20ClNO3/c1-16-11-8-10(4-6-15-7-5-14)9-12(17-2)13(11)18-3/h8-9,15H,4-7H2,1-3H3

PubChem CID: 418528; ChemSpider: 370487

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 28

7629
Analogue 10: Adding Cyclopropyl at N

N-cPr-M

IUPAC: N-[2-(3,4,5-Trimethoxyphenyl)ethyl]cyclopropanamine

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

InChI=1S/C14H21NO3/c1-16-12-8-10(6-7-15-11-4-5-11)9-13(17-2)14(12)18-3/h8-9,11,15H,4-7H2,1-3H3

PubChem CID: 14089101; ChemSpider: 10729058

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 29

7630
Analogue 11: Adding Propyl at N

N-Pr-M

IUPAC: N-[2-(3,4,5-Trimethoxyphenyl)ethyl]propan-1-amine

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

InChI=1S/C14H23NO3/c1-5-7-15-8-6-11-9-12(16-2)14(18-4)13(10-11)17-3/h9-10,15H,5-8H2,1-4H3

PubChem CID: 3046359; ChemSpider: 2308981

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 30

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

7631
Analogue 12: Adding Cyclopropylmethyl at N

N-CPM-M

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

Formula: C15H23NO3 Molecular weight: 265.34802 g/mol InChI Key: DFDALGJXCBUKHT-UHFFFAOYSA-N

InChI=1S/C15H23NO3/c1-17-13-8-12(6-7-16-10-11-4-5-11)9-14(18-2)15(13)19-3/h8-9,11,16H,4-7,10H2,1-3H3

PubChem CID: 3046361; ChemSpider: 2308983

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 31

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

16 α analogues:
1
Analogue 1: Adding Ethyl at α

AEM
α-Ethylmescaline
α-Ethyl-3,4,5-trimethoxyphenethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1-(3,4,5-Trimethoxyphenyl)-2-aminobutane

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

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

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

PubChem CID: 204932; ChemSpider: 177522; Wikipedia: AEM (psychedelic)

Shulgin Index: #1 AEM; Table: 5 Page: 350 Row: 11

See also PiHKAL: #157 TMA    

See also Transcripts: 1.20

See also Pharmacology notes I: p. 20, AEM: Subacute evaluation

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

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

Daley, PF; Morris, H. Pages from the lab notebook of Alexander Shulgin: A glance through the history of psychedelic chemistry. Vice, 1 Oct 2012.

157
Analogue 2: Adding Methyl at α

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

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

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.

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

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.

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

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

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

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

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

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

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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

180
Analogue 3: Adding Propyl at α

APM
α-Propylmescaline
α-Propyl-3,4,5-trimethoxyphenethylamine

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

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

InChI=1S/C14H23NO3/c1-5-6-11(15)7-10-8-12(16-2)14(18-4)13(9-10)17-3/h8-9,11H,5-7,15H2,1-4H3

PubChem CID: 3051170; ChemSpider: 2313134

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 12

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

181
Analogue 4: Adding Butyl at α

ABM
α-Butylmescaline
α-n-Butyl-3,4,5-trimethoxyphenethylamine

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

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

InChI=1S/C15H25NO3/c1-5-6-7-12(16)8-11-9-13(17-2)15(19-4)14(10-11)18-3/h9-10,12H,5-8,16H2,1-4H3

PubChem CID: 204173; ChemSpider: 176854

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 13

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

182
Analogue 5: Adding Pentyl at α

AAM
α-Amylmescaline
α-n-Amyl-3,4,5-trimethoxyphenethylamine

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

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

InChI=1S/C16H27NO3/c1-5-6-7-8-13(17)9-12-10-14(18-2)16(20-4)15(11-12)19-3/h10-11,13H,5-9,17H2,1-4H3

PubChem CID: 3051169; ChemSpider: 2313133

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 14

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

2057
Analogue 6: Adding Hexyl at α

AHM
α-Hexylmescaline

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

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

InChI=1S/C17H29NO3/c1-5-6-7-8-9-14(18)10-13-11-15(19-2)17(21-4)16(12-13)20-3/h11-12,14H,5-10,18H2,1-4H3

PubChem CID: 3051165; ChemSpider: 2313129

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 15

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

2058
Analogue 7: Adding Heptyl at α

ASM
α-Heptylmescaline

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

Formula: C18H31NO3 Molecular weight: 309.44364 g/mol InChI Key: UKLPFTJPSYHWML-UHFFFAOYSA-N

InChI=1S/C18H31NO3/c1-5-6-7-8-9-10-15(19)11-14-12-16(20-2)18(22-4)17(13-14)21-3/h12-13,15H,5-11,19H2,1-4H3

PubChem CID: 3051164; ChemSpider: 2313128

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 16

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

2059
Analogue 8: Adding Nonyl at α

ANM
α-Nonylmescaline

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

Formula: C20H35NO3 Molecular weight: 337.4968 g/mol InChI Key: DSGREKFHMOAVGY-UHFFFAOYSA-N

InChI=1S/C20H35NO3/c1-5-6-7-8-9-10-11-12-17(21)13-16-14-18(22-2)20(24-4)19(15-16)23-3/h14-15,17H,5-13,21H2,1-4H3

PubChem CID: 3051168; ChemSpider: 2313132

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 18

See also PiHKAL: #1 AEM    

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

2094
Analogue 9: Adding Dideutero at α

α-D
α,α-Dideutero-3,4,5-trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(1,1-2H2)ethan-1-amine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-BFWBPSQCSA-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/i5D2

See also PiHKAL: #51 β-D    
7604
Analogue 10: Adding Hydroxymethyl at α

α-HMe-M

IUPAC: 2-Amino-3-(3,4,5-trimethoxyphenyl)propan-1-ol

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: BQBVLVURBOVNIG-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-15-10-5-8(4-9(13)7-14)6-11(16-2)12(10)17-3/h5-6,9,14H,4,7,13H2,1-3H3

PubChem CID: 20192102

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 4

7605
Analogue 11: Adding Chloromethyl at α

α-CMe-M

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

Formula: C12H18ClNO3 Molecular weight: 259.72922 g/mol InChI Key: JQXARIHJXXXTKR-UHFFFAOYSA-N

InChI=1S/C12H18ClNO3/c1-15-10-5-8(4-9(14)7-13)6-11(16-2)12(10)17-3/h5-6,9H,4,7,14H2,1-3H3

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 5

7609
Analogue 12: Adding Dimethyl at α

α-MM-M

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

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

InChI=1S/C13H21NO3/c1-13(2,14)8-9-6-10(15-3)12(17-5)11(7-9)16-4/h6-7H,8,14H2,1-5H3

PubChem CID: 3029803; ChemSpider: 2295076

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 9

7610
Analogue 13: Adding Methyl and 1,3-Benzodioxol-5-ylmethyl at α

α-MV-M

IUPAC: 1-(1,3-Benzodioxol-5-yl)-2-methyl-3-(3,4,5-trimethoxyphenyl)propan-2-amine

Formula: C20H25NO5 Molecular weight: 359.4162 g/mol InChI Key: FSKCIYSNAGOSJF-UHFFFAOYSA-N

InChI=1S/C20H25NO5/c1-20(21,10-13-5-6-15-16(7-13)26-12-25-15)11-14-8-17(22-2)19(24-4)18(9-14)23-3/h5-9H,10-12,21H2,1-4H3

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 10

7617
Analogue 14: Adding Octyl at α

AOM

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

Formula: C19H33NO3 Molecular weight: 323.47022 g/mol InChI Key: MCFRJYPZIDTASB-UHFFFAOYSA-N

InChI=1S/C19H33NO3/c1-5-6-7-8-9-10-11-16(20)12-15-13-17(21-2)19(23-4)18(14-15)22-3/h13-14,16H,5-12,20H2,1-4H3

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 17

458
Analogue 15: Adding Trifluoromethyl at α

α-TFMM

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

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

InChI=1S/C12H16F3NO3/c1-17-8-4-7(6-10(16)12(13,14)15)5-9(18-2)11(8)19-3/h4-5,10H,6,16H2,1-3H3

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

2331
Analogue 16: Adding Carboxy at α

α-Carboxy-mescaline
3,5-Dimethoxy-O-methyltyrosine

IUPAC: 2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

Formula: C12H17NO5 Molecular weight: 255.26708 g/mol InChI Key: AYPXBNMIJGVJDE-UHFFFAOYSA-N

InChI=1S/C12H17NO5/c1-16-9-5-7(4-8(13)12(14)15)6-10(17-2)11(9)18-3/h5-6,8H,4,13H2,1-3H3,(H,14,15)

PubChem CID: 13406760; ChemSpider: 11345055

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). III. Some derivatives of 3-phenylalanine. Can. J. Chem., 1 Feb 1974, 52 (3), 390–394. 316 kB. doi:10.1139/v74-062

Three β analogues:
17
Analogue 1: Adding Methoxy at β

BOM
β-Methoxymescaline
3,4,5,β-Tetramethoxyphenethylamine

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

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: GAKIJEPUVBHWCK-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-14-9-5-8(11(7-13)16-3)6-10(15-2)12(9)17-4/h5-6,11H,7,13H2,1-4H3

PubChem CID: 44719490; ChemSpider: 21106265; Wikipedia: BOM (psychedelic)

Shulgin Index: #16 BOM; Table: 5 Page: 350 Row: 22

See also PiHKAL: #13 BOB    

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

51
Analogue 2: Adding Dideutero at β

β-D
β,β-Dideutero-3,4,5-trimethoxyphenethylamine
3,4,5-Trimethoxy-β,β-dideuterophenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(2,2-2H2)ethan-1-amine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-APZFVMQVSA-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/i4D2

PubChem CID: 44719547; ChemSpider: 21106267; Wikipedia: Beta-D

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 19

See also PiHKAL: #50 4-D #96 M  
7620
Analogue 3: Adding Hydroxy at β

β-HOM

IUPAC: 2-Amino-1-(3,4,5-trimethoxyphenyl)ethanol

Formula: C11H17NO4 Molecular weight: 227.25698 g/mol InChI Key: BHURFCFBOPXSCN-UHFFFAOYSA-N

InChI=1S/C11H17NO4/c1-14-9-4-7(8(13)6-12)5-10(15-2)11(9)16-3/h4-5,8,13H,6,12H2,1-3H3

PubChem CID: 28894; ChemSpider: 26875

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 20

Three R2 analogues:
455
Analogue 1: Adding Methoxy at R2

TeMPEA

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

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: GJKJPCJLMHZZFK-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-14-9-7-8(5-6-13)10(15-2)12(17-4)11(9)16-3/h7H,5-6,13H2,1-4H3

PubChem CID: 611405; ChemSpider: 531480

Shulgin Index: #114 TeMPEA; Table: 6 Page: 355 Row: 3

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

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. II. Tetra- and penta-methoxy-β-phenethylamines. J. Org. Chem., 1 Jan 1955, 20 (1), 102–108. 534 kB. doi:10.1021/jo01119a017

7851
Analogue 2: Adding Chloro at R2

2-CM

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

Formula: C11H16ClNO3 Molecular weight: 245.70264 g/mol InChI Key: LNEOIKLZQLPCLZ-UHFFFAOYSA-N

InChI=1S/C11H16ClNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3

Shulgin Index: See #114 TeMPEA; Table: 6 Page: 355 Row: 1

7852
Analogue 3: Adding Bromo at R2

2-BM

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

Formula: C11H16BrNO3 Molecular weight: 290.15364 g/mol InChI Key: UXQBKANLBLUVMK-UHFFFAOYSA-N

InChI=1S/C11H16BrNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3

PubChem CID: 16637783; ChemSpider: 17574207

Shulgin Index: See #114 TeMPEA; Table: 6 Page: 355 Row: 2

Parker, MA. Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 1998. 2719 kB.

Five R3 analogues:
119
Analogue 1: Substituting Ethoxy for Methoxy at R3

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

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

163
Analogue 2: Substituting Ethylthio for Methoxy at R3

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

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

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

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

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

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

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

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

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

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

2212
Analogue 3: Substituting Hydroxy for Methoxy at R3

3-DESMETHYL
3-Demethylmescaline
3-Hydroxy-4,5-dimethoxyphenethylamine

IUPAC: 5-(2-Aminoethyl)-2,3-dimethoxyphenol

Formula: C10H15NO3 Molecular weight: 197.231 g/mol InChI Key: PDKPJPTZKPCMKR-UHFFFAOYSA-N Properties: Peyote alkaloid

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

PubChem CID: 44559361; ChemSpider: 25038773

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

7512
Analogue 4: Substituting Chloro for Methoxy at R3

3-Cl-4,5-DMPEA

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

Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: YPCHSTYBWRNMKH-UHFFFAOYSA-N

InChI=1S/C10H14ClNO2/c1-13-9-6-7(3-4-12)5-8(11)10(9)14-2/h5-6H,3-4,12H2,1-2H3

PubChem CID: 13697586; ChemSpider: 20503802

Shulgin Index: See #19 2C-C; Table: 5 Page: 348 Row: 12

Hellot, J; Violland-Duperret, N; Pacheco, H. Psychotropes potentiels VI. Synthèse de nouveaux mescalinoïdes. Chimie Therapeutique, 1 Jan 1970, 5 (1), 55–64. 472 kB. HNMR, anal. chem. In French.

7573
Analogue 5: Substituting Bromo for Methoxy at R3

3,4,5-BMM

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

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

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

PubChem CID: 60906541; ChemSpider: 26492099

Shulgin Index: See #18 2C-B; Table: 5 Page: 349 Row: 23

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

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

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

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

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

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

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

See also PiHKAL: #99 MAL #123 MEPEA  

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

10
Analogue 2: Substituting Butoxy for Methoxy 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 Methoxy 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 Methoxy 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 Methoxy at R4

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

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

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

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

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

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

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

72
Analogue 6: Substituting Ethoxy for Methoxy at R4

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

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

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

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

PubChem CID: 38240; ChemSpider: 35053; Wikipedia: Escaline

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

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

See also 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

92
Analogue 7: Substituting Isopropoxy for Methoxy 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

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

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

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

99
Analogue 8: Substituting Methallyloxy for Methoxy 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

140
Analogue 9: Substituting Propoxy for Methoxy 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

See also Pharmacology notes II: p. 209, Proscaline

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

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

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

141
Analogue 10: Substituting Phenethyloxy for Methoxy at R4

PE
Phenescaline
3,5-Dimethoxy-4-phenethyloxyphenethylamine

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

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

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

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

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

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

143
Analogue 11: Substituting Prop-2-ynyloxy for Methoxy 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    
149
Analogue 12: Substituting Butylthio for Methoxy 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  

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 Methoxy 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

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 Methoxy 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 Methoxy at R4

TP
Thioproscaline
4-Propylthio-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-n-propylthiophenethylamine

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

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

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

PubChem CID: 44349931; ChemSpider: 21106393; Wikipedia: Thioproscaline

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 351 Row: 30

See also PiHKAL: #151 4-TE    

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

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

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

318
Analogue 16: Substituting Benzyloxy for Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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 Methoxy 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

Four R5 analogues:
60
Analogue 1: Removing Methoxy at R5

DMPEA
3,4-Dimethoxyphenethylamine

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

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3

PubChem CID: 8421; ChemSpider: 8114; Wikipedia: 3,4-Dimethoxyphenethylamine

Shulgin Index: #49 DMPEA; Table: 4 Page: 330 Row: 5

See also PiHKAL: #20 2C-B
#115 MDPEA
#142 PEA
#152 2-TIM
#154 4-TIM

See also Transcripts: 1.107

See also Pharmacology notes I: p. 107, DMPEA: Subjective response

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

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

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

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

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

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

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.

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

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!

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

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; Sargent, T; Naranjo, C. Role of 3,4-dimethoxyphenethylamine in schizophrenia. Nature, 1 Jan 1966, 212, 1606–1607. 267 kB. doi:10.1038/2121606a0

Butterick, JR; Unrau, AM. Studies on theoretical psychotogens. Synthesis of O-methylated analogs of catecholamine neurotransmitters and metabolic precursors. Can. J. Chem., 1 Jan 1974, 52 (16), 2873–2879. 305 kB. doi:10.1139/v74-418

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.

Sargent, TW; Israelstam, DM; Shulgin, AT; Landaw, SA; Finley, NN. A note concerning the fate of the 4-methoxyl group in 3,4-dimethoxyphenethylamine (DMPEA). Biochem. Biophys. Res. Commun., 1 Jan 1967, 29 (1), 126–130. 262 kB. doi:10.1016/0006-291X(67)90552-9

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

137
Analogue 2: Substituting Propoxy for Methoxy at R5

MP
Metaproscaline
3,4-Dimethoxy-5-propoxyphenethylamine
3,4-Dimethoxy-5-n-propoxyphenethylamine

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

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

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

PubChem CID: 44375097; ChemSpider: 21106345; Wikipedia: Metaproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 5

See also PiHKAL: #119 ME #163 3-TME  

See also Transcripts: 3.430

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

155
Analogue 3: Substituting Methylthio for Methoxy at R5

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

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

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

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

PubChem CID: 44276881; ChemSpider: 21106411; Wikipedia: Thiomescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 32

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

See also Transcripts: 3.355, 3.411, 3.432, 3.433

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

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

7634
Analogue 4: Substituting Propylthio for Methoxy at R5

3,4,5-2C-T-7

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

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

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

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 350 Row: 34

One R4,5 analogue:
95
Analogue 1: Substituting Methylenedioxy for Dimethoxy at R4,5

LOPHOPHINE
Lophophine
3-Methoxy-4,5-methylenedioxyphenethylamine

IUPAC: 2-(7-Methoxy-1,3-benzodioxol-5-yl)ethan-1-amine

Formula: C10H13NO3 Molecular weight: 195.21512 g/mol InChI Key: ORXQUAPZHKCCAX-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3

PubChem CID: 90239; ChemSpider: 81465; Wikipedia: Lophophine

Shulgin Index: #73 Lophophine; Table: 5 Page: 352 Row: 8

See also PiHKAL: #132 MMDA    

See also Transcripts: 1.127, 2.228

See also Pharmacology notes I: p. 127, Lophophine: Subacute evaluation
See also Pharmacology notes II: p. 228, Lophophine

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

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.

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

Bruhn, JG; EI-Seedi, HR; Stephanson, N; Beck, O; Shulgin, AT. Ecstasy analogues found in cacti. J. Psychoactive Drugs, 1 Jun 2008, 40 (2), 219–222. 884 kB. doi:10.1080/02791072.2008.10400635

27 skeleton analogues:
229
Analogue 1: With 2-Phenylcyclopropan-1-amine skeleton

MCPA
TMT
3,4,5-Trimethoxytranylcypromine
trans-2-(3,4,5-Trimethoxyphenyl)cyclopropylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)cyclopropanamine

Formula: C12H17NO3 Molecular weight: 223.26828 g/mol InChI Key: HNYWYOQSLRJIMG-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-14-10-4-7(8-6-9(8)13)5-11(15-2)12(10)16-3/h4-5,8-9H,6,13H2,1-3H3

PubChem CID: 28236; ChemSpider: 26269

Shulgin Index: See #41 DMCPA; Table: 5 Page: 350 Row: 6

See also PiHKAL: #56 DMCPA #142 PEA  
See also TiHKAL: #8 α,N-DMT    

See also Transcripts: 1.158

See also Pharmacology notes I: p. 158, TMT

Arvidsson, L; Johansson, AM; Hacksell, U; Nilsson, JLG; Svensson, K; Hjorth, S; Magnusson, T; Carlsson, A; Lindberg, P; Andersson, B; Sanchez, D; Wikström, H; Sundell, S. N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists. J. Med. Chem., 1 Jan 1988, 31 (1), 92–99. 1162 kB. doi:10.1021/jm00396a014

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

Cooper, PD. Stereospecific synthesis of cis- and trans-2-(3,4,5-trimethoxyphenyl)-cyclopropylamines. Can. J. Chem., 1 Dec 1970, 48 (24), 3882–3888. 452 kB. doi:10.1139/v70-653

265
Analogue 2: With 2-Phenoxyethan-1-amine skeleton

2-(3,4,5-Trimethoxyphenoxy)ethylamine

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

Formula: C11H17NO4 Molecular weight: 227.25698 g/mol InChI Key: AFJZAAPPTLXGHC-UHFFFAOYSA-N

InChI=1S/C11H17NO4/c1-13-9-6-8(16-5-4-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 3028345; ChemSpider: 2293772

See also PiHKAL: #96 M    

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.

1041
Analogue 3: With Prop-2-en-1-ylbenzene skeleton

Elemicin
3,4,5-Trimethoxyphenylprop-2-ene

IUPAC: 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: BPLQKQKXWHCZSS-UHFFFAOYSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3

PubChem CID: 10248; ChemSpider: 9830; Wikipedia: Elemicin

See also PiHKAL: #132 MMDA #157 TMA  

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Shulgin, AT. Composition of the myristicin fraction from oil of nutmeg. Nature, 1 Jan 1963, 197, 379. 107 kB. doi:10.1038/197379a0 Rhodium.

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. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

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. Concerning the pharmacology of nutmeg. Mind, 1 Jan 1963, 1, 299–302. 578 kB.

1042
Analogue 4: With (1Z)-Prop-1-en-1-ylbenzene skeleton

cis-Isoelemicin
cis-3,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,3-Trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RRXOQHQFJOQLQR-WAYWQWQTSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5-8H,1-4H3/b6-5-

PubChem CID: 5851118; ChemSpider: 4722632

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

1043
Analogue 5: With (1E)-Prop-1-en-1-ylbenzene skeleton

Isoelemicin
trans-3,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,3-Trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RRXOQHQFJOQLQR-AATRIKPKSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5-8H,1-4H3/b6-5+

PubChem CID: 5318557; ChemSpider: 4477101

See also PiHKAL: #157 TMA    

Shulgin, AT; Kerlinger, HO. Isolation of methoxyeugenol and trans-isoelemicin from oil of nutmeg. Naturwissenschaften, 1 Jan 1964, 51 (15), 360–361. 330 kB. doi:10.1007/BF00637880

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

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.

2245
Analogue 6: With Phenylethyl-cyclic-amine skeleton

Mescaline succinimide
N-(3,4,5-Trimethoxyphenethyl)succinimide

IUPAC: 1-[2-(3,4,5-Trimethoxyphenyl)ethyl]pyrrolidine-2,5-dione

Formula: C15H19NO5 Molecular weight: 293.31506 g/mol InChI Key: BASCTZKHLMXTBL-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C15H19NO5/c1-19-11-8-10(9-12(20-2)15(11)21-3)6-7-16-13(17)4-5-14(16)18/h8-9H,4-7H2,1-3H3

PubChem CID: 57478615; ChemSpider: 25746881

2246
Analogue 7: With Phenylethyl-cyclic-amine skeleton

Mescaline malimide
N-(3,4,5-Trimethoxyphenethyl)malimide

IUPAC: 3-Hydroxy-1-[2-(3,4,5-trimethoxyphenyl)ethyl]pyrrolidine-2,5-dione

Formula: C15H19NO6 Molecular weight: 309.31446 g/mol InChI Key: LZIIMOKSBCMVHC-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C15H19NO6/c1-20-11-6-9(7-12(21-2)14(11)22-3)4-5-16-13(18)8-10(17)15(16)19/h6-7,10,17H,4-5,8H2,1-3H3

PubChem CID: 57478616

2247
Analogue 8: With Phenylethyl-cyclic-amine skeleton

Mescaline citrimide
N-(3,4,5-Trimethoxyphenethyl)citrimide

IUPAC: {3-Hydroxy-2,5-dioxo-1-[2-(3,4,5-trimethoxyphenyl)ethyl]pyrrolidin-3-yl}acetic acid

Formula: C17H21NO8 Molecular weight: 367.35054 g/mol InChI Key: HHPKCGRYGJVOQI-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C17H21NO8/c1-24-11-6-10(7-12(25-2)15(11)26-3)4-5-18-13(19)8-17(23,16(18)22)9-14(20)21/h6-7,23H,4-5,8-9H2,1-3H3,(H,20,21)

PubChem CID: 57478617

2248
Analogue 9: With Phenylethyl-cyclic-amine skeleton

Mescaline maleimide
N-(3,4,5-Trimethoxyphenethyl)maleimide

IUPAC: 1-[2-(3,4,5-Trimethoxyphenyl)ethyl]-1H-pyrrole-2,5-dione

Formula: C15H17NO5 Molecular weight: 291.29918 g/mol InChI Key: KBHCXDREVKDXOE-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C15H17NO5/c1-19-11-8-10(9-12(20-2)15(11)21-3)6-7-16-13(17)4-5-14(16)18/h4-5,8-9H,6-7H2,1-3H3

ChemSpider: 25746095

2249
Analogue 10: With Phenylethyl-cyclic-amine skeleton

Mescaline isocitrimide lactone
N-(3,4,5-Trimethoxyphenethyl)isocitrimide lactone

IUPAC: 5-[2-(3,4,5-Trimethoxyphenyl)ethyl]dihydro-2H-furo[2,3-c]pyrrole-2,4,6(3H,5H)-trione

Formula: C17H19NO7 Molecular weight: 349.33526 g/mol InChI Key: GZUQMXTYIBHNAM-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C17H19NO7/c1-22-11-6-9(7-12(23-2)15(11)24-3)4-5-18-16(20)10-8-13(19)25-14(10)17(18)21/h6-7,10,14H,4-5,8H2,1-3H3

2256
Analogue 11: With Phenylethyl-cyclic-amine skeleton

Peyonine
N-(3,4,5-Trimethoxyphenethyl)-2-carboxypyrrole

IUPAC: 1-[2-(3,4,5-Trimethoxyphenyl)ethyl]-1H-pyrrole-2-carboxylic acid

Formula: C16H19NO5 Molecular weight: 305.32576 g/mol InChI Key: DDYNENGLSGKEPO-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C16H19NO5/c1-20-13-9-11(10-14(21-2)15(13)22-3)6-8-17-7-4-5-12(17)16(18)19/h4-5,7,9-10H,6,8H2,1-3H3,(H,18,19)

PubChem CID: 602258; ChemSpider: 523536

2257
Analogue 12: With Phenylethyl-cyclic-amine skeleton

Peyoglunal
N-(3,4,5-Trimethoxyphenethyl)-2-formyl-5-(hydroxymethyl)pyrrole

IUPAC: 5-(Hydroxymethyl)-1-[2-(3,4,5-trimethoxyphenyl)ethyl]-1H-pyrrole-2-carbaldehyde

Formula: C17H21NO5 Molecular weight: 319.35234 g/mol InChI Key: WIGMDTGVKPNGIX-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C17H21NO5/c1-21-15-8-12(9-16(22-2)17(15)23-3)6-7-18-13(10-19)4-5-14(18)11-20/h4-5,8-10,20H,6-7,11H2,1-3H3

2218
Analogue 13: With 1-(2,3-Dihydro-1H-inden-1-yl)methanamine skeleton

Jimscaline

IUPAC: 1-(4,5,6-Trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine

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

InChI=1S/C13H19NO3/c1-15-11-6-10-8(7-14)4-5-9(10)12(16-2)13(11)17-3/h6,8H,4-5,7,14H2,1-3H3

PubChem CID: 44413589; ChemSpider: 21376014; Wikipedia: Jimscaline

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

McLean, TH; Chambers, JJ; Parrish, JC; Braden, MR; Marona-Lewicka, D; Kurrasch-Orbaugh, D; Nichols, DE. C-(4,5,6-trimethoxyindan-1-yl)methanamine: A mescaline analogue designed using a homology model of the 5-HT2A receptor. J. Med. Chem., 1 Jan 2006, 49 (14), 4269–4274. 370 kB. doi:10.1021/jm060272y

McLean, TH; Chambers, JJ; Parrish, JC; Braden, MR; Marona-Lewicka, D; Kurrasch-Orbaugh, D; Nichols, DE. C-(4,5,6-trimethoxyindan-1-yl)methanamine: A mescaline analogue designed using a homology model of the 5-HT2A receptor (additions and corrections). J. Med. Chem., 1 Jan 2006, 49 (25), 7558–7558. 51 kB. doi:10.1021/jm0612259

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.

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

619
Analogue 14: With 3-Phenylpropan-1-amine skeleton

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

7607
Analogue 15: With Benzyl-cyclic-amine skeleton

α,N-Butenyl-M

IUPAC: 2-(3,4,5-Trimethoxybenzyl)-1,2,3,6-tetrahydropyridine

Formula: C15H21NO3 Molecular weight: 263.33214 g/mol InChI Key: DQNJGXONRDHTII-UHFFFAOYSA-N

InChI=1S/C15H21NO3/c1-17-13-9-11(8-12-6-4-5-7-16-12)10-14(18-2)15(13)19-3/h4-5,9-10,12,16H,6-8H2,1-3H3

PubChem CID: 3046367; ChemSpider: 2308989

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 7

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

7608
Analogue 16: With Phenylethyl-cyclic-amine skeleton

N,N-Butenyl-M

IUPAC: 1-[2-(3,4,5-Trimethoxyphenyl)ethyl]-2,5-dihydro-1H-pyrrole

Formula: C15H21NO3 Molecular weight: 263.33214 g/mol InChI Key: AKDGIMIIYKLFLT-UHFFFAOYSA-N

InChI=1S/C15H21NO3/c1-17-13-10-12(6-9-16-7-4-5-8-16)11-14(18-2)15(13)19-3/h4-5,10-11H,6-9H2,1-3H3

PubChem CID: 3046365; ChemSpider: 2308987

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 8

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

7623
Analogue 17: With 2-Amino-1-phenylethanone skeleton

M-βk

IUPAC: 2-Amino-1-(3,4,5-trimethoxyphenyl)ethanone

Formula: C11H15NO4 Molecular weight: 225.2411 g/mol InChI Key: KWZWUFCLUMUDRD-UHFFFAOYSA-N

InChI=1S/C11H15NO4/c1-14-9-4-7(8(13)6-12)5-10(15-2)11(9)16-3/h4-5H,6,12H2,1-3H3

PubChem CID: 22281600; ChemSpider: 24794588

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 23

7855
Analogue 18: With 1,2,3,4-Tetrahydronaphthalen-2-amine skeleton

TMAT

IUPAC: 5,6,7-Trimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine

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

InChI=1S/C13H19NO3/c1-15-11-7-8-6-9(14)4-5-10(8)12(16-2)13(11)17-3/h7,9H,4-6,14H2,1-3H3

ChemSpider: 25795647

Shulgin Index: See #117 TMA; Table: 6 Page: 355 Row: 5

504
Analogue 19: With Phenyl-cyclic-amine skeleton

IUPAC: 3-(3,4,5-Trimethoxyphenyl)pyrrolidine

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

InChI=1S/C13H19NO3/c1-15-11-6-10(9-4-5-14-8-9)7-12(16-2)13(11)17-3/h6-7,9,14H,4-5,8H2,1-3H3

PubChem CID: 16754845; ChemSpider: 25433803

Świst, M; Wilamowski, J; Zuba, D; Kochana, J; Parczewski, A. Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA. Forensic Sci. Int., 10 May 2005, 149 (2–3), 181–192. 594 kB. doi:10.1016/j.forsciint.2004.06.016

Barreto, RL; Nascimbem, LBLR; Correiaa, CRD. Synthesis of the 3-(3,4,5-trimethoxyphenyl)-pyrrolidine: a new conformationally constrained mescaline analogue. Synth. Commun., 1 Jan 2007, 37 (12), 2011–2018. 76 kB. doi:10.1080/00397910701356504

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

1310
Analogue 20: With Benzyl-cyclic-amine skeleton

IUPAC: 2-(3,4,5-Trimethoxybenzyl)piperidine

Formula: C15H23NO3 Molecular weight: 265.34802 g/mol InChI Key: MCEXVSPHYNHEBP-UHFFFAOYSA-N

InChI=1S/C15H23NO3/c1-17-13-9-11(8-12-6-4-5-7-16-12)10-14(18-2)15(13)19-3/h9-10,12,16H,4-8H2,1-3H3

ChemSpider: 25580642

Wolters, RJ; Bej, AJ; Tanner, NS. Conformationally constrained analogs of mescaline. J. Pharm. Sci., 1 Jan 1974, 63 (1), 1379–1382. 451 kB. doi:10.1002/jps.2600630909

1311
Analogue 21: With Phenyl-cyclic-amine skeleton

IUPAC: 3-(3,4,5-Trimethoxyphenyl)piperidine

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

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

PubChem CID: 24904284; ChemSpider: 21394279

Wolters, RJ; Bej, AJ; Tanner, NS. Conformationally constrained analogs of mescaline. J. Pharm. Sci., 1 Jan 1974, 63 (1), 1379–1382. 451 kB. doi:10.1002/jps.2600630909

1312
Analogue 22: With Phenyl-cyclic-amine skeleton

IUPAC: 2-(3,4,5-Trimethoxyphenyl)morpholine

Formula: C13H19NO4 Molecular weight: 253.29426 g/mol InChI Key: HFNYSVVSGSCBTA-UHFFFAOYSA-N

InChI=1S/C13H19NO4/c1-15-10-6-9(12-8-14-4-5-18-12)7-11(16-2)13(10)17-3/h6-7,12,14H,4-5,8H2,1-3H3

PubChem CID: 24271528; ChemSpider: 23913884

Wolters, RJ; Bej, AJ; Tanner, NS. Conformationally constrained analogs of mescaline. J. Pharm. Sci., 1 Jan 1974, 63 (1), 1379–1382. 451 kB. doi:10.1002/jps.2600630909

1528
Analogue 23: With Phenylethyl-cyclic-amine skeleton

IUPAC: 1-Methyl-4-[2-(3,4,5-trimethoxyphenyl)ethyl]-1,4-diazepane

Formula: C17H28N2O3 Molecular weight: 308.41582 g/mol InChI Key: IUIIJNWSSCADDA-UHFFFAOYSA-N

InChI=1S/C17H28N2O3/c1-18-7-5-8-19(11-10-18)9-6-14-12-15(20-2)17(22-4)16(13-14)21-3/h12-13H,5-11H2,1-4H3

PubChem CID: 55460; ChemSpider: 50082

Majchrzak, MW; Kotełko, A; Guryn, R; Lambert, JB; Szadowska, A; Kowalczyk, K. Synthesis and action on the central nervous system of mescaline analogues containing piperazine or homopiperazine rings. J. Pharm. Sci., 1 Mar 1983, 72 (3), 304–306. 404 kB. doi:10.1002/jps.2600720324

1529
Analogue 24: With Phenylethyl-cyclic-amine skeleton

IUPAC: 1-Methyl-4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazine

Formula: C16H26N2O3 Molecular weight: 294.38924 g/mol InChI Key: YHFIBOIUDOXFTP-UHFFFAOYSA-N

InChI=1S/C16H26N2O3/c1-17-7-9-18(10-8-17)6-5-13-11-14(19-2)16(21-4)15(12-13)20-3/h11-12H,5-10H2,1-4H3

PubChem CID: 3070230; ChemSpider: 2329943

Majchrzak, MW; Kotełko, A; Guryn, R; Lambert, JB; Szadowska, A; Kowalczyk, K. Synthesis and action on the central nervous system of mescaline analogues containing piperazine or homopiperazine rings. J. Pharm. Sci., 1 Mar 1983, 72 (3), 304–306. 404 kB. doi:10.1002/jps.2600720324

1530
Analogue 25: With Phenylethyl-cyclic-amine skeleton

IUPAC: 1,4-Bis[2-(3,4,5-trimethoxyphenyl)ethyl]-1,4-diazepane

Formula: C27H40N2O6 Molecular weight: 488.6163 g/mol InChI Key: QDLANCOTZZOXRP-UHFFFAOYSA-N

InChI=1S/C27H40N2O6/c1-30-22-16-20(17-23(31-2)26(22)34-5)8-12-28-10-7-11-29(15-14-28)13-9-21-18-24(32-3)27(35-6)25(19-21)33-4/h16-19H,7-15H2,1-6H3

PubChem CID: 55462; ChemSpider: 50084

Majchrzak, MW; Kotełko, A; Guryn, R; Lambert, JB; Szadowska, A; Kowalczyk, K. Synthesis and action on the central nervous system of mescaline analogues containing piperazine or homopiperazine rings. J. Pharm. Sci., 1 Mar 1983, 72 (3), 304–306. 404 kB. doi:10.1002/jps.2600720324

1531
Analogue 26: With Phenylethyl-cyclic-amine skeleton

IUPAC: 1,4-Bis[2-(3,4,5-trimethoxyphenyl)ethyl]piperazine

Formula: C26H38N2O6 Molecular weight: 474.58972 g/mol InChI Key: WQYNOTLFJQARMW-UHFFFAOYSA-N

InChI=1S/C26H38N2O6/c1-29-21-15-19(16-22(30-2)25(21)33-5)7-9-27-11-13-28(14-12-27)10-8-20-17-23(31-3)26(34-6)24(18-20)32-4/h15-18H,7-14H2,1-6H3

PubChem CID: 3070232; ChemSpider: 2329945

Majchrzak, MW; Kotełko, A; Guryn, R; Lambert, JB; Szadowska, A; Kowalczyk, K. Synthesis and action on the central nervous system of mescaline analogues containing piperazine or homopiperazine rings. J. Pharm. Sci., 1 Mar 1983, 72 (3), 304–306. 404 kB. doi:10.1002/jps.2600720324

932
Analogue 27: With Phenylmethanamine skeleton

3,4,5-Trimethoxybenzylamine

IUPAC: 1-(3,4,5-Trimethoxyphenyl)methanamine

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

InChI=1S/C10H15NO3/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-5H,6,11H2,1-3H3

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

31 isomers:
16
Isomer 1

BOHD
2,5-Dimethoxy-β-hydroxy-4-methylphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: WCURBUJUIMRCCJ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7-4-11(15-3)8(9(13)6-12)5-10(7)14-2/h4-5,9,13H,6,12H2,1-3H3

PubChem CID: 44719489; ChemSpider: 21106263; Wikipedia: BOHD (psychedelic)

See also PiHKAL: #14 BOD #57 DME  

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

91
Isomer 2

IM
Isomescaline
2,3,4-Trimethoxyphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: PVLFQRLVSMMSQK-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-5-4-8(6-7-12)10(14-2)11(9)15-3/h4-5H,6-7,12H2,1-3H3

PubChem CID: 414332; ChemSpider: 366878; Wikipedia: Isomescaline

Shulgin Index: #72 IM; Table: 5 Page: 338 Row: 14

See also PiHKAL: #92 IP #153 3-TIM  

See also Transcripts: 3.363

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

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

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

168
Isomer 3

TMPEA
TMPEA-2
2C-O
2,4,5-Trimethoxyphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: GKATTZLSNLYADI-UHFFFAOYSA-N

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

PubChem CID: 151954; ChemSpider: 133931; Wikipedia: 2C-O

Shulgin Index: #124 TMPEA-2; Table: 5 Page: 344 Row: 21

See also PiHKAL: #35 2C-O-4 #157 TMA #158 TMA-2
See also TiHKAL: #13 Harmaline    

Jansen, MPJM. β-2,4,5-Trimethoxyphenylethylamine, an isomer of mescaline. Recl. Trav. Chim. Pays-Bas, 1931, 50 (4), 291–312. 1227 kB. doi:10.1002/recl.19310500403

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

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

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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

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.

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

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

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

307
Isomer 4

TMPEA-5
2C-TMA-5
2,3,6-Trimethoxyphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: SOARXDWNNULVNL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-4-5-10(14-2)11(15-3)8(9)6-7-12/h4-5H,6-7,12H2,1-3H3

PubChem CID: 414331; ChemSpider: 366877

Shulgin Index: See #121 TMA-5; Table: 5 Page: 353 Row: 1

See also PiHKAL: #161 TMA-5    

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

Matsuhiro, B; Furst, A. 2,3,6-Trimethoxynitrostyrene and its β-phenethylamine. J. Med. Chem., 1 Sep 1970, 13 (5), 973. 140 kB. doi:10.1021/jm00299a042

308
Isomer 5

TMPEA-6
2C-TMA-6
2,4,6-TMPEA
Ψ-2C-O
2,4,6-Trimethoxyphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CGUNKAXAEZSOFA-UHFFFAOYSA-N

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

PubChem CID: 21679959; ChemSpider: 10296635

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 25

See also PiHKAL: #162 TMA-6    

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

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

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

2213
Isomer 6

N-Me-3-DESMETHYL
N-Methyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N-methylphenethylamine

IUPAC: 2,3-Dimethoxy-5-[2-(methylamino)ethyl]phenol

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

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

PubChem CID: 57478610

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 6

5396
Isomer 7

2C-pEtOH
4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AYJLNTOOEWDDBF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6,13H,3-4,7,12H2,1-2H3

PubChem CID: 57474313

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

2414
Isomer 8

DOOH
4-Hydroxy-2,5-dimethoxyamphetamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: XZYTWVYCADLTTI-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-11(15-3)9(13)6-10(8)14-2/h5-7,13H,4,12H2,1-3H3

PubChem CID: 44265202; ChemSpider: 23108622

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 11

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

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

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

2394
Isomer 9

β-HO-2,5-DMA
2,5-Dimethoxynorephedrine

IUPAC: 2-Amino-1-(2,5-dimethoxyphenyl)propan-1-ol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: WJAJPNHVVFWKKL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3

PubChem CID: 6082; ChemSpider: 5857

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 26

Rusterholz, DB; Dryer, SE; Long, JP; Barfknecht, CF; Mott, J. Sedative and analgesic actions of methoxylated 2-aminotetralins; involvement of α1- and α2-adrenoreceptors. Eur. J. Pharmacol., 25 Jul 1980, 65 (2–3), 201–211. 870 kB. doi:10.1016/0014-2999(80)90393-3

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

6522
Isomer 10

β,3,4-HO-N-iPr-DHPEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: JWZZKOKVBUJMES-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3

PubChem CID: 3779; ChemSpider: 3647

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 22

6565
Isomer 11

MHMAOH

IUPAC: 4-{2-[Hydroxy(methyl)amino]propyl}-2-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CFCCDEBKSDYMQE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-8(12(2)14)6-9-4-5-10(13)11(7-9)15-3/h4-5,7-8,13-14H,6H2,1-3H3

Shulgin Index: See #33 DHA; Table: 4 Page: 329 Row: 15

6584
Isomer 12

N,N-Me-HME

IUPAC: 5-[2-(Dimethylamino)-1-hydroxyethyl]-2-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: VDYIKJCBMMLENB-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12(2)7-10(14)8-4-5-11(15-3)9(13)6-8/h4-6,10,13-14H,7H2,1-3H3

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 34

6608
Isomer 13

N-Me-DME

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: QSUCQAULQIAOEP-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-9(13)8-4-5-10(14-2)11(6-8)15-3/h4-6,9,12-13H,7H2,1-3H3

PubChem CID: 3084840; ChemSpider: 2341843

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 8

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!

6611
Isomer 14

β,3,4-TMPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CFEHWNSMGUKJEU-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-5-4-8(6-10(9)14-2)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 3014315; ChemSpider: 2282798

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 11

6619
Isomer 15

DMAOH
HOT-DMA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: QESZBOZKJCHKCL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-8(12-13)6-9-4-5-10(14-2)11(7-9)15-3/h4-5,7-8,12-13H,6H2,1-3H3

PubChem CID: 5190226; ChemSpider: 4361999

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 19

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

6626
Isomer 16

β-HO-DMA

IUPAC: 2-Amino-1-(3,4-dimethoxyphenyl)propan-1-ol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: JTIPLNDENHDFNZ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)11(13)8-4-5-9(14-2)10(6-8)15-3/h4-7,11,13H,12H2,1-3H3

PubChem CID: 13585934; ChemSpider: 12956236

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 26

6634
Isomer 17

β-HO-4,3-EMPEA

IUPAC: 2-Amino-1-(4-ethoxy-3-methoxyphenyl)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: TYSLQHFYCCDHQF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-10-5-4-8(9(13)7-12)6-11(10)14-2/h4-6,9,13H,3,7,12H2,1-2H3

PubChem CID: 16768023; ChemSpider: 11852804

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 34

6856
Isomer 18

β,2-HO-N-Me-5-MA

IUPAC: 2-[1-Hydroxy-2-(methylamino)propyl]-4-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: OZBWNQQJAATCCF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12-2)11(14)9-6-8(15-3)4-5-10(9)13/h4-7,11-14H,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 6

6865
Isomer 19

β-HO-N-Me-2,5-DMPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AFGIOLGUENMUPF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-10(13)9-6-8(14-2)4-5-11(9)15-3/h4-6,10,12-13H,7H2,1-3H3

PubChem CID: 46244; ChemSpider: 42102

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 15

6867
Isomer 20

BODM

IUPAC: 2-(2,5-Dimethoxyphenyl)-2-methoxyethan-1-amine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: HRQOYIJXQHSHOE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-8-4-5-10(14-2)9(6-8)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 10420680; ChemSpider: 8596110

Shulgin Index: See #14 BOB; Table: 4 Page: 335 Row: 17

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

6868
Isomer 21

β-HO,Me-2,5-DMPEA

IUPAC: 1-Amino-2-(2,5-dimethoxyphenyl)propan-2-ol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AURMVDWBJNLYHE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-11(13,7-12)9-6-8(14-2)4-5-10(9)15-3/h4-6,13H,7,12H2,1-3H3

PubChem CID: 46246; ChemSpider: 42104

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 18

6906
Isomer 22

β,2-HO-N-Me-5-EPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: YOIOXOFQHDQNEP-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-8-4-5-10(13)9(6-8)11(14)7-12-2/h4-6,11-14H,3,7H2,1-2H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 6

6909
Isomer 23

β,2-HO-5-EA

IUPAC: 2-(2-Amino-1-hydroxypropyl)-4-ethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: LQFDWMDHTDNEFB-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-8-4-5-10(13)9(6-8)11(14)7(2)12/h4-7,11,13-14H,3,12H2,1-2H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 9

6926
Isomer 24

β-HO-N-Me-3,5-DMPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RJKGQUALUZJVGM-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-11(13)8-4-9(14-2)6-10(5-8)15-3/h4-6,11-13H,7H2,1-3H3

PubChem CID: 62774486

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 26

6972
Isomer 25

β-HO-N-Me-2,6-DMPEA

IUPAC: 1-(2,6-Dimethoxyphenyl)-2-(methylamino)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: HSYSLTPRNLNOAG-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-8(13)11-9(14-2)5-4-6-10(11)15-3/h4-6,8,12-13H,7H2,1-3H3

PubChem CID: 22574395; ChemSpider: 11474127

Shulgin Index: See #48 2,6-DMPEA; Table: 4 Page: 337 Row: 22

7071
Isomer 26

TMPEA-4

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: GERNGXILVRWWGB-UHFFFAOYSA-N

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

PubChem CID: 413872; ChemSpider: 366438

Shulgin Index: See #120 TMA-4; Table: 5 Page: 339 Row: 21

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

7210
Isomer 27

N-HO-2C-D

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: YRZMJKDZPVHTBF-UHFFFAOYSA-N

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

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 10

7559
Isomer 28

α-Me-3-DESMETHYL

IUPAC: 5-(2-Aminopropyl)-2,3-dimethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CEDBRNZPRXITHE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-9(13)11(15-3)10(6-8)14-2/h5-7,13H,4,12H2,1-3H3

ChemSpider: 26495745

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 9

7568
Isomer 29

DESMETHYL-M

IUPAC: 2,6-Dimethoxy-4-[2-(methylamino)ethyl]phenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CQRXQNMRCIMDPZ-UHFFFAOYSA-N

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

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 18

7572
Isomer 30

α-Me-DESMETHYL

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: NCPDWXQFKKIRGY-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-9(14-2)11(13)10(6-8)15-3/h5-7,13H,4,12H2,1-3H3

ChemSpider: 26495039

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 22

933
Isomer 31

N-Methyl-3,4,5-trimethoxybenzylamine

IUPAC: N-Methyl-1-(3,4,5-trimethoxyphenyl)methanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: LFULMNRPABTDDQ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-8-5-9(13-2)11(15-4)10(6-8)14-3/h5-6,12H,7H2,1-4H3

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

Show all 135 analogues and isomers Show only the 12 N analogues Show only the 16 α analogues Show only the three β analogues Show only the three R2 analogues Show only the five R3 analogues Show only the 33 R4 analogues Show only the four R5 analogues Show only the one R4,5 analogues Show only the 27 skeleton analogues
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