3C-CPM
4-Cyclopropylmethoxy-3,5-dimethoxyamphetamine

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

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

InChI=1S/C15H23NO3/c1-10(16)6-12-7-13(17-2)15(14(8-12)18-3)19-9-11-4-5-11/h7-8,10-11H,4-6,9,16H2,1-3H3

PubChem CID: 54929189

See also PiHKAL:	#37 CPM	#72 E

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

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

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.

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

IUPAC: 2-(4-Butoxy-3,5-dimethoxyphenyl)ethanamine

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

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

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

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

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.

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

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

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

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

IUPAC: 2-(3,5-Dimethoxy-4-methylphenyl)ethanamine

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

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

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

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

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

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

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

See also Pharmacology notes II:	p. 217, Escaline

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

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

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

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

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

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.

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

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

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

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

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

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

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

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

Nichols, DE; 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.

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

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

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

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

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

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

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

See also Pharmacology notes I:	p. 1, Mescaline: Subjective response p. 2, Mescaline: Subjective response p. 3, Mescaline: Subjective response p. 4, Mescaline: Subjective response p. 5, Mescaline: Subjective response p. 6, Mescaline: Subjective response p. 7, Mescaline: Basis for M.U. calculation
See also Pharmacology notes II:	app. 5, Untitled p. 321, Mescaline

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

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

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

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

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

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

Ogunbodede, O; McCombs, D; Trout, K; Daley, P; 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

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

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

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

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

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

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

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

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

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

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

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.

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.

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

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.

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

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

Fenderson5555. Two syntheses of mescaline. 21 Mar 2011.

MAL
Methallylescaline
3,5-Dimethoxy-4-methallyloxyphenethylamine

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

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

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

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine

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

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

PubChem CID: 15102790; ChemSpider: 10439596; Wikipedia: Proscaline

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

See also PiHKAL:	#72 E #80 F-22	#123 MEPEA #141 PE	#163 3-TME

See also Pharmacology notes II:	p. 209, Proscaline

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

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

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

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

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.

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

PE
Phenescaline
3,5-Dimethoxy-4-phenethyloxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(2-phenylethoxy)phenyl]ethanamine

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

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]ethanamine

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

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

IUPAC: 2-[4-(Butylsulfanyl)-3,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C14H23NO2S/c1-4-5-8-18-14-12(16-2)9-11(6-7-15)10-13(14)17-3/h9-10H,4-8,15H2,1-3H3

PubChem CID: 44349865; ChemSpider: 21106390; Wikipedia: Thiobuscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 31

See also PiHKAL:	#151 4-TE	#174 TP

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

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

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

IUPAC: 2-[4-(Ethylsulfanyl)-3,5-dimethoxyphenyl]ethanamine

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

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

PubChem CID: 44349999; ChemSpider: 21106391; Wikipedia: Thioescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 28

See also PiHKAL:	#150 3-TE	#163 3-TME	#174 TP

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

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

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

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

IUPAC: 2-[3,5-Dimethoxy-4-(methylsulfanyl)phenyl]ethanamine

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

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

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

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

See also PiHKAL:	#150 3-TE	#151 4-TE	#153 3-TIM	#163 3-TME

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

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

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

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

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 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

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.

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

IUPAC: 2-[3,5-Dimethoxy-4-(propylsulfanyl)phenyl]ethanamine

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

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

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

BZ
4-Benzyloxy-3,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Benzyloxy)-3,5-dimethoxyphenyl]ethanamine

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.

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

IUPAC: 2-[3,5-Dimethoxy-4-(pentyloxy)phenyl]ethanamine

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’.

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

IUPAC: 2-[4-(Hexyloxy)-3,5-dimethoxyphenyl]ethanamine

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

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

IUPAC: 2-[4-(Heptyloxy)-3,5-dimethoxyphenyl]ethanamine

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

FEM
4-(2-Fluoroethyloxy)-3,5-dimethoxyphenethylamine

IUPAC: 2-[4-(2-Fluoroethoxy)-3,5-dimethoxyphenyl]ethanamine

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

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

F2EM
4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine

IUPAC: 2-[4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenyl]ethanamine

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

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

F3EM
3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine

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

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

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

IUPAC: 2-[4-(3-Fluoropropoxy)-3,5-dimethoxyphenyl]ethanamine

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

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

IB
4-Isobutoxy-3,5-dimethoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(2-methylpropoxy)phenyl]ethanamine

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

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

IUPAC: 2-[3,5-Dimethoxy-4-(2-methoxyethoxy)phenyl]ethanamine

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

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

IUPAC: 2-(4-Bromo-3,5-dimethoxyphenyl)ethanamine

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.

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

3,5-DMPEA

IUPAC: 2-(3,5-Dimethoxyphenyl)ethanamine

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

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

Difluoroisoproscaline

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

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

Trifluoroproscaline

IUPAC: 2-[3,5-Dimethoxy-4-(3,3,3-trifluoropropoxy)phenyl]ethanamine

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

Trifluoromescaline

IUPAC: 2-[3,5-Dimethoxy-4-(trifluoromethoxy)phenyl]ethanamine

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

Difluoromescaline

IUPAC: 2-[4-(Difluoromethoxy)-3,5-dimethoxyphenyl]ethanamine

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

MAL
Methallylescaline
3,5-Dimethoxy-4-methallyloxyphenethylamine

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

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

3C-AL
4-Allyloxy-3,5-dimethoxyamphetamine

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

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

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

PubChem CID: 44350107; ChemSpider: 23206506

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 16

See also PiHKAL:	#2 AL

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

DOCOE
2,5-Dimethoxy-4-propanonylamphetamine

IUPAC: 1-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]propan-1-one

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

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

PubChem CID: 44265278; ChemSpider: 23108731

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 28

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

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

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

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