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

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

IUPAC: N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine

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

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

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

IUPAC: N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine

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

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

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

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

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)ethanamine

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.

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-CCCI-M

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

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

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

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

N-CPM-M

IUPAC: N-(Cyclopropylmethyl)-2-(3,4,5-trimethoxyphenyl)ethanamine

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

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

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

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

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

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

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

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

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

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

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

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

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

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

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

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

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. 1175 kB. doi:10.1021/jm00256a016

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

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

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.

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; 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

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

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

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

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

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

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.

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. 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.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

ChemSpider: 23553050

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

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

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

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

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

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

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

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

IUPAC: 2-Methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine

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

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

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)ethanamine

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

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

TeMPEA

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

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

2-CM

IUPAC: 2-(2-Chloro-3,4,5-trimethoxyphenyl)ethanamine

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

2-BM

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

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.

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

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

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

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

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

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

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

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

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

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

3-Cl-4,5-DMPEA

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

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

3,4,5-BMM

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

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

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

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

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

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

CPM
Cyclopropylmescaline
4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine

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

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

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

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

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

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

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

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; 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

DMPEA
3,4-Dimethoxyphenethylamine

IUPAC: 2-(3,4-Dimethoxyphenyl)ethanamine

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

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

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.

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

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

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

Glennon, RA; 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

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!.

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

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

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

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

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

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

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

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

3-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]ethanamine

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

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

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

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

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

LOPHOPHINE
Lophophine
3-Methoxy-4,5-methylenedioxyphenethylamine

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

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

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

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. 874 kB. doi:10.1080/02791072.2008.10400635

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

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

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

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

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

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

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

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; 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.

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

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

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

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; 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; 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.

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

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

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

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

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

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

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

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

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

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 (additions and corrections). J. Med. Chem., 1 Jan 2006, 49 (25), 7558–7558. 51 kB. doi:10.1021/jm0612259

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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)

IM
Isomescaline
2,3,4-Trimethoxyphenethylamine

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

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

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

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

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

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

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

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

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

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

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.

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

IUPAC: 2-(2,3,6-Trimethoxyphenyl)ethanamine

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

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

IUPAC: 2-(2,4,6-Trimethoxyphenyl)ethanamine

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

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

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

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.

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

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

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

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

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

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

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

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

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!.

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

β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine

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

DMAOH

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

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

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

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

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

BODM

IUPAC: 2-(2,5-Dimethoxyphenyl)-2-methoxyethanamine

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

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

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

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

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

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

TMPEA-4

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

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

N-HO-2C-D

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxyethanamine