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

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

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

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

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

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

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

See also Pharmacology notes I:

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

See also Pharmacology notes II:

p. 227, TMA: Subjective response

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

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.

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.

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

N-HO-TMA

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

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

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

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 1

IUPAC: N,N-Bis[1-(3,4,5-trimethoxyphenyl)propan-2-yl]formamide

Formula: C25H35NO7 Molecular weight: 461.5479 g/mol InChI Key: RBGOWSGUCNDBNE-UHFFFAOYSA-N

InChI=1S/C25H35NO7/c1-16(9-18-11-20(28-3)24(32-7)21(12-18)29-4)26(15-27)17(2)10-19-13-22(30-5)25(33-8)23(14-19)31-6/h11-17H,9-10H2,1-8H3

Błachut, D; Danikiewicz, W; Wojtasiewicz, K; Olejnik, M; Kalinowska, I; Szawkało, J; Czarnocki, Z. The synthesis, mass spectrometric properties and identification of some N,N-di-(β-arylisopropyl)formamides related to the synthesis of ring-modified amphetamines. Forensic Sci. Int., 20 Mar 2011, 206 (1), 197–206. 760 kB. doi:10.1016/j.forsciint.2010.08.007

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

See also PiHKAL:	#96 M

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

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

TeMA

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

Formula: C14H23NO4 Molecular weight: 269.33672 g/mol InChI Key: COTALDZATVLUNM-UHFFFAOYSA-N

InChI=1S/C14H23NO4/c1-9(15-2)7-10-8-11(16-3)13(18-5)14(19-6)12(10)17-4/h8-9,15H,7H2,1-6H3

Shulgin Index: #113 TeMA; Table: 6 Page: 355 Row: 4

N-Me-3,5-DMA

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

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: WVKXXCDIUCCHOE-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-9(13-2)5-10-6-11(14-3)8-12(7-10)15-4/h6-9,13H,5H2,1-4H3

PubChem CID: 22706901; ChemSpider: 11575386

Shulgin Index: See #39 3,5-DMA; Table: 4 Page: 336 Row: 29

DMMA

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

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: BUWHCARWGYFQPE-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-9(13-2)7-10-5-6-11(14-3)12(8-10)15-4/h5-6,8-9,13H,7H2,1-4H3

PubChem CID: 12235308; ChemSpider: 10467995

MMDMA
3-Methoxy-N-methyl-4,5-methylenedioxyamphetamine

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

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

InChI=1S/C12H17NO3/c1-8(13-2)4-9-5-10(14-3)12-11(6-9)15-7-16-12/h5-6,8,13H,4,7H2,1-3H3

PubChem CID: 547094; ChemSpider: 476196; Wikipedia: MMDMA (drug)

Shulgin Index: See #97 MMDA; Table: 5 Page: 352 Row: 11

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

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

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

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

PubChem CID: 28236; ChemSpider: 26269

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

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

See also Pharmacology notes I:	p. 158, TMT

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

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

See also PiHKAL:	#96 M

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

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

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

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

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

See also PiHKAL:	#132 MMDA	#157 TMA

Shulgin, AT. 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

See also PiHKAL:	#157 TMA

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

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

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

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

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

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

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

See also PiHKAL:	#157 TMA

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

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

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

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

IUPAC: 2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine

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

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

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

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

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

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

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

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

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

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

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

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

See also PiHKAL:	#72 E

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

2C-O-4
4-Isopropoxy-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropoxyphenethylamine

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

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

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

PubChem CID: 44719510; ChemSpider: 21106225; Wikipedia: 2C-O-4

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 5

EMM
2-Ethoxy-4,5-dimethoxyamphetamine
4,5-Dimethoxy-2-ethoxyamphetamine

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

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

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

PubChem CID: 44719565; ChemSpider: 21106299; Wikipedia: EMM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 28

See also PiHKAL:	#73 EEE #121 MEE	#122 MEM #136 MME

See also Pharmacology notes I:	p. 60, EMM: Subacute evaluation

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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

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.

MEM
2,5-Dimethoxy-4-ethoxyamphetamine

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

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

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

PubChem CID: 542053; ChemSpider: 472023; Wikipedia: 2,5-Dimethoxy-4-ethoxyamphetamine

Shulgin Index: #87 MEM; Table: 5 Page: 344 Row: 32

See also PiHKAL:	#35 2C-O-4 #72 E #73 EEE	#74 EEM #76 EMM #93 IRIS	#121 MEE #136 MME #138 MPM
See also TiHKAL:	#19 5-HO-DMT	#46 5-MeS-DMT

See also Pharmacology notes I:	p. 78.1, Subacute effects of MEM (XV-136) p. 80, MEM: Marginal effects p. 112, MEM: Subjective response p. 151, MEM
See also Pharmacology notes II:	app. 4, Experiment for Death Valley p. 229, MEM p. 260, MEM p. 270, MEM p. 380, MEM

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

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

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

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

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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.

MME
2,4-Dimethoxy-5-ethoxyamphetamine

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

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

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

PubChem CID: 44719602; ChemSpider: 21106338; Wikipedia: MME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 26

See also PiHKAL:	#73 EEE #75 EME	#121 MEE #122 MEM

See also Pharmacology notes I:	p. 77, MME: Subacute evaluation

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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

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

See also PiHKAL:	#119 ME	#163 3-TME

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

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.

SB
Symbescaline
3,5-Diethoxy-4-methoxyphenethylamine

IUPAC: 2-(3,5-Diethoxy-4-methoxyphenyl)ethanamine

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

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

PubChem CID: 44374890; ChemSpider: 21106384; Wikipedia: Symbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 33

See also PiHKAL:	#9 ASB	#163 3-TME

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

1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane

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

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

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

See also PiHKAL:	#8 ARIADNE

4C-TMPEA-6
1-(2,4,6-Trimethoxyphenyl)-2-aminobutane

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

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

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

PubChem CID: 43565966

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 28

See also PiHKAL:	#8 ARIADNE

BOED
2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-2-ethoxyethanamine

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

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

See also PiHKAL:	#14 BOD

Coutts, RT; Malicky, JL. The synthesis of analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some ring-methoxylated 1-amino- and 2-aminoindanes. Can. J. Chem., 1 Feb 1974, 52 (3), 381–389. 615 kB. doi:10.1139/v74-061

Z-7.2
4-Methyl-2,3,6-trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxy-4-methylphenyl)propan-2-amine

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

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

See also PiHKAL:	#69 Ψ-DOM

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

See also PiHKAL:	#96 M

N-Me-TMA-2
METHYL-TMA-2
N-Methyl-2,4,5-trimethoxyamphetamine

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

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

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

PubChem CID: 69454104

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 24

See also PiHKAL:	#126 METHYL-DMA

See also Pharmacology notes I:	p. 59, N-Me-TMA-2: Subacute evaluation

N-Me-TMA-6
METHYL-TMA-6
N-Methyl-2,4,6-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,6-trimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 69393054

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 27

See also PiHKAL:	#126 METHYL-DMA

2C-O-7
2C-O-7
2,5-Dimethoxy-4-n-propoxyphenethylamine

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

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

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

PubChem CID: 57474252

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 35

See also PiHKAL:	#35 2C-O-4

Salbutamol
N-tert-Butyl-β,4-dihydroxy-3-(hydroxymethyl)phenethylamine

IUPAC: 4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

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

InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

PubChem CID: 2083; ChemSpider: 1999; Wikipedia: Salbutamol

homo-TMA-2

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

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

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

PubChem CID: 3839009; ChemSpider: 3064644

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 27

homo-TMA-3

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

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

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

PubChem CID: 3041182; ChemSpider: 2304487

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 29

homo-TMA-6

IUPAC: 4-(2,4,6-Trimethoxyphenyl)butan-2-amine

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

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

PubChem CID: 3041180; ChemSpider: 2304485

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 30

N,N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethanamine

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

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

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 13

β-HO-β,N,N-Me-2,5-DMPEA

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

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

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

PubChem CID: 50632; ChemSpider: 45892

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 20

β-HO-N,N-Me-2,5-DMA

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

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

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

PubChem CID: 46240; ChemSpider: 42098

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 28

β-HO-N-Me-2,5-DEPEA

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

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

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

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 13

β-HO-2,5-DEA

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

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

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

PubChem CID: 11253430; ChemSpider: 9428457

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 15

N-Me-TMA-3

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

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

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

ChemSpider: 21476716

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 16

4C-TMPEA-3

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

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

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

PubChem CID: 43566032

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 17

4C-HM

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

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

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

PubChem CID: 20315288

Shulgin Index: See #118 TMA-2; Table: 5 Page: 343 Row: 5

BOE

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethanamine

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

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

PubChem CID: 10331826; ChemSpider: 8507286

Shulgin Index: See #14 BOB; Table: 5 Page: 343 Row: 12

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

DOEH

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

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

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

PubChem CID: 14201978; ChemSpider: 21415075

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 25

4C-MeO

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

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

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

PubChem CID: 43566022

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 27

DESMETHYL-iPr

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

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

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

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 20

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

DOMOM

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

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

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

PubChem CID: 10934687; ChemSpider: 9109923

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B