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PiHKAL#162 TMA-6; SI#122 TMA-6
162
Variant: N α R2 R3 R4 R6 skeleton isomers all
Analogues: 2 2 3 2 15 2 1 29 56

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

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

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

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

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

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

See also Transcripts: 1.72, 1.93, 1.93.2, 1.98, 1.99, 1.150, 1.188, 1.189, 2.253

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

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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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.

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

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

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

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

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

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

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

Shulgin, AT; Sargent, T; Naranjo, C. 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.

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

Two N analogues:
290
Analogue 1: Adding Methyl at N

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    

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

541
Analogue 2: Adding Benzyloxy at N

N-Benzoyl-TMA-6

IUPAC: N-[1-(2,4,6-Trimethoxyphenyl)propan-2-yl]benzamide

Formula: C19H23NO4 Molecular weight: 329.39022 g/mol InChI Key: QKIRRXZGIIENOO-UHFFFAOYSA-N

InChI=1S/C19H23NO4/c1-13(20-19(21)14-8-6-5-7-9-14)10-16-17(23-3)11-15(22-2)12-18(16)24-4/h5-9,11-13H,10H2,1-4H3,(H,20,21)

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

Two α analogues:
190
Analogue 1: Substituting Ethyl for Methyl at α

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    
308
Analogue 2: Removing Methyl at α

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

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

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

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

PubChem CID: 21679959; ChemSpider: 10296635

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

See also PiHKAL: #162 TMA-6    

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

Three R2 analogues:
7772
Analogue 1: Substituting Bromo for Methoxy at R2

2,4,6-DOB

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

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: QEZQLIBEVDLHCE-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(12)5-8(14-2)6-11(9)15-3/h5-7H,4,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 22

7774
Analogue 2: Substituting Ethyl for Methoxy at R2

2,4,6-DOET

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

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: QQJTYGJGZRETQO-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-11(15-3)8-13(16-4)12(10)6-9(2)14/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57486957

Shulgin Index: See #56 DOET; Table: 5 Page: 353 Row: 24

573
Analogue 3: Substituting Chloro for Methoxy at R2

2,4,6-DOC
2-Chloro-4,6-dimethoxyamphetamine

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

Formula: C11H16ClNO2 Molecular weight: 229.70324 g/mol InChI Key: LETSMZRHUXLNTC-UHFFFAOYSA-N

InChI=1S/C11H16ClNO2/c1-7(13)4-9-10(12)5-8(14-2)6-11(9)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 11184685; ChemSpider: 9359770

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

Two R3 analogues:
7874
Analogue 1: Adding Methoxy at R3

TeMA-2

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

Formula: C13H21NO4 Molecular weight: 255.31014 g/mol InChI Key: DJUKQNSUJQBHFW-UHFFFAOYSA-N

InChI=1S/C13H21NO4/c1-8(14)6-9-10(15-2)7-11(16-3)13(18-5)12(9)17-4/h7-8H,6,14H2,1-5H3

Shulgin Index: See #115 TeMPEA-3; Table: 6 Page: 355 Row: 24

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

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

1077
Analogue 2: Adding Iodo at R3

3-I-TMA-6

IUPAC: 1-(3-Iodo-2,4,6-trimethoxyphenyl)propan-2-amine

Formula: C12H18INO3 Molecular weight: 351.18069 g/mol InChI Key: PSDRKRQLERYHON-UHFFFAOYSA-N

InChI=1S/C12H18INO3/c1-7(14)5-8-9(15-2)6-10(16-3)11(13)12(8)17-4/h6-7H,5,14H2,1-4H3

Dawson, BA; Black, DB; Sy, W; Graham, K. 13C NMR of some iodinated methoxy-amphetamines. Magn. Reson. Chem., 1 Sep 1994, 32 (9), 557–558. 171 kB. doi:10.1002/mrc.1260320913

15 R4 analogues:
69
Analogue 1: Substituting Methyl for Methoxy at R4

Ψ-DOM
Z-7
4-Methyl-2,6-dimethoxyamphetamine
2,6-Dimethoxy-4-methylamphetamine

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

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

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

PubChem CID: 13753734; ChemSpider: 21106372; Wikipedia: psi-DOM

Shulgin Index: See #60 DOM; Table: 5 Page: 353 Row: 18

See also PiHKAL: #42 Ψ-2C-T-4 #68 DOM #162 TMA-6

See also Transcripts: 1.166, 1.167, 1.190

See also Pharmacology notes I: p. 166, Ψ-DOM
p. 167, Ψ-DOM
p. 190, Ψ-DOM

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

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Chambers, JJ; Kurrasch-Orbaugh, DM; Nichols, DE. Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: Effects on 5-HT2A/2C receptor affinity. Bioorg. Med. Chem. Lett., 1 Jan 2002, 12 (15), 1997–1999. 100 kB. doi:10.1016/S0960-894X(02)00306-2

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

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

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

2163
Analogue 2: Removing Methoxy at R4

2,6-DMA
2,6-Dimethoxyamphetamine

IUPAC: 1-(2,6-Dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 141048; ChemSpider: 124412

Shulgin Index: #37 2,6-DMA; Table: 4 Page: 337 Row: 23

See also PiHKAL: #55 3,4-DMA #124 META-DOB  

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

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

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Anal. Chem., 1974, 57 (1), 70–78. 426 kB.

2336
Analogue 3: Substituting Phenylpropyl for Methoxy at R4

2,6-Dimethoxy-4-phenylpropylamphetamine

IUPAC: 1-[2,6-Dimethoxy-4-(3-phenylpropyl)phenyl]propan-2-amine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: BLTUEXQAJVYGCR-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-15(21)12-18-19(22-2)13-17(14-20(18)23-3)11-7-10-16-8-5-4-6-9-16/h4-6,8-9,13-15H,7,10-12,21H2,1-3H3

PubChem CID: 10064188; ChemSpider: 8239728

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

371
Analogue 4: Substituting Methylthio for Methoxy at R4

Ψ-ALEPH
2,6-Dimethoxy-4-methylthioamphetamine

IUPAC: 1-[2,6-Dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine

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

InChI=1S/C12H19NO2S/c1-8(13)5-10-11(14-2)6-9(16-4)7-12(10)15-3/h6-8H,5,13H2,1-4H3

PubChem CID: 11300389; ChemSpider: 9475366

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 31

See also PiHKAL: #162 TMA-6    

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

374
Analogue 5: Substituting Bromo for Methoxy at R4

4,2,6-DOB
Ψ-DOB
4-Bromo-2,6-dimethoxyamphetamine

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

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: LLTVNYHNUJIHOU-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(14-2)5-8(12)6-11(9)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 158251; ChemSpider: 139237

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 15

See also PiHKAL: #162 TMA-6    

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

373
Analogue 6: Substituting Ethyl for Methoxy at R4

4,2,6-DOET
Ψ-DOET
4-Ethyl-2,6-dimethoxyamphetamine

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

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: DVBZPPVSVLQDKE-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-12(15-3)11(6-9(2)14)13(8-10)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57498518

Shulgin Index: See #56 DOET; Table: 5 Page: 353 Row: 19

See also PiHKAL: #162 TMA-6    

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

372
Analogue 7: Substituting Iodo for Methoxy at R4

Ψ-DOI
4-Iodo-2,6-dimethoxyamphetamine

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

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: JKWXVAUZJUBUFC-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-7(13)4-9-10(14-2)5-8(12)6-11(9)15-3/h5-7H,4,13H2,1-3H3

See also PiHKAL: #162 TMA-6    

Sy, W. Iodination of methoxyamphetamines with iodine and silver sulphate. Tetrahedron Lett., 24 Sep 1993, 34 (39), 6223–6224. 133 kB. doi:10.1016/S0040-4039(00)73715-4

7766
Analogue 8: Substituting Trifluoromethyl for Methoxy at R4

DOTFM-6

IUPAC: 1-[2,6-Dimethoxy-4-(trifluoromethyl)phenyl]propan-2-amine

Formula: C12H16F3NO2 Molecular weight: 263.2561496 g/mol InChI Key: DZZWUCOCRKSNLR-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2/c1-7(16)4-9-10(17-2)5-8(12(13,14)15)6-11(9)18-3/h5-7H,4,16H2,1-3H3

Shulgin Index: See #63 DOTFM; Table: 5 Page: 353 Row: 16

7782
Analogue 9: Substituting Ethylthio for Methoxy at R4

Ψ-ALEPH-2

IUPAC: 1-[4-(Ethylsulfanyl)-2,6-dimethoxyphenyl]propan-2-amine

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

InChI=1S/C13H21NO2S/c1-5-17-10-7-12(15-3)11(6-9(2)14)13(8-10)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 11335306; ChemSpider: 9510252

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 32

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

481
Analogue 10: Substituting 2,2-Difluoroethyl for Methoxy at R4

Ψ-DODFE

IUPAC: 1-[4-(2,2-Difluoroethyl)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H19F2NO2 Molecular weight: 259.2922664 g/mol InChI Key: QVTWZVXRAGWKCV-UHFFFAOYSA-N

InChI=1S/C13H19F2NO2/c1-8(16)4-10-11(17-2)5-9(7-13(14)15)6-12(10)18-3/h5-6,8,13H,4,7,16H2,1-3H3

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

479
Analogue 11: Substituting 2,2,2-Trifluoroethoxy for Methoxy at R4

Ψ-MTFEM

IUPAC: 1-[2,6-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]propan-2-amine

Formula: C13H18F3NO3 Molecular weight: 293.2821296 g/mol InChI Key: PGMSUWCSIAGHKB-UHFFFAOYSA-N

InChI=1S/C13H18F3NO3/c1-8(17)4-10-11(18-2)5-9(6-12(10)19-3)20-7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3

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

478
Analogue 12: Substituting 2,2-Difluoroethoxy for Methoxy at R4

Ψ-MDFEM

IUPAC: 1-[4-(2,2-Difluoroethoxy)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H19F2NO3 Molecular weight: 275.2916664 g/mol InChI Key: NBJZLMLXGXIWJW-UHFFFAOYSA-N

InChI=1S/C13H19F2NO3/c1-8(16)4-10-11(17-2)5-9(6-12(10)18-3)19-7-13(14)15/h5-6,8,13H,4,7,16H2,1-3H3

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

477
Analogue 13: Substituting 2-Fluoroethyoxy for Methoxy at R4

Ψ-MFEM

IUPAC: 1-[4-(2-Fluoroethoxy)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H20FNO3 Molecular weight: 257.3012032 g/mol InChI Key: ZWTSZKWQJSFARQ-UHFFFAOYSA-N

InChI=1S/C13H20FNO3/c1-9(15)6-11-12(16-2)7-10(18-5-4-14)8-13(11)17-3/h7-9H,4-6,15H2,1-3H3

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

951
Analogue 14: Substituting 2,2,2-Trifluoroethyl for Methoxy at R4

Ψ-DOTFE

IUPAC: 1-[4-(2,2,2-Triifluoroethyl)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H18F3NO2 Molecular weight: 277.2827296 g/mol InChI Key: VULLDPCMWBQMSH-UHFFFAOYSA-N

InChI=1S/C13H18F3NO2/c1-8(17)4-10-11(18-2)5-9(6-12(10)19-3)7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3

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

786
Analogue 15: Substituting Difluoromethoxy for Methoxy at R4

Ψ-DODFMO

Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: XEJQGOZXVLCLQY-UHFFFAOYSA-N

InChI=1S/C12H17F2NO3/c1-7(15)4-9-10(16-2)5-8(18-12(13)14)6-11(9)17-3/h5-7,12H,4,15H2,1-3H3

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

Two R6 analogues:
53
Analogue 1: Removing Methoxy at R6

2,4-DMA
2,4-Dimethoxyamphetamine

IUPAC: 1-(2,4-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DQWOZMUBHQPFFF-UHFFFAOYSA-N Properties: Essential amphetamine

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

PubChem CID: 417604; ChemSpider: 124411; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #35 2,4-DMA; Table: 4 Page: 327 Row: 11

See also PiHKAL: #55 3,4-DMA #124 META-DOB #157 TMA

See also Transcripts: 1.144

See also Pharmacology notes I: p. 144, 2,4-DMA

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Anal. Chem., 1974, 57 (1), 70–78. 426 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.

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; 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

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; 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

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

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

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

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

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

243
Analogue 2: Substituting Methyl for Methoxy at R6

6-Me-2,4-DOM
Z-7.1
2,4-Dimethoxy-6-methylamphetamine

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

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

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

Shulgin Index: See #60 DOM; Table: 5 Page: 353 Row: 23

See also PiHKAL: #69 Ψ-DOM    

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

One skeleton analogue:
623
Analogue 1: With 3-Phenylpropan-1-amine skeleton

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

29 isomers:
14
Isomer 1

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

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

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

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

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

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

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

See also Transcripts: 4.462

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

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

72
Isomer 2

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

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

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

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

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

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

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

See also Transcripts: 2.217, 3.365, 3.397

See also Pharmacology notes II: p. 217, Escaline

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

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

Benington, F; Morin, RD; Clarke, LC. Synthesis of 4-hydroxy- and 4-ethoxy-3,5-dimethoxy-β-phenethylamines. J. Am. Chem. Soc., 1 Nov 1954, 76 (21), 5555–5556. 307 kB. doi:10.1021/ja01650a084

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

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

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

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

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

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

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

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

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

119
Isomer 3

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

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

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

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

PubChem CID: 44350068; ChemSpider: 21106344; Wikipedia: Metaescaline

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

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

See also Transcripts: 3.409

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

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

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

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

157
Isomer 4

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

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

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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

158
Isomer 5

TMA-2
2,4,5-Trimethoxyamphetamine

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

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

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

PubChem CID: 31014; ChemSpider: 28773; Drugs Forum: TMA-2; Erowid: TMA-2; Wikipedia: Trimethoxyamphetamine

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

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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

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

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

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

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

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

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

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

Anon. Report on the risk assessment of TMA-2, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

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

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

159
Isomer 6

TMA-3
2,3,4-Trimethoxyamphetamine

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

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

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

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

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

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

See also Transcripts: 1.72, 1.85, 1.85.2

See also Pharmacology notes I: p. 72, SARs
p. 85.1, Subacute evaluation TMA-3 (XVI-13)

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

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

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

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

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

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; 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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

160
Isomer 7

TMA-4
2,3,5-Trimethoxyamphetamine

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

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

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

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

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

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

See also Transcripts: 1.61, 1.72

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

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

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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

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

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

161
Isomer 8

TMA-5
2,3,6-Trimethoxyamphetamine

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

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

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

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

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

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

See also Transcripts: 1.72, 1.97

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

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

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

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

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

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

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

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

262
Isomer 9

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

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

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

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

PubChem CID: 138365; ChemSpider: 121990

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

See also PiHKAL: #96 M    

See also Transcripts: 1.142

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

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

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

2068
Isomer 10

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

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

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

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

PubChem CID: 57474251

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

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

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

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

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

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

PubChem CID: 57478611

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

5383
Isomer 12

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

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

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

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

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

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

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

333
Isomer 13

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

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

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

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

ChemSpider: 25045865

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

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

619
Isomer 14

homo-Mescaline

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

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

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

PubChem CID: 614460; ChemSpider: 534098

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

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

6559
Isomer 15

β-HO-N-iPr-GEA

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

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

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

PubChem CID: 68951; ChemSpider: 62174

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

6612
Isomer 16

N-Me-β,3,4-TMPEA

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

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

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

PubChem CID: 15612893; ChemSpider: 26711698

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

6625
Isomer 17

DMMAOH

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

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

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

PubChem CID: 11368108; ChemSpider: 9543025

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

6655
Isomer 18

DEE

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

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

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

PubChem CID: 18627975

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

6866
Isomer 19

β-HO-N,N-Me-2,5-DMPEA

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

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

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

PubChem CID: 46242; ChemSpider: 42100

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

6869
Isomer 20

β-HO-β,N-Me-2,5-DMPEA

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

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

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

PubChem CID: 50630; ChemSpider: 45890

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

6877
Isomer 21

β-HO-N-Me-2,5-DMA

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

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

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

PubChem CID: 3027653; ChemSpider: 2293151

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

6910
Isomer 22

β,2-HO-N-Me-5-EA

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

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

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

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

6912
Isomer 23

β-HO-2,5-DEPEA

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

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

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

PubChem CID: 18627950

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

6927
Isomer 24

β-HO-N,N-Me-3,5-DMPEA

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

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

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

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

7217
Isomer 25

N-HO-DOM

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

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

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

PubChem CID: 597107; ChemSpider: 519067

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

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

7569
Isomer 26

DESMETHYL-MM

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

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

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

PubChem CID: 24971842; ChemSpider: 21404060

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

1019
Isomer 27

β-HO-DOM

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

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

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

ChemSpider: 26711720

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

1016
Isomer 28

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

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

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

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

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

701
Isomer 29

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

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

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

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

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

Show all 56 analogues and isomers Show only the two N analogues Show only the two α analogues Show only the three R2 analogues Show only the two R3 analogues Show only the 15 R4 analogues Show only the two R6 analogues Show only the one skeleton analogues
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