Exploring TMA-4. To explore a different substance…

Names:
TMA-4 · 2,3,5-Trimethoxyamphetamine
IUPAC name:
1-(2,3,5-Trimethoxyphenyl)propan-2-amine
ID: 160 · Formula: C12H19NO3 · Molecular weight: 225.284
InChI: 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

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. http://dx.doi.org/10.1002/jms.1347

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7.7 MB.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1970; pp 21–41. 8.6 MB.

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

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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, 1978; Vol. 11, pp 243–333. 2.6 MB. http://dx.doi.org/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. http://dx.doi.org/10.1002/omr.1270210611

TMPEA-4
3,5-DMA
2,3,5-DOB · 2-Br-3,5-DMA
2-I-3,5-DMA
2-Me-3,5-DOM
2,3,5-DOET
2,5-DMA
3-DOB
3-DON
3-DOM
3,2,5-DOET
TA
2,3-DMA
5,2,3-DOB · 5-Br-2,3-DMA
5-Me-2,3-DOM
5,2,3-DOET
TeMA-3
314
315
MMDA-4
DMA-2-hemiFLY
BOD
E
ME
TMA
TMA-2
TMA-3
TMA-5
TMA-6
METHYL-MESCALINE
2C-O-2
N,N-Me-3-DESMETHYL
N,N-Me-DME · Macromerine
2C-pEtOH
4C-HO
homo-Mescaline
β-HO-N-iPr-GEA
N-Me-β,3,4-TMPEA
DMMAOH
DEE
β-HO-N,N-Me-2,5-DMPEA
β-HO-β,N-Me-2,5-DMPEA
β-HO-N-Me-2,5-DMA
β,2-HO-N-Me-5-EA
β-HO-2,5-DEPEA
β-HO-N,N-Me-3,5-DMPEA
N-HO-DOM
DESMETHYL-MM
β-HO-DOM
1016
N-MeO-3,4-DMA
TMPEA-4
3,5-DMA
2,3,5-DOB · 2-Br-3,5-DMA
2-I-3,5-DMA
2-Me-3,5-DOM
2,3,5-DOET
2,5-DMA
3-DOB
3-DON
3-DOM
3,2,5-DOET
TA
2,3-DMA
5,2,3-DOB · 5-Br-2,3-DMA
5-Me-2,3-DOM
5,2,3-DOET
TeMA-3
314
315
MMDA-4
DMA-2-hemiFLY
BOD
E
ME
TMA
TMA-2
TMA-3
TMA-5
TMA-6
METHYL-MESCALINE
2C-O-2
N,N-Me-3-DESMETHYL
N,N-Me-DME · Macromerine
2C-pEtOH
4C-HO
homo-Mescaline
β-HO-N-iPr-GEA
N-Me-β,3,4-TMPEA
DMMAOH
DEE
β-HO-N,N-Me-2,5-DMPEA
β-HO-β,N-Me-2,5-DMPEA
β-HO-N-Me-2,5-DMA
β,2-HO-N-Me-5-EA
β-HO-2,5-DEPEA
β-HO-N,N-Me-3,5-DMPEA
N-HO-DOM
DESMETHYL-MM
β-HO-DOM
1016
N-MeO-3,4-DMA
21 September 2017 · Creative Commons BY-NC-SA ·