Exploring TMA-5. To explore a different substance…

Names:
TMA-5
2,3,6-Trimethoxyamphetamine
IUPAC name:
1-(2,3,6-Trimethoxyphenyl)propan-2-amine
161 · C12H19NO3 · 225.284
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
OASZJWLOOFXASO-UHFFFAOYSA-N This stereoisomer Any stereoisomer

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

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. https://doi.org/10.1002/jms.1347

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

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.

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. https://doi.org/10.1016/S0968-0896(03)00437-1

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

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. https://doi.org/10.1002/omr.1270210611

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. https://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. https://doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB.

Zhang, S; Fan, Y; Shi, Z; Cheng, S. DFT-based QSAR and action mechanism of phenylalkylamine and tryptamine hallucinogens. Chin. J. Chem., 1 Apr 2011, 29 (4), 623–630. 166 kB. https://doi.org/10.1002/cjoc.201190132 #54

BOD
E
ME
TMA
TMA-2
TMA-3
TMA-4
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
2-Me-M
β-HO-DOM
Hydroxy-DOM
N-MeO-3,4-DMA
Terbutaline
10423
10411
10406
β-Methylmescaline
ψ-2C-O-2
α-Methoxy-2C-D
2C-MOM
HOT-E
19 June 2018 · Creative Commons BY-NC-SA ·