Chemistry:Methyl-TMA-2

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Methyl-TMA-2, or N-methyl-TMA-2, also known as N-methyl-2,4,5-trimethoxyamphetamine, is a drug of the phenethylamine, amphetamine, and DOx families.[1][2] It is the N-methyl derivative of 2,4,5-trimethoxyamphetamine (TMA-2) as well as the α,N-dimethyl derivative of 2C-O (2,4,5-trimethoxyphenethylamine).[1][2]

Use and effects

N-Methylation of psychedelic phenethylamines has invariably greatly reduced or eliminated their hallucinogenic activity.[3][1][4][5] Examples of this include related compounds like Beatrice (N-methyl-DOM) and methyl-DOB (N-methyl-DOB), which at assessed doses appear to be inactive as psychedelics in humans.[6][1][4][5] In accordance with the preceding findings, per Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), methyl-TMA-2 was inactive at doses of up to 120 mg.[1] For comparison, the active dose range of TMA-2 is 20 to 40 mg.[1]

History

Methyl-TMA-2 was first described in the scientific literature by at least 1984.[2][7] It was subsequently described further by Shulgin in PiHKAL in 1991.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  "Three additional N-methylated homologues of known psychedelics warrant mention, but do not really deserve separate recipes. This is because they have had only the most cursory assaying, which I have learned about by personal correspondence. [...] METHYL-TMA [...] had been run up in several trials to a maximum of 240 [mg], with some mental disturbances mentioned only at this highest level. METHYL-TMA-2 [...] had been tried at up to 120 [mg] without any effects. METHYL-TMA-6 [...] had been tried at up to 30 [mg] and it, too, was apparently without effects. These are reports that I have heard from others, but I have had no personal experience with them. Those that I can describe from personal experience are entered separately as recipes of their own. And there are many, many other N-methyl homologues which have been prepared and characterized in the literature, and have yet to be tasted. So far, however, the only consistent thing seen is that, with N-methylation, the potency of the psychedelics is decreased, but the potency of the stimulants appears to be pretty much maintained."
  2. ↑ 2.0 2.1 2.2 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. pp. 344. ISBN 978-0-9630096-3-0. 
  3. ↑ Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. https://bitnest.netfirms.com/external/10.1007/7854_2017_475. "Although the most active tryptamine hallucinogens are N,N-dialkylated, the phenethylamines generally cannot tolerate even a single N-substitution. Even small groups such as methyl or ethyl (see Table 2) abolish their hallucinogenic activity." 
  4. ↑ 4.0 4.1 "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. 1980. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5. "Of all the variously substituted phenylisopropylamines that have been N-methylated and titrated in man (including the homologs of TMA-2, 2,5-DMA, DOM, and DOB: 60.22b, 60.22i, 60.22aa, and 60.22ff, respectively), it is only the methylenedioxy compound 60.23a that has maintained quantitative potency (94). As with mescaline itself, dimethylation of this compound eliminates any central action." 
  5. ↑ 5.0 5.1 "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. 74–91. https://bibliography.maps.org/resources/download/11534. "[MDA] is also remarkable because the N-methyl homolog 3,4 (MDMA) has biological activity, although the nature of its action places it outside of this review. No other phenethylamine hallucinogen retains central activity on N-methylation." 
  6. ↑ (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 834–835, 878. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. "8.5.26. N-Substitution von 2,4,5-trisubstituierten Phenylalkylaminen: Einerseits wurde der Einfluss von N-Alkyl-, andererseits derjenige von N-Heterogruppen-Substituenten geprüft. Allgemein ist bekannt, dass das Einführen von Alkylsubstituenten am Stickstoff von psychedelischen Phenylalkylaminen eine Abnahme der HT2-Rezeptoraffinitäten zur Folge hat [29, 150, 151]. Die Wirkungsabschwächung konnte mit den potenten Substanzen DOB (2) und DOM (8) im Menschen bestätigt werden [8]: N-Methyl-DOM (316; BEATRICE) und METHYL-DOB (317) erwiesen sich im Vergleich zu den beiden unmethylierten Verbindungen als massiv weniger aktiv; die aktive Dosis wurde dabei noch nicht eruiert. METHYL-DOET (318; DOETM) erwies sich bei einer Dosierung von 18mg bereits als deutlich aktiv [140]; die Wirkungen wurden im Vergleich zu DOET (14) als ruhiger und angenehmer beschrieben. [...] 318; METHYL-DOET, 18mg, 8-10h. [...] [140] P. Rausch. Persönliche Mitteilung, 2009." 
  7. ↑ "The Identification of Methoxy-N-Methylamphetamines". Journal of Forensic Sciences 29 (4): 1056–1071. 1 October 1984. doi:10.1520/JFS11772J. ISSN 0022-1198. 




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