2,3,6-Trimethoxyphenethylamine
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| Other names | 2,3,6-TMPEA; TMPEA-5; 2C-TMA-5 |
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| Formula | C11H17NO3 |
| Molar mass | 211.261 g·mol−1 |
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2,3,6-Trimethoxyphenethylamine (2,3,6-TMPEA), also known as TMPEA-5 or as 2C-TMA-5, is a chemical compound of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2][3][4] It is one of the possible positional isomers of trimethoxyphenethylamine and is a positional isomer of mescaline.[1][2][3][4] According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), 2,3,6-TMPEA is not known to have ever been tested in humans.[1][3] It is either a competitive substrate or inhibitor of monoamine oxidase (MAO).[3][1][2] The chemical synthesis of 2,3,6-TMPEA has been described.[4] 2,3,6-TMPEA was first described in the scientific literature by J. R. Merchant and A. J. Mountwala in 1958.[2] As a positional isomer of mescaline, it is a Schedule I controlled substance in the United States.[2]
See also
- Trimethoxyphenethylamine
- Substituted methoxyphenethylamine
- 2,3,6-Trimethoxyamphetamine (2,3,6-TMA; TMA-5)
- 2C-O (2,4,5-TMPEA)
- Isomescaline (2,3,4-TMPEA)
- ψ-2C-O (2,4,6-TMPEA)
- 2C-TMA-4 (2,3,5-TMPEA)
References
- ^ a b c d Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The two-carbon analogue of TMA-5 is 2,3,6-trimethoxyphenethylamine (or 2C-TMA-5 or 2,3,6-TMPEA). This is a known material, although there has been some controversy as to its physical properties. It has been studied in monoamine oxidase systems, and appears to be either a competitive substrate or an inhibitor of that enzyme. But as far as I know, no one has nibbled it, so its human activity is unknown."
- ^ a b c d e Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ^ a b c d Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 669, 883. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
- ^ a b c Merchant J, Mountwala A (1958). "Notes - Synthesis of Some β-Phenethylamine Derivatives. I.". The Journal of Organic Chemistry. 23 (11): 1774–1776. doi:10.1021/jo01105a601. ISSN 0022-3263. Retrieved 29 November 2025.