2,3,6-Trimethoxyphenethylamine

vanc 6 2,3,6-Trimethoxyphenethylamine.svg skin-invert-image None 15806-31-2 3166-84-5 (HCl) 414331 366877 2,3,6-TMPEA; TMPEA-5; 2C-TMA-5 2-(2,3,6-trimethoxyphenyl)ethanamine 11 17 1 3 COC1=C(C(=C(C=C1)OC)OC)CCN 1S/C11H17NO3/c1-13-9-4-5-10(14-2)11(15-3)8(9)6-7-12/h4-5H,6-7,12H2,1-3H3 SOARXDWNNULVNL-UHFFFAOYSA-N 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). "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." Shulgin A, Manning T, Daley P The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley 1 2011 Transform Press 978-0-9630096-3-0 Trachsel D, Lehmann D, Enzensperger C Phenethylamine: von der Struktur zur Funktion Solothurn 669, 883 2013 Phenethylamines: From Structure to Function 1 Nachtschatten-Verlag Nachtschatten-Science 978-3-03788-700-4 858805226 https://books.google.com/books?id=-Us1kgEACAAJ de https://web.archive.org/web/20251113135159/https://books.google.com/books?id=-Us1kgEACAAJ 13 November 2025 29 November 2025 bot: unknown Merchant J, Mountwala A Notes - Synthesis of Some β-Phenethylamine Derivatives. I. The Journal of Organic Chemistry 23 11 1774–1776 1958 10.1021/jo01105a601 0022-3263 https://pubs.acs.org/doi/abs/10.1021/jo01105a601 29 November 2025 subscription It is one of the possible positional isomers of trimethoxyphenethylamine and is a positional isomer of mescaline. 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. It is either a competitive substrate or inhibitor of monoamine oxidase (MAO). The chemical synthesis of 2,3,6-TMPEA has been described. 2,3,6-TMPEA was first described in the scientific literature by J. R. Merchant and A. J. Mountwala in 1958. As a positional isomer of mescaline, it is a Schedule I controlled substance in the United States. The drug is a controlled substance in Canada under phenethylamine blanket-ban language.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 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 External links 2,3,6-Trimethoxyphenethylamine - Isomer Design Category:Phenethylamines Category:Trimethoxyphenyl compounds