2,3,5-Trimethoxyphenethylamine

vanc 6 2,3,5-Trimethoxyphenethylamine.svg skin-invert-image None 3166-77-6 413872 366438 1741591 2,3,5-TMPEA; TMPEA-4; 2C-TMA-4 2-(2,3,5-trimethoxyphenyl)ethanamine 11 17 1 3 COC1=CC(=C(C(=C1)OC)OC)CCN 1S/C11H17NO3/c1-13-9-6-8(4-5-12)11(15-3)10(7-9)14-2/h6-7H,4-5,12H2,1-3H3 GERNGXILVRWWGB-UHFFFAOYSA-N 2,3,5-Trimethoxyphenethylamine (2,3,5-TMPEA), also known as TMPEA-4 or as 2C-TMA-4, is a chemical compound of the phenethylamine family related to mescaline (3,4,5-trimethoxyphenethylamine). "This 2,3,5-orientation of the methoxy groups on the aromatic ring is far and away the most difficult tri-substitution pattern known to chemists. There just isn’t any simple way to put it together. The 2-carbon phenethylamine (2,3,5-trimethoxyphenethylamine) had been synthesized quite a while ago. Its role as a substrate for liver amine oxidase in in vitro studies has been explored, but it has never been tried in man." 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 663, 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://archive.org/details/phenethylamine-von-der-struktur-zur-funktion-trachsel-lehmann-enzensperger-2013 21 August 2025 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 Clark LC, Benington F, Morin RD The Effects of Ring-Methoxyl Groups on Biological Deamination of Phenethylamines Journal of Medicinal Chemistry 8 3 353–355 May 1965 14323146 10.1021/jm00327a016 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), 2,3,5-TMPEA has never been tested in humans. Unlike mescaline, 2,3,5-TMPEA does not appear to be a substrate for amine oxidase. The chemical synthesis of 2,3,5-TMPEA has been described. The 2,3,5- substitution pattern, as in 2,3,5-TMPEA, is said to be the most difficult tri-substitution pattern in terms of synthesis. 2,3,5-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 also 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 2,3,5-Trimethoxyamphetamine (2,3,5-TMA; TMA-4) 2C-O (2,4,5-TMPEA) Isomescaline (2,3,4-TMPEA) ψ-2C-O (2,4,6-TMPEA) References External links TMPEA-4 - Isomer Design Category:Phenethylamines Category:Trimethoxyphenyl compounds