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." 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.
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