2,4,6-Trimethoxyphenethylamine (2,4,6-TMPEA), also known as TMPEA-6, 2C-TMA-6, or ψ-2C-O, is a drug of the phenethylamine and Ψ-PEA families. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and 2C-O (2,4,5-trimethoxyphenethylamine) as well as the α-desmethyl analogue of 2,4,6-trimethoxyamphetamine (TMA-6). The drug has been encountered online as a novel designer drug.
Use and effects According to Daniel Trachsel in 2012, who cited personal communication with P. Rausch in 2009, the drug has been reported to be inactive in humans at a dose of up to 300mg or more. This is similar to the case of 2C-O (inactive at >300mg), but is in contrast to mescaline (active at ~180–360mg) as well as TMA-6 (active at 25–50mg).
Pharmacology Pharmacodynamics Unlike mescaline, but similarly to 2C-O, 2,4,6-TMPEA does not appear to be a substrate for amine oxidase.
Chemistry Derivatives A variety of derivatives of 2,4,6-TMPEA are known.
History 2,4,6-TMPEA was first described in the scientific literature by 1954. Alexander Shulgin mentioned 2,4,6-TMPEA in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and stated that its activity in humans was unknown at the time. "The phenethylamine homologue of TMA-6 is well known, but is virtually unexplored pharmacologically. The above benzaldehyde with nitromethane in glacial acetic acid containing ammonium acetate gave the appropriate β-nitrostyrene as yellow crystals with a mp 177–177.5 °C. This, with LAH in ether, gave 2,4,6-trimethoxyphenethylamine (2,4,6-TMPEA, or 2C-TMA-6) as the picrate salt (mp 204–205 °C) or the hydrochloride salt (mp 234–235 °C). It has been shown not to be a substrate to the soluble amine oxidase from rabbit liver, a property it shares with mescaline, but whether it is or is not active in man is at present unknown." The compound was encountered as a novel designer drug in Russia in 2023.
Society and culture Legal status Canada 2,4,6-TMPEA is a controlled substance in Canada under phenethylamine blanket-ban language.
See also Trimethoxyphenethylamine Ψ-PEA (psychedelics) Substituted methoxyphenethylamine 2,4,6-Trimethoxyamphetamine (2,4,6-TMA; TMA-6) Mescaline (3,4,5-trimethoxyphenethylamine) 2C-O (2,4,5-trimethoxyphenethylamine)
References
External links 2C-TMA-6 - Isomer Design