2,4,6-Trimethoxyphenethylamine

vanc 6 2,4,6-Trimethoxyphenethylamine.svg skin-invert-image 225px None Schedule I (isomer of mescaline) 15873-23-1 21679959 10296635 2,4,6-TMPEA; TMPEA-6; 2C-TMA-6; ψ-2C-O 2-(2,4,6-trimethoxyphenyl)ethanamine 11 17 1 3 COC1=CC(=C(C(=C1)OC)CCN)OC 1S/C11H17NO3/c1-13-8-6-10(14-2)9(4-5-12)11(7-8)15-3/h6-7H,4-5,12H2,1-3H3 CGUNKAXAEZSOFA-UHFFFAOYSA-N 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. Shulgin A, Manning T, Daley P The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley 1 353 2011 Transform Press 978-0-9630096-3-0 Trachsel D, Lehmann D, Enzensperger C Phenethylamine: von der Struktur zur Funktion Solothurn 881–885 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 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. Trachsel D Fluorine in psychedelic phenethylamines Drug Testing and Analysis 4 7–8 577–590 2012 22374819 10.1002/dta.413 Similar to 2C-O (43: >300 mg[3]), Ψ-2C-O (2,4,6-TMPEA, 61: >300 mg) did not show any human activity (P. Rausch, personal communication in 2009) and interestingly, the 3,4,5-trimethoxy isomer mescaline (22: 180–360 mg) does.[3] A couple of fluorinated Ψ-2C and Ψ-3C derivatives have been prepared (compounds 62–69, Figure 4). 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 Synthesis The chemical synthesis of 2,4,6-TMPEA has been described. 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. Benington F, Morin RD, Clark LC MESCALINE ANALOGS. I. 2,4,6-TRIALKOXY-β-PHENETHYLAMINES The Journal of Organic Chemistry 19 1 11–16 1954 10.1021/jo01366a003 0022-3263 Clark LC, Benington F, Morin RD The effects of ring-methoxyl groups on biological deamination of phenethylamines Journal of Medicinal Chemistry 8 353–355 May 1965 3 14323146 10.1021/jm00327a016 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. 2C-TMA-6 1 July 2012 АИПСИН https://aipsin.com/newsubstance/1143/ ru 18 July 2025 2C-TMA-6 (2,4,6-TMPEA) 1 July 2012 АИПСИН https://aipsin.com/newsubstance/1271/ ru 18 July 2025 Society and culture Legal status Canada 2,4,6-TMPEA 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 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 Category:Ψ-PEA Category:Daniel Trachsel Category:Designer drugs Category:Phenethylamines Category:Trimethoxyphenyl compounds