2,3,5,6-Tetramethoxyphenethylamine

vanc 6 TeMPEA-3 TeMPEA-3.svg skin-invert-image 225px None 121008955 62993366 2,3,5,6-TeMPEA; TeMPEA-3 2-(2,3,5,6-tetramethoxyphenyl)ethanamine 12 19 1 4 COC1=CC(=C(C(=C1OC)CCN)OC)OC 1S/C12H19NO4/c1-14-9-7-10(15-2)12(17-4)8(5-6-13)11(9)16-3/h7H,5-6,13H2,1-4H3 MRCWRNATBFUERI-UHFFFAOYSA-N 2,3,5,6-Tetramethoxyphenethylamine (2,3,5,6-TeMPEA), also known as TeMPEA-3, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). Shulgin A, Manning T, Daley PF #115. TeMPEA-3 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley, CA 1 282–283 2011 https://archive.org/details/shulgin-index-vol-1/page/282/mode/1up Transform Press 978-0-9630096-3-0 709667010 It is one of the possible positional isomers of tetramethoxyphenethylamine (TeMPEA). The in-vitro metabolism and effects of TeMPEA-3 on behavior in animals have been studied. Clark LC, Benington F, Morin RD The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related β-phenethylamines The Alabama Journal of Medical Sciences 1 417–429 October 1964 14230671 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 Unlike mescaline, TeMPEA-3 was inactive in the conditioned avoidance response test in rats. Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups Psychopharmacologia 10 5 379–387 1967 5588333 10.1007/BF00403978 The effects of TeMPEA-3 in humans have not been reported and are unknown. The drug was first described in the scientific literature by 1955. Benington F, Morin RD, Clark LC Mescaline Analogs. II. Tetra- and Penta-Methoxy-β-Phenethylamines The Journal of Organic Chemistry 20 1 102–108 1955 10.1021/jo01119a017 0022-3263 TeMPEA-3 was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. It 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 Substituted methoxyphenethylamine Tetramethoxyphenethylamine (TeMPEA) 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA, TeMPEA-1) 2,3,4,6-Tetramethoxyphenethylamine (TeMPEA-2) 2,3,5,6-Tetramethoxyamphetamine (TeMA-3) Pentamethoxyphenethylamine (PeMPEA) Trimethoxyphenethylamine (TMPEA) References External links TeMPEA-3 - Isomer Design Category:2C (psychedelics) Category:Methoxyphenethylamines