2,3,4,6-Tetramethoxyphenethylamine

vanc 6 TeMPEA-2 2,3,4,6-Tetramethoxyphenethylamine.svg skin-invert-image 250px None 3166-92-5 121008956 62993367 2,3,4,6-TeMPEA; TeMPEA-2 2-(2,3,4,6-tetramethoxyphenyl)ethanamine 12 19 1 4 COC1=CC(=C(C(=C1CCN)OC)OC)OC 1S/C12H19NO4/c1-14-9-7-10(15-2)12(17-4)11(16-3)8(9)5-6-13/h7H,5-6,13H2,1-4H3 BIJGTHTWKBFOCK-UHFFFAOYSA-N 2,3,4,6-Tetramethoxyphenethylamine (2,3,4,6-TeMPEA), also known as TeMPEA-2, 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 Trachsel D, Lehmann D, Enzensperger C Phenethylamine: von der Struktur zur Funktion Solothurn 883, 923 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 one of the possible positional isomers of tetramethoxyphenethylamine (TeMPEA). The in-vitro metabolism and effects of TeMPEA-2 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 The drug showed little or no activity as a norepinephrine releasing agent in vitro. Daly JW, Creveling CR, Witkop B The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines Journal of Medicinal Chemistry 9 3 273–280 May 1966 5960887 10.1021/jm00321a001 It does not seem to have been tested in humans. TeMPEA-2 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 https://pubs.acs.org/doi/abs/10.1021/jo01119a017 subscription 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) 2,3,5,6-Tetramethoxyphenethylamine (TeMPEA-3) 2,3,4,6-Tetramethoxyamphetamine (TeMA-2) Pentamethoxyphenethylamine (PeMPEA) Trimethoxyphenethylamine (TMPEA) References External links TeMPEA-2 - Isomer Design Category:Methoxyphenethylamines