2,3,4-Trimethoxyamphetamine

vanc 6 TMA-3 Trimethoxyamphetamine-3.svg skin-invert-image Oral Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen None Unknown 1082-23-1 31012 28771 9T3SO4A6HM 30777 2,3,4-TMA; TMA-3; α-Methylisomescaline 1-(2,3,4-trimethoxyphenyl)propan-2-amine 12 19 1 3 CC(CC1=C(C(=C(C=C1)OC)OC)OC)N 1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3 LWDQPPLPHGXYLG-UHFFFAOYSA-N 2,3,4-Trimethoxyamphetamine (2,3,4-TMA), also known as TMA-3 or as α-methylisomescaline, is a putative psychedelic drug of the phenethylamine and amphetamine families. https://erowid.org/library/books_online/pihkal/pihkal159.shtml Shulgin A, Manning T, Daley P The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley 1 2011 Transform Press 978-0-9630096-3-0 It is one of the possible positional isomers of trimethoxyamphetamine and is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA or TMA-1). Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2,3,4-TMA's dose as greater than 100mg orally and its duration as unknown. Jacob P, Shulgin AT Lin GC, Glennon RA Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs Hallucinogens: An Update 146 74–91 1994 8742795 National Institute on Drug Abuse Research Monograph Series National Institute on Drug Abuse https://archives.nida.nih.gov/sites/default/files/monograph146.pdf https://bibliography.maps.org/resources/download/11534 https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 13 July 2025 Shulgin AT Laing RR Basic Pharmacology and Effects Hallucinogens: A Forensic Drug Handbook 67–137 2003 Elsevier Science Forensic Drug Handbook Series 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC https://bibliography.maps.org/resources/download/12634 https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 13 July 2025 The drug produced no effects whatsoever at a dose of 100mg in three separate individuals. Higher doses were not tested, but 2,3,4-TMA could possibly be active at higher doses. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics 2,3,4-TMA shows affinity for serotonin receptors. Glennon RA, Rosecrans JA Indolealkylamine and phenalkylamine hallucinogens: a brief overview Neuroscience and Biobehavioral Reviews 6 4 489–497 1982 6757811 10.1016/0149-7634(82)90030-6 Glennon RA, Liebowitz SM, Anderson GM Serotonin receptor affinities of psychoactive phenalkylamine analogues Journal of Medicinal Chemistry 23 3 294–299 March 1980 7365744 10.1021/jm00177a017 Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, Smith C, Egan C, Davis K, Mattson MV Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors Drug and Alcohol Dependence 60 2 121–132 August 2000 10940539 10.1016/s0376-8716(99)00148-9 11380/17721 free It substituted for DOM in rodent drug discrimination tests. Glennon RA, Young R Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines Pharmacology, Biochemistry, and Behavior 17 4 603–607 October 1982 6965276 10.1016/0091-3057(82)90330-6 Chemistry Synthesis The chemical synthesis of 2,3,4-TMA has been described. History 2,3,4-TMA was first described in the scientific literature by Alexander Shulgin in 1964. Shulgin AT Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines Experientia 20 7 366–367 July 1964 5855670 10.1007/BF02147960 Shulgin AT The six trimethoxyphenylisopropylamines (trimethoxyamphetamines) Journal of Medicinal Chemistry 9 3 445–446 May 1966 5960939 10.1021/jm00321a058 Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Society and culture Legal status Canada 2,3,4-TMA 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 United States As a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), 2,3,4-TMA is a Schedule I controlled substance in the United States. See also Trimethoxyamphetamine Substituted methoxyphenethylamine Isomescaline (2,3,4-TMPEA; TMPEA-4) References External links TMA-3 - Isomer Design TMA-3 - PiHKAL - Erowid TMA-3 - PiHKAL - Isomer Design TMA-3 - The Shulgin Index Category:Phenethylamines Category:Psychedelic phenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines Category:Trimethoxyphenyl compounds