2,3,5-Trimethoxyamphetamine

vanc 6 TMA-4 Trimethoxyamphetamine-4.svg skin-invert-image 250px Oral Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen None ~6 hours 23693-14-3 602804 523988 LEL94CV318 103331 2,3,5-TMA; TMA-4 1-(2,3,5-trimethoxyphenyl)propan-2-amine 12 19 1 3 CC(CC1=C(C(=CC(=C1)OC)OC)OC)N 1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3 MJIBJXKJBRLSQA-UHFFFAOYSA-N 2,3,5-Trimethoxyamphetamine (2,3,5-TMA), also known as TMA-4, is a psychedelic drug of the phenethylamine and amphetamine families. https://erowid.org/library/books_online/pihkal/pihkal160.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 2,3,5-TMA's dose as greater than 80mg orally and its duration as perhaps or about 6hours. 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 Based on limited testing, it produced threshold effects including much introspection among others, along with no subjective physical symptoms. The drug at 80mg was described as comparable to 50μg LSD or 120mg TMA and as being roughly 4-fold as potent as mescaline. Per Shulgin, more testing is needed to fully characterize the drug in humans. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics 2,3,5-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 The drug substitutes 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 2,3,5-TMA has been described. History 2,3,5-TMA was first described in the scientific literature by Alexander Shulgin in 1966. 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 2,3,5-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), 2,3,5-TMA is a Schedule I controlled substance in the United States. See also Trimethoxyamphetamine Substituted methoxyphenethylamine 2,3,5-Trimethoxyphenethylamine (2,3,5-TMPEA; TMPEA-4) References External links TMA-4 - Isomer Design TMA-4 - PiHKAL - Erowid TMA-4 - PiHKAL - Isomer Design TMA-4 - The Shulgin Index Category:Methoxyphenethylamines Category:Psychedelic phenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines Category:Trimethoxyphenyl compounds