TMA-2 is aserotonergic psychedelic and produceshallucinogenic effects.[1][2] It is said to be active at doses of 20 to 40mg and to have aduration of 8 to 12hours.[1][4] It is much morepotent than its positional isomer3,4,5-trimethoxyamphetamine (3,4,5-TMA, TMA, or TMA-1), which is said to be active at doses of 100 to 250mg and to have a duration of 6 to 8hours.[5] However,DOM (2,5-dimethoxy-4-methylamphetamine), theanalogue of TMA-2 in which its 4-methoxy group has been replaced with a morelipophilic 4-methyl group, is about 10times more potent than TMA-2.[6]
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:[7][8][9][10][11][12][13][14][15]
^Glennon RA (January 1987). "Central serotonin receptors as targets for drug research".J Med Chem.30 (1):1–12.doi:10.1021/jm00384a001.PMID3543362.Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
^Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)".Eur J Pharmacol.102 (1):23–29.doi:10.1016/0014-2999(84)90333-9.PMID6479216.
^abShulgin AT (1978)."Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.).Stimulants. Boston, MA: Springer US. pp. 243–333.doi:10.1007/978-1-4757-0510-2_6.ISBN978-1-4757-0512-6.3.1.6. 2,4,5-Trimethoxyphenylisopropylamine This geometric isomer of TMA was first synthesized by Bruckner (1933) and its psychotomimetic properties were first observed some 30 years later (Shulgin, 1964a), 2,4,5-Trimethoxyphenylisopropylamine (34, TMA-2, 2,4,5-trimethoxyamphetamine) was the second of the six possible positional isomers found to be psychotomimetic, and was thus called TMA-2.
^Bruckner, Viktor (24 October 1933). "Über das Pseudonitrosit des Asarons".Journal für Praktische Chemie.138 (9–10):268–274.doi:10.1002/prac.19331380907.ISSN0021-8383.
^Shulgin AT (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines".Experientia.20 (7):366–367.doi:10.1007/BF02147960.PMID5855670.
^Shulgin AT (May 1966). "The six trimethoxyphenylisopropylamines (trimethoxyamphetamines)".J Med Chem.9 (3):445–446.doi:10.1021/jm00321a058.PMID5960939.
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages. See also:Receptor/signaling modulators
