2,4-Dimethoxyamphetamine

2,4-DMA.svg skin-invert-image 250px DMA-3d-sticks.png bg-transparent 225px Oral Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Psychoactive drug; Stimulant, Serotonergic psychedelic; Hallucinogen None "Short" 23690-13-3 52850-81-4 141047 124411 GT33R7Q58G 282734 2,4-DMA; 2,4-Dimethoxy-α-methylphenethylamine; DMA-3 1-(2,4-dimethoxyphenyl)propan-2-amine 11 17 1 2 CC(CC1=C(C=C(C=C1)OC)OC)N 1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3 DQWOZMUBHQPFFF-UHFFFAOYSA-N 2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a psychoactive drug of the phenethylamine and amphetamine families. Shulgin AT, Shulgin A #53 2,4-DMA; 2,4-DIMETHOXYAMPHETAMINE PiHKAL: A Chemical Love Story 1991 Transform Press 9780963009609 1st Berkeley, CA 25627628 https://www.erowid.org/library/books_online/pihkal/pihkal053.shtml Shulgin A, Manning T, Daley PF #35. 2,4-DMA The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press Berkeley 1 2011 978-0-9630096-3-0 https://archive.org/details/shulgin-index-vol-1/page/54/mode/1up?view=theater It is one of the dimethoxyamphetamine (DMA) series of positional isomers. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2,4-DMA's dose as greater than 60mg orally and its duration as "short". At a dose of 60mg orally, the effects of 2,4-DMA were reported to include definite threshold effects or even a bit more, a lot of amphetamine-like effects, some euphoria, and a psychedelic-like "diffusion of association". The drug's effects started to wear off after 3hours. According to Shulgin, 2,4-DMA could be a full stimulant and/or a full psychedelic at sufficiently high doses, but higher doses were not tested. 2,4-DMA has been found to act as a low-potency full agonist of the serotonin 5-HT2A receptor, with an EC50 half-maximal effective concentration of 2,950nM and an Emax half-maximal effective concentration of 117%. Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore ACS Pharmacol Transl Sci 4 2 488–502 April 2021 33860179 8033619 10.1021/acsptsci.0c00063 It fully substitutes for DOM in rodent drug discrimination tests. Glennon RA, Young R Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines Pharmacol Biochem Behav 17 4 603–607 October 1982 6965276 10.1016/0091-3057(82)90330-6 Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists ACS Chem Neurosci 11 9 1238–1244 May 2020 32212672 10.1021/acschemneuro.0c00129 Removal of the 2- or 5-position methoxy group in 2,4,5-substituted compounds is also detrimental for their in vivo activity. For example, 2,4-dimethoxyamphetamine (13, Figure 2) and 3,4-dimethoxyamphetamine (14, Figure 2) are less potent than 8 in humans and in rats trained to discriminate 9. 14,15 The drug is less potent in this regard than 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2), but is more potent than 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1). 2,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects. Glennon RA Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships NIDA Res Monogr 94 43–67 1989 2575229 https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 https://web.archive.org/web/20230511144224/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 dead May 11, 2023 The chemical synthesis of 2,4-DMA has been described. 2,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967.Alexander T. Shulgin Thornton Sargent Claudio Naranjo The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines 202–214 Efron DH, Holmstedt B, Kline NS Ethnopharmacologic Search for Psychoactive Drugs: Proceedings of a Symposium Held in San Francisco, California, January 28–30, 1967 Raven Press New York 1967 978-0-89004-047-8 14498182 OL14623132M https://bibliography.maps.org/resources/download/15578 https://books.google.com/books?id=IvfBDethZkYC https://web.archive.org/web/20250712212357/https://bibliography.maps.org/resources/download/15578 12 July 2025 Shulgin AT, Sargent T, Naranjo C Structure–activity relationships of one-ring psychotomimetics Nature 221 5180 537–541 February 1969 5789297 10.1038/221537a0 1969Natur.221..537S https://bibliography.maps.org/resources/download/11267 https://web.archive.org/web/20250712213646/https://bibliography.maps.org/resources/download/11267 2025-07-12 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991. See also Dimethoxyamphetamine Substituted methoxyphenethylamine 2,4,5-Trimethoxyamphetamine (TMA-2) 2,4,6-Trimethoxyamphetamine (TMA-6; ψ-TMA-2) 2,4-Dimethoxyphenethylamine References External links 2,4-DMA - Isomer Design 2,4-DMA - PiHKAL - Erowid 2,4-DMA - PiHKAL - Isomer Design 2,4-DMA - The Shulgin Index Category:5-HT2A agonists Category:Methoxyphenethylamines Category:Monoamine releasing agents Category:PiHKAL Category:Psychedelic phenethylamines Category:Stimulants Category:Substituted amphetamines Category:2,4-Substituted phenethylamines Category:Dimethoxyphenyl compounds