2,3-Dimethoxyamphetamine

2,3-Dimethoxyamphetamine.svg skin-invert-image 250px Serotonin receptor modulator None 15402-81-0 91255 82404 P5Z6ZU6N7S 280855 2,3-DMA; DMA-2; NSC-172189 1-(2,3-dimethoxyphenyl)propan-2-amine 11 17 1 2 CC(CC1=C(C(=CC=C1)OC)OC)N 1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3 DHLWJXGSZDJWKK-UHFFFAOYSA-N 2,3-Dimethoxyamphetamine (2,3-DMA), also known as DMA-2, is a drug of the phenethylamine and amphetamine families. Shulgin A, Manning T, Daley PF #34. 2,3-DMA 51–54 https://archive.org/details/shulgin-index-vol-1/page/51/mode/1up The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press Berkeley, CA 1 2011 978-0-9630096-3-0 709667010 Brimblecombe RW, Pinder RM Phenylalkylamines and Their Derivatives Hallucinogenic Agents Bristol 55–97 1975 Wright-Scientechnica https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 It is one of the positional isomers of dimethoxyamphetamine. 2,3-DMA does not appear to have been tested in humans. The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A2 = 2,880nM). Glennon RA, Liebowitz SM, Anderson GM Serotonin receptor affinities of psychoactive phenalkylamine analogues J Med Chem 23 3 294–299 March 1980 7365744 10.1021/jm00177a017 In a subsequent study, 2,3-DMA showed very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 4,280nM and >10,000nM, respectively). Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists J Med Chem 43 16 3074–3084 August 2000 10956215 10.1021/jm9906062 It did not show activity as a norepinephrine releasing agent in vitro. The drug is behaviorally active in mice. 2,3-DMA did not substitute 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 However, it did partially substitute for 5-MeO-DMT in these tests. Glennon RA, Rosecrans JA, Young R Behavioral properties of psychoactive phenylisopropylamines in rats Eur J Pharmacol 76 4 353–360 December 1981 7327208 10.1016/0014-2999(81)90106-0 As with DOM, the drug did not substitute for dextroamphetamine in drug discrimination tests. Glennon RA, Young R, Hauck AE Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology Pharmacol Biochem Behav 22 5 723–729 May 1985 3839309 10.1016/0091-3057(85)90520-9 It produced behavioral disruption at higher doses. Glennon RA Discriminative stimulus properties of phenylisopropylamine derivatives Drug Alcohol Depend 17 2–3 119–134 June 1986 2874967 10.1016/0376-8716(86)90003-7 The chemical synthesis of 2,3-DMA has been described. 2,3-DMA was first described in the scientific literature by F. Benington and colleagues by 1968. Benington F, Morin RD The chemorelease of norepinephrine from mouse hearts by substituted amphetamines J Med Chem 11 4 896–897 July 1968 5677681 10.1021/jm00310a048 Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects. 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 See also Dimethoxyamphetamine Substituted methoxyphenethylamine 2,3-Dimethoxyphenethylamine References External links 2,3-DMA - Isomer Design 2,3-DMA - The Shulgin Index Category:Methoxyphenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines Category:Dimethoxyphenyl compounds