2,6-Dimethoxyamphetamine

2,6-Dimethoxyamphetamine.svg skin-invert-image 200px Serotonin receptor modulator None 23690-14-4 141048 124412 GCG9F6BC2R 30577 2,6-DMA; DMA-5 1-(2,6-dimethoxyphenyl)propan-2-amine 11 17 1 2 CC(CC1=C(C=CC=C1OC)OC)N 1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3 OHGNLLDQBKOWJW-UHFFFAOYSA-N 2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families. Shulgin A, Manning T, Daley PF #37. 2,6-DMA 63–65 https://archive.org/details/shulgin-index-vol-1/page/63/mode/1up The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press Berkeley, CA 1 2011 978-0-9630096-3-0 709667010 It is one of the positional isomers of dimethoxyamphetamine. The drug has not been tested in humans and its effects in humans are unknown. 2,6-DMA showed very low affinity for serotonin receptors in rat stomach fundus strips (A2 = 8,130nM). 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, it showed no affinity for the serotonin 5-HT2A or 5-HT2C receptors (Ki = >10,000nM). 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 2,6-DMA only partially substituted for DOM in rodent drug discrimination tests, with a maximum responding of 41% and behavioral disruption at higher doses. 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 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 It did not substitute for dextroamphetamine in these 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 The chemical synthesis of 2,6-DMA has been described. 2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969. 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 At that time, he had not yet synthesized it and did not report its effects. 2,6-DMA is a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA) and hence is a Schedule I controlled substance in the United States. See also Dimethoxyamphetamine Substituted methoxyphenethylamine 2,6-Dimethoxyphenethylamine References External links 2,6-DMA - Isomer Design 2,6-DMA - The Shulgin Index Category:Methoxyphenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines Category:Dimethoxyphenyl compounds