2-Methoxyamphetamine

Chemical compound changed 477213867 1-(2-methoxyphenyl)propan-2-amine 2-Methoxyamphetamine.svg skin-invert-image 200px Oral changed ?? 15402-84-3 correct FDA 8NC8ZCZ6JE none 159755 correct chemspider 140465 correct EBI 16451 2-MA; ortho-Methoxyamphetamine; OMA 10 15 1 1 O(c1ccccc1CC(N)C)C correct chemspider 1S/C10H15NO/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3 correct chemspider VBAHFEPKESUPDE-UHFFFAOYSA-N 2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine family. It is substantially weaker in inhibiting the reuptake of and inducing the release of the monoamine neurotransmitters compared to related agents such as amphetamine, MMA, and PMA, Tseng LF, Menon MK, Loh HH Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue The Journal of Pharmacology and Experimental Therapeutics 197 2 263–271 May 1976 1271280 http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1271280 Horace Loh and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine. Shulgin A, Shulgin A Pihkal: A Chemical Love Story Transform Press 1991 0-9630096-0-5 http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=97 The drug also shows relatively weak affinity for serotonin receptors, including the serotonin 5-HT1 and 5-HT2 receptors (Ki = 3,500nM and 8,130nM, respectively). Glennon RA Central serotonin receptors as targets for drug research J Med Chem 30 1 1–12 January 1987 3543362 10.1021/jm00384a001 Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites 2-MA fully substitutes for dextroamphetamine in rodent 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 See also Substituted methoxyphenethylamine Methoxyphenamine 3-Methoxyamphetamine (MMA) 4-Methoxyamphetamine (PMA) References External links IsomerDesign - OMA; 2-Methoxyamphetamine Category:Methoxyphenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines