2-Methoxyphenethylamine

vanc 6 2-Methoxyphenethylamine.svg skin-invert-image 200px Trace amine-associated receptor 1 (TAAR1) agonist None 2045-79-6 74896 67459 A87YWS9XM3 100635 2-MPEA; ortho-Methoxyphenethylamine; o-Methoxyphenethylamine 2-(2-methoxyphenyl)ethanamine 9 13 1 1 COC1=CC=CC=C1CCN 1S/C9H13NO/c1-11-9-5-3-2-4-8(9)6-7-10/h2-5H,6-7,10H2,1H3 WSWPCNMLEVZGSM-UHFFFAOYSA-N 2-Methoxyphenethylamine (2-MPEA) is a drug of the phenethylamine family. Shulgin A, Manning T, Daley PF #100. 2-MPEA The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley, CA 1 241–243 2011 https://archive.org/details/shulgin-index-vol-1/page/241/mode/1up Transform Press 978-0-9630096-3-0 709667010 It is one of the methoxyphenethylamine positional isomers. Use and effects The effects of 2-MPEA in humans have not been reported and are unknown. Pharmacology The drug showed very low affinity for the serotonin receptors in the rat stomach fundus strip (A2 = 3,020nM). Glennon RA, Liebowitz SM, Anderson GM Serotonin receptor affinities of psychoactive phenalkylamine analogues Journal of Medicinal Chemistry 23 3 294–299 March 1980 7365744 10.1021/jm00177a017 In another study, it showed no affinity for the serotonin 5-HT2A or 5-HT2C receptors (Ki = >10,000nM). Rangisetty JB, Dukat M, Dowd CS, Herrick-Davis K, DuPre A, Gadepalli S, Teitler M, Kelley CR, Sharif NA, Glennon RA 1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character Journal of Medicinal Chemistry 44 20 3283–3291 September 2001 11563927 10.1021/jm0100739 2-MPEA is a potent full agonist of the human trace amine-associated receptor 1 (TAAR1) (EC50 half-maximal effective concentration = 144nM; Emax maximal efficacy = 95%). Lewin AH, Navarro HA, Mascarella SW Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1 Bioorganic & Medicinal Chemistry 16 15 7415–7423 August 2008 18602830 2601700 10.1016/j.bmc.2008.06.009 History 2-MPEA was first described in the scientific literature by at least 1943. Alles GA, Heegaard EV Substrate specificity of amine oxidase Journal of Biological Chemistry 147 3 487–503 1943 10.1016/S0021-9258(18)72344-2 free Clark LC, Benington F, Morin RD The effects of ring-methoxyl groups on biological deamination of phenethylamines Journal of Medicinal Chemistry 8 3 353–355 May 1965 14323146 10.1021/jm00327a016 It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. See also Substituted methoxyphenethylamine Methoxyphenethylamine 2-Methoxyamphetamine Methoxyphenamine References External links 2-MPEA Category:Methoxyphenethylamines Category:TAAR1 agonists