2,4-Dimethoxyphenethylamine

2,4-Dimethoxyphenethylamine.svg skin-invert-image Serotonin 5-HT2A receptor agonist None 15806-29-8 417604 369665 4535193 2,4-DMPEA; DMPEA-3; 24; 24DMP 2-(2,4-dimethoxyphenyl)ethanamine 10 15 1 2 COC1=CC(=C(C=C1)CCN)OC 1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)10(7-9)13-2/h3-4,7H,5-6,11H2,1-2H3 YDTQAPOROITHCN-UHFFFAOYSA-N 2,4-Dimethoxyphenethylamine (2,4-DMPEA), also known as DMPEA-3, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). Shulgin A, Manning T, Daley PF #47. 2,4-DMPEA 82–83 https://archive.org/details/shulgin-index-vol-1/page/82/mode/1up The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press Berkeley, CA 1 2011 978-0-9630096-3-0 709667010 Clark LC, Benington F, Morin RD The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines Ala J Med Sci 1 417–429 October 1964 14230671 Clark LC, Benington F, Morin RD The effects of ring-methoxyl groups on biological deamination of phenethylamines J Med Chem 8 3 353–355 May 1965 14323146 10.1021/jm00327a016 It is one of the positional isomers of dimethoxyphenethylamine. The in-vitro metabolism of 2,3-DMPEA and its effects on cat behavior have been studied. The drug is known to act as a low-potency partial agonist of the serotonin 5-HT2A receptor (Ki = 202–999nM; EC50 half-maximal effective concentration = 832–4,034nM; Emax maximal efficacy = 67–83%). Braden MR, Parrish JC, Naylor JC, Nichols DE Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists Mol Pharmacol 70 6 1956–1964 December 2006 17000863 10.1124/mol.106.028720 Braden MR Towards a biophysical understanding of hallucinogen action 2007 Ph.D. Purdue University 304838368 https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=9a30faca37ad48466b87a192ccd542401dc24012 The effects of 2,4-DMPEA in humans have not been reported and are unknown. 2,4-DMPEA was first described in the scientific literature by at least 1964. It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. NBOMe and NBOH derivatives with potent serotonin 5-HT2A receptor agonism, such as 24-NBOMe and 24-NBOH, have been synthesized and studied. See also Substituted methoxyphenethylamine Dimethoxyphenethylamine 2,4-Dimethoxyamphetamine Isomescaline (2,3,4-trimethoxyphenethylamine) 2C-O (2,4,5-trimethoxyphenethylamine) References External links 2,4-DMPEA - Isomer Design 2,4-DMPEA - The Shulgin Index Category:5-HT2A agonists Category:Methoxyphenethylamines Category:2,4-Substituted phenethylamines Category:Dimethoxyphenyl compounds