2,6-Dimethoxyphenethylamine

vanc 6 2,6-Dimethoxyphenethylamine.svg skin-invert-image 185px None 486-95-3 417602 369663 2,6-DMPEA; DMPEA-5 2-(2,6-dimethoxyphenyl)ethanamine 10 15 1 2 COC1=C(C(=CC=C1)OC)CCN 1S/C10H15NO2/c1-12-9-4-3-5-10(13-2)8(9)6-7-11/h3-5H,6-7,11H2,1-2H3 VIHNHLSXVPNVPY-UHFFFAOYSA-N 2,6-Dimethoxyphenethylamine (2,6-DMPEA), also known as DMPEA-5, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). Shulgin A, Manning T, Daley PF #48. 2,6-DMPEA The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Berkeley, CA 1 84–85 2011 https://archive.org/details/shulgin-index-vol-1/page/84/mode/1up Transform Press 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 dimethoxyphenethylamine. Its in-vitro metabolism and effects on cat behavior have been described. Clark LC, Benington F, Morin RD The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines The Alabama Journal of Medical Sciences 1 417–429 October 1964 14230671 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 Ernst AM Relation between the structure of certain methoxyphenylethylaminederivatives and the occurrence of a hypokinetic rigid syndrome Psychopharmacologia 7 6 383–390 May 1965 5890661 10.1007/BF00402360 The drug showed no activity as a norepinephrine reuptake inhibitor or releasing agent in vitro. Rotman A, Lundstrom J, McNeal E, Daly J, Creveling CR Norepinephrine uptake sites in cardiac tissue. Lack of affinity of 6-hydroxynorepinephrine and related compounds Journal of Medicinal Chemistry 18 2 138–142 February 1975 1120979 10.1021/jm00236a005 It is relatively unaffected by monoamine oxidase (MAO) and is said to be behaviorally inactive in animals. The effects of 2,6-DMPEA in humans have not been reported and are unknown. 2,6-DMPEA was first described in the scientific literature by at least 1962. Marley E Action of some sympathomimetic amines on the cat's iris, in situ or isolated The Journal of Physiology 162 2 193–211 July 1962 14470081 1359651 10.1113/jphysiol.1962.sp006926 It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Notable derivatives of 2,6-DMPEA include the psychedelic and related drugs Ψ-2C-T-4 (psi-2C-T-4), ψ-DOM (psi-DOM), and CT-5172. Shulgin AT Laing RR Basic Pharmacology and Effects Hallucinogens: A Forensic Drug Handbook 67–137 2003 Elsevier Science Forensic Drug Handbook Series 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 See also Substituted methoxyphenethylamine Dimethoxyphenethylamine 2,6-Dimethoxyamphetamine TMA-6 (2,4,6-trimethoxyamphetamine) References External links 2,6-DMPEA - Isomer Design 2,6-DMPEA - The Shulgin Index Category:Dimethoxyphenyl compounds Category:Methoxyphenethylamines