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'''4-Chloro-2,5-dimethoxyamphetamine''' (also known as '''DOC''') is a [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. | '''4-Chloro-2,5-dimethoxyamphetamine''' (also known as '''DOC''') is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. | ||
DOC was first synthesized by a team at the University of Alberta in 1972.<ref>Coutts, Ronald T; Malicky, Jerry L. (1973). "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry, 1973, 51(9): 1402-1409, 10.1139/v73-210 | http://www.nrcresearchpress.com/doi/abs/10.1139/v73-210</ref> However, its usage in humans was not popularized until the 1991 publication [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]].<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref> Preceding this, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref>Brian A. Dawson & George A. Neville (1989) "Identification of Two New 'Designer' Amphetamines by NMR Techniques", Canadian Society of Forensic Science Journal, 22:2, 195-202, https://doi.org/10.1080/00085030.198</ref> | DOC was first synthesized by a team at the University of Alberta in 1972.<ref>Coutts, Ronald T; Malicky, Jerry L. (1973). "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry, 1973, 51(9): 1402-1409, 10.1139/v73-210 | http://www.nrcresearchpress.com/doi/abs/10.1139/v73-210</ref> However, its usage in humans was not popularized until the 1991 publication [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]].<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref> Preceding this, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.<ref>Brian A. Dawson & George A. Neville (1989) "Identification of Two New 'Designer' Amphetamines by NMR Techniques", Canadian Society of Forensic Science Journal, 22:2, 195-202, https://doi.org/10.1080/00085030.198</ref> | ||