title: Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures.
abstract: The Russian Federation prohibited the distribution of herbal mixtures with synthetic aminoalkylindoles JWH-018 and JWH-073, agonist cannabinoid receptors, on January 22, 2010. The lack or low content of their native compounds in urine requires detailed identification of their metabolites, which are excreted with urine and are present in blood. Using gas and liquid chromatography-mass spectrometry, we identified a series of metabolites in urine samples from humans and rats that were products of the following reactions: (a) mono- and dihydroxylation of the parent compounds with hydroxyl groups located at aromatic and aliphatic residues, (b) carboxylation, (c) N-dealkylation and (d) N-dealkylation and hydroxylation. The prevailing urinary metabolites in humans are monohydroxylated forms, while N-dealkylated and N-dealkyl monohydroxylated forms are found in rats. Twenty-six samples of herbal smoking mixtures with JWH-018, purchased in Russia, were analysed.
authors.affiliation: Bureau of Forensic-Medical Expertise's, Forensic-Chemical Division, Belgorod, Russia. chrzond4250@yandex.ru
authors.forename: Andrej
authors.initials: A
authors.lastname: Grigoryev
authors.forename: Sergey
authors.initials: S
authors.lastname: Savchuk
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Melnik
authors.forename: Natal'ja
authors.initials: N
authors.lastname: Moskaleva
authors.forename: Jurij
authors.initials: J
authors.lastname: Dzhurko
authors.forename: Mihail
authors.initials: M
authors.lastname: Ershov
authors.forename: Aleksandr
authors.initials: A
authors.lastname: Nosyrev
authors.forename: Aleksandr
authors.initials: A
authors.lastname: Vedenin
authors.forename: Boris
authors.initials: B
authors.lastname: Izotov
authors.forename: Irina
authors.initials: I
authors.lastname: Zabirova
authors.forename: Vladimir
authors.initials: V
authors.lastname: Rozhanets
mesh_terms: D000478:Alkylation; D000818:Animals; D002853:Chromatography, Liquid / Q000379:methods*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D006900:Hydroxylation; D013287:Illicit Drugs / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism* / Q000652:urine; D008385:Marijuana Smoking / Q000378:metabolism* / Q000652:urine; D009281:Naphthalenes / Q000378:metabolism* / Q000652:urine; D051381:Rats; D017208:Rats, Wistar; D043884:Receptor, Cannabinoid, CB1
chemical_list: D013287:Illicit Drugs; D007211:Indoles; D009281:Naphthalenes; D043884:Receptor, Cannabinoid, CB1; C552597:1-pentyl-3-(1-naphthoyl)indole