title: Characterization of in vitro metabolites of JWH-018, JWH-073 and their 4-methyl derivatives, markers of the abuse of these synthetic cannabinoids.
abstract: In vitro incubation with human liver microsomes of JWH-018, JWH-073, JWH-122 and for the first time 1-butyl-3-(1-(4-methyl)naphthoyl)indole (the 4-methylnaphthoyl analogue of JWH-073) was investigated to identify the principal metabolites of alkylindole synthetic cannabinoids, thus helping the discovering of synthetic cannabinoids abusers. The results obtained showed that the most abundant metabolites were mono-hydroxylated derivatives either on the alkyl chain (ω or ω-1 position) or on the indole (presumably in position 5 or 6) and naphthalene moieties. Moreover the extraction conditions of these derivatives from biological fluids, mainly plasma and urine spiked with commercially available metabolite standards, and the incubation procedure were investigated to obtain a fast, reliable and suitable extraction protocol to detect either the parent drugs or their metabolites by means of GC/MS.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Veniero
authors.initials: V
authors.lastname: Gambaro
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Sebastiano
authors.initials: S
authors.lastname: Arnoldi
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Stefania
authors.initials: S
authors.lastname: Bellucci
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Eleonora
authors.initials: E
authors.lastname: Casagni
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Lucia
authors.initials: L
authors.lastname: Dell'Acqua
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Fumagalli
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Pallavicini
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy. Electronic address: gabriella.roda@unimi.it.
authors.forename: Gabriella
authors.initials: G
authors.lastname: Roda
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Chiara
authors.initials: C
authors.lastname: Rusconi
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
authors.forename: Ermanno
authors.initials: E
authors.lastname: Valoti
mesh_terms: D002186:Cannabinoids / Q000737:chemistry* / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006801:Humans; D013287:Illicit Drugs / Q000737:chemistry / Q000378:metabolism; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism*; D008862:Microsomes, Liver / Q000378:metabolism; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism*; D015203:Reproducibility of Results
chemical_list: D002186:Cannabinoids; D013287:Illicit Drugs; D007211:Indoles; D009281:Naphthalenes; C568258:JWH-073; C552597:1-pentyl-3-(1-naphthoyl)indole
keywords: Alkylindole metabolites; GC/FID; GC/MS; JWH-018; JWH-073; JWH-122 ;1-Butyl-3-(1-(4-methyl)naphthoyl)indole