title: Detection and tentative identification of urinary phase I metabolites of phenylacetylindole cannabimimetics JWH-203 and JWH-251, by GC-MS and LC-MS/MS.
abstract: The synthetic phenylacetylindole cannabimimetics, JWH-203 and JWH-251, have been identified in 'herbal' smoking mixtures following the widespread legislative control of 'first generation' compounds such as JWH-018 and CP47, 497(C8). N-Alkylindole cannabimimetics (including phenylacetylindoles) undergo extensive metabolism and little or none of the parent compounds are found in urine. Utilizing GC-MS and LC-MS/MS, a series of JWH-203 and JWH-251 urinary metabolites have been tentatively identified. These are products of mono- and dihydroxylation, monohydroxylation combined with formation of carbonyl group on the N-pentyl chain, carboxylation of N-pentyl chain and N-dealkylation combined with monohydroxylation. Additionally, trihydroxylated metabolites were detected for JWH-203. No parent compounds were detected. The monohydroxylated metabolites with the hydroxyl group positioned on the N-pentyl chain were the most abundant and were found to be suitable for establishing ingestion of JWH-203 or JWH-250. Maximum urinary concentrations of chain-monohydroxylated metabolites were observed at 2.5-3h (JWH-203) and 6-10h (JWH-251) following ingestion. These metabolites were observed (GC-MS) for to 10 and 8 days (JWH-203 and JWH-251, respectively).
authors.affiliation: Department of Pharmacology and Therapeutics, Trinity College, School of Medicine, Dublin 8, Ireland.
authors.forename: Pierce
authors.initials: P
authors.lastname: Kavanagh
authors.forename: Andrej
authors.initials: A
authors.lastname: Grigoryev
authors.forename: Alexandra
authors.initials: A
authors.lastname: Melnik
authors.forename: Sergey
authors.initials: S
authors.lastname: Savchuk
authors.forename: Anton
authors.initials: A
authors.lastname: Simonov
authors.forename: Vladimir
authors.initials: V
authors.lastname: Rozhanets
mesh_terms: D002853:Chromatography, Liquid / Q000379:methods*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D013287:Illicit Drugs / Q000737:chemistry / Q000378:metabolism / Q000652:urine*; D007211:Indoles / Q000737:chemistry / Q000378:metabolism / Q000652:urine*; D015394:Molecular Structure; D015813:Substance Abuse Detection / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: C586414:1-(1-pentyl-1H-indol-3-yl)-2-o-tolylethanone; C568288:1-pentyl-3-(2'-chlorophenylacetyl)indole; D013287:Illicit Drugs; D007211:Indoles
keywords: GC–MS; JWH-203; JWH-251; LC–MS/MS; Metabolite; Synthetic cannabinoid