title: The identification of the urinary metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by gas chromatography-mass spectrometry.
abstract: 3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indole-derived cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction via the Early Warning System by Hungarian authorities in 2010 and later identified in head shop test purchases in Ireland. Using gas chromatography-mass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. The O-demethylated metabolites were found to be the most useful metabolic markers for the identification of RCS-4 ingestion.
authors.affiliation: Department of Pharmacology and Therapeutics, School of Medicine, Trinity College, Dublin, Ireland.
authors.forename: Pierce
authors.initials: P
authors.lastname: Kavanagh
authors.forename: Andrej
authors.initials: A
authors.lastname: Grigoryev
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Melnik
authors.forename: Anton
authors.initials: A
authors.lastname: Simonov
mesh_terms: D000328:Adult; D015415:Biomarkers / Q000652:urine; D002186:Cannabinoids / Q000737:chemistry / Q000652:urine*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D006900:Hydroxylation; D013287:Illicit Drugs / Q000032:analysis*; D007211:Indoles / Q000737:chemistry / Q000652:urine*; D008297:Male; D010084:Oxidation-Reduction; D015813:Substance Abuse Detection / Q000379:methods*; D055815:Young Adult
chemical_list: C574712:3-(4-methoxybenzoyl)-1-pentylindole; D015415:Biomarkers; D002186:Cannabinoids; D013287:Illicit Drugs; D007211:Indoles