The identification of the urinary metabolites of 3-(4-methoxybenzoyl)-1-pentylindole (RCS-4), a novel cannabimimetic, by gas chromatography-mass spectrometry

Journal of Analytical Toxicology
Pierce KavanaghAnton Simonov

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.

References

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Citations

Jan 16, 2014·Analytical and Bioanalytical Chemistry·Robert KronstrandMartin Josefsson
Apr 9, 2015·Drug Metabolism Reviews·Marisol S CastanetoMarilyn A Huestis
Oct 9, 2012·Drug Testing and Analysis·Tim SobolevskyGrigory Rodchenkov
Sep 20, 2015·Science & Justice : Journal of the Forensic Science Society·Karim M Abdel-HayC Randall Clark
Nov 28, 2014·Drug Testing and Analysis·Tim SobolevskyGrigory Rodchenkov
Sep 19, 2014·Drug Testing and Analysis·Marisol S CastanetoMarilyn A Huestis
Apr 25, 2016·Journal of Pharmaceutical and Biomedical Analysis·Karim M Abdel-HayC Randall Clark
Dec 10, 2013·Forensic Science International : Synergy·Piotr AdamowiczKarolina Sekuła
May 23, 2014·Forensic Science International : Synergy·Allan J BarnesMarilyn A Huestis
Jun 20, 2018·Journal of Chromatographic Science·Amber Thaxton-WeissenfluhC Randall Clark

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