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Kavanagh P.,Trinity College Dublin | Grigoryev A.,Bureau of Forensic Medical Expertise | Melnik A.,Bureau of Forensic Medical Expertise | Simonov A.,Chemical Toxicology Laboratory
Journal of Analytical Toxicology | Year: 2012

3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indolederived 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/oxidationof 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. © The Author [2012]. Published by Oxford University Press. All rights reserved. Source


Grigoryev A.,Bureau of Forensic Medical Expertise | Kavanagh P.,Trinity College Dublin | Melnik A.,Bureau of Forensic Medical Expertise
Drug Testing and Analysis | Year: 2013

AM-694 (1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone), a synthetic indole-based cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS) by Irish authorities in 2010. Using gas chromatography-mass spectrometry (GC-MS), we have identified six AM-694 metabolites in post-ingestion samples. The metabolites were tentatively identified as products of (1) hydrolytic defluorination, (2) carboxylation, (3) monohydroxylation of N-alkyl chain, and (4) hydrolytic defluorination combined with monohydroxylation of N-alkyl chain. The parent compound was not detected. The excretion of major metabolites was observed up to 117h following administration. One metabolite (a product of hydrolytic defluorination) was also identified in urine samples from two individuals admitted to hospital suffering from suspected drug overdoses. Copyright © 2012 John Wiley & Sons, Ltd. Six metabolites of AM-694 the psychoactive ingredient some of herbal smoking mixtures were identified in human post-administration urine samples. The major metabolites were found to be products of metabolic hydrolytic defluorination and oxidative ones. Both parent AM-694 and its N-defluoropentylated metabolites were not found in one of the samples. © 2012 John Wiley & Sons, Ltd. Source


Grigoryev A.,Bureau of Forensic Medical Expertise | Kavanagh P.,Trinity College Dublin | Melnik A.,Bureau of Forensic Medical Expertise
Drug Testing and Analysis | Year: 2012

3-[(Adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a synthetic cannabimimetic, was identified in head shop products in Ireland in 2010. German authorities also reported it to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS) in 2011. As indole-derived cannabimimetics, such as JWH-018, JWH-073, and JWH-250, undergo extensive metabolism, it was expected that AB-001 would behave similarly. To include it in our toxicological screening protocols, we have identified its urinary metabolites in humans following oral administration. The major metabolites were found to be adamantane mono-hydroxylated and adamantane mono-hydroxylated/N-dealkylated products. No parent compound was found in urine, and metabolites were detectable for up to 160h following administration. © 2011 John Wiley & Sons, Ltd. Source


Grigor'Ev A.M.,Bureau of Forensic Medical Expertise | Savchuk S.A.,Moscow State University | Mel'Nik A.A.,Bureau of Forensic Medical Expertise | Ershov M.B.,Chemical Toxicology Laboratory | And 5 more authors.
Journal of Analytical Chemistry | Year: 2012

The consumption of JWH-018, an agonist of cannabinoid receptors within a number of smoking mixtures, can be established though the detection of its metabolites in human blood and urine. Using gas and liquid chromatography coupled with mass spectrometry, we identified 14 metabolites of JWH-018, products of mono- and dihydroxylation of aromatic and aliphatic moieties in the initial structure, carboxylation, dealkylation, and dealkylation followed by hydroxylation processes, in human and rat urine. The predominant metabolites excreted with urine, which can also be detected in human blood serum, were found to be products of monohydroxylation and in urine of rats, products of dealkylation with monohydroxylation. © 2012 Pleiades Publishing, Ltd. Source

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