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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 Expertises | Melnik A.,Bureau of Forensic Medical Expertises | Savchuk S.,Moscow State University | Simonov A.,Chemical Toxicology Laboratory | Rozhanets V.,Nacional Research Center on Addictions
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences | Year: 2011

Prohibition of some synthetic cannabimimetics (e.g., JWH-018, JWH-073 and CP 47497) in a number of countries has led to a rise in new compounds in herbal mixtures that create marijuana-like psychotropic effects when smoked. The cannabimimetic JWH-250 (1-pentyl-3-(2-methoxyphenylacetyl)indole) was identified in May 2009 by the German Federal Criminal Police as an new ingredient in herbal smoking mixtures. The absence or low presence of the native compound in urine samples collected from persons who had consumed JWH-250 necessitates a detailed identification of their metabolites, which are excreted with urine and present in blood. Using gas and liquid chromatography-mass spectrometry (GC-MS and LC-MS/MS), we identified a series of metabolites in urine samples and serum sample from humans and urine samples from rats that were products of the following reactions: (a) mono- and dihydroxylation of aromatic and aliphatic residues of the parent compound, (b) trihydroxylation and dehydration of the N-alkyl chain, (c) N-dealkylation and (d) N-dealkylation and monohydroxylation. The prevailing urinary metabolites in humans were the monohydroxylated forms, while N-dealkylated and N-dealkyl monohydroxylated forms were found in rats. The detection of the mono- and dihydroxylated metabolites of JWH-250 in urine and serum samples by GC-MS and LC-MS/MS proved to be effective in determining consumption of this drug. © 2011 Elsevier B.V. Source


Grigoryev A.,Bureau of Forensic Medical Expertises | Kavanagh P.,Trinity College Dublin | Melnik A.,Bureau of Forensic Medical Expertises | Savchuk S.,National Research Center on Addiction | Simonov A.,Chemical Toxicology Laboratory
Journal of Analytical Toxicology | Year: 2013

Studies on the pyrolysis of the synthetic cannabinoid agonist UR-144 ((1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone) have shown that its major pyrolysis product is a tetramethylcyclopropane ring-opened alkene. Considering that smoking is a common way of ingesting synthetic cannabimimetics, the presence of the metabolites of this pyrolysis product would be expected in biological fluids. Using GC-MS and LC-MS-MS methods, a series of phase I metabolites of UR-144 and its pyrolysis product were detected in the urine samples from patients admitted to hospital with suspected drug intoxication. The metabolites were tentatively identified as the products of mono-hydroxylation, di-hydroxylation, mono-hydroxylation with formation of the carbonyl group on the N-alkyl chain, carboxylation and N-dealkylation with mono-hydroxylation. In the case of the UR-144 pyrolysis product, metabolites with hydration of the aliphatic double bond were also identified. The parent compounds were detected as trace amounts in some urine samples, and the hydrated derivative of the UR-144 pyrolysis product was detected in the majority of samples. The detection of mono-hydroxylated metabolites of UR-144 (LC-MS-MS) and mono-hydroxylated/with hydration metabolites of the UR-144 pyrolysis product (GC-MS) was found to be the most useful method of establishing UR-144 ingestion. © The Author [2013]. Published by Oxford University Press. All rights reserved. Source


Kavanagh P.,Trinity College Dublin | Grigoryev A.,Bureau of Forensic Medical Expertises | Melnik A.,Bureau of Forensic Medical Expertises | Savchuk S.,National Research Center on Addiction | And 2 more authors.
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences | Year: 2013

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 2.5-3. h (JWH-203) and 6-10. h (JWH-251) following ingestion. These metabolites were observed (GC-MS) for to 10 and 8 days (JWH-203 and JWH-251, respectively). © 2013 Elsevier B.V. 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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