Gas and Liquid Chromatography-Mass Spectrometry Detection of the Urinary Metabolites of UR-144 and Its Major Pyrolysis Product

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 cannab...

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Bibliographic Details
Published in:Journal of analytical toxicology 2013-06, Vol.37 (5), p.265-276
Main Authors: Grigoryev, Andrej, Kavanagh, Pierce, Melnik, Alexandra, Savchuk, Sergey, Simonov, Anton
Format: Article
Language:English
Subjects:
Cannabinoids - urine
Chromatography, High Pressure Liquid
Controlled Substances - urine
Gas Chromatography-Mass Spectrometry - methods
Hot Temperature
Humans
Smoking
Substance Abuse Detection - methods
Tandem Mass Spectrometry
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Summary: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.
ISSN:0146-4760
1945-2403
DOI:10.1093/jat/bkt028