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Metabolism of synthetic cannabinoid receptor agonists encountered in clinical casework: major in vivo phase I metabolites of JWH-007, JWH-019, JWH-203, JWH-307, UR-144, XLR-11, AM-2201, MAM-2201 and AM-694 in human urine using LC-MS/MS

Hutter, M, Broecker, S, Kneisel, S, Franz, F, Brandt, SD and Auwärter, V (2018) Metabolism of synthetic cannabinoid receptor agonists encountered in clinical casework: major in vivo phase I metabolites of JWH-007, JWH-019, JWH-203, JWH-307, UR-144, XLR-11, AM-2201, MAM-2201 and AM-694 in human urine using LC-MS/MS. Current Pharmaceutical Biotechnology. ISSN 1389-2010

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Abstract

Background: `Herbal mixtures` containing synthetic cannabinoid receptor agonists (SCRAs) are promoted as legal alternative to marihuana and are easily available via the Internet. Keeping analytical methods for the detection of these SCRAs up-to-date is a continuous challenge for clinicians and toxicologists due to the high diversity of the chemical structures and the frequent emergence of new compounds. Since many SCRAs are extensively metabolized, analytical methods used for urine testing require previous identification of the major metabolites of each compound. Objective: The aim of this study was to identify the in vivo major metabolites of nine SCRAs (AM-694, AM-2201, JWH-007, JWH-019, JWH-203, JWH-307, MAM-2201, UR-144, XLR-11) for unambiguous detection of a drug uptake by analysis of urine samples. Method: Positive urine samples from patients of hospitals, detoxification and therapy centers as well as forensic-psychiatric clinics were analyzed by means of liquid chromatography-tandem mass spectrometry (LC-MS/MS) and liquid chromatography-quadrupol time-of-flight mass spectrometry (LC-qToF-MS) for investigation of the in vivo major metabolites. Results: For all investigated SCRAs, monohydroxylation, dihydroxylation and/or formation of the N-pentanoic acid metabolites were among the most abundant metabolites detected in human urine samples. Substitution of the fluorine atom was observed to be an important metabolic reaction for compounds carrying an N-(5-fluoropentyl) chain. Dealkylated metabolites were not detected in vivo. Conclusion: The investigated metabolites facilitate the reliable detection of drug uptake by analysis of urine samples. For distinction between uptake of the fluorinated and the non-fluorinated analogs, the N-(4-hydroxypentyl) metabolite of the non-fluorinated analog was identified as a useful analytical target and consumption marker.

Item Type: Article
Uncontrolled Keywords: 1004 Medical Biotechnology, 1115 Pharmacology And Pharmaceutical Sciences
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Bentham Science Publishers
Date Deposited: 15 May 2018 10:59
Last Modified: 15 May 2018 10:59
DOI or Identification number: 10.2174/1389201019666180509163114
URI: http://researchonline.ljmu.ac.uk/id/eprint/8670

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