Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in 'herbal mixtures' using LC-MS/MS techniques

• Published in: Journal of mass spectrometry. Vol. 47; no. 1; pp. 54 - 65
• Main Authors: Hutter, M., Broecker, S., Kneisel, S., Auwärter, V.
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.01.2012; Wiley
• Subjects: aminoalkylindoles; Biological and medical sciences; Cannabinoids - metabolism; Cannabinoids - urine; Chromatography, Liquid - methods; Drug addictions; Humans; Indoles - chemistry; Indoles - metabolism; Indoles - urine; Ions; JWH; LC-MS/MS; Medical sciences; metabolism; Naphthalenes - chemistry; Naphthalenes - metabolism; Naphthalenes - urine; Street Drugs - urine; Substance Abuse Detection; synthetic cannabinoids; Tandem Mass Spectrometry - methods; Toxicology; Biological fluid; Tandem mass spectrometry; Metabolite; Psychotropic; HPLC chromatography; Fraud; Cannabinoid; Electrospray; LC-MS/MS; aminoalkylindoles; Illicit preparation; Qualitative analysis; Drug of abuse; JWH; Adulteration; synthetic cannabinoids; Urine; Terpenoid; Hydroxylation; Coupled method; Metabolism; Synthetic product; Quality control; Carboxylation; Mass spectrometry
• ISSN: 1076-5174; 1096-9888
• DOI: 10.1002/jms.2026

Herbal mixtures, such as ‘Spice’, containing cannabimimetic compounds are easily available on the Internet and have become increasingly popular among people having to undergo urine drug testing, as these compounds are not detected by current immunochemical tests. For analysis of urine samples, knowledge of the main metabolites is necessary as the unchanged compounds are usually not found in urine after consumption. In this paper, the identification of the major metabolites of the currently most common seven synthetic cannabinoids is presented. Urine samples from patients of psychiatric facilities known to have consumed synthetic cannabinoids were screened by LC‐MS/MS and HR‐MS/MS techniques, and the major metabolites for each of the following synthetic cannabinoids were identified by their enhanced product ion spectra and accurate mass measurement: JWH‐018, JWH‐073, JWH‐081, JWH‐122, JWH‐210, JWH‐250 and RCS‐4. The major metabolic pathway is monohydroxylation either at the N‐alkyl side chain, the naphthyl moiety or the indole moiety. In addition, metabolites with carboxylated alkyl chains were identified for some of the compounds. These results facilitate the design of urine screening methods for detecting consumption of synthetic cannabinoids. Copyright © 2012 John Wiley & Sons, Ltd.