title: A sensitive GC-EIMS method for simultaneous detection and quantification of JWH-018 and JWH-073 carboxylic acid and hydroxy metabolites in urine.
abstract: Synthetic cannabinoids, including JWH-018 and JWH-073, belong to a class of aminoalkylindoles (AAIs) that are smoked to produce an effect similar to tetrahydrocannabinol. Compounds in this class are often collectively known as 'Spice'. After ingestion, these compounds are extensively metabolized to their hydroxy and carboxylic acid metabolites. During forensic analysis, detection of these metabolites in urine is an indication of past exposure to the parent compounds. The analytical process involved hydrolysis of conjugated metabolites by glucuronidase, solvent extraction, derivatization by trifluoroacetic anhydride and hexafluoroisopropanol and GC-EIMS detection. Identification of the unknown was based on the criteria of GC retention time within ±2% and mass spectral ion ratio within ±20% of that of a standard. Deuterated internal standards of the carboxylic acid metabolites were used for quantification. The acid (JWH-018-COOH, JWH-073-COOH) and hydroxy (JWH-018-OH, JWH-073-OH) metabolites were linear over the concentration range of 0.1-10 and 0.2-10 ng/mL, respectively, with a correlation coefficient-square, R(2) > 0.999 (N = 5). Extraction recoveries of the metabolites were within 79 and 87%. The method was applied to 17 urine specimens collected as part of a military law enforcement investigation. Nine of the specimens tested positive for one or more of the metabolites. When the procedure was extended to screen other AAI compounds, two of the specimens were found to contain JWH-210, JWH-250 (JWH-302 or JWH-201) and JWH-250 (C4 isomers). The GC-EIMS method presented here was found to be suitable for detecting JWH-018 and JWH-073 metabolites and other AAI compounds in urine.
authors.affiliation: Division of Forensic Toxicology, Office of the Armed Forces Medical Examiner, Dover AFB, DE, USA buddha_paul@yahoo.com.
authors.forename: Buddha D
authors.initials: BD
authors.lastname: Paul
authors.affiliation: Division of Forensic Toxicology, Office of the Armed Forces Medical Examiner, Dover AFB, DE, USA.
authors.forename: Thomas
authors.initials: T
authors.lastname: Bosy
mesh_terms: D001711:Biotransformation; D002138:Calibration; D002264:Carboxylic Acids / Q000652:urine*; D002851:Chromatography, High Pressure Liquid; D053593:Forensic Toxicology / Q000379:methods*; D008401:Gas Chromatography-Mass Spectrometry / Q000592:standards; D006801:Humans; D006900:Hydroxylation; D013287:Illicit Drugs / Q000652:urine*; D007211:Indoles / Q000652:urine*; D057230:Limit of Detection; D016014:Linear Models; D008889:Military Personnel; D009281:Naphthalenes / Q000652:urine*; D011237:Predictive Value of Tests; D012015:Reference Standards; D015203:Reproducibility of Results; D012907:Smoking; D015813:Substance Abuse Detection / Q000379:methods* / Q000592:standards; D019966:Substance-Related Disorders / Q000175:diagnosis / Q000652:urine*; D053719:Tandem Mass Spectrometry
chemical_list: D002264:Carboxylic Acids; D013287:Illicit Drugs; D007211:Indoles; D009281:Naphthalenes; C568258:JWH-073; C552597:1-pentyl-3-(1-naphthoyl)indole