title: A GC-MS study of three major acidic metabolites of delta 1-tetrahydrocannabinol.
abstract: The major urinary metabolite of delta 1-tetrahydrocannabinol (delta 1-THC) (1), delta 1-THC-7-oic acid (2), has been extensively studied for several purposes, including testing in the workplace for drug abuse. Immunoassays in combination with more specific methods such as gas chromatography-mass spectrometry (GC-MS), are commonly used for verification of positive results in the screening. Two additional and recently synthesized acidic metabolites of 1, 4",5"-bisnor-delta 1-THC-7,3"-dioic acid (3) and 4"-hydroxy-delta 1-THC-7-oic acid (4), were studied to widen the scientific basis in the analysis. Five different derivatives were examined using GC-MS. In addition, a new deuterated internal standard for 2, [2H10]-2, was evaluated. According to our results, suitable derivatives of 2, 3, and 4, according to chromatographic properties, are the methyl ester/silyl ether (procedure a), the methyl ester/trifluoroacetate (procedure b), or the silyl ester/silyl ether (procedure c). The estimated recoveries of [2H5]-3 and [2H6]-4 using liquid-liquid extraction were 24% and 50%, respectively. The properties of [2H10]-2 as internal standard were equivalent to those of [2H9]-2 and, under the conditions used, did not appear to give rise to a significantly higher chromatographic resolution from that of 2. However, [2H10]-2 produces ions at different mass numbers, which makes it useful as a complement to the existing deuterated internal standards of 2.
authors.affiliation: Division of Pharmacognosy, Uppsala University, Sweden.
authors.forename: M
authors.initials: M
authors.lastname: Szirmai
authors.forename: O
authors.initials: O
authors.lastname: Beck
authors.forename: N
authors.initials: N
authors.lastname: Stephansson
authors.forename: M M
authors.initials: MM
authors.lastname: Halldin
mesh_terms: D013759:Dronabinol / Q000378:metabolism* / Q000652:urine*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods* / Q000592:standards; D006801:Humans; D012015:Reference Standards; D015813:Substance Abuse Detection / Q000379:methods*; D013997:Time Factors
chemical_list: D013759:Dronabinol