Studies on the metabolism of the Δ9-tetrahydrocannabinol precursor Δ9-tetrahydrocannabinolic acid A (Δ9-THCA-A) in rat using LC-MS/MS, LC-QTOFMS and GC-MS techniques

Journal of Mass Spectrometry

Volumn 44, Issue 10, 2009, Pages 1423-1433

  Jung, Julia ^a   Meyer, Markus R ^b   Maurer, Hans H ^b   Neusüß, Christian ^c   Weinmann, Wolfgang ^a   Auwärter, Volker ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

^c AALEN UNIVERSITY   (Germany)

Author keywords

9 Tetrahydrocannabinolic acid A ( 9 THCA A); GC MS; LC MS MS; LC QTOF MS; Metabolism

Indexed keywords

ACCURATE MASS; BODY MASS; CANNABIS SATIVA; FRESH PLANTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GC-MS; GLUCURONIDATION; GLUCURONIDES; HIGH RESOLUTION; IN-VIVO; LC-MS/MS; LC-QTOF MS; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; ORAL INTAKE; PARENT COMPOUNDS; RAT URINE; TIME OF FLIGHT; URINE SAMPLE;

ACIDS; ALDEHYDES; BIOCHEMISTRY; BIOMOLECULES; BODY FLUIDS; CHROMATOGRAPHIC ANALYSIS; GAS CHROMATOGRAPHY; HEMP; HYDROXYLATION; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETERS; MASS SPECTROMETRY; METABOLITES; ORGANIC POLYMERS;

METABOLISM;

11 HYDROXYDRONABINOL; DRONABINOL; GLUCURONIDE; TETRAHYDROCANNABINOLIC ACID; TETRAHYDROCANNABINOL;

ANIMAL EXPERIMENT; ARTICLE; DEHYDRATION; DRUG DETERMINATION; GAS CHROMATOGRAPHY; GLUCURONIDATION; HYDROXYLATION; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; TANDEM MASS SPECTROMETRY; ANIMAL; BLOOD; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; ORAL DRUG ADMINISTRATION; URINE; WISTAR RAT;

CANNABIS; CANNABIS SATIVA; RATTUS;

ADMINISTRATION, ORAL; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MALE; MASS SPECTROMETRY; RATS; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TETRAHYDROCANNABINOL;

EID: 70349868313     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1624     Document Type: Article

References (33)

1. C. E. Turner, M. A. Elsohly, E. G. Boeren. Constituents of Cannabis Sativa L. XVII. A review of natural constituents. Journal of Natural Products 1980, 43, 169.
2. R. Mechoulam, S. Ben-Shabat. From gan-zi-gun-nu to anandamide and 2-arachidonoylglycerol: the ongoing story of cannabis. Natural Product Reports 1999, 16, 131.
3. T. Yamauchi, Y. Shoyama, H. Aramaki, T. Azuma, I. Nishioka. Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol. Chemical and Pharmaceutical Bulletin 1967, 15, 1075.
4. Y. Shoyama, I. Yamauchi, V. Nishioka. Cannabis, Cannabigerolic acid monomethyl ether and cannabinolic acid. Chemical and Pharmaceutical Bulletin 1970, 18, 1327.
5. G. S. Lewis, C. E. Turner. Constituents of Cannabis sativa L. XIII-Stability of dosage form prepared by impregnating synthetic (-)-Δ9-trans-tetrahydrocannabinol on placebo Cannabis plant material. Journal of Pharmaceutical Sciences 1978, 67, 876.
6. R. K. Razdan, A. J. Puttick, B. A. Zitko, G. R. Handrick. Hashish VI: conversion of (-)-1(6)-tetrahydrocannabinol to (-)- 1(7)-tetrahydrocannabinol. Stability of (-)-1- and (-)-1(6)- tetrahydrocannabinols. Experientia 1972, 28, 121.
7. 9-THC in cannabis products. Forensic Science International 2005, 149, 3.
8. J. Jung, J. Kempf, H. Mahler, W. Weinmann. Detection of Δ9-tetrahydrocannabinolic acid in human urine and blood serum by LC-MS/MS. Journal ofMass Spectrometry 2006, 42, 354.
9. J. Jung, V. Auwaerter, G. Herzog, H. Mahler, J. Kempf, W. Weinmann. Determination of Δ9-Tetrahydrocannabinolic Acid A in Serum Samples by GC-MS. In Proceedings of the XV. GTFCh-Symposium, F. Pragst, R. Aderjan (eds). Mosbach (Baden): Bad Vilbel, 2007, 378.
10. C. Moore, S. Rana, C. Coulter. Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid. Journal of Chromatography B 2007, 852, 459.
11. B. Costa. On the pharmacological properties of Δ9- tetrahydrocannabinol (THC). Chemistry and Biodiversity 2007, 4, 1664.
12. D. Baker, G. Pryce, G. Giovannoni, A. J. Thompson. The therapeutic potential of cannabis. Lancet Neurology 2003, 2, 291.
13. J. L. Croxford. Therapeutic potential of cannabinoids in CNS disease. CNS Drugs 2003, 17, 179.
14. E. M. Williamson, F. J. Evans. Cannabinoids in clinical practice. Drugs 2000, 60, 1303.
15. M. Guzmán. Cannabinoids: potential anticancer agents. Nature reviews. Cancer 2003, 3, 745.
16. J. L. Croxford, S. D. Miller. Towards cannabis and cannabinoid treatment of multiple sclerosis. Drugs of Today 2004, 40, 663.
17. H. H. Maurer, C. Sauer, D. S. Theobald. Toxicokinetics of drugs of abuse: current knowledge of the isoenzymes involved in the human metabolism of tetrahydrocannabinol, cocaine, heroin, morphine and codein. Therapeutic DrugMonitoring 2006, 28, 447.
18. T. M. Bland, R. L. Haining, T. S. Tracy, P. S. Callery. CYP2C-catalyzed delta(9)-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochemical Pharmacology 2005, 70, 1096.
19. K. Watanabe, T. Matsunaga, I. Yamamoto, Y. Funae, H. Yoshimura. Involvement of CYP2C in the metabolism of cannabinoids by human hepatic microsomes from an old woman. Biological and Pharmaceutical Bulletin 1995, 18, 1138.
20. 1-tetrahydrocannabinol. Drug metabolism and Disposition: the Biological Fate of Chemicals 1992, 20, 421.
21. 1- tetrahydrocannabinol formed by human livers. Drug Metabolism and Disposition: the Biological Fate of Chemicals 1982, 10, 297.
22. 9-tetrahydrocannabinol by rat liver microsomes. Drug Metabolism and Disposition 1990, 18(6), 943.
23. 9-tetrahydrocannabinol by liver microsomes of adult female rats. Drug Metabolism and Disposition 1992, 20(1), 79.
24. M. E. Wall, M. Perez-Reyes. The metabolism of Δ9- tetrahydrocannabinol and related cannabinoids in man. Journal of Clinical Pharmacology 1981, 21, 178S.
25. M. M. Halldin, M. Widman. Glucuronic acid conjugate of Δ1-tetrahydrocannabinol in the urine of man. Arzneimittelforschung 1983, 33, 177.
26. 9- tetrahydrocannabinol-11-oic acid glucuronide: a tetrahydrocannabinol metabolite. The Journal of Pharmacy and Pharmacology 1980, 32, 445.
27. M. A. Huestis, M. Elsohly, W. Nebro, A. Barnes, R. A. Gustafson, M. L. Smith. Estimating time of last oral ingestion of cannabis from plasma THC and THCCOOH concentrations. Therapeutic Drug Monitoring 2006, 28, 540.
28. 9-tetrahydrocannabinol concentrations. Clinical Chemistry 2005, 51, 2289.
29. M. A. Huestis, J. E. Henningfield, E. J. Cone. Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smokingmarijuana. JournalofAnalytical Toxicology 1992, 16, 276.
30. 9-tetrahydrocannabinol (THC-COOH). Journal of Analytical Toxicology 1992, 16, 283.
31. T. Daldrup, I. Meininger. Cannabis imStraßenverkehr, 1st ed.Gustav Fischer Verlag: Stuttgart, Jena, Lübeck, Ulm, 1998, 193.
32. 9-THCA-A) from Cannabis sativa. Poster at the 46th International Meeting of the TIAFT, 2-8 June 2008, Martinique, French West Indies. (Annales de Toxicologie Analytique 2008, 20(S1), 75).
33. F. Grotenhermen. Pharmacokinetics and pharmacodynamics of cannabinoids. Clinical Pharmacokinetics 2003, 42(4), 327.