Metabolites of cannabidiol identified in human urine

References

• Binder M., Agurell S., Leander K., Lindgren J.-E. Zur Identifikation potentieller Metabolite von Cannabis-Inhaltstoffen: Kernresonanz- und massenspektroskopische Untersuchungen an seitenketten-hydroxylierten Cannabinoiden. Helvetica Chimica Acta 1974; 57: 1626–1641
   PubMed Web of Science ®Google Scholar
• Consroe P., Snider S. R. Therapeutic potential of cannabinoids in neurological disorders. Cannabinoids as Therapeutic Agents, R. Mechoulam. CRC Press, Boca Raton, FL 1986; 21–49
   Google Scholar
• Cunha J. M., Carlini E. A., Periera E. E., Ramos O. L., Pimentel C., Gagliardi R., Sanvito W. L., Lander N., Mechoulam R. Chronic administration of cannabidiol to healthy volunteers and epileptic patients. Pharmacology 1980; 21: 175–185
   PubMed Web of Science ®Google Scholar
• Fernandes M., Waring N., Christ W., Hill R. Interactions of several cannabinoids with the hepatic drug metabolising system. Biochemical Pharmacology 1973; 22: 2981–2987
   Google Scholar
• Harvey D. J. The mass spectrometry of the trimethylsilyl derivatives of hydroxy and acid metabolites of delta-1- and delta-6-tetrahydro-cannabinol. Biomedical Mass Spectrometry 1981; 8: 579–588
   PubMedGoogle Scholar
• Harvey D. J. Mass spectrometry of the cannabinoids and their metabolites. Mass Spectrometry Reviews 1987; 6: 135–229
   Web of Science ®Google Scholar
• Harvey D. J. Oxidative cleavage of the pentyl side-chain of cannabinoids: Identification of new biotransformation pathways in the metabolism of 4′-hydroxy-delta-9-tetrahydrocannabinol in the mouse. Drug Metabolism and Disposition 1989a, in press
   Google Scholar
• Harvey D. J. Further studies on the oxidative cleavage of the pentyl side-chain of cannabinoids: Identification of new biotransformation products in the metabolism of 3′-hydroxy-delta-9-tetrahydrocannabinol by the mouse. Xenobiotica 1989; 19: 1437–1447
   PubMed Web of Science ®Google Scholar
• Harvey D. J., Leuschner J. T. A. Studies on the beta-oxidative metabolism of delta-1- and delta-6-tetrahydrocannabinol in the mouse. The in vivo biotransformation of metabolites oxidized in the side-chain. Drug Metabolism and Disposition 1985; 13: 215–219
   PubMed Web of Science ®Google Scholar
• Harvey D. J., Mechoulam R. (1987) Identification of cannabidiol metabolites in human urine. Presented at the 35th conference of the American Society for Mass Spectrometry and Allied Topics Abstracts, Denver, CO, May, 24-291987, 1020–1021
   Google Scholar
• Harvey D. J., Paton W. D. M. The use of deuterium labelling in structural and quantitative studies of tetrahydrocannabinol metabolites by mass spectrometry. Advances in Mass Spectrometry 1980; 8: 1194–1203
   Google Scholar
• Harvey D. J., Paton W. D. M. Metabolism of the cannabinoids. Reviews in Biochemical Toxicology 1984; 6: 221–264
   Google Scholar
• Harvey D. J., Martin B. R., Paton W. D. M. Identification of the glucuronides of cannabidiol and hydroxycannabidiols in mouse liver. Biochemical Pharmacology 1976; 25: 2217–2219
   PubMed Web of Science ®Google Scholar
• Harvey D. J., Martin B. R., Paton W. D. M. Identification of in vivo liver metabolites of delta-1-tetrahydrocannabinol, cannabidiol and cannabinol produced by the guinea pig. Journal of Pharmacy and Pharmacology 1980; 23: 267–271
   Google Scholar
• Karler R., Turkanis S. A. The cannabinoids as potential antiepileptics. Journal of Clinical Pharmacology 1981; 21: 437s–448s
   Google Scholar
• Kochen W., Scheffner H. On unsaturated metabolites of the valproic acid (VPA) in serum of epileptic children. Antiepileptic Therapy: Advances in Drug Monitoring, S. I. Jokannssen, P. L. Morselli, C. E. Pippinger, A. Richens, D. Schmidt, H. Meinardi. Raven Press, New York 1980; 111–120
   Google Scholar
• Lyle M. A., Pallante S., Head K., Fenselau C. Synthesis and characterization of glucuronides of cannabinol, cannabidiol, delta-9-tetrahydrocannabinol and delta-8-tetrahydrocannabinol. Biomedical Mass Spectrometry 1977; 4: 190–196
   PubMedGoogle Scholar
• Martin B., Nordqvist M., Agurell S., Lindgren J.-E., Leander K., Binder B. Identification of monohydroxylated metabolites of cannabidiol formed by a rat liver. Journal of Pharmacy and Pharmacology 1976; 28: 275–279
   PubMed Web of Science ®Google Scholar
• Martin B., Agurell S., Nordqvist M., Lindgren J.-E. Dioxygenated metabolites of cannabidiol formed by rat liver. Journal of Pharmacy and Pharmacology 1976; 28: 603–608
   PubMedGoogle Scholar
• Martin B. R., Harvey D. J., Paton W. D. M. Biotransformation of cannabidiol in mice: identification of new acid metabolites. Drug Metabolism and Disposition 1977; 5: 259–267
   PubMed Web of Science ®Google Scholar
• McCloskey J. A., Stillwell R. N., Lawson A. M. Use of deuterium-labelled trimethylsilyl derivatives in mass spectrometry. Analytical Chemistry 1968; 40: 233–236
   Web of Science ®Google Scholar
• Meese C. O., Fischer C., Eichelbaum M. Stereoselectivity of the 4-hydroxylation of debrisoquin in man, detected by gas chromatography/mass spectrometry. Biomedical and Environmental Mass Spectrometry 1988; 15: 63–66
   PubMedGoogle Scholar
• Narimatsu S., Watanabe K., Yamamoto I., Yoshimura H. Mechanism for inhibitory effect of cannabidiol on microsomal testosterone oxidation in male rat liver,. Drug Metabolism and Disposition 1988; 16: 880–889
   PubMed Web of Science ®Google Scholar
• Pallante S., Lyle M. A., Fenselau C. Synthesis and characterization of glucuronides of 5′-hydroxy-delta-9-tetrahydro-cannabinol and 11-hydroxy-delta-9-tetrahydrocannabinol. Drug Metabolism and Disposition 1978; 6: 389–395
   Google Scholar
• Paton W. D. M., Pertwee R. G. Effect of cannabis and certain of its constituents on pentobarbitone sleeping time and phenazone metabolism. British Journal of Pharmacology 1972; 44: 250–261
   Google Scholar
• Rettenmeier A. W., Gordon W. P., Prickett K. S., Levy R. H., Lockard J. S., Thummel K. E., Baillie T. A. Metabolic fate of valproic acid in the rhesus monkey. Formation of a toxic metabolite, 2-n-propyl-4-pentenoic acid. Drug Metabolism and Disposition 1986; 14: 443–453
   PubMed Web of Science ®Google Scholar
• Samara E., Bialer M., Harvey D. J. Identification of urinary metabolites of cannabidiol in the dog. Drug Metabolism and Disposition 1900a, in press
   Google Scholar
• Samara E., Bialer M., Harvey D. J. Identification and pharmacokinetics of cannabidiol metabolites in the rat. Drug Metabolism and Disposition 1990b, submitted
   Google Scholar
• Siemens A. J., Kalant H., Khanna J. M., Marshman J., Ho G. Effect of cannabis on pentobarbitone sleeping-time and pentobarbital metabolism in the rat. Biochemical Pharmacology 1974; 23: 477–188
   PubMedGoogle Scholar
• Turner C. E., ElSohly M. A., Boeren E. G. Constituents of Cannabis sativa L: XVII. A review of the natural constituents. Journal of Natural Products (Lloydia) 1980; 43: 169–234
   PubMed Web of Science ®Google Scholar
• Yamamoto I., Watanabe K., Narimatsu S., Gohda H., Arai M., Yoshimura H. Action mechanism of cannabidiol to inactivate cytochrome P-450. Marijuana: An International Research Report, G. Chesher, P. Consroe, R. Musty. National Campaign Against Drug Abuse, Monograph series, No. 7, Australian Government Printing Service, Canberra 1988; 383–387
   Google Scholar
• Zuardi A. W., Shirakawa I., Finkelfarb E., Karniol I. G. Action of cannabidiol on the anxiety and other effects produced by delta-9-THC in normal subjects. Psychopharmacology 1982; 76: 245–250
   PubMed Web of Science ®Google Scholar