Abstract
Great progress has been made in recent years in elucidating the metabolism of Δ9-tetrahydrocannabinol (Δ9-THC), the major psychoactive constituent of marihuana. The main metabolites of Δ9-THC, resulting from the liver microsomal oxidase reactions, have been identified as 11-hydroxy-Δ9-THC (11-OH-Δ9-THC) and 8,11-diOH-Δ9-THC [1,3,20]. In addition, the formation of acidic metabolites has been proven [4,17,21]. Treatment of rats with SKF-525-A before administering Δ9-THC resulted in a substantial reduction of all three metabolites [7]. Some reports indicate that the monohydroxylated metabolite is as active as Δ9-THC behavior-ally and pharmacologically [8,12,19,20], although others imply that unchanged Δ9-THC is responsible for certain effects of marihuana [13,18]. The dihydroxylated product is behaviorally inactive [5,19,20].
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References
Agurell, S., I. M. Nilsson, A. Ohlsson, and F. Sandberg (1969) Elimination of tritium-labelled cannabinols in the rat with special reference to the development of tests for the identification of cannabis users. Biochem. Pharmacol. 18:1195.
Agurell, S., I. M. Nilsson, A. Ohlsson, and F. Sandberg (1970) On the metabolism of tritium-labelled Δ1-tetrahydrocannabinol in the rabbit. Biochem. Pharmacol. 19:1333.
Ben-Zvi, Z., R. Mechoulam, and S. Burstein (1970) Identification through synthesis of an active Δ1(6) -tetrahydrocannabinol metabolite. J. Am. Chem. Soc. 92:3468.
Burstein, S., J. Rosenfeld, and T. Wittstruck (1972) Isolation and characterization of two major metabolites of Δ1-tetrahydrocannabinol. Science 176:422.
Christensen, H. D., R. I. Freudenthal, J. R. Gidley, R. Rosenfeld, G. Boegli, L. Testino, D. R. Brine, C. G. Pitt, and M. E. Wall (1971) Activity of Δ8- and Δ9-tetrahydrocannabinol and related compounds in the mouse. Science 172:165.
Estevez, V. S., L. F. Englert, and B. T. Ho (1973) A new metabolite of (-)-11-hydroxy-Δ8-tetrahydrocannabinol in rats. Res. Commun. Chem. Pathol. Pharmacol. 6:821.
Estevez, V. S., L. F. Englert, and B. T. Ho (1974) Effect of SKF-525-A on the metabolism of (-)-Δ9-tetrahydrocannabinol in the rat brain and liver. Res. Commun. Chem. Pathol. Pharmacol. 8:389.
Gill, E. W. and G. Jones (1972) Brain levels of Δ1-tetrahydrocan-nabinol and its metabolites in mice—correlation with behavior, and the effect of the metabolic inhibitor SKF-525-A, and piperonyl butoxide. Biochem. Pharmacol. 21:2237.
Ho, B. T., V. S. Estevez, L. F. Englert, and W. M. McIsaac (1972) Δ9-Tetrahydrocannabinol and its metabolites in monkey brains. J. Pharm. Pharmacol. 24:414.
Ho, B. T., V. S. Estevez, and L. F. Englert (1973) Effect of repeated administration on the metabolism of (-)-Δ9-tetrahydrocannabinol in rats. Res. Commun. Chem. Pathol. Pharmacol. 5:215.
Ho, B. T., V. S. Estevez, and L. F. Englert (1973) The uptake and metabolic fate of cannabinoids in rat brains. J. Pharm. Pharmacol. 25:490.
Irwin, S. (1968) Comprehensive observation assessment: 1A. A systematic, quantitative procedure for assessing the behavioral and physiological state of the mouse. Psychopharmacologia 13:222.
Kubena, R. K. and H. Barry, III (1970) Interactions of Δ1-tetrahydrocannabinol with barbiturates and methamphetamine. J. Pharmacol. Exp. Ther. 173:94.
Lemberger, L., S. Silberstein, J. Axelrod, and I. Kopin (1970) Marihuana: studies on the disposition and metabolism of delta-9-tetrahydrocannabinol in man. Science 170:1320.
Lemberger, L., N. Tamarkin, J. Axelrod, and I. Kopin (1971) Delta-9-tetrahydrocannabinol—metabolism and disposition in long-term marihuana smokers. Science 173:12.
Mikes, F., A. Hoffman, and P. G. Waser (1971) Identification of (-)-Δ9–6a,10a-trans-tetrahydrocannabinol and two of its metabolites in rats by use of combination gas chromatography-mass spectrometry and mass fragmentography. Biochem. Pharmacol. 20:2469.
Nordqvist, M., S. Agurell, M. Binder, and J. M. Nilsson (1974) Structure of an acidic metabolite of Δ1-tetrahydrocannabinol isolated from rabbit urine. J. Pharm. Pharmacol. 26:471.
Sofia, R. D. and H. Barry, III (1970) Depressant effect of Δ1-tetra-hydrocannabinol enhanced by inhibition of its metabolism. Eur. J. Pharmacol. 13:134.
Truitt, E. B. (1970) Pharmacological activity in a metabolite of l-trans-Δ8-tetrahydrocannabinol. Fed. Proc. 29:619.
Wall, M. E., O. R. Brine, G. A. Brine, C. G. Pitt, R. I. Freudenthal, and H. D. Christensen (1970) Isolation, structure and biological activity of several metabolites of delta-9-tetrahydrocannabinol. J. Am. Chem. Soc. 92:3466.
Wall, M. E., O. R. Brine, and M. Pérez-Reyes (1973) Studies on the in vitro and in vivo metabolism of Δ9-tetrahydrocannabinol. Abstracts 33rd International Congress of Pharmaceutical Sciences, Stockholm, p. 258.
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Schoolar, J.C., Ho, B.T., Estevez, V.S. (1976). Comparison of Various Solvent Extractions for the Chromatographic Analysis of Δ9-THC and Its Metabolites. In: Nahas, G.G., Paton, W.D.M., Idänpään-Heikkilä, J.E. (eds) Marihuana. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-51624-5_6
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DOI: https://doi.org/10.1007/978-3-642-51624-5_6
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