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Comparison of Various Solvent Extractions for the Chromatographic Analysis of Δ9-THC and Its Metabolites

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Marihuana

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

  1. 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.

    Article  PubMed  Google Scholar 

  2. 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.

    Article  PubMed  Google Scholar 

  3. 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.

    Article  PubMed  Google Scholar 

  4. Burstein, S., J. Rosenfeld, and T. Wittstruck (1972) Isolation and characterization of two major metabolites of Δ1-tetrahydrocannabinol. Science 176:422.

    Article  PubMed  Google Scholar 

  5. 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.

    Article  PubMed  Google Scholar 

  6. 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.

    PubMed  Google Scholar 

  7. 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.

    PubMed  Google Scholar 

  8. 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.

    Article  PubMed  Google Scholar 

  9. 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.

    Google Scholar 

  10. 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.

    PubMed  Google Scholar 

  11. 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.

    Article  Google Scholar 

  12. Irwin, S. (1968) Comprehensive observation assessment: 1A. A systematic, quantitative procedure for assessing the behavioral and physiological state of the mouse. Psychopharmacologia 13:222.

    Article  PubMed  Google Scholar 

  13. Kubena, R. K. and H. Barry, III (1970) Interactions of Δ1-tetrahydrocannabinol with barbiturates and methamphetamine. J. Pharmacol. Exp. Ther. 173:94.

    PubMed  Google Scholar 

  14. 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.

    Article  PubMed  Google Scholar 

  15. Lemberger, L., N. Tamarkin, J. Axelrod, and I. Kopin (1971) Delta-9-tetrahydrocannabinol—metabolism and disposition in long-term marihuana smokers. Science 173:12.

    Article  Google Scholar 

  16. 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.

    Article  PubMed  Google Scholar 

  17. 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.

    Article  PubMed  Google Scholar 

  18. 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.

    Article  PubMed  Google Scholar 

  19. Truitt, E. B. (1970) Pharmacological activity in a metabolite of l-trans-Δ8-tetrahydrocannabinol. Fed. Proc. 29:619.

    Google Scholar 

  20. 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.

    Article  PubMed  Google Scholar 

  21. 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.

    Google Scholar 

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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

  • Publisher Name: Springer, Berlin, Heidelberg

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