THE IN VITRO AND IN VIVO METABOLISM OF TETRAHYDROCANNABINOL (THC) *
Published Dec 1, 1971 · M. Wall
Annals of the New York Academy of Sciences
61
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Abstract
Introduction With the exception of an early study by Miras,’ until recently there have been no reports on the metabolism of marijuana constituents. Lack of progress in this field, as well as allied areas in biochemistry and pharmacology of the cannabinoids, was due largely to the unavailability of synthetic, pure, “cold,” or radiolabeled compounds for use as analytical standards, and this, of course, hindered the development of analytical methodology. Largely because of the work of Mechoulam 2a-2c and Petrzilka? excellent synthetic procedures for As-THC=A1-THC and L ~ ~ T H C = A ~ ( ~ ) T H C have been devised, and several laboratories have described the preparation of tritium labeled A8or A9-THC,&’ and using carbon 14-labeled olivetol, we have also prepared carbon 14-labeled A8and AS-THC. With availability of pure reference compounds, a number of papers dealing with analysis of the cannabinoids by gas-liquid chromatography have appeared.”-l0 With the accessibility of reference standards and analytical methods, several groups in the United States (Battelle Memorial Institute” and Research Triangle Institute12 and abroad. Hebrew University,13 Israel, and Faculty of Pharmacy,I4 Stockholm, Sweden almost simultaneously commenced in vitro and, in some cases, in vivo studies on the metabolism of Asand A*-THC. This report will deal largely with studies in this area carried out at the Research Triangle Institute. In Vitro Metabolism of Ag-THC The structure of AQ-THC and related cannabinoids is shown in FIGURE 1. In vitro studies of the metabolism of this compound were conducted with liver homogenates prepared from mouse, rat, rabbit, guinea pig and man (autopsy specimen). Most of the work reported has been carried out with rat liver.