CHEMICAL SYNTHESIS AND BIOLOGICAL OCCURRENCE OF CARBOXYLIC-ACID METABOLITES OF DELTA-1(6)-TETRAHYDROCANNABINOL

  • 1 January 1979
    • journal article
    • research article
    • Vol. 7  (3) , 155-161
Abstract
Potential metabolites of (-)-3,4-trans-tetrahydrocannabinol (THC) with a carboxylic acid function in the side chain were synthesized as their methyl esters in the .DELTA.1(6)-series. The chromatographic and mass-spectrometric properties of 5 side-chain homologs were studied and used to facillitate the isolation and the identification of the corresponding monocarboxylic acid metabolites of .DELTA.1(6)-THC in the mouse, guinea pig and rabbit formed after i.p. administration. The metabolites were identified by gas chromatography and mass fragmentography. In mouse liver .DELTA.1(6)-THC-7-oic acid and 3",4",5"-trisnor-.DELTA.1(6)-THC-2"-oic acid were identified as metabolites. In guinea pig liver these acids occurred together with 4",5"-bisnor-.DELTA.1(6)-THC-3"-oic acid and 5"-nor-.DELTA.1(6)-THC-4"-oic acid. Rabbit liver contained .DELTA.1(6)-THC-7-oic acid, 2",3",4",5"-tetranor-.DELTA.1(6)-THC-1"-oic acid and 4",5"-bisnor-.DELTA.1(6)-THC-3"-oic acid. The structure of 3 dicarboxylic acid metabolites of .DELTA.1(6)-THC in rabbit kidney were determined by mass spectrometry and proton magnetic resonance spectroscopy.

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