PMID: 38086May 1, 1979

Chemical synthesis and biological occurrence of carboxylic acid metabolites of delta1(6)-tetrahydrocannabinol

Drug Metabolism and Disposition : the Biological Fate of Chemicals
S AgurellA Ohlsson

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 delta1(6)-series. The chromatographic and mass-spectrometric properties of the five side-chain homologues were examined and utilized to facilitate the isolation and the identification of the corresponding monocarboxylic acid metabolites of delta1(6)-THC in the mouse, guinea pig, and rabbit formed after ip administration. The metabolites were identified by gas chromatography and mass fragmentography. In mouse liver delta1(6)-THC-7-oic acid and 3'',4'',5''-trisnor delta1(6)-THC-2''-oic acid were identified as metabolites. In guinea pig liver these acids occurred together with 4'',5''-bisnor-delta1(6)-THC-3''-oic acid and 5''-nor-delta1(6)-THC-4''-oic acid. Rabbit liver contained delta1(6)-THC-7-oic acid, 2'',3'',4'',5''-tetranor-delta1(6)-THC-1''-oic acid and 4'',5''-bisnor-delta1(6)-THC-3''-oic acid. Further, the structure of three dicarboxylic acid metabolites of delta1(6)-THC in rabbit kidney were determined by mass spectrometry and proton magnetic resonance spectroscopy.

Related Concepts

Tetrahydrocannabinol
DLK1 gene
Cavia
Gas Chromatography-Mass Spectrometry
Dicarboxylic Acids
Mass Spectrometry
DLK1 wt Allele
Chromatography, Gas-Liquid
Acids
Esters

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