Urinary metabolites of delta 1-tetrahydrocannabinol in man

The metabolism of delta 1-tetrahydrocannabinol (delta 1-THC) was studied in man after oral administration. Twelve acidic metabolites were isolated from human urine and identified by gas chromatography-mass spectrometry. One additional metabolite was tentatively identified. Hitherto, only one of the metabolites (delta 1-THC-7-oic acid, ) has been identified in man. Three of the metabolites have not been identified in any species before. delta 1-THC-7-oic acid (1) corresponding to 27% of the urinary metabolites was the most abundant metabolite. 4"-Hydroxy-delta 1-THC-7-oic acid (6) was the second most abundant monocarboxylic acid. The remaining eleven monocarboxylic acids predominantly oxidized at C-7 and at C-2" and C-3" of the side-chain, unsubstituted as well as monohydroxylated, were present in small amounts.