Further urinary metabolites of delta 1-tetrahydrocannabinol in man.

The in vivo metabolism of delta 1-tetrahydrocannabinol (delta 1-THC) was further investigated in man after oral administration. Five dicarboxylic acids were isolated from the urine and identified by gas chromatography-mass spectrometry. None of these acids have been identified in man before and two of them (3",4",5"-trisnor-delta 1-THC-7,2"-dioic acid (15) and 5"-nor-delta 1-THC-7,4"-dioic acid (17)) have hitherto not been found in any species. The major dicarboxylic acid was 4",5"-bisnor-delta 1-THC-7,3"-dioic acid (16) corresponding to 8% of the excreted radioactivity in the urine. The other dicarboxylic acids (14, 18) were present in small amounts.