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  • Title: In vivo metabolism of the n-propyl homologues of delta-8- and delta-9-tetrahydrocannabinol in the mouse.
    Author: Brown NK, Harvey DJ.
    Journal: Biomed Environ Mass Spectrom; 1988 Apr 01; 15(7):403-10. PubMed ID: 2839261.
    Abstract:
    n-Propyl-delta-8-tetrahydrocannabinol (n-propyl-delta-8-THC and n-propyl-delta-9-THC were synthesized by condensation of (1S)-cis-verbenol with 5-n-propyl-1,3-dihydroxybenzene and administered to male Charles River CD-1 mice. Hepatic metabolites were isolated by solvent extraction and chromatography on Sephadex LH-20 and identified by gas chromatography/mass spectrometry. Seven metabolites were identified from each cannabinoid. Metabolism was similar to that previously observed from the penyl homologues, with the major biotransformation pathway being the production of 11-hydroxy-propyl-THCs and their oxidation to carboxylic acid metabolites. Other metabolites were mainly hydroxylated derivatives of these compounds and the corresponding 11-alcohol. Less hydroxylation at C(8) was found with n-propyl-delta-9-THC than with the pentyl homologue, and the monohydroxy metabolite, 8-alpha-hydroxy-n-propyl-delta-9-THC, was not observed, even though it was a prominent metabolite from delta-9-THC itself. Hydroxylation occurred in the side-chain at C(2').
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