Metabolic Transformation of (3R, 4R)‐Δ1(7)‐Tetrahydrocannabinol by a Rat Liver Microsomal Preparation

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Abstract
The metabolism of the non‐psychotropic cannabinoid (3R, 4R)Δ1(7)‐tetrahydrocannabinol (1) (=Δ 1(7)‐THC) was investigated in a rat liver microsomal preparation. The metabolites obtained from the incubation mixture were separated, purified and identified by 1H‐NMR. spectroscopy and combined gas‐liquid chromatography/mass spectrometry. Metabolites 3–10 are derived from Δ1(7)‐THC (1) by mono‐hydroxylation in the isoprenoid moiety or the side chain of the molecule. Metabolites 11–16 are hydroxylated in the isoprenoid ring and the side chain simultaneously. The third group, metabolites 18–22, is derived from the 1,7‐epoxide 17 by hydrolysis of the oxirane ring, three of these metabolites bearing additional hydroxyl‐groups in the isoprenoid part or the side chain. The mass spectra of the metabolites are discussed in detail and a new rule for the fragmentations of tetrahydrocannabinols is presented.