Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse. 1988

N K Brown, and D J Harvey
University Department of Pharmacology, Oxford, UK.

n-Hexyl-delta-8-tetrahydrocannabinol (n-hexyl-delta-8-THC) and n-hexyl-delta-9-THC were synthesized by condensation of (1S)-cis-verbenol with 5-n-hexyl-1,3-dihydroxybenzene and administered intraperitoneally to male Charles-River CD-1 mice. Hepatic metabolites were isolated by solvent extraction and chromatography on Sephadex LH-20 and identified by GC/MS. Eleven metabolites were identified from n-hexyl-delta-8-THC and sixteen from n-hexyl-delta-9-THC. The pattern of metabolites was intermediate between that previously observed from the pentyl homologues and that from n-heptyl-delta-9-THC with the major biotransformation pathway being hydroxylation and oxidation at C-11. Other metabolites were mainly hydroxylated derivatives of these compounds. Metabolites containing two hydroxy groups in the side-chain were present in low concentration. These have not been observed from lower homologues but are major metabolites of n-heptyl-delta-9-THC. Compared with the metabolism of the n-pentyl homologue, there was a trend towards the production of more hydroxy metabolites at the expense of carboxylic acids, in keeping with the general reduction of oxidation observed with other homologous cannabinoids as the chain length increases.

UI MeSH Term Description Entries
D008099 Liver A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances. Livers
D008297 Male Males
D008401 Gas Chromatography-Mass Spectrometry A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds. Chromatography, Gas-Liquid-Mass Spectrometry,Chromatography, Gas-Mass Spectrometry,GCMS,Spectrometry, Mass-Gas Chromatography,Spectrum Analysis, Mass-Gas Chromatography,Gas-Liquid Chromatography-Mass Spectrometry,Mass Spectrometry-Gas Chromatography,Chromatography, Gas Liquid Mass Spectrometry,Chromatography, Gas Mass Spectrometry,Chromatography, Mass Spectrometry-Gas,Chromatography-Mass Spectrometry, Gas,Chromatography-Mass Spectrometry, Gas-Liquid,Gas Chromatography Mass Spectrometry,Gas Liquid Chromatography Mass Spectrometry,Mass Spectrometry Gas Chromatography,Spectrometries, Mass-Gas Chromatography,Spectrometry, Gas Chromatography-Mass,Spectrometry, Gas-Liquid Chromatography-Mass,Spectrometry, Mass Gas Chromatography,Spectrometry-Gas Chromatography, Mass,Spectrum Analysis, Mass Gas Chromatography
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001711 Biotransformation The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D013759 Dronabinol A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound. THC,Tetrahydrocannabinol,delta(9)-THC,9-ene-Tetrahydrocannabinol,Marinol,Tetrahydrocannabinol, (6a-trans)-Isomer,Tetrahydrocannabinol, (6aR-cis)-Isomer,Tetrahydrocannabinol, (6aS-cis)-Isomer,Tetrahydrocannabinol, Trans-(+-)-Isomer,Tetrahydrocannabinol, Trans-Isomer,delta(1)-THC,delta(1)-Tetrahydrocannabinol,delta(9)-Tetrahydrocannabinol,9 ene Tetrahydrocannabinol,Tetrahydrocannabinol, Trans Isomer
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus

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