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

  title={Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse},
  author={N. K. Brown and David J. Harvey},
  journal={European Journal of Drug Metabolism and Pharmacokinetics},
  • N. K. Brown, D. Harvey
  • Published 1 July 1988
  • Biology, Chemistry
  • European Journal of Drug Metabolism and Pharmacokinetics
Summaryn-Hexyl-delta-8-tetrahydrocannabiol (n-hexyl-dclta-8-THC) andn-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 fromn-hexyl-delta-8-THC and sixteen fromn-hexyl-delta-9-THC. The pattern of metabolites was… 

GC-MS Metabolite Profile and Identification of Unusual Homologous Cannabinoids in High Potency Cannabis sativa.

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Biotransformation of Tetrahydrocannabinol

This review article assesses the current knowledge on the biotransformation of tetrahydrocannabinol and with particular focus on ∆9-THC.



In vivo metabolism of the methyl homologues of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol and abn-delta-8-tetrahydrocannabinol in the mouse.

Metabolites from methyl-delta-8-THC were similar with respect to the positions substituted to those produced by higher homologues, with the exception that less metabolism occurred at C(8) and a higher percentage of the total metabolic fraction was accounted for by the 11-oic acid metabolite.

Identification of the in vivo liver metabolites of (--)-delta 7-tetrahydrocannabinol produced by the mouse.

The major in vivo metabolites of (--)-delta 7-tetrahydrocannabinol were extracted from the livers of mice after a single intraperitoneal dose and were examined by combined gas-liquid

Identification of in vivo liver metabolites of delta 6-tetrahydrocannabinol produced by the mouse.

  • D. HarveyW. Paton
  • Chemistry, Biology
    Drug metabolism and disposition: the biological fate of chemicals
  • 1980
Delta 6-THC was found to be metabolized more extensively via the epoxide-diol pathway than the delta 1-isomer, and was the major biotransformation pathways.

Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse.

  • D. Harvey
  • Biology, Chemistry
    Xenobiotica; the fate of foreign compounds in biological systems
  • 1985
Nineteen metabolites of heptyl-delta-1-THC have been identified in mouse liver using combined g.l.c. and mass spectrometry following i.p. administration of the drug. All metabolites contained either

In vivo metabolites of Δ1(6)‐tetrahydrocannabinol produced by the mouse via the epoxide‐diol pathway

The characterization of a similar epoxide (lI), together with the derived diol, la,68dihydroxyhexahydrocannabinol (IIIa) and its 3"-, (IIIb) and 4"-hydroxy (IIIc) derivatives as in vivo liver metabolites of A1@)-THC in the mouse is reported.

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The mass spectra of the trimethylsilyl derivatives of the hydroxy and acid metabolites of Δ1‐ and Δ6‐tetrahydrocannabinol

Deuterium labelling and high resolution mass measurements have been used to investigate the fragmentation mechanisms leading to diagnostic ions in the mass spectra of the trimethylsilyl derivatives

Identification of di‐ and tri‐substituted hydroxy and ketone metabolites of Δ1‐tetrahydrocannabinol in mouse liver

In vivo liver metabolites of Δ1‐tetrahydrocannabinol (Δ1‐THC) were examined with a gas chromatograph—mass spectrometer—computer system as trimethylsilyl (TMS), [2H9]TMS and methyloxime‐TMS

Zur Identifikation potentieller Metabolite von Cannabis‐Inhaltstoffen: Kernresonanz‐ und massenspektroskopische Untersuchungen an seitenkettenhydroxylierten Cannabinoiden

The 100-MHz-NMR-spectra of 11 side chain hydroxylated derivatives of cannabidiol (1), Δ6-tetrahydrocannabinol (2) and cannabinol (3) were analysed for signals specific for the position of hydroxyl

Structural studies of cannabinoids. A theoretical and proton magnetic resonance analysis.

A conformational analysis of the major active constituent of marijuana and its analogs is described and conclusions are reached, concerning the conformation of the pyran ring, the preferred orientation of the phenolic O-H bond, and ring C conformational preferences in 1, 2, 3, and A-THC, are in substantial agreement with pmr observations resulting from nuclear Overhauser effect and solvent effect studies.