Comparative in vitro metabolism of the cannabinoids

@article{Harvey1991ComparativeIV,
  title={Comparative in vitro metabolism of the cannabinoids},
  author={David J. Harvey and N. K. Brown},
  journal={Pharmacology Biochemistry and Behavior},
  year={1991},
  volume={40},
  pages={533-540}
}
  • D. Harvey, N. K. Brown
  • Published 1 November 1991
  • Biology, Chemistry
  • Pharmacology Biochemistry and Behavior
Recent advances in the metabolism of cannabinoids.
Decarbonylation: A metabolic pathway of cannabidiol in humans.
TLDR
Results of this study indicate a prolonged detectability of DCBD (in serum) in comparison to CBD after oral CBD ingestion, which appears to be an important supplementary human metabolite that might be helpful for the analytical confirmation of a CBD uptake and might improve the interpretation of the consumption of CBD-containing products.
11-Nor-9-carboxy-∆ 9 -tetrahydrocannabinol - a ubiquitous yet underresearched cannabinoid. A re- view of the literature
TLDR
A literature review on the reported pharmacological effects of THC-COOH is provided and further studies are advocated to reveal any potential involvement of this abundant metabolite in the complex pharmacology and in the proven therapeutic effects of cannabis extracts.
Mini-Review 11-Nor-9-carboxy-∆ 9-tetrahydrocannabinol – a ubiquitous yet underresearched cannabinoid . A review of the literature
TLDR
A literature review on the reported pharmacological effects of THC-COOH is provided and further studies are advocated to reveal any potential involvement of this abundant metabolite in the complex pharmacology and in the proven therapeutic effects of cannabis extracts.
Monkey Hepatic Microsomal Alcohol Oxygenase: Purification and Characterization of a Cytochrome P450 Enzyme Catalyzing the Stereoselective Oxidation of 7α- and 7β-Hydroxy-Δ8-tetrahydrocannabinol to 7-Oxo-Δ8-tetrahydrocannabinol
TLDR
Results indicate that P450JM-E (CYP3A8) is a major enzyme of the oxidation of 7-OH-Δ8-THC in monkey hepatic microsomes, although this stereoselective dehydration differentiates between two epimers.
Pharmacokinetics and Pharmacodynamics of Cannabinoids
TLDR
Properties of cannabis that might be of therapeutic use include analgesia, muscle relaxation, immunosuppression, sedation, improvement of mood, stimulation of appetite, antiemesis, lowering of intraocular pressure, bronchodilation, neuroprotection and induction of apoptosis in cancer cells.
Emergence of the less common cannabinoid Δ8 -Tetrahydro-cannabinol in a doping sample.
TLDR
In vitro experiments using human liver microsomes showed, that Δ8 -THC is metabolized in the same way as Δ9 - THC, and additional investigations of doping control samples containing Δ9-THC-COOH revealed the simultaneous presence of Δ8-THc-CooH in low concentrations.
Stimulatory Effects of Testosterone and Progesterone on the NADH-and NADPH-dependent Oxidation of 7β-Hydroxy-Δ8-tetrahydrocannabinol to 7-Oxo-Δ8-tetrahydrocannabinol in Monkey Liver Microsomes
TLDR
Kinetic analyses revealed that both the NADH- and NADPH-dependent 7-oxo-delta8-THC formation showed sigmoid kinetics, and proposed a kinetic model involving at least three binding sites, for the mechanism of activation by testosterone.
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References

SHOWING 1-10 OF 36 REFERENCES
In vitro metabolism of cannabigerol in several mammalian species.
Microsomal incubations were prepared from the livers of male mice, rats, cats, guinea-pigs, hamsters and gerbils and both male and female rabbits and were incubated with cannabigerol (CBG), a
In vitro metabolism of cannabidiol in the rabbit: identification of seventeen new metabolites including thirteen dihydroxylated in the isopropenyl chain.
TLDR
The metabolism of cannabidiol (CBD) was studied in liver microsomes from the female New Zealand white rabbit and 17 metabolites, mainly mono-, di- and tri-hydroxy compounds, were identified; 17 of these have not been reported before.
In vitro metabolism of delta-11-tetrahydrocannabinol in the mouse, rat, guinea pig, rabbit, hamster, gerbil and cat.
  • D. Harvey, N. K. Brown
  • Biology, Chemistry
    Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology
  • 1990
In vivo metabolism of the methyl homologues of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol and abn-delta-8-tetrahydrocannabinol in the mouse.
TLDR
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.
In vivo metabolism of cannabinol by the mouse and rat and a comparison with the metabolism of Δ1‐tetrahydrocannabinol and cannabidiol
TLDR
The in vivo liver metabolism of cannabinol has been studied in the mouse and rat by combined gas chromatography and mass spectrometry and by reduction of acid metabolites with lithium aluminium deuteride to the corresponding alcohols.
Metabolic Transformation of (3R, 4R)‐Δ1(7)‐Tetrahydrocannabinol by a Rat Liver Microsomal Preparation
TLDR
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 and a new rule for the fragmentations of tetrahydroannabinols is presented.
Difference in epoxides formation and their further metabolism between delta 9- and delta 8-tetrahydrocannabinols by human liver microsomes.
TLDR
Results indicate that 9 alpha, 10 alpha-EHHC formed from delta 9-THC is further metabolized not by epoxide hydrolase but by monooxygenase system involving cytochrome P-450, and that, on the contrary, 8 alpha, 9 alpha- and 8 beta, 9 beta-EH HCs derived from delta 8-THCs may be metabolized by epoxides rather than cy tochrome P -450 in the human liver.
In vivo metabolites of Δ1(6)‐tetrahydrocannabinol produced by the mouse via the epoxide‐diol pathway
TLDR
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.
Identification of in vivo liver metabolites of Δ1 ‐tetrahydrocannabinol, cannabidiol, and cannabinol produced by the guinea‐pig
TLDR
The metabolites of Δ1 ‐trahydrocannabinol, cannabidiol (CBD), and cannabinol produced in vivo by the guinea‐pig have been studied by combined gas‐liquid chromatography‐mass spectrometry and differed considerably from that observed in mouse and rat.
Identification of cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymes, and its pharmacological activity in mice.
TLDR
CBE was formed from CBD as a novel metabolite, and that the amount was about one-sixth of 7-hydroxy-CBD, which was the most abundant metabolite under in vitro conditions in the presence of microsomal monooxygenase (cytochrome P-450).
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