Cannabielsoin as a new metabolite of cannabidiol in mammals

@article{Yamamoto1991CannabielsoinAA,
  title={Cannabielsoin as a new metabolite of cannabidiol in mammals},
  author={Ikuo Yamamoto and Hiroshi Gohda and Shizuo Narimatsu and Kazuhito Watanabe and Hidetoshi Yoshimura},
  journal={Pharmacology Biochemistry and Behavior},
  year={1991},
  volume={40},
  pages={541-546}
}
Recent advances in the metabolism of cannabinoids.
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This review provides an overview of the chemical structure of natural and synthetic CBD derivatives including the molecular targets associated with these compounds.
Molecular Targets of the Phytocannabinoids: A Complex Picture.
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This contribution focuses on the molecular pharmacology of the phytocannabinoids, including Δ9-THC and CBD, from the prospective of the targets at which these important compounds act.
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References

SHOWING 1-10 OF 25 REFERENCES
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).
In vivo and in vitro metabolism of cannabidiol monomethyl ether and cannabidiol dimethyl ether in the guinea pig: on the formation mechanism of cannabielsoin-type metabolite from cannabidiol.
TLDR
Results indicate that 1S,2R-epoxide are formed from CBD, CBDM and CBDD and that the epoxides are quickly converted to elsoin-type metabolites in the cases of CBD and CBDM.
Biotransformation of cannabidiol in mice. Identification of new acid metabolites.
TLDR
The in vivo metabolism of cannabidiol was investigated in mice and the most significant biotransformations were glucuronide conjugation and, to a lesser extent, formation of CBD-7-oic acid.
Metabolites of cannabidiol identified in human urine.
  • D. Harvey, R. Mechoulam
  • Chemistry, Biology
    Xenobiotica; the fate of foreign compounds in biological systems
  • 1990
TLDR
This is the first metabolic study of CBD in humans; most observed metabolic routes were typical of those found for CBD and related cannabinoids in other species.
Dioxygenated metabolites of cannabidiol formed by rat liver
TLDR
The metabolism of cannabidiol (CBD) was studied in vitro using a 10 000 g supernatant from rat liver using mass spectrometry and nuclear magnetic resonance spectroscopy to identify metabolites that reflected the quantity of monohydroxy metabolites that was previously found.
Identification of monohydroxylated metabolites of cannabidiol formed by rat liver
TLDR
Cannabidiol (CBD) was metabolized in vitro by rat liver enzymes and hydroxylation occurred in all positions of the pentyl side chain, 4″‐hydroxy‐CBD being most abundant.
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.
9 alpha, 10 alpha-epoxyhexahydrocannabinol formation from delta 9-tetrahydrocannabinol by liver microsomes of phenobarbital-treated mice and its pharmacological activities in mice.
TLDR
It is suggested that 9 alpha, 10 alpha-EHHC can contribute to the pharmacological effects of delta 9-THC as an active metabolite.
Enzymatic oxidation of 7-hydroxylated delta 8-tetrahydrocannabinol to 7-oxo-delta 8-tetrahydrocannabinol by hepatic microsomes of the guinea pig.
TLDR
It is likely that hepatic microsomal monooxygenase (probably cytochrome P-450) plays a main role in the oxidation of delta 8-tetrahydrocannabinol and 7-oxo-delta 8-THC.
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