Tags

Type your tag names separated by a space and hit enter

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.
Chem Pharm Bull (Tokyo). 1990 Jun; 38(6):1697-701.CP

Abstract

Oxidative metabolism of cannabidiol monomethyl ether (CBDM), one of the components of marihuana, was studied in the guinea pig. Cannabielsoin monomethyl ether (CBEM) was found to be formed with hepatic microsomes by gas chromatography-mass spectrometry (GC-MS). Experiments using various modifiers of enzymatic reaction suggested that, as in the case of cannabielsoin (CBE) formation from canabidiol (CBD), CBEM was formed from CBDM by the monooxygenase system including cytochrome P450. When cannabidiol dimethyl ether (CBDD), in which phenolic hydroxyl groups of CBD are masked with methyl groups, was incubated with liver microsomes and an reduced nicotinamide adenine dinucleotide phosphate-generating system, 1S,2R-epoxy-CBDD was identified by GC-MS. The epoxy metabolite was also found in the liver of a guinea pig pretreated with CBDD (100 mg/kg, intraperitoneally) 1 h before sacrifice. Rate of 1S,2R-epoxide metabolism was slower than that of 1R,2S-epoxy-CBDD under the conditions, as in the microsomal oxidation of CBDD described above. These results indicate that 1S,2R-epoxides 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.

Authors+Show Affiliations

Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

2208386

Citation

Gohda, H, et al. "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." Chemical & Pharmaceutical Bulletin, vol. 38, no. 6, 1990, pp. 1697-701.
Gohda H, Narimatsu S, Yamamoto I, et al. 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. Chem Pharm Bull (Tokyo). 1990;38(6):1697-701.
Gohda, H., Narimatsu, S., Yamamoto, I., & Yoshimura, H. (1990). 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. Chemical & Pharmaceutical Bulletin, 38(6), 1697-701.
Gohda H, et al. 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. Chem Pharm Bull (Tokyo). 1990;38(6):1697-701. PubMed PMID: 2208386.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Gohda,H, AU - Narimatsu,S, AU - Yamamoto,I, AU - Yoshimura,H, PY - 1990/6/1/pubmed PY - 1990/6/1/medline PY - 1990/6/1/entrez SP - 1697 EP - 701 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 38 IS - 6 N2 - Oxidative metabolism of cannabidiol monomethyl ether (CBDM), one of the components of marihuana, was studied in the guinea pig. Cannabielsoin monomethyl ether (CBEM) was found to be formed with hepatic microsomes by gas chromatography-mass spectrometry (GC-MS). Experiments using various modifiers of enzymatic reaction suggested that, as in the case of cannabielsoin (CBE) formation from canabidiol (CBD), CBEM was formed from CBDM by the monooxygenase system including cytochrome P450. When cannabidiol dimethyl ether (CBDD), in which phenolic hydroxyl groups of CBD are masked with methyl groups, was incubated with liver microsomes and an reduced nicotinamide adenine dinucleotide phosphate-generating system, 1S,2R-epoxy-CBDD was identified by GC-MS. The epoxy metabolite was also found in the liver of a guinea pig pretreated with CBDD (100 mg/kg, intraperitoneally) 1 h before sacrifice. Rate of 1S,2R-epoxide metabolism was slower than that of 1R,2S-epoxy-CBDD under the conditions, as in the microsomal oxidation of CBDD described above. These results indicate that 1S,2R-epoxides 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. SN - 0009-2363 UR - https://www.unboundmedicine.com/medline/citation/2208386/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_ L2 - https://www.lens.org/lens/search/patent/list?q=citation_id:2208386 DB - PRIME DP - Unbound Medicine ER -