9α, 10α-EPOXYHEXAHYDROCANNABINOL FORMATION FROM Δ^9-TETRAHYDROCANNABINOL BY LIVER MICROSOMES OF PHENOBARBITAL-TREATED MICE AND ITS PHARMACOLOGICAL ACTIVITIES IN MICE
スポンサーリンク
概要
- 論文の詳細を見る
9α, 10α-Epoxyhexahydrocannabinol (9α, 10α-EHHC) was found to be formed from Δ^9-tetrahydrocannabinol (Δ^9-THC) by liver microsomes of mice pretreated with phenobarbital. Further, pharmacological effects of 9α, 10α-EHHC in mice were compared with those of Δ^9-THC using catalepsy, hypothermia, pentobarbital-induced sleep prolongation and anticonvulsant activity against pentylenetetrazol as indices. 9α, 10α-EHHC was approximately equipotent with Δ^9-THC in the pharmacological indices except for catalepsy. The cataleptogenic effect of the epoxide was about 4 times as potent as the parent compound. From these results, it is suggested that 9α, 10α-EHHC can contribute to the pharmacological effects of Δ^9-THC as an active metabolite.
- 公益社団法人日本薬学会の論文
著者
-
中村 紳一郎
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
-
Yamamoto Ikuo
北陸大学 薬 衛化
-
Yamamoto Ikuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
Nakamura S
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
-
Nakamura Satoko
Osaka University Of Pharmaceutical Sciences
-
Watanabe Kazuhito
Department Of Chemistry And Chemical Engineering Faculty Of Engineering Yamagata University
-
Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen University
-
Narimatsu Shizuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
Watanabe Kazuhito
Faculty Of Pharmaceutical Sciences Kyushu University
-
Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen
-
Yamamoto Ikuo
Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University
関連論文
- Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain(Biochemistry)
- Differential Expression of Dipeptidyl Peptidase IV (CD26)and Thyroid Peroxidase in Neoplastic Thyroid Tissues
- Butyrylcholinesterase and Erythrocyte Sulfhydryl-dependent Enzyme Hydrolyze Gabexate in Human Blood
- Involvement of Human Blood Arylesterases and Liver Microsomal Carboxylesterases in Nafamostat Hydrolysis
- P2-18 Golgi retention mechanism of CALNUC : NH2-terminal proline plays an essential role for retention
- Effect of Several Cellulosic Binders on Particle Size Distribution in Fluidized Bed Granulation
- Effect of Several Cellulosic Binders on Particle Size Distribution of Granules Prepared by a High-Speed Mixer
- Hepatic Metabolism of Methyl Anthranilate and Methyl N-Methylanthranilate as Food Flavoring Agents in Relation to Allergenicity in the Guinea Pig
- Stereospecific and Regioselective Hydrolysis of Cannabinoid Esters by ES46.5K, an Esterase from Mouse Hepatic Microsomes, and Its Differences from Carboxylesterases of Rabbit and Porcine Liver(Biochemistry)
- In Vitro Inhibitory Effects of Cannabinoids on Progesterone 17α-Hydroxylase Activity in Rat Testis Microsomes
- Synthesis of N^3-Substituted Uridine and Related Pyrimidine Nucleosides and Their Antinociceptive Effects in Mice
- Major Cytochrome P450 Enzymes Responsible for Microsomal Aldehyde Oxygenation of 11-Oxo-〓^8-tetrahydrocannabinol and 9-Anthraldehyde in Human Liver
- Skin Reaction Induced by Aldehydes for Food Flavoring Agents
- Possible Existence of a Novel Receptor for Uridine Analogues in the Central Nervous System Using Two Isomers, N^3-(S)-(+)-and N^3-(R)-(-)-α-Hydroxy-β-phenethyluridines
- Hypnotic Action of N^3-Substituted Arabinofuranosyluracils on Mice
- Cross-Reactivity of Various Tetrahydrocannabinol Metabolites with a Monoclonal Antibody against Tetrahydrocannabinolic Acid
- A Carbonyl Reductase-Catalyzing Reduction of N^3-Phenacyluridine in Rabbit Liver
- Synthesis and Pharmacological Evaluation in Mice of Halogenated Cannabidiol Derivatives.
- Characterization of Microsomal Alcohol Oxygenase Catalyzing the Oxidation of 7-Hydroxy-Δ^8-tetrahydrocannabinol to 7-Oxo-Δ^8-tetrahydrocannabinol in Rat Liver
- Synthesis and Central Nervous System Depressant Effects of N^3-Substituted 2', 3'-O-Isopropylideneuridines
- Synthesis and Pharmacological Evaluation in Mice of Halogenated Cannabidiol Derivatives
- Pharmacologica Efects in Mice of Anandamide and Its Related Fatty Acid Ethanolamides, and Enhancement of Cataleptogenic Effect of Anandamide by Phenylmethylsulfonyl Fluoride
- Effects of Heavy Oil from the Nakhodka on Hepatic and Pulmonary Enzymes of Mice(PROCEEDINGS OF 24TH SYMPOSIUM ON TOXICOLOGY AND ENVIRONMENTAL HEALTH)
- Synthesis and Pharmacological Activities in Mice of Halogenated Δ^9-Tetrahydrocannabinol Derivatives
- Synthesis and Sedative-Hypnotic Effects of N^3-Allyl-and N^1-Allyl-5,6-substituted 2-Thiouracil Derivatives in Mice
- Effective NADH-Dependent Oxidation of 7β-Hydroxy-Δ^8-tetrahydrocannabinol to the Corresponding Ketone by Japanese Monkey Hepatic Microsomes(Toxicology)
- Monkey Hepatic Microsomal Alcohol Oxygenase: Purification and Characterization of a Cytochrome P450 Enzyme Catalyzing the Stereoselective Oxidation of 7α-and 7β-Hydroxy-Δ^8-tetrahydrocannabinol to 7-Oxo-Δ^8-tetrahydrocannabinol
- A Cytochrome P450 Enzyme Responsible for the Carbon Monoxide Formation by Cannabidiol in Mouse Hepatic Microsomes.
- Inhibition of Mouse Hepatic Glutathione S-Transferase by Δ^8-Tetrahydrocannabinol p-Quinone and Cannabidiol Hydroxy-quinone.
- Microsomal Aldehyde Oxygenase (MALDO) for Tolualdehydes, Active Metabolites of Xylenes, in the Mouse Liver and Lung
- "B-4 Hydrolysis of Xenobiotics by ES46.5K, a Novel Esterase from Mouse Liver Microsomes
- Stereoselectivity in Bunitrolol 4-Hydroxylation in Liver Microsomes from Marmosets and Japanese Monkeys
- Microsomal Aldehyde Oxygenase (MALDO): Purification and Characterization of a Cytochrome P450 Isozyme Responsible for Oxidation of 9-Anthraldehyed to 9-Anthracenecarboxylic Acid in Monkey Liver
- A-3 PHARMACOTOXICITY OF A NITROGEN CONTAINING CONSTITUENT IN CANNABIS SATIVA L. : II FERUROYLTYRAMINE AS A NEW CONSTITUENT
- Determination of Heavy Metal Contents in Human Gallstones Using X-Ray Fluorescence Spectrometry (Regular Presentations) (Proceedings of the 15 th Symposium on Environmental Pollutants and Toxicology)
- B05 Pharmacotoxicity of p-Coumaroyltyramine, A Nitrogen Containing Constituent in Cannabis sativa L.
- Determination of Metal Contents in River Sediment Near a Closed Mine by X-ray Fluorescence Spectrometry (Proceedings of the 14th Symposium on Environmental Pollutants and Toxicology)
- Determination of Metal Contents in Biological and Environmental Materials by Energy-Dispersive X-Ray Fluorescence Analysis
- CADMIUM, COPPER AND ZINC CONCENTRATIONS IN HUMAN RENAL CALCULUS AND GALL STONE, AND ITS ANALYTICAL IMPLICATIONS
- MECHANISM OF SLEEP-PROLONGATING EFFECT OF Δ^8-TETRAHYDROCANNABINOL (Δ^8-THC) AND ITS METABOLITES
- IDENTIFICATION AND DETERMINATION OF 11-OXO-Δ^8-TETRAHYDROCANNABINOL AS AN INTERMEDIATE METABOLITE OF Δ^8-TETRAHYDROCANNABINOL IN THE MOUSE BRAIN AND LIVER
- UDP-GLUCURONYLTRANSFERASE ACTIVITIES OF RABBIT LIVER MICROSOMES FOR CANNABINOIDS
- METABOLIC CONVERSION OF Δ^8-TETRAHYDROCANNABINOL (Δ^8-THC) TO Δ^8-THC-11-OIC ACID AND ITS PHARMACOLOGICAL IMPLICATIONS
- METABOLISM OF 11-HYDROXY-Δ^8-THC TO 11-OXO-Δ^8THC IN RATS (The Fourth Meeting for the Study of Toxic Effect)
- Critical Anomaly of the Third-Order Elastic Constants in CsPbCl_3
- Mechanism of Inhibitory Effects of Cannabidiol and Cannabidiol Hydroxy-quinone on the Hepatic Microsomal Drug-Metabolizing Enzymes in Mice (Proceedings of the 23rd Symposium on Toxicology and Environmental Health)
- Involvement of a Novel Mouse Hepatic Microsomal Esterase, ES46.5K, in the Hydrolysis of Phthalate Esters
- Mechanism of Hepatic Microsomal Oxidation of 11-Hydroxy-Δ^8-tetra-hydrocannabinol to 11-Oxo-Δ^8-tetrahydrocannabinol. Evidence for Hydration of the Aldehyde Formed
- Inhibitory Effect of Cannabidiol Hydroxy-quinone, and Oxidative Product of Cannabidiol, on the Hepatic Microsomal Drug-Metabolizing Enzymes of Mice
- INTERACTION OF CANNABINOIDS WITH HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEM IN THE RAT
- PURIFICATION AND CHARACTERIZATION OF MOUSE HEPATIC MICROSOMAL ALDEHYDE OXYGENASE
- MECHANISM OF CANNABIELSOIN FORMATION FROM CANNABIDIOL, ONE OF THE MAJOR CMPONENTS OF MARIHUANA
- CYTOCHROME P450 ISOZYMES INVOLVED IN METABOLIC ACTIVATION OF Δ^9-TETRAHYDROCANNABINOL BY RAT LIVER MICROSOMES
- Mechanism of Biological Formation of Cannabielsoin from Cannabidiol in the Guinea-Pig, Mouse, Rat and Rabbit
- HEPATIC MICROSOMAL OXYGENATION OF METHYL GROUP TO CARBOXYLIC ACID IN XENOBIOTICS : METABOLISM OF Δ^8-TETRAHYDROCANNABINOL AT THE 11-POSITION
- Identification of Cannabielsoin, a New Metabolite of Cannabidiol Formed by Guinea-Pig Hepatic Microsomal Enzymes, and Its Pharmacological Activity in Mice
- IN VIVO EFFECTS OF TETRAHYDROCANNABINOLS AND THEIR EIGHT MONOOXYGENATED METABOLITES ON THE HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEMS OF MICE
- METABOLIC ACTIVATION OF CANNABIDIOL BY HEPATIC MICROSOMES. COMPLEX FORMATION WITH CYTOCHROME P-450
- MECHANISM OF THE PROLONGATION OF BARBITURATE-INDUCED SLEEPING TIME AND THE INHIBITION OF THE HEPATIC MICROSOMAL DRUG METABOLIZING ENZYMES BY CANNABIDIOL, A COMPONENT OF CANNABIS
- EFFECTS OF TWO CANNABINOIDS ON HEPATIC MICROSOMAL CYTOCHROME P-450
- METABOLIC ACTIVATION OF Δ^8-THTRAHYDROCANNABINOL (Δ^8-THC) AT THE 7-POSITION AND MECHANISM OF THE OXIDATION OF 7-HYDROXY-Δ^8-THC TO 7-OXO-Δ^8-THC WITH LIVER MICROSOMES
- METABOLIC DISPOSITION OF 8α, 9α-AND 8β, 9β-EPOXYHEXAHYDROCANNABINOLS IN THE MOUSE
- IN VITRO METABOLISM OF TETRAHYDROCANNABINOL (THC) BY HUMAN LIVER MICROSOMES. EPOXIDE-DIOL PATHWAY OF THC
- DIFFERENCE IN EPOXIDES FORMATION AND THEIR FURTHER METABOLISM BETWEEN Δ^9 -AND Δ^8-TETRAHYDROCANNABINOLS BY HUMAN LIVER MICROSOMES
- THE PROPERTIES OF UDP-GLUCURONYLTRANSFERASE FOR CANNABINOIDS IN RAT LIVER MICROSOMES
- The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries
- c-Kit Proto-oncogene Is More Likely to Lose Expression in Differentiated Thyroid Carcinoma Than Three Thyroid-specific Genes : Thyroid Peroxidase, Thyroglobulin, and Thyroid Stimulating Hormone Receptor
- Compertitive Inhibition of Δ^8-Tetrahydrocannabinol and Its Active Metabolites for Cannabinoid Receptor Binding
- Anandamide, an Endogenous Cannabinoid Receptor Ligand, Also Interacts with 5-Hydroxytryptamine (5-HT) Receptor
- Synthesis and Hypnotic Activities of 4-Thio Analogues of N^3-Substituted Uridines
- Establishment by Adriamycin Exposure of Multidrug-resistant Rat Ascites Hepatoma AH130 Cells Showing Low DT-diaphorase Activity and High Cross Resistance to Mitomycins
- Inhibition of P-Glycoprotein-Dependent Multidrug Resistance by an Isoquinolinesulfonamide Compound H-87 in Rat Ascites Hepatoma AH66 Cells
- A Novel Series of Thromboxane A_2 Synthetase Inhibitors with Free Radical Scavenging and Anti-peroxidative Activities
- Bioavailable Acyl-CoA : Cholesterol Acyltransferase Inhibitor with Anti-peroxidative Activity : Synthesis and Biological Activity of Novel Indolinyl Amide and Urea Derivatives
- Studies on the Constituents of Broussonetia Species. V. Two New Pyrrolidine Alkaloids, Broussonetines K and L, as Inhibitors of Glycosidase, from Broussonetia Kazinoki SIEB.
- Reductive Dimerization of Alkylidenemalonates Using Samarium(II) Diiodide and ^1H-NMR Behavior of the Dimers, 2,3-Diaryl-1,1,4,4-butanetetracarboxylates
- Central Nervous System Depressant Effects of N^3-Substituted Derivatives of Deoxyuridine in Mice
- STRUCTURE-ACTIVITY RELATIONSHIP OF URIDINE DERIVATIVES FOR HYPNOTIC ACTIVITY
- Accurate Measurements and Determination of the Magnetic Anisotropies of Several Manganese Crystals
- INHIBITORY EFFECT OF CANNABIDIOL ON THE HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEM IN THE RAT
- Studies on the Constituents of Broussonetia Species. IV. Two New Pyrrolidinyl Piperidine Alkaloids, Broussonetines I and J, from Broussonetia kazinoki SIEB.
- Studies on the Constituents of Broussonetia Species. III. Two New Pyrrolidine Alkaloids, Broussonetines G and H, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.
- Studies on the Constituents of Broussonetia Species. II. Six New Pyrrolidine Alkaloids, Broussonetine A, B, E, F and Broussonetinine A and B, as Inhibitors of Glycosidases from Broussonetia kazinoki SIEB.
- Fluorometric Determination of Hydrogen Peroxide Based on Formation of Amprochrome
- Rapid Determination of Trace Metals in Foods by Using the Microwave Oven-Digestion Method. II. Determination of Zinc, Copper, Manganese, Lead and Cadmium
- Rapid Determination of Trace Metals in Foods by Using the Microwave Oven-Digestion Method. I. Determination of Arsenic
- Mechanism of Pulmonary Cytochrome P450 Inactivation by Tolualdehydes, Active Metabolites of Xylenes (Proceedings of the 22nd Symposium on Toxicology and Environmental Health)
- Metabolic Reaction of Tolualdehydes by Microsomal Aldehyde Oxygenase (MALDO) in Lung (Proceedings of the 19th Symposium on Toxicology and Environmental Health)
- Histidine-Related Dipeptides, Carnosine, Anserine and Homocarnosine, Possess the CNS Depressant Effects on Mice and their Action Mechanism
- TOLERANCE DEVELOPMENT TO HYPOTHERMIC EFFECT OF Δ^8-TETRAHYDROCANNABINOL AND ITS ACTIVE METABOLITES
- INTERACTIONS OF ACTIVE CANNABINOID METABOLITES WITH GABA_A RECEPTOR
- INHIBITION OF ANANDAMIDE AMIDASE ACTIVITY IN MOUSE BRAIN MICROSOMES BY CANNABINOIDS
- Involvement of a Novel Mouse Hepatic Esterase (ES46.5K) in the Hydrolysis of Phthalate Esters (Proceedings of the 21st Symposium on Toxicology and Environmental Health)
- Involvement of Microsomal Aldehyde Oxygenase (MALDO) in the Metabolism of Aliphatic Aldehydes in the Mouse Liver (Proceedings of the 20th Symposium on Toxicology and Environmental Health)
- Studies on Metabolism and Toxicity of Organic Solvents, Toluene and Related Compounds : Metabolism of Benzaldehydes by Microsomal Aldehyde Oxygenase (MALDO) (Proceedings of the 18th Symposium on Toxicology, and Environmental Health)
- METABOLIC DISPOSITION OF 8α, 9α- AND 8β, 9β-EPOXYHEXAHYDROCANNABINOL (EHHC) IN THE MOUSE
- 9α, 10α-EPOXYHEXAHYDROCANNABINOL FORMATION FROM Δ^9-TETRAHYDROCANNABINOL BY LIVER MICROSOMES OF PHENOBARBITAL-TREATED MICE AND ITS PHARMACOLOGICAL ACTIVITIES IN MICE
- IN VITRO METABOLIC FORMATION OF 8α, 9α-EPOXYHEXAHYDROCANNABINOL AND ITS IMPLICATION IN THE PHARMACOLOGICAL ACTIVITY OF Δ^8-TETRAHYDROCANNABINOL
- IN VITRO AND IN VIVO INTERACTIONS OF Δ^8-TETRAHYDROCANNABINOL AND ITS METABOLITES WITH HEPATIC MICROSOMAL DRUG METABOLIZING ENZYME SYSTEMS OF MICE
- A Colorimetric Method for the Determination of Cannabinoids with Fast Blue BB Salt