Pharmacologica Efects in Mice of Anandamide and Its Related Fatty Acid Ethanolamides, and Enhancement of Cataleptogenic Effect of Anandamide by Phenylmethylsulfonyl Fluoride
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概要
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Anandamide (N-arachidonoylethanolamine) and six fatty acid ethanolamides were synthesized and their pharmacological effects in mice were assessed using catalepsy, hypothermia and pentobarbital-induced sleep prolongation as indices. The effects of phenylmethysulfonyl fluride (PMSF) pretreatment on anandamide effects were also evaluated and discussed in relation to inhibition of anandamide amidohydrolase in mouse brain and liver. The cataleptogenic effect of anandamide (ED_<50>=6.0 mg/kg, i.v.) was 4 to 6 times more active than those of N-oleoyl-(ED_<50>=26.5 mg/kg, i.v.) and N-linoleoylethanolamine (ED_<50>=37.5 mg/kg, i.v.), although the peak time in the effect was observed within 1 min after i.v. administration. None of the saturated fatty acid ethanolamides (N-myristoyl-, N-palmitoyl-, N-stearoyl- and N-arachidoylethanolamine) showed a positive response in the cataleptogenic effect even at a dose up to 40 mg/kg i.v. Anandamide, N-linoleoyl-, N-oleoyl- and N-myristoylethanolamine (10 mg/kg, i.v.) produced a significant hypothermia (0.19 to 0.59℃) at 5 to 15 min after administration. The duration of the effects of these ethanolamides was also relatively short. Anandamide, N-linoleoyl-, N-oleovl- and N-palmitoylethanolamine (5 or 10 mg/kg, i.v.) significantly prolonged pentobarbital-induced sleeping time by 148-207% of control sleeping time. The cataleptogenic effect of anandamide was markedly potentiated by pretreatment of mice with PMSF (100 mg/kg, i.p.). The ED_<50> (mg/kg, i.v.) of anandamide was 0.48 (0.24-0.96) in PMSF-pretreated mice. The pretreatment of mice with PMSF significantly decreased the metabolic clearance rate of anandamide in microsomal fractions of liver and brain. Thus, the V_<max>/K_m values of brain and hepatic microsomes were 26 and 10%, respectively, as compared with those of control mice. The present study demonstrated that anandamide and N-acylethanolamines of unsaturated fatty acids exhibited cannabinoid-like effects in mice, and that anandamide amidohydrolase has an important role in the pharmacological effects of anandamide in vivo.
- 社団法人日本薬学会の論文
- 1999-04-15
著者
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NAKAMURA Seikou
Kyoto Pharmaceutical University
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中村 紳一郎
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
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YAMAMOTO IKUO
Department of Laboratory Medicine, Miyazaki Medical College
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景山 節
京大・霊長類研・生化学
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Yamamoto Ikuo
Department Of Hygienic Chemistry School Of Pharmaceutical Sciences Kyushu University Of Health And W
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Kimura Toshiyuki
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
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Watanabe Kazuhito
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
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MATSUNAGA Tamihide
Department of Pharmacy, Shinshu University Hospital
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Nakamura S
Toyama Univ. Toyama Jpn
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HO Ing
University of Mississippi Medical Center
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HO Ing
Department of Pharmacology and Toxicology, University of Mississippi Medical Center
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YOSHIMURA Hidetoshi
Department of Food and Nutrition, Nakamura Gakuen University
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NAKAMURA Shizuko
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University
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Yamamoto Ikuo
北陸大学 薬 衛化
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Yamamoto Ikuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Nakamura S
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
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YAMAMOTO IKUO
Hygienic Chemistry
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Kimura T
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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景山 節
京都大学霊長類研究所人類進化モデル研究センター
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景山 節
京大・霊長研
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Ho Ing
ミシシッピ大学医学部薬毒理学教室
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Nakamura Satoko
Osaka University Of Pharmaceutical Sciences
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Kimura Toshiyuki
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Narimatsu Shizuo
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
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Watanabe Kazuhito
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Watanabe Kazuhito
Department Of Chemistry And Chemical Engineering Faculty Of Engineering Yamagata University
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Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen University
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Yoshimura Hidetoshi
Faculty Of Pharmaceutical Sciences Kyushu University(present):department Of Food And Nutrition Nakam
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Kimura T
Department Of Medicinal Chemistry Center For Frontier Research In Medicinal Science 21st Century Coe
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Ho Ing
Department Of Pharmacology & Toxicology University Of Mississippi Medical Center
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Yoshida H
Lab. Of Food & Nutritional Sciences Dep. Of Nutritional Sci. Kobe-gakuin Univ.
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Narimatsu Shizuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Yoshimura H
Faculty Of Pharmaceutical Sciences Kyushu University(present):department Of Food And Nutrition Nakam
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Nakamura S
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
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Yamamoto I
Hygienic Chemistry
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Yoshida Hiromi
Department Of Nutritional Science Kobe Gakuin University
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Matsunaga Tamihide
Department Of Pharmacy Shinshu University Hospital
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Watanabe Kazuhito
Faculty Of Pharmaceutical Sciences Kyushu University
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Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen
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Yamamoto Ikuo
Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University
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Kimura T
Peptide Inst. Inc. Minoh Jpn
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Matsunaga Tamihide
Department of Clinical Pharmacy, Graduate School of Pharmaceutical Sciences, Nagoya City University
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吉村 英敏
Department of Nutritional Science, Kobe Gakuin University
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