Comparison in mice of pharmacological effects of Δ8-tetrahydrocannabinol and its metabolites oxidized at 11-position

European Journal of Pharmacology - Tập 63 - Trang 1-6 - 1980
Kazuhito Watanabe1,2, Ikuo Yamamoto1, Kazuta Oguri1,2, Hidetoshi Yoshimura2
1Department of Hygienic Chemistry, School of Pharmacy, Hokuriku University, Kanazawa 920-11, Japan
2Department of Hygienic and Forensic Chemistry, Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka 812, Japan

Tài liệu tham khảo

Adams, 1973, Interaction of chloramphenicol and Δ1-THC on barbital-anesthetized mice, Experientia, 29, 181, 10.1007/BF01945462 Ben-Zvi, 1974, 7-Oxo-Δ1-tetrahydrocannabinol: a novel metabolite of Δ1-tetrahydrocannabinol, Res. Commun. Chem. Pathol. Pharmacol., 8, 223 Ben-Zvi, 1970, Synthesis of Δ1 and Δ1(6)-tetrahydrocannabinol metabolites, Tetrahedron Lett., 4495, 10.1016/S0040-4039(01)83959-9 Burstein, 1970, Metabolism of Δ1(6)-tetrahydrocannabinol, an active marihuana constituent, Nature, 225, 88, 10.1038/225087a0 Burstein, 1972, Isolation and characterization of two major urinary metabolites of Δ1-tetrahydrocannabinol, Science, 176, 422, 10.1126/science.176.4033.422 Christensen, 1971, Activity of Δ8- and Δ9-tetrahydrocannabinol and related compounds in the mouse, Science, 172, 165, 10.1126/science.172.3979.165 Estevez, 1974, Effect of SKF 525-A on the metabolism of (−)-Δ9-tetrahydrocannabinol in the rat brain and liver, Res. Commun. Chem. Pathol. Pharmacol., 8, 389 Foltz, 1970, Metabolite of (−)-trans-Δ8-tetrahydrocannabinol: identification and synthesis, Science, 168, 844, 10.1126/science.168.3933.844 Gill, 1972, Brain levels of Δ1-tetrahydrocannabinol and its metabolites in mice — correlation with behavior, and the effect of the metabolic inhibitors SKF 525-A and piperonyl butoxide, Biochem. Pharmacol., 21, 2237, 10.1016/0006-2952(72)90039-1 Gill, 1973, Contribution of the metabolite 7-hydroxy-Δ1-tetrahydrocannabinol towards the pharmacological activity of Δ1-tetrahydrocannabinol in mice, Biochem. Pharmacol., 22, 175, 10.1016/0006-2952(73)90271-2 Harvey, 1976, Characterization of three monohydroxy acid and two dihydroxy acid metabolites of Δ1-tetrahydrocannabinol in mouse liver, Res. Commun. Chem. Pathol. Pharmacol., 13, 585 Hollister, 1974, Structure-activity relations in man of cannabis constituents and homologs and metabolites of Δ9-tetrahydrocannabinol, Pharmacology, 11, 3, 10.1159/000136462 Inayama, 1974, Oxidation of Δ1- and Δ6-tetrahydrocannabinol with selenium dioxide, Chem. Pharm. Bull. (Tokyo), 22, 1519, 10.1248/cpb.22.1519 Lemberger, 1973, Comparative pharmacology of Δ9-tetrahydrocannabinol and its metabolites, 11-OH-Δ9-tetrahydrocannabinol, J. Clin. Invest., 52, 2411, 10.1172/JCI107431 Lemberger, 1970, Marihuana: studies on the disposition and metabolism of delta-9-tetrahydrocannabinol in man, Science, 170, 1320, 10.1126/science.170.3964.1320 Litchfield, 1949, A simple method of evaluating dose-effect experiments, J. Pharmacol. Exp. Ther., 96, 99 Mantilla-Plata, 1974, Effects of phenobarbital and SKF 525-A pretreatment, sex, liver injury and vehicle on Δ9-tetrahydrocannabinol toxicity, Toxicol. Appl. Pharmacol., 27, 123, 10.1016/0041-008X(74)90179-3 Mechoulam, 1970, Marihuana Chemistry, Science, 168, 1159, 10.1126/science.168.3936.1159 Mechoulam, 1973, Δ6-Tetrahydrocannabinol-7-oic acid, a urinary Δ6-THC metabolite: isolation and synthesis, Experientia, 29, 1193, 10.1007/BF01935065 Nilsson, 1970, Δ1-Tetrahydrocannabinol: structure of a majore metabolite, Science, 168, 1228, 10.1126/science.168.3936.1228 Nordqvist, 1979, Acidic metabolites of Δ1-tetrahydrocannabinol isolated from rabbit urine, J. Pharm. Pharmacol., 13, 134 Sofia, 1974, The lethal effects of Δ9-tetrahydrocannabinol in mice enhanced by pretreatment with SKF 525-A or chloramphenicol, European J. Pharmacol., 26, 383, 10.1016/0014-2999(74)90251-9 Sofia, 1970, Depressant effect of Δ1-tetrahydrocannabinol enhanced by inhibition of its metabolism, European J. Pharmacol., 13, 134, 10.1016/0014-2999(70)90195-0 Wall, 1970, Isolation, structure, and biological activity of several metabolites of Δ9-tetrahydrocannabinol, J. Am. Chem. Soc., 92, 3466, 10.1021/ja00714a042 Wall, 1976, Metabolism of cannabinoids in man, 93 Watanabe, 1979, Microsomal oxygenase catalyzed oxidation of 11-hydroxy-Δ8-tetrahydrocannabinol to 11-oxo-Δ8-tetrahydrocannabinol, Biochem. Biophys. Res. Commun., 88, 178, 10.1016/0006-291X(79)91713-3 Yoshimura, 1978, Synthesis and pharmacological activity of a phosphate ester of Δ8-tetrahydrocannabinol, J. Med. Chem., 21, 1079, 10.1021/jm00208a014