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Comparison of local anesthetic activities between cis and trans isomers of DL-1-benzoyloxy-2-dimethylamino-1,2,3,4-tetrahydronaphthalene

, : Comparison of local anesthetic activities between cis and trans isomers of DL-1-benzoyloxy-2-dimethylamino-1,2,3,4-tetrahydronaphthalene. Japanese Journal of Pharmacology: 13-19

The local anesthetic activities of cis- and trans- dl-1-benzoyloxy-2-dimethylamino-1,2,3,4-tetrahydronaphthalene were compared using several methods with guinea-pigs. The cis compound (YAU-17) was 2.9 to 6 times as potent as its trans isomer and exceeded procaine, lidocaine and cocaine in potencies of corneal anesthesia, intracutaneous anesthesia and sciatic nerve block. In another experiment on isolated frog sartorius muscle, all of the local anesthetics suppressed the twitch contractions elicited by stimulation of the sciatic nerve. The neuromuscular blocking activity of the cis compound was more pronounced than that of the trans form. Supersensitivity to noradrenaline was produced by both of the stereoisomers in isolated vas deferens of guinea-pigs although there was no difference in the activity. The sensitizing action was also demonstrable with cocaine and lidocaine but not with procaine. When injected intravenously into mice, the cis compound was twice as toxic as its isomer. It is postulated that stereoselectivity is to some extent involved in the mechanisms of action of the local anesthetic agents.


PMID: 1263353

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