ORIENTATION OF OXYGEN ATOM AT C-6 AS A DETERMINANT OF AGONISTIC ACTIVITY IN OXYMORPHONE SERIES

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  • 1 January 1977
    • journal article
    • research article
    • Vol. 200  (3) , 496-500
Abstract
The kinetics of various oxymorphones, their 6-methylene analogs and the 6-hydroxyepimers corresponding to naloxone and naltrexone [narcotic antagonists] were studied in the longitudinal muscle strip of the guinea-pig ileum. Substitution of the oxygen at C-6 by a methylene group slightly increased antagonistic activity of the resulting structures, without significantly influencing agonistic activity relative to the parent compound. The .alpha.-orientation of the hydroxy group at C-6 enhanced the agonistic property of both naloxone and naltrexone. The .beta.-compounds were pure antagonists with potencies similar to those of the parent keto structures.