Oxilorphan and Butorphanol. Potent Narcotic Antagonists and Nonaddicting Analgesics in the 3,14-Dihydroxymorphinan Series. Part V
- 15 October 1975
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 53 (20), 3094-3102
- https://doi.org/10.1139/v75-439
Abstract
A series of 3,14-dihydroxymorphinans 8 was synthesized via a method of (a) acylation of 3-methoxy-Δ8,14-morphinan 4a (b) stereospecific epoxidation of the resultant amides to β-epoxides 5 (c) simultaneous reduction of amide and epoxide functions and (d) demethylation of the resultant 3-methoxy-14-hydroxymorphinans 7. Alternatively deblocking of the amine function in 5b by hydrolysis followed by reduction of the resultant amino epoxide 5e afforded 14-hydroxy-3-methoxymorphinan 7e, which is readily alklyated and demethylated to give various 8. On a basis of interesting pharmacological profiles compounds l-8c (oxilorphan) and l-8d (butorphanol) were selected for clinical studies.This publication has 3 references indexed in Scilit:
- Use of Writhing Test for Evaluating Analgesic Activity of Narcotic AntagonistsExperimental Biology and Medicine, 1965
- SOME NARCOTIC ANTAGONISTS IN BENZOMORPHAN SERIES1964
- A Method for Evaluating both Non-Narcotic and Narcotic AnalgesicsExperimental Biology and Medicine, 1957