ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of several 14-hydroxymorphinans, using oxymorphone (= 3, 14-dihydroxy-4,5-epoxy-N-methylmorphinan-6-one, 1) as starting material, is described. The antinociceptive potency of the N-methyl substituted 14-hydroxy-morphinans was determined. Thus, in order of antinociceptive potency, 14-hydroxy-4-methoxy-N-methylmorphinan-6-one (5) 〉4,5-epoxy-14-hydroxy-N-methyl-morphinan-6-one (3)〉4, 14-dihydroxy-N-methylmorphinan-6-one (4)〉14-hydroxy-4-methoxy-N-methylmorphinan (11) ≈4, 14-dihydroxy-N-methylmorphinan (12). The most potent compound in this series, 14-hydroxy-4-methoxy-N-methyl-morphinan-6-one (5), was found to have about six times the potency of morphine; it was equipotent with levorphanol.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640809
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