A number of diverse N-substituted-N-normetazocine heterocycles ((-)-1R,5R,9R)- and (+)-(1S,5S,9S)-5,9-dimethyl-2′-hydroxy-2-substituted-6,7-benzomorphans) were synthesized and evaluated. Conversion of an antinociceptively inactive alcohol to an ether (-)-1R,5R,9R)-5,9-dimethyl-2′-hydroxy-2-(2-methoxyethyl)-6,7-benzomorph an ((-)-N-methoxyethylnormetazocine, 4), gave a compound that was 10 to 40 times more potent than morphine as an antinociceptive agent, but did not attenuate morphine withdrawal in monkeys. Other (-)-enantiomers also had potent antinociceptive activity and one, (-)-N-fluoropropylnormetazocine (9), was a potent opioid antagonist.
|Original language||English (US)|
|Number of pages||8|
|Journal||Medicinal Chemistry Research|
|State||Published - 2000|
ASJC Scopus subject areas
- Pharmacology, Toxicology and Pharmaceutics(all)
- Organic Chemistry