99134-12-0Relevant articles and documents
Enantiomeric (-)-(1R,5R,9R) and (+)-(1S,5S,9S) heterocyclic N-substituted-normetazocines: Synthesis of potent and selective antinociceptives and opioid antagonists through N-substituent modification
May,Aceto,Bowman,Traynor,Woods,Jacobson,Harris
, p. 178 - 185 (2007/10/03)
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.