Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one, a selective mu opioid receptor antagonist

J Med Chem. 1989 Feb;32(2):418-21. doi: 10.1021/jm00122a021.

Abstract

(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation, rat and mouse vas deferens preparation, acetic acid writhing antagonism test) indicate that 2 is a selective mu opioid receptor antagonist.

MeSH terms

  • Animals
  • Guinea Pigs
  • In Vitro Techniques
  • Male
  • Mice
  • Morphinans / chemical synthesis
  • Morphinans / pharmacology*
  • Narcotic Antagonists / chemical synthesis
  • Narcotic Antagonists / pharmacology*
  • Rats
  • Receptors, Opioid / drug effects*
  • Receptors, Opioid, mu

Substances

  • Morphinans
  • Narcotic Antagonists
  • Receptors, Opioid
  • Receptors, Opioid, mu
  • cyprodime