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

Article abstract of DOI:10.1021/jm00122a021

(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methyl-morphinan-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 μ opioid receptor antagonist.