(−)‐<i>N</i>‐[(Cyclopropyl) methyl]‐3,4‐dimethoxy‐5‐methylmorphinan‐6‐one, an opioid agonist with preference for kappa opioid receptors

Abstract

Abstract N ‐Allyl‐ and N ‐[(Cyclopropyl)methyl]‐3,4‐dimethoxy‐5‐methylmorphinan‐6‐one ( 9 and 10, resp.) were synthesized from 5‐methyldih drothebainone ( 1 ). This essential intermediate was prepared from the baine via 5‐methylthebaine (5) employing a novel route. The Pharmacological studies showed 9 and 10 to be potent opioid agonists. Compound 10 was found to have preference for kappa rather than mu opioid receptors.