Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone

J Med Chem. 1978 Apr;21(4):398-400. doi: 10.1021/jm00202a018.

Abstract

(+)-Naloxone was prepared in 26% overall yield in eight steps from (+)-7-bromodihydrocodeinone dimethyl ketal by a synthesis which excluded enantiomeric contamination. (+)-Naloxone was examined in three assay systems and found to have no more than 1/1000(-1)/10 000th the activity of (-)-naloxone; it can, thus, serve to test the stereospecificity of the biochemical and pharmacological actions of (-)-naloxone.

MeSH terms

  • Adenylyl Cyclases / metabolism
  • Animals
  • Binding, Competitive
  • Electric Stimulation
  • Guinea Pigs
  • Hybrid Cells / enzymology
  • In Vitro Techniques
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Naloxone / chemical synthesis*
  • Naloxone / metabolism
  • Naloxone / pharmacology
  • Rats
  • Receptors, Opioid / metabolism
  • Stereoisomerism

Substances

  • Receptors, Opioid
  • Naloxone
  • Adenylyl Cyclases