Synthesis and antinociceptive activity of 7-methoxycodeine

J Med Chem. 1978 Dec;21(12):1320-2. doi: 10.1021/jm00210a031.

Abstract

(-)-7-Methoxycodeine was synthesized from (-)-1-bromosinomeninone in three steps with an overall yield of 29%. The introduction of the 7-methoxy group into the C ring of codeine did not decrease its oral activity. 7-Methoxycodeine was unstable in acidic media. Its oral activity was however, not likely to be due to conversion to the acid-stable (-)-sinomeninone, since the latter was orally inactive.

MeSH terms

  • Administration, Oral
  • Analgesics / chemical synthesis*
  • Animals
  • Codeine / administration & dosage
  • Codeine / analogs & derivatives*
  • Codeine / chemical synthesis
  • Codeine / pharmacology
  • Injections, Subcutaneous
  • Mice
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Codeine