Synthesis and antinociceptive activity of 7-methoxycodeine.
(-)-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.
D000284:Administration, Oral; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D003061:Codeine / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D007279:Injections, Subcutaneous; D051379:Mice; D013329:Structure-Activity Relationship
D000700:Analgesics; D003061:Codeine