Synthesis and pharmacological activity of some N-alkyl-substituted 9alpha-ethyl-2'-hydroxy-5-methyl-6,7-benzomorphans

A series of N-substituted 9alpha-ethyl-2'-hydroxy-5-methyl-6,7-benzomorphans was synthesized and evaluated for their narcotic analgesic and antagonistic activities. Compounds 2a and 22 were as potent as morphine in the writhing (PPQ) and hot-plate tests, while a number of compounds demonstrated antagonistic activities greater than nalorphine. Generally, the compounds in this series show activities somewhat greater than the comparable compounds in the 5,9alpha-dimethyl-6,7-benzomorphan series for analgesic effect and similar or slightly less antagonistic potency.