Azabicycloalkanes as analgetics. IV. 4-Phenyl-2-azabicyclo[2,2,1]heptanes.

Abstract

As part of the study on the structure-activity relationships of azabicycloalkane antagonist-analgetics, 4-phenyl-2-azabicyclo[2,2,1]heptane was synthesized. The phenols (XII and XIII) with a bridged 3-phenylpyrrolidine moiety were analgetically inactive. A shape of the alicyclic ring may play an important role on the analgetic effectiveness of these derivatives. XII and XIII displayed apparent properties of narcotic antagonism on the order of 1-phenyl-6-azabicyclo[3,2,1]octane and pentazocine, the result suggesting that the structural requisite for the antagonist activity in these derivatives, differing from those for analgesia, may be a N-methylphenylethanamine chain.