Synthesis of exo-3-phenylbicyclo[3.2.1]oct-3-en-2-amine and related compounds as potential analgesics

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Abstract
Several analogs of exo-3-phenylbicyclo[3.2.1]oct-3-en-2-amine (1) were prepared, a compound that was marked antinociceptive activity in the inflamed-paw pressure test in rats. Two synthetically versatile methods leading to these compounds are described. In this series, antinociceptive activity increases with increasing size of the amine substituent, reaching an optimum with N(Me)Et, but this is always associated with CNS stimulant activity. The antinociceptive activity of these compounds is most likely due to an action that is similar to that of amphetamine rather than to an interaction with an opiate receptor. The endo diastereoisomer 22 [N,N-dimethyl-3-phenylbicyclo[3.2.1]oct-3-en-2-amine] and the benzo analog 11 [exo-5,6-dihydro-7-phenyl-5,9-methano-9H-benzocyclohepten-6-amine hydrochloride] were both devoid of antinociceptive and CNS stimulant activity.

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