Synthesis of Hexahydro-[2]pyrindine(=Hexahydrocyclopenta[c]pyridine) Derivatives as Conformationally Restricted Analogs of the Nicotinic Ligands Arecolone and Isoarecolone

Two hexahydropyrindine derivatives and their methiodides were synthesized. They can be considered rigid analogs of the known nicotinic agonists arecolone and isoarecolone. The affinity for the central nicotinic receptor was measured on rat cerebral cortex. Although only one methiodide, among the four confomationally restricted compounds, shows an appreciable affinity, the results obtained provide useful information on the molecular requirementes at the interaction site of the central nicotinic receptors.