The synthesis and nicotinic binding activity of (±)-epiquinamide and (±)-C(1)-epiepiquinamide

The synthesis of (±)-epiquinamide 1 and (±)-C(1)-epiepiquinamide 2 based on the use of a Curtius rearrangement to introduce the C(1) amino residue is reported. In a competition binding assay for [3H]epibatidine binding to rat brain membranes neither (±)-1 nor (±)-2 showed any significant level of nicotinic activity.