A series of ethers containing pyrrolidine and/or pyridine bioisosteres was synthesized and evaluated as nicotinic ligands. The dimethylaminoethoxypyridines 6 and 7 inhibited the specific binding of (-)⁻³H_N indicating with Ki values of 300 nM and 450 nM, respectively. Compounds 8 and 9 were found to have Ki values of 3390 nM and 360 nM. These results suggest that dialkylamino and appropriately substituted benzene rings (NO2, 8; OH, 9) are bioisosteric replacements for pyrrolidine and pyridine, respectively.