Anabasine served as a starting material for the synthesis of two series of novel, drug-like compounds. On the one hand, anabasine was subjected to a direct Chichibabin amination and elaborated into medicinally relevant, racemic 6-(piperidin-2-yl)imidazo[1,2-a]pyridines via the Groebke-Blackburn reaction. On the other hand, anabasine was used as an amine for the Ugi reaction to provide novel non-racemic anabasine-containing 2-[(2-pyridin-3-yl)piperidin-1-yl] acetamide peptidomimetics with high diastereoselectivity.