(-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia Tupa with Agonist Activity at Nicotinic Acetylcholine Receptor

Abstract

Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at α3β2/α3β4 nAChR and α7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR.