anabaseine

Description

Anabaseine is a bipyridine derivative and piperidine analogue of anabasine1, the Molecule of the Week for December 29, 2008. Both molecules are chemically related to nicotine, the August 20, 2018, MOTW.
Anabaseine was first synthesized in 1936 by E. Sp?th* and L. Mamoli at the University of Vienna via a Claisen condensation. In 1971, William R. Kem*, Bernard C. Abbott*, and Robert M. Coates at the University of Illinois at Champaign–Urbana reported the isolation of anabaseine from a nemertean (ribbon worm), which uses the molecule to paralyze prey and repel predators. In 1981, J. W. Wheeler, R. M. Duffield, and co-workers at Howard University (Washington, DC) isolated it from the poison glands of Aphaenogaster ants, which use anabaseine as a pheromone and a chemical defense.
Because of its chemically reactive imine group, anabaseine is a useful scaffold for synthesizing nicotinic receptor drug candidates. These include GTS-212 (synthesized by Kem), which has been clinically tested to improve cognition in schizophrenics and pre–Alzheimer’s disease patients.
In 2009, Palmer Taylor, Yves Bourne, and coauthors at the University of California, San Diego, the University of Aix-Marseille (France), and the University of Florida (Gainesville) reported on the interactions of GTS-21 and several other substituted anabaseines with molluscan acetylcholine-binding proteins. The following year, a quantitative structure–activity relationship analysis of benzylidene–anabaseines by Kem, Alan R. Katritzky, and co-workers at the University of Florida provided additional insights concerning ligand–nicotinic receptor interactions.
1. CAS Reg. No. 494-52-0. 2. CAS Reg. No. 156223-05-1.

Chemical properties

Brown Liquid

The Uses of anabaseine

A naturally occurring neurotoxin produced by hoplonemertine sea worms competes with the natural neurotransmitter acetylcholine when binding to nicotinic receptor sites.

What are the applications of Application

Anabaseine is A naturally occurring neurotoxin

Definition

ChEBI: Anabaseine is a member of bipyridines.