(+/-)-2-Acetyl-9-aza bicyclo[4.2.1]non-2-ene fumarate

Description

(+)-Anatoxin-a—(1R,6R)-5-acetyl-9-azabicyclo[4.2.1]non-4-ene—is an acute neurotoxin produced by cyanobacteria worldwide. In biological systems, it behaves similarly to acetylcholine, but it is not degraded by cholinesterase. Recent studies of anatoxin-a contamination of drinking water sources have been carried out in New York State; Quebec, Canada; southern France; and the Niger Delta in Africa.

Occurrence

An oily alkaloid, anatoxin-a has been isolated from Anabaena jfos-aquae.

The Uses of (+/-)-2-Acetyl-9-aza bicyclo[4.2.1]non-2-ene fumarate

(+)-Anatoxin-a is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. The toxin is produced by at least four different genera of cyanobacteria and has been reported in North America, Europe, Africa, Asia, and New Zealand. Symptoms of anatoxin exposure are loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis.

What are the applications of Application

(±)-Anatoxin A Fumarate is a cyanotoxin agonist of AChR

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 4539, 1984 DOI: 10.1021/ja00328a040

Biological Activity

A potent nicotinic agonist (K i values are 1.25 and 1840 nM for α 4 β 2 and α 7 nicotinic receptors respectively). Stimulates [ 3 H]-dopamine release from rat striatal synaptosomes (EC 50 = 136 nM).

Safety Profile

Poison by intraperitoneal route.An experimental teratogen. When heated todecomposition it emits toxic fumes of NOx.