(+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE

Acute toxicity

Intraperitoneal-mouse LDL0: 0.25 mg/kg

Occurrence

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

Uses

(+)-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.

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.