Anatoxin-a

Anatoxin-a
IUPAC name 1-[(1R,6R)-9-azabicyclo[4.2.1]non-4-en-5-yl]ethanone
Other names Anatoxin A
Identifiers
CAS number	64285-06-9 Y
PubChem	431734
ChemSpider	381822 Y
KEGG	C10841 Y
ChEMBL	CHEMBL25619 Y
Jmol-3D images	Image 1
SMILES CC(=O)C1=CCCC2CCC1N2
InChI InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3 Y Key: SGNXVBOIDPPRJJ-UHFFFAOYSA-N Y InChI=1/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3 Key: SGNXVBOIDPPRJJ-UHFFFAOYAZ
Properties
Molecular formula	C10H15NO
Molar mass	165.232
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Anatoxin-a, also known as Very Fast Death Factor, 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. The toxin is much less likely to be identified in the southern hemisphere. Symptoms of anatoxin exposure are loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor where it acts as an analogue of acetylcholine. The molecule is not degraded by cholinesterase, thus causing permanent stimulation of muscle cells leading to paralysis. Information on carcinogenicity is not available.

See also

• Cyanotoxin

References

• Wood, S. A., J. P. Rasmussen, P. T. Holland, R. Campbell, and A. L. M. Crowe. 2007. "First Report of the Cyanotoxin Anatoxin-A from Aphanizomenon issatschenkoi (cyanobacteria)" Journal of Phycology 43:356-365.
• National Center for Environmental Assessment. "Toxicological Reviews of Cyanobacterial Toxins: Anatoxin-a" NCEA-C-1743