Anatoxin-a

Not to be confused with Anatoxin-a(S).
Anatoxin-a
Ball-and-stick model of the anatoxin-a molecule
Names
IUPAC name
1-(9-azabicyclo[4.2.1]non-2-en-2-yl)ethan-1-one
Other names
Anatoxin A
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.215.761 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: SGNXVBOIDPPRJJ-UHFFFAOYSA-N checkY
  • 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
  • CC(=O)C1=CCCC2CCC1N2
Properties
C10H15NO
Molar mass 165.232
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anatoxin-a, also known as Very Fast Death Factor (VFDF), is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by multiple genera of cyanobacteria and has been reported in North America, South America, Central America, Europe, Africa, Asia, and Oceania. Symptoms of anatoxin-a toxicity include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor (nAchR) where it mimics the binding of the receptor's natural ligand, acetylcholine. As such, anatoxin-a has been used for medicinal purposes to investigate diseases characterized by low acetylcholine levels. Due to its high toxicity and potential presence in drinking water, anatoxin-a poses a threat to animals, including humans. While methods for detection and water treatment exist, scientists have called for more research to improve reliability and efficacy. Anatoxin-a is not to be confused with guanitoxin (formerly anatoxin-a(S)), another potent cyanotoxin that has a similar mechanism of action to that of anatoxin-a and is produced by many of the same cyanobacteria genera, but is structurally unrelated.[1]

  1. ^ Aráoz R, Molgó J, Tandeau de Marsac N (October 2010). "Neurotoxic cyanobacterial toxins". Toxicon. 56 (5): 813–28. doi:10.1016/j.toxicon.2009.07.036. PMID 19660486.