Saxitoxin
1266996
224409761
2008-07-08T18:52:24Z
Bosco911
2976963
{{OrganicBox small
| C=10 | H=17 | N=7 | O=4
| cat =nd
| image =[[Image:Saxitoxin_structure.png|250px|Chemical structure of saxitoxin]]
| name =(3aS-(3a-α,4-α,10aR*))2,6-diamino-<br />4-(((amino-carbonyl)oxy)methyl)-3a,4,8,9-tetrahydro-<br />1H,10H-pyrrolo(1,2-c)purine-10,10-diol
| CAS =35523-89-8
| DrugBank =
| PubChem =37165
| SMILES =N=C1N[C@@H](COC(N)=O)[C@H]3[C@]<br />2(N=C(N)N3)N1CCC2(O)O
| mass =299.29
}}
''
'''Saxitoxin''' ('''STX''') is a neurotoxin naturally produced by certain species of marine [[dinoflagellate]]s (''Alexandrium sp., Gymnodinium sp., Pyrodinium sp.'') and cyanobacteria (''Anabaena sp., Aphanizomenon sp., Cylindrospermopsis sp., Lyngbya sp.,
''Planktothrix sp.'')<ref>Landsberg JH, 2002. The effects of harmful algal blooms on aquatic organisms. Reviews in Fisheries Science, 10(2): 113–390.</ref>. The term saxitoxin originates from the butter clam (''Saxidomus giganteus'') in which it was first recognized. It is a [[neurotoxin]] that acts as a selective [[sodium channel]] blocker. The human illness associated with ingestion of harmful levels of saxitoxin is known as [[paralytic shellfish poisoning]], or PSP, and saxitoxin and its derivatives are often referred to as "PSP toxins".
The [[medical]] and ecological importance of saxitoxin lies mainly in effects of [[harmful algal bloom]]s on [[shellfish]] and certain finfish which can concentrate the toxin, making it available both for human consumption as well as by various marine organisms. The blocking of neuronal sodium channels which occurs in PSP produces a flaccid paralysis that leaves its victim calm and conscious through the progression of [[symptom]]s. Death often occurs from [[respiratory failure]]. PSP toxins have been implicated in various marine animal mortalities involving trophic transfer of the toxin from its algal source up the food web to higher predators.
It is listed in [[List of Schedule 1 substances (CWC)|schedule 1]] of the [[Chemical Weapons Convention]]. According to the book Spycraft, [[Lockheed U-2|U-2]] spyplane pilots were provided with needles containing Saxitoxin to be used in the event escape was impossible. The [[United States military]] isolated saxitoxin and assigned it the [[chemical weapon designation]] '''TZ'''. Though its early isolation and characterization were related to military efforts, saxitoxin has been more important to cellular research in delineating the function of the sodium channel.
== See also ==
* [[Harmful algal bloom]]
* [[Paralytic shellfish poisoning]]
* [[Alexandrium tamarense]] sp.
* [[Anabaena_circinalis|Anabaena circinalis]]
* [[Action potential]]
* [[Tetrodotoxin]]
== External links==
*http://www.uaf.edu/seagrant/issues/PSP/PSP.pdf
*http://www.chm.bris.ac.uk/motm/stx/saxi.htm
[[Category:Alkaloids]]
[[Category:Chemical weapons]]
[[Category:Neurotoxins]]
[[Category:Nitrogen heterocycles]]
[[de:Saxitoxin]]
[[it:Saxitossina]]
[[ja:サキシトキシン]]
[[no:Saxitoxin]]
[[ru:Сакситоксин]]
{{biochem-stub}}