Saxitoxin

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Saxitoxin
Systematic (IUPAC) name
(3aS-(3a-α,4-α,10aR*))2,6-diamino- 4-(((amino-carbonyl)oxy)methyl)-3a,4,8,9-tetrahydro- 1H,10H-pyrrolo(1,2-c)purine-10,10-diol
Identifiers
CAS number	35523-89-8
PubChem	37165
Chemical data
Formula	C₁₀H₁₇N₇O₄
Molar mass	299.29
SMILES	N=C1N[C@@H](COC(N)=O)[C@H]3[C@] 2(N=C(N)N3)N1CCC2(O)O
Complete data

Saxitoxin (STX) is a cyanotoxin found in marine dinoflagellates (algae). It is a neurotoxin that is a selective sodium channel blocker. The United States military isolated saxitoxin and assigned it the chemical weapon designation TZ. It is almost unique among toxins in that it acts very quickly, in a matter of minutes. The median lethal concentration (LCt₅₀) of TZ is 5 mg·min/m³.

The medical importance of saxitoxin is in relation to red tide in shellfish and causes the paralytic shellfish poisoning (PSP) food poisoning. The blocking of the sodium channel produces a flaccid paralysis that leaves its victim calm and conscious through the progression of symptoms. Death is from respiratory failure.

It is listed in schedule 1 of the Chemical Weapons Convention. According to the book spycraft, U2 spyplane pilots were provided with needles containing Saxitoxin to be used in the event escape was impossible. 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.