Tetrodotoxin

Tetrodotoxin

Names
IUPAC name (4R,4aR,5R,6S,7S,8S,8aR,10S,12S)-2-azaniumylidene-4,6,8,12-tetrahydroxy-6-(hydroxymethyl)-2,3,4,4a,5,6,7,8-octahydro-1H-8a,10-methano-5,7-(epoxymethanooxy)quinazolin-10-olate
Other names anhydrotetrodotoxin, 4-epitetrodotoxin, tetrodonic acid, TTX
Identifiers
CAS Number	4368-28-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:9506 N
ChEMBL	ChEMBL507974 N
ChemSpider	9349691 N
ECHA InfoCard	100.022.236
IUPHAR/BPS	2616
KEGG	C11692 N
PubChem	11174599
InChI InChI=1S/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1 N Key: CFMYXEVWODSLAX-QOZOJKKESA-N N InChI=1/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1 Key: CFMYXEVWODSLAX-QOZOJKKEBM
SMILES O1[C@@H]4[C@@](O)([C@@H]3O[C@@]1(O)[C@@H](O)[C@]2(N\C(=N/[C@H](O)[C@H]23)N)[C@@H]4O)CO
Properties
Chemical formula	C11H17N3O8
Molar mass	319.268
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several species that carry the toxin. Although tetrodotoxin was discovered in these fish and found in several other aquatic animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails), it is actually produced by certain infecting or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in the animals.

Tetrodotoxin inhibits the firing of action potentials in nerves by binding to the voltage-gated sodium channels in nerve cell membranes and blocking the passage of sodium ions (responsible for the rising phase of an action potential) into the nerve cell (in layman terms, it prevents the nervous system from carrying messages and prevents muscles from flexing).

Its mechanism of action, selective blocking of the sodium channel, was shown definitively in 1964 by Toshio Narahashi and John W. Moore at Duke University, using the sucrose gap voltage clamp technique.

Apart from their bacterial species of most likely ultimate biosynthetic origin (see below), tetrodotoxin has been isolated from widely differing animal species, including: