Tetrodotoxin

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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 (JSmol)	Interactive image zwitterion: Interactive image
ChEBI	CHEBI:9506 N
ChEMBL	ChEMBL507974 N
ChemSpider	9349691 N
ECHA InfoCard	100.022.236
IUPHAR/BPS	2616
KEGG	C11692 N
PubChem CID	11174599
UNII	3KUM2721U9 Y
CompTox Dashboard (EPA)	DTXSID10881342
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 zwitterion: 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)=[NH2+])[C@@H]4O)CO
Properties
Chemical formula	C11H17N3O8
Molar mass	319.270 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (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 of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopi, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants.^[1][2]

Although it produces thousands of intoxications annually and several deaths,^[3] it has shown efficacy for the treatment of cancer-related pain in phase II and III clinical trials.^[4]

Tetrodotoxin is a sodium channel blocker. It inhibits the firing of action potentials in neurons 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 neuron. This prevents the nervous system from carrying messages and thus muscles from contracting in response to nervous stimulation.^[5]

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.^[6]