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Substance Name: Tetrodotoxin
RN: 4368-28-9
UNII: 3KUM2721U9
InChIKey: CFMYXEVWODSLAX-QOZOJKKESA-N

Note

  • An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.

Molecular Formula

  • C11-H17-N3-O8

Molecular Weight

  • 319.268
 

Classification Codes

  • Anesthetics
  • Anesthetics, Local
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Membrane Transport Modulators
  • Natural Product
  • Noxae
  • Peripheral Nervous System Agents
  • Poisons
  • Sensory System Agents
  • Sodium Channel Blockers
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Names and Synonyms

Name of Substance

  • Tetrodotoxin

MeSH Heading

  • Tetrodotoxin

Synonyms

  • (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d) pyrimidine-4,7,10,11,12-pentol
  • 4-27-00-08206 (Beilstein Handbook Reference)
  • 5,9:7,10a-Dimethano-10ah-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-
  • Babylonia japonica toxin 1
  • BJT 1
  • BRN 0049176
  • CCRIS 9328
  • EINECS 224-458-8
  • Fugu poison
  • HSDB 3543
  • Maculotoxin
  • Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol
  • Spheroidine
  • Tarichatoxin
  • Tetrodontoxin
  • Tetrodotoxin
  • Tetrodotoxine
  • Tetrodoxin
  • TTX
  • UNII-3KUM2721U9

Systematic Names

  • 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-
  • 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-
  • Tetrodotoxin

Registry Numbers

CAS Registry Number

  • 4368-28-9

FDA UNII

  • 3KUM2721U9

Other Registry Numbers

  • 11005-69-9
  • 11026-09-8
  • 12626-86-7
  • 17289-88-2
  • 2229-61-0
  • 9014-39-5

System Generated Number

  • 0004368289

Structure Descriptors

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

InChIKey

CFMYXEVWODSLAX-QOZOJKKESA-N

Smiles

NC1=N[C@H](O)[C@H]2[C@H]3O[C@]4(O)O[C@@H]([C@@H](O)[C@@]2(N1)[C@@H]4O)[C@]3(O)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 intraperitoneal 14ug/kg (0.014mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Toxicon. Vol. 5, Pg. 25, 1967.
frog LDLo unreported 15ug/kg (0.015mg/kg)   Science. Vol. 144, Pg. 1100, 1964.
mouse LD50 intracrebral 600ng/kg (0.0006mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 14, Pg. 186, 1973.
mouse LD50 intraperitoneal 8ug/kg (0.008mg/kg)   Science. Vol. 144, Pg. 1100, 1964.
mouse LD50 intravenous 7300ng/kg (0.0073mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 14, Pg. 186, 1973.
mouse LD50 oral 334ug/kg (0.334mg/kg)   Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 14, Pg. 186, 1973.
mouse LD50 subcutaneous 8ug/kg (0.008mg/kg)   Clinical Toxicology. Vol. 4, Pg. 331, 1971.
mouse LD50 unreported 8700pg/kg (0.0000087mg/kg)   Igaku No Ayumi. Progress in Medicine. Vol. 112, Pg. 861, 1980.
rabbit LDLo intracrebral 25ug/kg (0.025mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo intramuscular 400ug/kg (0.4mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo intraspinal 80ug/kg (0.08mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo intravenous 400ug/kg (0.4mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo oral 7500ug/kg (7.5mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo parenteral 4ug/kg (0.004mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rabbit LDLo subcutaneous 650ug/kg (0.65mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 63, 1938.
rat LDLo unreported 15ug/kg (0.015mg/kg)   Science. Vol. 144, Pg. 1100, 1964.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.76 (none)   EXP
log P (octanol-water) -6.210 (none)   EST
Atmospheric OH Rate Constant 3.71E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.