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T8024

Sigma-Aldrich

Tetrodotoxin

≥98% (HPLC), powder

Synonym(s):

Fugu poison, Maculotoxin, TTX, Tarichatoxin

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About This Item

Empirical Formula (Hill Notation):
C11H17N3O8
CAS Number:
4368-28-9
Molecular Weight:
319.27
Beilstein/REAXYS Number:
49176
EC Number:
224-458-8
MDL number:
MFCD00213719
UNSPSC Code:
12352200
PubChem Substance ID:
24900493

assay

≥98% (HPLC)

form

powder

color

white

solubility

dilute citrate or acetate buffer: 1 mg/mL (dissolve at pH 4-5. Aqueous solutions, pH 4-5, are stable if stored frozen.)
strong acid or alkaline solutions: unstable (destroyed by boiling at pH 2.)

storage temp.

2-8°C

SMILES string

[H][C@]12OC3(O)OC(C4[C@@H](O)NC(=N)NC4([C@@H]1O)[C@@H]3O)[C@@]2(O)CO

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

InChI key

CFMYXEVWODSLAX-IXUBDLNJSA-N

Gene Information

rat ... Scnn1g(24768)

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Application

Tetrodotoxin has been used as standard during HPLC-based analysis of biotoxins from P. punctata tentacles whole crude extract (PHY-N). Tetrodotoxin has also been used to study its effects on low-threshold transient (LTT) Ca2+ currents in rat hippocampal interneurons.

Biochem/physiol Actions

Reversible, selective blocker of Na+ channels; blocks propagation of impulses in excitable membranes. Used to characterize sodium channels in excitable membranes and to study the role of sodium channels in normal physiology and disease.

Preparation Note

Tetrodotoxin is soluble in dilute citrate or acetate buffer at 1 mg/ml (pH 4-5). Aqueous solutions are stable at pH 4-5 if stored frozen. However, tetrodotoxin is unstable in strong acid or alkaline solutions and is destroyed by boiling at pH2.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bradley Watmuff et al.
PloS one, 7(2), e31999-e31999 (2012-03-03)
The obvious motor symptoms of Parkinson's disease result from a loss of dopaminergic neurons from the substantia nigra. Embryonic stem cell-derived neural progenitor or precursor cells, adult neurons and fetal midbrain tissue have all been used to replace dying dopaminergic
Rocky Chau et al.
Aquatic toxicology (Amsterdam, Netherlands), 104(1-2), 61-72 (2011-05-06)
The potent neurotoxin tetrodotoxin (TTX) has been identified from taxonomically diverse marine organisms. TTX possesses a unique cage-like structure, however, its biosynthesis has yet to be elucidated. Biosynthetic studies in the TTX-producing newt Taricha torosa, and in bacterial genera, including
Simone Berkel et al.
Human molecular genetics, 21(2), 344-357 (2011-10-14)
Mutations in the postsynaptic scaffolding gene SHANK2 have recently been identified in individuals with autism spectrum disorder (ASD) and intellectual disability. However, the cellular and physiological consequences of these mutations in neurons remain unknown. We have analyzed the functional impact
D D Fraser et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 11(9), 2812-2820 (1991-09-01)
Interneurons from the CA1 lacunosum-moleculare (L-M) region were isolated by trypsin-hyaluronidase treatment and mechanical trituration of the L-M. Interneurons isolated in this manner were multipolar with several dendritic processes and could be distinguished from CA1 pyramidal neurons. The properties of
Raquel Felipe Vasconcelos Carneiro et al.
Journal of applied toxicology : JAT, 31(8), 720-729 (2011-02-15)
Phyllorhiza punctata (P. punctata) is a jellyfish native to the southwestern Pacific. Herewith we present the biochemical and pharmacological characterization of an extract of the tentacles of P. punctata. The tentacles were subjected to three freeze-thaw cycles, homogenized, ultrafiltered, precipitated
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