13072-89-4

Basic information

• Product Name: anhydrotetrodotoxin
• Synonyms: anhydrotetrodotoxin;(8S)-4,9-Dideoxy-4β,9β-epoxytetrodotoxin;4,9-Anhydrotetrodotoxin;4,9-Dideoxy-4β,9β-epoxytetrodotoxin
• CAS NO: 13072-89-4
• Molecular Formula: C11H15N3O7
• Molecular Weight: 301.254
• Mol File: 13072-89-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 725.6°Cat760mmHg
• Flash Point: 392.6°C
• Appearance: /
• Density: 3.07g/cm³
• Vapor Pressure: 2.63E-24mmHg at 25°C
• Refractive Index: 2.298
• Storage Temp.: -20°
• Solubility: Soluble in Ethanol (up to 10 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Protect from exposure to light or moisture. Solutions are not stable. Solutions must be prepared fresh and used within 1 working day.
• CAS DataBase Reference: anhydrotetrodotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: anhydrotetrodotoxin(13072-89-4)
• EPA Substance Registry System: anhydrotetrodotoxin(13072-89-4)

Safety Data

• Hazardous Substances Data: 13072-89-4(Hazardous Substances Data)

Usage

Description

4,9-Anhydrotetrodotoxin (4,9-anhydro-TTX) is a derivative of TTX that selectively blocks inward sodium current through Nav1.6 voltage-activated sodium channels (IC50 = 7.8 nM in Xenopus oocytes). It demonstrates IC50 values of 1.3, 0.34, 0.99, 78.5, 1.3, and >30 μM for Nav1.2, Nav1.3, Nav1.4, Nav1.5, Nav1.7, and Nav1.8, respectively.

References

1) Rosker?et al. (2007),?The TTX metabolite 4,9-anhydro-TTX is a highly specific blocker of the Na(v1.6) voltage-dependent sodium channel; Am.J.Physiol.Cell Physiol.,?293?C783. 2) Denomme?et al.?(2020),??The voltage-gated sodium channel inhibitor, 4,9-anhydrotetrodotoxin, blocks human Nav1.1 in addition to Nav1.6;?Neurosci. Lett.?724?134853

InChI:InChI=1/C11H15N3O7/c12-8-13-6-2-4-9(17,1-15)5-3(16)10(2,14-8)7(19-6)11(18,20-4)21-5/h2-7,15-18H,1H2,(H3,12,13,14)/t2?,3-,4?,5-,6?,7+,9+,10-,11+/m1/s1

Upstream product

• 4368-28-9 tetradotoxin 
• 13285-84-2 (5S)-8t-acetoxy-8c-acetoxymethyl-2-amino-(3at,7at,10bt)-3a,7a,8,9,10,10b-hexahydro-1⁽³⁾H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazoline-6,10c-diol 
• 5141-89-9 (5S)-6,8t,10c-triacetoxy-8c-acetoxymethyl-(3at,7at,10bt)-3a,5,6,7a,8,9,10,10b-octahydro-1⁽³⁾H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazolin-2-ylamine; toluene-4-sulfonate 

Downstream Products

• 7724-38-1 Amino-desoxy-tetrodotoxin 

Related news

Actions of 4-epitetrodotoxin and anhydrotetrodotoxin (cas 13072-89-4) on the squid axon09/09/2019

The actions of the newly discovered 4-epitetrodotoxin and of anhydrotetrodotoxin have been studied on the internally perfused squid giant axon under voltage-clamped conditions. Both compounds are selective in blocking only the sodium channel. The concentration for reducing the sodium current to ...detailed

Relevant articles and documents

Total Synthesis of (?)-Tetrodotoxin and 11-norTTX-6(R)-ol

The enantioselective total synthesis of (?)-tetrodotoxin [(?)-TTX] and 4,9-anhydrotetrodotoxin, which are selective blockers of voltage-gated sodium channels, was accomplished from the commercially available p-benzoquinone. This synthesis was based on efficient stereocontrol of the six contiguous stereogenic centers on the core cyclohexane ring through Ogasawara's method, [3,3]-sigmatropic rearrangement of an allylic cyanate, and intramolecular 1,3-dipolar cycloaddition of a nitrile oxide. Our synthetic route was applied to the synthesis of the tetrodotoxin congeners 11-norTTX-6(R)-ol and 4,9-anhydro-11-norTTX-6(R)-ol through late-stage modification of the common intermediate. Neutral deprotection at the final step enabled easy purification of tetrodotoxin and 11-norTTX-6(R)-ol without competing dehydration to their 4,9-anhydro forms.

Tetrodotoxin.

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