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

Anhydrotetrodotoxin (4,9-anhydro-TTX) is a derivative of tetrodotoxin (TTX) that selectively blocks inward sodium current through Nav1.6 voltage-activated sodium channels with high specificity and potency (IC50 = 7.8 nM in Xenopus oocytes). It exhibits varying degrees of potency against other sodium channel subtypes, including Nav1.2, Nav1.3, Nav1.4, Nav1.5, Nav1.7, and Nav1.8.

Uses

Used in Pharmaceutical Industry:
Anhydrotetrodotoxin is used as a pharmacological tool for studying the function and role of voltage-activated sodium channels in various physiological and pathological processes. Its high selectivity and potency make it a valuable compound for investigating the specific contributions of different sodium channel subtypes to pain, epilepsy, and other neurological disorders.
Used in Drug Development:
Anhydrotetrodotoxin is used as a lead compound in the development of novel therapeutics targeting voltage-activated sodium channels. Its selective blocking activity against specific sodium channel subtypes, particularly Nav1.6, makes it a promising candidate for the treatment of conditions such as chronic pain, epilepsy, and potentially other neurological disorders.
Used in Neurophysiological Research:
Anhydrotetrodotoxin is used as a research tool in neurophysiological studies to investigate the role of sodium channels in the generation and propagation of action potentials in neurons. Its ability to selectively block specific sodium channel subtypes allows researchers to gain insights into the underlying mechanisms of various neurological conditions and the development of targeted therapies.
Used in Ion Channel Screening:
Anhydrotetrodotoxin is used as a reference compound in ion channel screening assays to identify and characterize new modulators of voltage-activated sodium channels. Its well-defined activity against different sodium channel subtypes serves as a benchmark for evaluating the potency and selectivity of newly discovered compounds with potential therapeutic applications.

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

• 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 
• 4368-28-9 tetradotoxin 

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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