Anhydrotetrodotoxin

Base Information

• Chemical Name: Anhydrotetrodotoxin
• CAS No.: 13072-89-4
• Molecular Formula: C11H15 N3 O7
• Molecular Weight: 301.25
• DSSTox Substance ID: DTXSID301019835
• Wikidata: Q104375947
• Mol file: 13072-89-4.mol

Synonyms:4,9-anhydro-TTX;4,9-anhydrotetrodotoxin;anhydrotetrodotoxin

Chemical Property of Anhydrotetrodotoxin

Chemical Property:

• Vapor Pressure: 2.63E-24mmHg at 25°C
• Boiling Point: 725.6°Cat760mmHg
• Flash Point: 392.6°C
• PSA: 56.06000
• Density: 3.07g/cm³
• LogP: 0.87730
• Storage Temp.: -20°
• Solubility.: Soluble in Ethanol (up to 10 mg/ml).
• XLogP3: -4.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 301.09099983
• Heavy Atom Count: 21
• Complexity: 574

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

4,9-Anhydrotetrodotoxin ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1(C2C3C4N=C(NC35C(C1OC(C5O4)(O2)O)O)N)O)O
• Isomeric SMILES: C([C@]1([C@@H]2[C@H]([C@@]34[C@H]5[C@@](O2)(OC1C3C(O5)N=C(N4)N)O)O)O)O
• 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.

Technology Process of Anhydrotetrodotoxin

There total 23 articles about Anhydrotetrodotoxin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

C19H21N3O9 → anhydrotetrodotoxin (13072-89-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 3h;

DOI:10.1002/anie.201611574

Reference yield:

(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 (5141-89-9) → 4,9-anhydrotetrodotoxin (13072-89-4)

Guidance literature:

With triethylamine; In methanol; water;

DOI:10.1016/S0040-4020(01)98344-9

Reference yield:

C35H54N2O10SSi → anhydrotetrodotoxin (13072-89-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: palladium 10% on activated carbon; quinoline; hydrogen / ethanol; ethyl acetate / 1.5 h / 20 °C

2.1: cesium fluoride / acetonitrile / 2 h / Inert atmosphere

2.2: 0.33 h / 20 °C / Inert atmosphere

3.1: N-chloromethanesulfonamide sodium salt; acetic acid / ethanol / 1.5 h / 20 °C / Inert atmosphere

3.2: 0.25 h / Inert atmosphere

4.1: ozone; sodium chlorite; sodium dihydrogenphosphate / dichloromethane; water; tert-butyl alcohol / 1 h / 20 °C / Inert atmosphere

4.2: 0.25 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

6.1: sodium tetrahydroborate; nickel dichloride / methanol; dichloromethane / 0.5 h / -40 °C / Inert atmosphere

6.2: 1.5 h / -40 - 0 °C / Inert atmosphere

7.1: lead(IV) tetraacetate / methanol / 3 h / 70 °C / Inert atmosphere

8.1: phenylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

8.2: 1.5 h / 20 °C / Inert atmosphere

9.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C

11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 20 °C / Inert atmosphere

11.2: 4 h / 20 °C / Inert atmosphere

12.1: trimethylsilyl iodide / acetonitrile / 0.17 h / 0 °C / Inert atmosphere

13.1: triethylamine; mercury dichloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

14.1: trifluoroacetic acid / water / 17 h / 60 °C / Inert atmosphere

15.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C

With quinoline; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl iodide; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; phenylsilane; hydrogen; lead(IV) tetraacetate; pyridinium p-toluenesulfonate; N-chloromethanesulfonamide sodium salt; potassium carbonate; ozone; acetic acid; triethylamine; cesium fluoride; trifluoroacetic acid; mercury dichloride; nickel dichloride; In methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1002/anie.201611574

upstream raw materials:

(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

(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

tetradotoxin

Downstream raw materials:

Amino-desoxy-tetrodotoxin