4-[(1E)-(hydroxyimino)methyl]-1-[({4-[(1E)-(hydroxyimino)methyl]pyridin-1-ium-1-yl}methoxy)methyl]pyridin-1-ium dichloride

• ChemBase ID: 153724
• Molecular Formular: C14H16Cl2N4O3
• Molecular Mass: 359.20784
• Monoisotopic Mass: 358.05994575
• SMILES: c1c(cc[n+](c1)COC[n+]1ccc(cc1)/C=N/O)/C=N/O.[Cl-].[Cl-]
• Canonical SMILES: O/N=C/c1cc[n+](cc1)COC[n+]1ccc(cc1)/C=N/O.[Cl-].[Cl-]
• InChI: InChI=1S/C14H14N4O3.2ClH/c19-15-9-13-1-5-17(6-2-13)11-21-12-18-7-3-14(4-8-18)10-16-20;;/h1-10H,11-12H2;2*1H
• InChIKey: ZIFJVJZWVSPZLE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1E)-(hydroxyimino)methyl]-1-[({4-[(1E)-(hydroxyimino)methyl]pyridin-1-ium-1-yl}methoxy)methyl]pyridin-1-ium dichloride; 4-[(hydroxyimino)methyl]-1-[({4-[(hydroxyimino)methyl]pyridin-1-ium-1-yl}methoxy)methyl]pyridin-1-ium dichloride
• IUPAC Traditional name: 4-[(1E)-(hydroxyimino)methyl]-1-[({4-[(1E)-(hydroxyimino)methyl]pyridin-1-ium-1-yl}methoxy)methyl]pyridin-1-ium dichloride; 4-[(hydroxyimino)methyl]-1-[({4-[(hydroxyimino)methyl]pyridin-1-ium-1-yl}methoxy)methyl]pyridin-1-ium dichloride
• Synonyms: 1,1’[Oxybis(methylene)]-bis[4-(hydroxyimino)methyl]pyridinium Dichloride; Toxogonin Dichloride; Toxogonine; Toxobidin; Toksobidin; Obidoxime Chloride; 1,1′-(Oxydimethylene)bis(pyridinium-4-carbaldoxime) dichloride; Bis(4-formylpyridiniomethyl) ether dioxime; Toxogonin; Obidoxime chloride

Database IDs

• CAS Number: 114-90-9
• EC Number: 204-059-5
• MDL Number: MFCD00038864
• Beilstein Number: 4117377
• PubChem SID: 162247863; 24873520
• PubChem CID: 5359290

CALCULATED PROPERTIES

• Acid pKa: 8.561568
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -6.930292
• LogD (pH = 7.4): -6.957366
• Log P: -6.929924
• Molar Refractivity: 79.6179 cm^3
• Polarizability: 29.490025 Å^3
• Polar Surface Area: 82.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 216-219°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: 1-10% Aqueous solution
• RTECS: UU6825000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C14H16Cl2N4O3

DETAILS

Sigma Aldrich - 51063

Biochem/physiol Actions
Antidote for organophosphate nerve agent poisoning1
Antidote for organophosphate nerve agent poisoning1, but, as with other oxime agents, not full spectrum. Obidoxime fails primarily to reactivate acetylcholinesterase that has been inhibited with cyclosarin.2
General description
active agent in Toxogonin®
Legal Information
TOXOGONIN is a registered trademark of Merck

Toronto Research Chemicals - O100000

Cholinesterase reactivator.