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114-90-9

114-90-9 Structure

114-90-9 Structure
IdentificationBack Directory
[Name]

OBIDOXIME CHLORIDE
[CAS]

114-90-9
[Synonyms]

bh6
luh6
bu-6
lueh6
D009768
Obidoxim
luh(sub6)
TOXOGONIN
toxobidin
Obidoxime
toxogonine
toksobidin
luh6-chloride
luh(sub6)-cl2
luh6dichloride
luh(sup6)-cl(sup2)
OBIDOXIME CHLORIDE
Chloride, obidoxime
toxogonindichloride
obidoximedichloride
obidoximehydrochloride
Obidoxime dihydrochloride
Merck brand of obidoxime chloride
BIS(4-FORMYLPYRIDINIOMETHYL) ETHER DIOXIME
bis(isonicotinaldoxime1-methyl)etherdichloride
1,3-bis(4-aldoximinopyridinium)dimethyletherbichloride
n,n-dimethylenoxid-bis-(pyridinium-4-aldoxim)-dichlorid
n,n-dimethyleneoxidebis(pyridinium-4-aldoxime)dichloride
bis(4-hydroxyiminomethylpyridinium-1-methyl)etherdichloride
1,1’-(oxydimethylene)bis(4-formylpyridinium)dichloridedioxime
1,1’-(oxydimethylene)bis(4-formylpyridinium)dioximedichloride
etherbis-14-hydroxy-iminomethylopyridine-(1)-metylodichloride
1,1'-(OXYDIMETHYLENE)BIS(PYRIDINIUM-4-CARBALDOXIME) DICHLORIDE
1,3-bis(4-hydroxyiminomethyl-1-pyridinio)-2-oxapropanedichloride
pyridinium,1,1’-(oxydimethylene)bis(4-formyl-,dichloride,dioxime
1,1'[OXYBIS(METHYLENE)]-BIS[4-(HYDROXYIMINO)METHYL]PYRIDINIUM DICHLORIDE
1,1’-[oxybis(methylene)]bis[4-[(hydroxyimino)methyl]-pyridiniudichloride
1,1’-(oxybis(methylene))bis(4-((hydroxyimino)methyl)-pyridiniudichloride
Pyridinium, 1,1'-(oxybis(methylene))bis(4-((hydroxyimino)methyl))-, dichloride
[EINECS(EC#)]

204-059-5
[Molecular Formula]

C14H16Cl2N4O3
[MDL Number]

MFCD00038864
[MOL File]

114-90-9.mol
[Molecular Weight]

359.21
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

216-219oC dec.
[storage temp. ]

-20°C Freezer
[solubility ]

Methanol (Slightly), Water (Slightly)
[form ]

powder or crystals
[color ]

Off-White to Light Beige
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[BRN ]

4117377
[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
[SMILES]

[Cl-].[Cl-].O\N=C\c1cc[n+](COC[n+]2ccc(cc2)\C=N\O)cc1
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Uses]

antibacterial
[Uses]

Cholinesterase reactivator
[Originator]

Toksobidin,Polfa-Starogard
[Manufacturing Process]

2 Methods of producing of obidoxime chloride: 1. Into a boiling agitated solution of 2.44 g pyridine-4-aldoxime in 10 ml absolute ethanol is added dropwise during the course of 25 min a solution of 1.14 g bis-chloromethyl ether in 5 ml absolute ethanol. The reaction mixture is then refluxed for 35 min, and then agitated for 5 h at room temperature. The precipitate of bis-[4-hydroxyimino-methyl-pyridinium-(1)-methyl]-ether Trade dichloride is thoroughly washed with absolute acetone. The yield is 3.5 g which is 98% of the theoretical, and the melting point is 229°C. If convenient, the mother liquor can be reused to make additional product.
2. 12.2 g (0.1 mole) pyridine-4-aldoxime are dissolved with heating in 125 ml chloroform. Within 25 min, 8.5 g (0.075 mole), α,α-dichlorodimethyl ether in 20 ml chloroform are dropped while stirring into the boiling solution. The reaction mixture is heated for another 35 min. After standing for several hours, the precipitate is filtered off, washed with absolute ethanol, acetone and ether and dried at 80°C. Yield: 17.0 g, 95% of the theoretical, and the melting point is 225°C (dec.).
[Therapeutic Function]

Antidote
[General Description]

active agent in Toxogonin
[Biochem/physiol Actions]

Antidote for organophosphate nerve agent poisoning, but, as with other oxime agents, not full spectrum. Obidoxime fails primarily to reactivate acetylcholinesterase that has been inhibited with cyclosarin.
[Safety Profile]

Poison by intraperitoneal,intravenous, intramuscular, and subcutaneous routes.Moderately toxic by ingestion. When heated todecomposition it emits toxic fumes of Cl- and NOx. Seealso BROMIDES.
Safety DataBack Directory
[WGK Germany ]

2
[RTECS ]

UU6825000
[Storage Class]

11 - Combustible Solids
[Toxicity]

LD50 in mice, rats (mg/kg): 70, 133 i.v.; 150, 225 i.p.; >2240, >4000 orally; in mice (mg/kg): 172 i.m. (Erdman, Engelhard)
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