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P9053

Sigma-Aldrich

Pyridine-2-aldoxime methochloride

Synonym(s):

2-PAM chloride, Pralidoxime chloride

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About This Item

Empirical Formula (Hill Notation):
C7H9N2O · Cl
CAS Number:
51-15-0
Molecular Weight:
172.61
EC Number:
200-080-9
MDL number:
MFCD00011981
UNSPSC Code:
12352202
PubChem Substance ID:
24899005
NACRES:
NA.77

biological source

synthetic (organic)

form

solid

mp

230 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

[Cl-].C[n+]1ccccc1\C=N\O

InChI

1S/C7H8N2O.ClH/c1-9-5-3-2-4-7(9)6-8-10;/h2-6H,1H3;1H

InChI key

HIGSLXSBYYMVKI-UHFFFAOYSA-N

Gene Information

human ... ACHE(43)

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Biochem/physiol Actions

The prototypical reactivator of acetylcholinesterase that has been inactivated by organophosphorus insecticides or nerve agents. It is now known that no reactivator is effective against a broad spectrum of organophosphorus agents.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Chennamaneni Srinivas Rao et al.
Bioorganic & medicinal chemistry letters, 16(8), 2134-2138 (2006-02-17)
In continuation of our investigations of unsymmetrical bisquaternary monooximes, we synthesized four new series of compounds bridged by hexyl, heptyl, octyl and nonyl groups. All eight monooximes viz., dibromides of 1-(4-hydroxyiminomethylpyridinium)6-(3/4-carbamoylpyridinium)hexane, 1-(4-hydroxyiminomethylpyridinium)-7-(3/4-carbamoylpyridinium)heptane, 1-(4-hydroxyiminomethylpyridinium)-8-(3/4-carbamoylpyridinium)octane, 1-(4-hydroxyiminomethylpyridinium)-9-(3/4-carbamoylpyridinium)nonane as well as the corresponding bis-oximes
Jyotiranjan Acharya et al.
European journal of medicinal chemistry, 46(9), 3926-3933 (2011-06-28)
A series of carbamoyl bis-pyridinium monooximes linked with xylene linker were synthesized and their in-vitro reactivation potential was evaluated against acetylcholinesterase (AChE) inhibited by organophosphorus inhibitors (OP) such as sarin, DFP and VX and the data were compared with reactivation
Kamil Musilek et al.
Bioorganic & medicinal chemistry letters, 16(21), 5673-5676 (2006-08-29)
Three asymmetrical AChE reactivators with cyano-moiety and propane linker were synthesized using modification of currently known synthetic pathways. Their potency to reactivate AChE inhibited by nerve agent tabun and insecticide paraoxon was tested in vitro and compared to pralidoxime, HI-6
Kamil Musilek et al.
Bioorganic & medicinal chemistry, 15(21), 6733-6741 (2007-09-04)
Acetylcholinesterase reactivators are crucial antidotes for the treatment of organophosphate intoxication. Fifteen new monooxime reactivators of acetylcholinesterase with a (E)-but-2-ene linker were developed in an effort to extend the properties of K-oxime (E)-1-(4-carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibromide (K203). The known reactivators (pralidoxime, HI-6
Kamil Musilek et al.
Journal of medicinal chemistry, 50(22), 5514-5518 (2007-10-11)
Acetylcholinesterase reactivators are crucial antidotes for the treatment of organophosphate intoxication. Among the organophosphates, with the exception of soman, tabun (GA) intoxications are the least responsive to treatment with commercially available therapeutics. A rational design was used to increase reactivation
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