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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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Jarosław Kalisiak et al.
Journal of medicinal chemistry, 55(1), 465-474 (2011-12-31)
A new class of amidine-oxime reactivators of organophosphate (OP)-inhibited cholinesterases (ChE) was synthesized and tested in vitro and in vivo. Compared with 2-PAM, the most promising cyclic amidine-oxime (i.e., 12e) showed comparable or greater reactivation of OP-inactivated AChE and OP-inactivated
Kamil Musilek et al.
Bioorganic & medicinal chemistry letters, 17(11), 3172-3176 (2007-03-27)
Six novel AChE reactivators with a (Z)-but-2-ene linker were synthesized using the known synthetic pathways. Their ability to reactivate AChE, which had been previously inhibited by nerve agent tabun or pesticide paraoxon, was tested in vitro and compared to pralidoxime
Jyotiranjan Acharya et al.
European journal of medicinal chemistry, 44(3), 1335-1340 (2008-04-09)
A series of novel bis-pyridinium oximes connected by bis-methoxymethyl benzene, 1,4-bis-methoxymethyl (cis)-but-2-ene and 1,4-bis-methoxymethyl but-2-yne linkers were synthesized and their in vitro reactivation efficacy was evaluated against diisopropyl phosphorofluoridate (DFP) inhibited acetylcholinesterase (AChE) and compared with the established antidote 2-PAM
F Worek et al.
Archives of toxicology, 72(4), 237-243 (1998-05-20)
The treatment of poisoning by highly toxic organophosphorus compounds (nerve agents) is unsatisfactory. Until now, the efficacy of new potential antidotes has primarily been evaluated in animals. However, the extrapolation of these results to humans is hampered by species differences.
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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