An AChE reactivator
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Small Molecule Modulators
Small Molecule Activators

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Neuroscience

Pralidoxime (chloride)

Item No. 23666

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(hydroxyimino)methyl]-1-methyl-pyridinium, monochloride
CAS Number
51-15-0
Synonyms
  • 2-PAM
Molecular Formula
C7H9N2O • Cl
Formula Weight
172.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
247, 300 nm
SMILES
C[N+]1=CC=CC=C1/C=N/O.[Cl-]
InChi Code
InChI=1S/C7H8N2O.ClH/c1-9-5-3-2-4-7(9)6-8-10;/h2-6H,1H3;1H
InChi Key
HIGSLXSBYYMVKI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $86

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    10 g

    $153

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    Product Description

    Pralidoxime reactivates acetylcholinesterase (AChE) that has been deactivated by binding of organophosphates to its esteratic site.1 Pralidoxime binds to the anionic site of AChE and displaces the phosphate from the esteratic site through formation of phosphate-pralidoxime conjugates. It reactivates paraoxon- and diisopropyl fluorophosphate-inactivated human red blood cell (RBC) AChE with IC50 shifts of 0.3 and 0.8 nM per μM of pralidoxime, respectively.2,3 At a concentration of 10 μM, it reactivates human RBC AChE that has been inactivated by chlorpyrifos (Item No. 21412), diazinon (Item No. 23769), and malathion (Item No. 22998) by 17, 61, and 36%, respectively.4 Pralidoxime binds to sarin-bound hAChE (Kd = 25.72 μM) and inhibits sarin-induced AChE deactivation (IC50 = 1.21 mM) in hemoglobin-free erythrocyte ghosts.5 Formulations containing pralidoxime have been used to treat organophosphate poisoning.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jokanović, M., and Stojiljković, M.P. Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate poisoning. Eur. J. Pharmacol. 553(1-3), 10-17 (2006).

    2. Petroianu, G.A., Arafat, K., Kuca, K., et al. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: In vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon. J. Appl. Toxicol. 26(1), 64-71 (2006).

    3. Lorke, D.E., Hasan, M.Y., Arafat, K., et al. In vitro oxime protection of human red blood cell acetylcholinesterase inhibited by diisopropyl-fluorophosphate. J. Appl. Toxicol. 28(4), 422-429 (2008).

    4. Costa, M.D., Freitas, M.L., Soares, F.A., et al. Potential of two new oximes in reactivate human acetylcholinesterase and butyrylcholinesterase inhibited by organophosphate compounds: An in vitro study. Toxicol. In Vitro 25(8), 2120-2123 (2011).

    5. Karade, H.N., Raviraju, G., Acharya, B.N., et al. Synthesis and in vitro reactivation study of isonicotinamide derivatives of 2-(hydroxyimino)-N-(pyridin-3-yl)acetamide as reactivators of Sarin and VX inhibited human acetylcholinesterase (hAChE). Bioorg. Med. Chem. 24(18), 4171-4176 (2016).