pralidoxime

Also known as 2-PAM

Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM, usually as the chloride or iodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosphate poisoning in conjunction with atropine and either diazepam or midazolam. It is a white solid.

Chemical data

Formula: C7H9N2O+
Molecular weight: 137.16 g/mol
IUPAC name: (NZ)-N-[(1-methylpyridin-1-ium-2-yl)methylidene]hydroxylamine
SMILES: C[N+]1=CC=CC=C1/C=N\O
InChIKey: JBKPUQTUERUYQE-UHFFFAOYSA-O
XLogP: 1
Polar surface area: 36.5 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 1

via PubChem

Research

1,679 papers

Pralidoxime.Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology · 2016
Pralidoxime safety and toxicity in children.Prehospital emergency care · 2007
Pralidoxime and pesticide poisoning: A question of severity?Biomedical journal · 2016
Pralidoxime improves the hemodynamics and survival of rats with peritonitis-induced sepsis.PloS one · 2021
Pralidoxime-like reactivator with increased lipophilicity - Molecular modeling and in vitro study.Chemico-biological interactions · 2023

via PubMed

Wikidata facts

Mass: 137.071488

Show 5 more facts

isomeric SMILES: C[N+]1=CC=CC=C1/C=N/O
canonical SMILES: CN1C=CC=CC1=C[NH+]=O
World Health Organisation international non-proprietary name: pralidoxime
Commons category: Pralidoxime
chemical formula: C₇H₉N₂O⁺

Sources (4)

via Wikidata · CC0

~4 min read

Article

8 sections

Contents

Chemical synthesis
Mechanism of action
Dosage
Interactions
Contraindications
See also
References
External links

==Chemical synthesis== Pralidoxime, 2-pyridinaldoxime methylchloride, is prepared by treating pyridine-2-carboxaldehyde with hydroxylamine. The resulting pyridine-2-aldoxime is alkylated with methyl iodide giving pralidoxime as the iodide salt. 500px|center