2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride

• ChemBase ID: 614
• Molecular Formular: C7H9ClN2O
• Molecular Mass: 172.61216
• Monoisotopic Mass: 172.0403406
• SMILES: O/N=C/c1cccc[n+]1C.[Cl-]
• Canonical SMILES: O/N=C/c1cccc[n+]1C.[Cl-]
• InChI: InChI=1S/C7H8N2O.ClH/c1-9-5-3-2-4-7(9)6-8-10;/h2-6H,1H3;1H
• InChIKey: HIGSLXSBYYMVKI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride; 2-[(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride
• IUPAC Traditional name: pralidoxime chloride; pralidoximum chloride; 2-[(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride
• Brand Name: Protopam; ComboPen
• Synonyms: Pralidoxime Chloride; Pralidoxime; Pyridine-2-aldoxime methochloride; 2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride; 2-PAM chloride; 2-[(Hydroxyimino)methyl]-1-methyl-pyridinium Chloride; 2-Formyl-1-methyl-pyridinium Chloride Oxime; 1-Methylpyridinium-2-aldoxime Chloride; 2-PAM Cl; 2-PAM; Protopam Chloride; 2-Pyridinealdoxime Methochloride; Pyridine-2-aldoxime Methochloride; Pralidoxime Chloride; Pyridine-2-carboxaldoxime methochloride; 2-PAM 氯化物; 氯解磷定; 2-吡啶醛肟甲氯; 2-吡啶醛肟 甲氯

Database IDs

• CAS Number: 51-15-0; 6735-59-7
• EC Number: 200-080-9
• MDL Number: MFCD00011981
• Beilstein Number: 4163981
• Merck Index: 147703
• PubChem SID: 160964077; 24899005
• PubChem CID: 57428996

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.7806177
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.4252226
• LogD (pH = 7.4): -4.3101006
• Log P: -3.257119
• Molar Refractivity: 40.3265 cm^3
• Polarizability: 14.695804 Å^3
• Polar Surface Area: 36.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.13
• LOG S: -1.0
• Solubility (Water): 1.71e+01 g/l

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 226-230°C (dec.); 230 °C(lit.); ca 223°C dec.
• Hydrophobicity(logP): 0.0; 1.564

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: UU4200000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 20/21/22; 36/37/38
• Safety Statements: 26-37; 36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 99%
• Empirical Formula (Hill Notation): C7H9N2O · Cl

DETAILS

DrugBank - DB00733

• Drug Groups: approved
• Description: Pralidoxime is an antidote to organophosphate pesticides and chemicals. Organophosphates bind to the esteratic site of acetylcholinesterase, which results initially in reversible inactivation of the enzyme. If given within 24 hours,after organophosphate exposure, pralidoxime reactivates the enzyme cholinesterase by cleaving the phosphate-ester bond formed between the organophosphate and acetylcholinesterase.
• Indication: For the treatment of poisoning due to those pesticides and chemicals of the organophosphate class which have anticholinesterase activity and in the control of overdosage by anticholinesterase drugs used in the treatment of myasthenia gravis.
• Pharmacology: Pralidoxime is to reactivate cholinesterase (mainly outside of the central nervous system) which has been inactivated by phosphorylation due to an organophosphate pesticide or related compound. The destruction of accumulated acetylcholine can then proceed, and neuromuscular junctions will again function normally. Pralidoxime also slows the process of "aging" of phosphorylated cholinesterase to a nonreactivatable form, and detoxifies certain organophosphates by direct chemical reaction. The drug has its most critical effect in relieving paralysis of the muscles of respiration. Because pralidoxime is less effective in relieving depression of the respiratory center, atropine is always required concomitantly to block the effect of accumulated acetylcholine at this site. Pralidoxime relieves muscarinic signs and symptoms, salivation, bronchospasm, etc., but this action is relatively unimportant since atropine is adequate for this purpose.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 74-77 minutes
• Protein Binding: No binding to plasma proteins
• Elimination: The drug is rapidly excreted in the urine partly unchanged, and partly as a metabolite produced by the liver.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - P9053

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.1

Sigma Aldrich - 131636

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.1

Toronto Research Chemicals - P701120

This compound binds to inactivated acetylcholinesterases and is used to combat poisoning from organophosphates and nerve agents

REFERENCES

• Lajmanovich, R., et al.: Toxicol. Env. Chem., 90, 1145 (2008)
• Eyer, P., et al.: Brit. J. Clin. Pharmacol., 66, 450 (2008)
• Goncalves, L., et al.: J. Pharm. Sci., 98, 1040 (2008)