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51-15-0 molecular structure
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2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride

ChemBase ID: 614
Molecular Formular: C7H9ClN2O
Molecular Mass: 172.61216
Monoisotopic Mass: 172.0403406
SMILES and InChIs

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

Cite this record

CBID:614 http://www.chembase.cn/molecule-614.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.7806177  H Acceptors
H Donor LogD (pH = 5.5) -3.4252226 
LogD (pH = 7.4) -4.3101006  Log P -3.257119 
Molar Refractivity 40.3265 cm3 Polarizability 14.695804 Å3
Polar Surface Area 36.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.13  LOG S -1.0 
Solubility (Water) 1.71e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
226-230°C (dec.) expand Show data source
230 °C(lit.) expand Show data source
ca 223°C dec. expand Show data source
Hydrophobicity(logP)
0.0 expand Show data source
1.564 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
RTECS
UU4200000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
20/21/22 expand Show data source
36/37/38 expand Show data source
Safety Statements
26-37 expand Show data source
36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
95% expand Show data source
97% expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C7H9N2O · Cl expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00733 external link
Item Information
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 external link
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 external link
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 external link
This compound binds to inactivated acetylcholinesterases and is used to combat poisoning from organophosphates and nerve agents

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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