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

• ChemBase编号: 614
• 分子式: C7H9ClN2O
• 平均质量: 172.61216
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride; 2-[(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride
• IUPAC传统名: pralidoxime chloride; pralidoximum chloride; 2-[(hydroxyimino)methyl]-1-methylpyridin-1-ium chloride
• 商标名: Protopam; ComboPen
• 别名: 2-PAM 氯化物; 氯解磷定; 2-吡啶醛肟甲氯; 2-吡啶醛肟 甲氯; 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

登记号

• CAS号: 6735-59-7; 51-15-0
• EC号: 200-080-9
• MDL号: MFCD00011981
• Beilstein号: 4163981
• 默克索引号: 147703
• PubChem SID: 160964077; 24899005
• PubChem CID: 57428996

理论计算性质

JChem

• Acid pKa: 5.7806177
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -3.4252226
• LogD (pH = 7.4): -4.3101006
• Log P: -3.257119
• 摩尔折射率: 40.3265 cm^3
• 极化性: 14.695804 Å^3
• 极化表面积: 36.47 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.13
• LOG S: -1.0
• 溶解度: 1.71e+01 g/l

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 226-230°C (dec.); 230 °C(lit.); ca 223°C dec.
• 疏水性(logP): 0.0; 1.564

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• RTECS编号: UU4200000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 20/21/22; 36/37/38
• 安全公开号: 26-37; 36
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332; H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

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

详细说明

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

参考文献

• 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)