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Quinidine sulfate dihydrate

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CAS:6591-63-5
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CAS:6591-63-5
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Quinidine sulfate dihydrate manufacturers

Quinidine sulfate dihydrate Basic information
Product Name:Quinidine sulfate dihydrate
Synonyms:Quinidin;Quinidine dihydrate sulfate salt;6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol hemisulfate hydrate;Cinchonan-9-ol, 6'-methoxy-, (9S)-, sulfate (2:1) (salt), monohydrate;Quinidine sulfate (2:1) (salt) monohydrate;Quinidine sulfate hydrate;Quinidine sulfate monohydrate;Unii-J13S2394he
CAS:6591-63-5
MF:C20H26N2O6S
MW:422.5
EINECS:678-472-8
Product Categories:Monovalent Ion Channels;Other Sodium Channel Modulators;Sodium Channel Modulators;Alkaloids;Biochemistry;for Resolution of Acids;Optical Resolution;Quinoline Alkaloids;Synthetic Organic Chemistry;chiral
Mol File:6591-63-5.mol
Quinidine sulfate dihydrate Structure
Quinidine sulfate dihydrate Chemical Properties
Melting point 212-214 °C (dec.)(lit.)
alpha [α]D20 +260~+270° (c=5, dil. HCl.10min)
refractive index 275 ° (C=2, 0.1mol/L HCl)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
solubility Slightly soluble in water, soluble in boiling water and in ethanol (96 per cent), practically insoluble in acetone.
color White to Off-White
Water Solubility Soluble in chloroform, water (11 mg/ml at 20°C), alcohol, and ethanol (50 mg/ml).
Sensitive Light Sensitive
Merck 14,8060
InChIKeyAKYHKWQPZHDOBW-ZAXYGKDDNA-N
SMILES[C@@H]([C@@]1([H])C[C@@H]2CC[N@]1C[C@@H]2C=C)(C1=CC=NC2=CC=C(OC)C=C12)O.S(O)(O)(=O)=O |&1:0,1,4,7,9,r|
CAS DataBase Reference6591-63-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22-20/21/22
Safety Statements 13-36
RIDADR UN 2811 6.1/PG III
WGK Germany 3
RTECS VA5605000
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 2939200050
MSDS Information
ProviderLanguage
SigmaAldrich English
Quinidine sulfate dihydrate Usage And Synthesis
DescriptionQuinidine sulfate dihydrate is a diastereomer of quinine and a Na+ channel blocker. Also a class I antiarrhythmic drug. Quinidine sulfate dihydrate is a white, odorless crystalline substance that has a bitter flavor. It has limited solubility in water and alcohol but dissolves easily in chloroform and ether. This compound is effective against bacteria resistant to erythromycin, including staphylococci and streptococci, and works by inhibiting cellular ATPases.
Chemical PropertiesQuinidine sulfate dihydrate is white to light yellow crystal powde
Usesantiarrhythmic, antimalarial
UsesQuinidine sulfate dihydrate (cas# 6591-63-5) is the hydrated, sulfate salt of Quinidine (Q685000), a dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial.
ApplicationQuinidine sulfate salt dihydrate has been used as an antiarrhythmic drug to study its effects on phosphorylation and mutations in the cardiac sodium channel Nav1.5.
Brand nameCin-Quin (Solvay Pharmaceuticals); Quinidex (Wyeth); Quinora (Schering).
General DescriptionQuinidine sulfate dihydrate is the sulfateof an alkaloid obtained from various species ofCinchona and their hybrids. It is a dextrorotatory diastereoisomerof quinine. The salt crystallizes from wateras the dihydrate, in the form of fine, needlelike, white crystals.Quinidine sulfate contains a hydroxymethyl groupthat serves as a link between a quinoline ring and a quinuclidinemoiety. The structure contains two basic nitrogens,of which the quinuclidine nitrogen is the stronger base(pKa 10). Quinidine sulfate dihydrate is bitter and light sensitive.Quinidine sulfate dihydrates are nearly neutral or slightly alkaline. Itis soluble to the extent of 1% in water and more highly solublein alcohol or chloroform.
HazardQuinidine sulfate dihydrate is acutely toxic and photosensitising. The photosensitisation reaction to quinidine sulphate was reproducible in the photopic test and after oral administration plus ultraviolet A (UVA) irradiation. Eczematous dermatitis was induced after intradermal injection of quinidine sulfate dihydrate irradiated by UVA in vitro only in the presence of the patient's serum. Three workers exposed to quinidine sulphate developed allergic reactions within a short period of time (2-3 months).
Biochem/physiol ActionsClass IA antiarrhythmic; potassium channel blocker.
Clinical UseQuinidine sulfate is the prototype of antiarrhythmicdrugs and a class IA antiarrhythmic agent according to theVaughan Williams classification. It reduces Na+ current bybinding the open ion channels (i.e., state A). The decreasedNa+entry into the myocardial cell depresses phase 4 diastolicdepolarization and shifts the intracellular threshold potentialtoward zero. These combined actions diminish thespontaneous frequency of pacemaker tissues, depress theautomaticity of ectopic foci, and, to a lesser extent, reduceimpulse formation in the SA node. This last action results inbradycardia. During the spike action potential, quinidinesulfate decreases transmembrane permeability to passiveinflux of Na+, thus slowing the process of phase 0 depolarization,which decreases conduction velocity. This is shownas a prolongation of the QRS complex of electrocardiograms.Quinidine sulfate also prolongs action potential duration,which results in a proportionate increase in the QTinterval. It is used to treat supraventricular and ventricularectopic arrhythmias, such as atrial and ventricular prematurebeats, atrial and ventricular tachycardia, atrial flutter, andatrial fibrillation.
Quinidine sulfate dihydrate Preparation Products And Raw materials
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