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Amiodarone hydrochloride

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Amiodarone hydrochloride Basic information
Amiodarone hydrochloride Chemical Properties
  • Melting point:154-158°C
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility Soluble in chloroform, methanol.
  • pkapKa (25°C) 6.56 ±0.06
  • form neat
  • λmax242nm(MeOH)(lit.)
  • Merck 14,482
  • CAS DataBase Reference19774-82-4(CAS DataBase Reference)
Safety Information
MSDS
Amiodarone hydrochloride Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • OriginatorCordarone,Labaz,France,1971
  • UsesAmiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death.
  • UsesAntiarrhythmic;Na+ channel blocker
  • UsesA non-selective ion channel blocker. Antiarrhythmic (class III)
  • Manufacturing Process135 grams of 2-n-butyl-3-(3,5-diiodo-4-hydroxybenzoyl)benzofuran dissolved in 600 cc of ethyl carbonate were treated with 5.7 grams of sodium in the form of sodium methoxide in methanol. Then, β-diethylaminoethyl chloride which had been obtained from 51.6 grams of the hydrochloride in ethyl carbonate was introduced into a suspension of the sodium salt. The mixture was heated to a temperature of approximately 90°C which was maintained for approximately 2 hours. The mixture was cooled and allowed to stand overnight during which time the sodium chloride settled down.
    The toluene solution containing diethylaminoethyl ether was extracted with increasingly diluted aqueous hydrochloric acid solutions while stirring. Extraction was continued until the alkalized solution produced no further precipitate. The combined aqueous solutions were washed with ether and then made strongly alkaline with aqueous sodium hydroxide. Extraction with ether was carried out three times. The organic layers were washed with water and then dried over anhydrous potassium carbonate. In order to produce the hydrochloride, the carbonate was filtered off and then the hydrochloride was precipitated from the ether solution with an ethereal hydrochloric acid solution. After the solution had been allowed to stand for a few hours, decantation was carried out and the syrupy hydrochloride residue was taken up in 500 cc of boiling acetone. The salt crystallized out by cooling. The substance was allowed to stand overnight at 0°C, and centrifuged, washed with ethyl acetate and then with ether and dried. 130 grams of 2-n-butyl-3- (3,5-diiodo-4-β-N-diethylaminoethoxybenzoyl)benzofuran hydrochloride in the form of a crystalline powder which melts at 156°C were obtained.
  • Therapeutic FunctionCoronary vasodilator
  • General Description
    Amiodarone, marketed as Pacerone?, Cordarone?, Aratac, and Atlansil, is an antiarrhythmic agent monitored by clinical labs using HPLC or LCMS to ensure patients remain within the drugs therapeutic range.
  • Veterinary Drugs and TreatmentsBecause of its potential toxicity and lack of experience with use in canine and equine patients, amiodarone is usually used when other less toxic or commonly used drugs are ineffective. It may be useful in dogs and horses to convert atrial fib into sinus rhythm and in dogs for arrhythmias associated with left ventricular dysfunction. In horses, one horse with Ventricular tachycardia was converted into sinus rhythm using amiodarone.
    As the risk of sudden death is high in Doberman pinschers exhibiting rapid, wide-complex ventricular tachycardia or syncope with recurrent VPC’s, amiodarone may be useful when other drug therapies are ineffective.
Amiodarone hydrochloride Preparation Products And Raw materials
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