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1-(2,6-Dimethylphenoxy)-2-propanamine

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1-(2,6-Dimethylphenoxy)-2-propanamine Basic information
1-(2,6-Dimethylphenoxy)-2-propanamine Chemical Properties
  • Melting point:203-205 °C
  • Boiling point:271.5±28.0 °C(Predicted)
  • Density 0.979±0.06 g/cm3(Predicted)
  • storage temp. 2-8°C
  • solubility ethanol: 50 mg/mL
  • form powder
  • pkapKa 9.14± 0.01(H2O,t =25±0.2,I=0.01(NaCl))(Approximate)
  • color white
  • CAS DataBase Reference31828-71-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceMexiletine(31828-71-4)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 20/21/22
  • Safety Statements 36
  • RIDADR 3249
  • WGK Germany 3
  • RTECS KR9300000
  • HazardClass 6.1(b)
  • PackingGroup III
1-(2,6-Dimethylphenoxy)-2-propanamine Usage And Synthesis
  • OriginatorMexitil,Boehringer Ingelheim,US,1976
  • UsesCardiac depressant (anti-arrhythmic).
  • UsesMexiletine is used for ventricular extrasystole and ventricular tachycardia, and ventricular fibrillation (including during the severe period of myocardial infarction).
  • DefinitionChEBI: An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.
  • Manufacturing ProcessThe sodium salt of dimethyl phenol was reacted with chloroacetone and this product with hydroxylamine to give the starting material.
    245 g of this 1-(2',6'-dimethyl-phenoxy)-propanone-(2)-oxime were dissolved in 1,300 cc of methanol, and the solution was hydrogenated at 5 atmospheres gauge and 60°C in the presence of Raney nickel. After the calculated amount of hydrogen had been absorbed, the catalyst was filtered off, the methanol was distilled out of the filtrate,and the residue, raw 1-(2',6'-dimethylphenoxy)-2-amino-propane, was dissolved in ethanol. The resulting solution was acidified with ethereal hydrochloric acid, the acidic solution was allowed to cool, and the precipitate formed thereby was collected by vacuum filtration. The filter cake was dissolved in ethanol and recystallized therefrom by addition of ether. 140.5 g (51.5% of theory) of a substance having a melting point of 203°C to 205°C were obtained, which was identified to be 1-(2',6'- dimethyl-phenoxy)-2-anino-propane hydrochloride.
  • brand nameMexitil (Boehringer Ingelheim).
  • Therapeutic FunctionAntiarrhythmic
  • Clinical UseMexiletine (Mexitil) is an antiarrhythmic agent with pharmacological and antiarrhythmic properties similar to those of lidocaine and tocainide. Like tocainide,mexiletine is available for oral administration.
    Mexiletine is useful as an antiarrhythmic agent in the management of patients with either acute or chronic ventricular arrhythmias.While it is not at present an indication for use, there is interest in using mexiletine to treat the congenital long QT syndrome when an abnormality in the SCN5A gene (LQTS 3) has been found.
  • Side effectsA very narrow therapeutic window limits mexiletine use. The first signs of toxicity manifest as fine tremor of the hands, followed by dizziness and blurred vision. Hypotension, sinus bradycardia, and widening of the QRS complex have been noted as the most common unwanted cardiovascular effects of IV mexiletine. The side effects of oral maintenance therapy include reversible upper gastrointestinal distress, tremor, lightheadedness, and coordination difficulties. These effects generally are not serious and can be reduced by downward dose adjustment or administering the drug with meals. Cardiovascular adverse effects, which are less common, include palpitations, chest pain, and angina or anginalike pain.
  • Chemical SynthesisMexiletine is 1-methyl-2-(2,2-dimethylphenoxy)ethylamine (18.1.11). Mexiletine is synthesized by reacting the sodium salt of 2,6-dimethylphenol with chloroacetone, forming 1-(2,6-dimethylphenoxy)-2-propanone (18.1.9). Reacting this with hydroxylamine gives the corresponding oxime (18.1.10). Reduction of the oximine group using hydrogen over Raney nickel gives mexiletine (18.1.11).

  • Drug interactionsAn upward adjustment in dose may be required when mexiletine is administered with phenytoin or rifampin, since these drugs stimulate the hepatic metabolism of mexiletine, reducing its plasma concentration.
  • PrecautionsMexiletine is contraindicated in the presence of cardiogenic shock or preexisting second- or third-degree heart block in the absence of a cardiac pacemaker. Caution must be exercised in administration of the drug to patients with sinus node dysfunction or disturbances of intraventricular conduction.
1-(2,6-Dimethylphenoxy)-2-propanamine Preparation Products And Raw materials
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