Mexiletin

Bezeichnung:Mexiletin

CAS-Nr31828-71-4

Englisch Name:1-(2,6-Dimethylphenoxy)-2-propanamine

CBNumberCB9497353

SummenformelC11H17NO

Molgewicht179.26

MOL-Datei31828-71-4.mol

Synonyma

Mexiletin

Mexiletin physikalisch-chemischer Eigenschaften

Schmelzpunkt	203-205 °C
Siedepunkt	271.5±28.0 °C(Predicted)
Dichte	0.979±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	ethanol: 50 mg/mL
pka	pKa 9.14± 0.01(H2O,t =25±0.2,I=0.01(NaCl))(Approximate)
Aggregatzustand	powder
Farbe	white
BCS Class	1
CAS Datenbank	31828-71-4(CAS DataBase Reference)
NIST chemische Informationen	Mexiletine(31828-71-4)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22
S-Sätze:	36
RIDADR	3249
WGK Germany	3
RTECS-Nr.	KR9300000
HazardClass	6.1(b)
PackingGroup	III

Gefahreninformationscode (GHS)

1-(2,6-Dimethylphenoxy)-2-propanamine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Mexiletine is effective both parenterally and orally , . Because the substance has a large distribution volume, a high initial dose is necessary.
Originator
Mexitil,Boehringer Ingelheim,US,1976
Verwenden
Mexiletine is a useful analgesia.It is used in treatment of amyotrophic lateral sclerosis comprising administering a bile acid and a phenylbutyrate compound and an additional therapeutic agent.
Verwenden
Mexiletine is used for ventricular extrasystole and ventricular tachycardia, and ventricular fibrillation (including during the severe period of myocardial infarction).
Verwenden
Cardiac depressant (anti-arrhythmic).
Definition
ChEBI: An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.
Manufacturing Process
The 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.
Trademarks
Mexitil (Boehringer Ingelheim).
Therapeutic Function
Antiarrhythmic
Clinical Use
Mexiletine (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.
Nebenwirkungen
A 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.
Synthese
Mexiletine 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).
Arzneimittelwechselwirkung
An 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.
Vorsichtsmaßnahmen
Mexiletine 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 Upstream-Materialien And Downstream Produkte

Mexiletin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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