1-Methyl-2-(2,6-xylyloxy)ethylammoniumchlorid

Bezeichnung:1-Methyl-2-(2,6-xylyloxy)ethylammoniumchlorid

CAS-Nr5370-01-4

Englisch Name:Mexiletine hydrochloride

CBNumberCB6114224

SummenformelC11H18ClNO

Molgewicht215.72

MOL-Datei5370-01-4.mol

Synonyma

1-Methyl-2-(2,6-xylyloxy)ethylammoniumchlorid

1-Methyl-2-(2,6-xylyloxy)ethylammoniumchlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	200-203°C
Dichte	1.12 g/cm3
storage temp.	2-8°C
Löslichkeit	ethanol: 50 mg/mL
Aggregatzustand	powder
pka	9.0(at 25℃)
Farbe	white
maximale Wellenlänge (λmax)	272nm(MeOH)(lit.)
Merck	14,6169
Stabilität	Hygroscopic
CAS Datenbank	5370-01-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38-22
S-Sätze:	36-26
WGK Germany	3
RTECS-Nr.	KR9300000
HS Code	2922190900
Toxizität	LD50 in male, female rats, mice, rabbits (mg/kg): 350, 400, 310, 400, 180, 160 orally; in male, female rats, mice (mg/kg): 27, 30, 43, 50 i.v. (Kast)

Gefahreninformationscode (GHS)

Mexiletine hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Mexiletine is a voltage-gated sodium channel blocker and class Ib antiarrhythmic agent that preferentially binds to open/inactive channels. It inhibits aconitine-induced dysrhythmias in mice with ED₅₀ values of 57 and 107 mg/kg for intraperitoneal and oral administration, respectively. Mexiletine decreases or inhibits conduction across the Purkinje fiber-muscle junction, shortens action potential duration, and decreases the refractory period when used at concentrations less than 5 μg/ml in isolated canine Purkinje fiber and ventricular muscle preparations.
Chemische Eigenschaften
White to Off-White Solid
Originator
Mexitil,Boehringer Ingelheim,US,1976
Verwenden
antipsychotic
Verwenden
Antiarrhythmic (class IB)
Verwenden
Mexiletine hydrochloride has been used as a sodium channel blocker:
- expressed in chinese hamster ovary cells
- in human embryonic kidney (HEK) cells for whole cell patch-clamp studies
- electrophysiology studies in HEK cells expressing Nav1.7 protein
Definition
ChEBI: A hydrochloride composed of equimolar amounts of mexiletine and hydrogen chloride.
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
Allgemeine Beschreibung
Mexiletine hydrochloride,1-methyl-2-(2,6-xylyloxy)ethylamine hydrochloride (Mexitil)(pKa 8.4), is a class IB antiarrhythmic agent that is effectivewhen given either intravenously or orally. It resembles lidocainein possessing a xylyl moiety but otherwise is differentchemically. Mexiletine hydrochloride is an ether and is notsubject to the hydrolysis common to the amides lidocaineand tocainide. Its mean half-life on oral administration isapproximately 10 hours.
Although not subject to hydrolysis, mexiletine hydrochlorideis metabolized by oxidative and reductiveprocesses in the liver. Its metabolites, p-hydroxymexiletineand hydroxymethylmexiletine, are not pharmacologicallyactive as antiarrhythmic agents.
Biologische Aktivität
Use-dependent sodium channel blocker (IC 50 values are 75.3 and 23.6 μ M for tonic and use-dependent block respectively). Class Ib antiarrhythmic, neuroprotective and antimyotonic agent.
Biochem/physiol Actions
Mexiletine is a potent sodium channel blocker. It is a cardiac antiarrhythmic and is used as an adjuvant in headache and neuropathic pain Mexiletine is used for treating myotonia in sodium channelopathies and reduces the cardiac action potential depolarization but shows no impact on atrial refractoriness. Its inhibitory effect on sodium channels is effective in treating potassium aggravated myotonia.
Clinical Use
Mexiletine hydrochloride, like class I antiarrhythmicagents, blocks the fast Na channel in cardiac cells. It isespecially effective on the Purkinje fibers in the heart. Thedrug increases the threshold of excitability of myocardialcells by reducing the rate of rise and amplitude of the actionpotential and decreases automaticity.
Mexiletine hydrochloride is used for long-term oral prophylaxisof ventricular tachycardia. The drug is given in200- to 400-mg doses every 8 hours.
Lager
Desiccate at +4°C

Mexiletine hydrochloride Upstream-Materialien And Downstream Produkte

1-Methyl-2-(2,6-xylyloxy)ethylammoniumchlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

5370-01-4, Mexiletine hydrochloride Verwandte Suche:

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