31828-71-4 Usage
Description
1-(2,6-Dimethylphenoxy)-2-propanamine, also known as Mexilitine, is an aromatic ether that is the 2,6-dimethylphenyl ether of 2-aminopropan-1-ol. It is a cardiac depressant with anti-arrhythmic properties and is used in the treatment of various cardiac conditions.
Uses
Used in Cardiology:
1-(2,6-Dimethylphenoxy)-2-propanamine is used as an anti-arrhythmic agent for the treatment of ventricular extrasystole, ventricular tachycardia, and ventricular fibrillation, including during the severe period of myocardial infarction. Its cardiac depressant properties help regulate abnormal heart rhythms and maintain a stable heart rate.
Used in Neurology:
1-(2,6-Dimethylphenoxy)-2-propanamine is used as an analgesic agent in the treatment of amyotrophic lateral sclerosis (ALS). It is administered alongside a bile acid and a phenylbutyrate compound, along with an additional therapeutic agent, to alleviate pain and improve the quality of life for ALS patients.
Brand Name:
Mexitil (Boehringer Ingelheim)
Originator
Mexitil,Boehringer Ingelheim,US,1976
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.
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.
Side effects
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.
Synthesis
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).
Drug interactions
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.
Precautions
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.
Check Digit Verification of cas no
The CAS Registry Mumber 31828-71-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,8,2 and 8 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 31828-71:
(7*3)+(6*1)+(5*8)+(4*2)+(3*8)+(2*7)+(1*1)=114
114 % 10 = 4
So 31828-71-4 is a valid CAS Registry Number.
InChI:InChI:1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3
31828-71-4Relevant articles and documents
Deracemization of mexiletine biocatalyzed by ω-transaminases
Koszelewski, Dominik,Pressnitz, Desiree,Clay, Dorina,Kroutil, Wolfgang
, p. 4810 - 4812 (2009)
(S)- as well as (R)-mexiletine [1-(2,6-dimethylphenoxy)-2-propanamine], a chiral orally effective antiarrhythmic agent, was prepared by deracemizatlon starting from the commercially available racemic amine using ω-transaminases In up to >99% ee and conver
Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol
Manna, Avrajit,Chatterjee, Sandip,Chakraborty, Ipsita,Bhaumik, Tanurima
, (2020/01/08)
Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.
Method for synthesizing mexiletine chloride
-
, (2019/03/15)
The invention discloses a method for synthesizing mexiletine chloride, wherein a reaction system takes 2,6-xylenol as a starting material to synthesize a corresponding target product. In the reaction,a transition metal gold complex and a ruthenium complex are used for catalysis, compared with the previous method for synthesizing mexiletine chloride, no alkali is added during a reaction process, no by-products are produced, the reaction atom economy is high, and the reaction conditions are mild. Therefore, the method has broad development prospects.
