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ChemicalBook--->CAS DataBase List--->31828-71-4

31828-71-4

31828-71-4 Structure

31828-71-4 Structure
IdentificationMore
[Name]

1-(2,6-Dimethylphenoxy)-2-propanamine
[CAS]

31828-71-4
[Synonyms]

1-(2,6-dimethylphenoxy)-2-propanamin
1-methyl-2-(2,6-xylyloxy)-ethylamin
1-Methyl-2-(2,6-xylyloxy)ethylamine
2-Propanamine, 1-(2,6-dimethylphenoxy)-
Ethylamine, 1-methyl-2-(2,6-xylyloxy)-
Mexilitine
1-(2,6-xylyloxy)-2-aminopropane hydrochloride
MEXILETIN
(+-)-2-Amino-1-(2',6'-dimethylphenoxy)propane
(RS)-Mexiletine
2-Amino-1-(2,6-dimethylphenoxy)propane
2-Propanamine, 1-(2,6-dimethylphenoxy)-(9CI)
dl-Mexiletine
Ethylamine, 1-methyl-2-(2,6-xylyloxy)-(8CI)
Mexiletine (base and/or unspecified salts)
1-(2,6-Dimethylphenoxy)-2-propanamine
Mexiletine
(2R)-1-(2,6-Dimethylphenoxy)propane-2-amine
(R)-1-Methyl-2-(2,6-xylyloxy)ethylamine
Mexilitine R
[EINECS(EC#)]

250-825-7
[Molecular Formula]

C11H17NO
[MDL Number]

MFCD00216024
[Molecular Weight]

179.259
[MOL File]

31828-71-4.mol
Chemical PropertiesBack Directory
[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
[pka]

pKa 9.14± 0.01(H2O,t =25±0.2,I=0.01(NaCl))(Approximate)
[color ]

white
[BCS Class]

1
[CAS DataBase Reference]

31828-71-4(CAS DataBase Reference)
[NIST Chemistry Reference]

Mexiletine(31828-71-4)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S36:Wear suitable protective clothing .
[RIDADR ]

3249
[WGK Germany ]

3
[RTECS ]

KR9300000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
Raw materials And Preparation ProductsBack Directory
[Raw materials]

2,6-Dimethylphenol-->HYDROXYLAMINE-->Benzene, 1,3-dimethyl-2-(2-propyn-1-yloxy)--->Carbamic acid, N-[2-(2,6-dimethylphenoxy)-1-methylethyl]-, 1,1-dimethylethyl ester-->Mexiletine hydrochloride-->1-(2,6-DIMETHYLPHENOXY)-2-PROPANOL-->1-(2,6-DIMETHYLPHENOXY)ACETONE
[Preparation Products]

N-[2-(2,6-DiMethylphenoxy)-1-Methylethyl]acetaMide
Hazard InformationBack Directory
[Description]

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
[Uses]

Cardiac depressant (anti-arrhythmic).
[Uses]

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.
[Uses]

Mexiletine is used for ventricular extrasystole and ventricular tachycardia, and ventricular fibrillation (including during the severe period of myocardial infarction).
[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.
[Brand name]

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.
[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).

Synthesis_31828-71-4

[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.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

31828-71-4(sigmaaldrich)
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