53012-41-2

Basic information

• Product Name: 1-(2,6-Dimethylphenoxy)propan-2-one
• Synonyms: 1-(2,6-Dimethylphenoxy)-2-propanone;1-(2,6-Dimethylphenoxy)acetone
• CAS NO: 53012-41-2
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.2277
• EINECS: 258-292-2
• Product Categories: Aromatics;Metabolites & Impurities
• Mol File: 53012-41-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 261.4 °C at 760 mmHg
• Flash Point: 104.9 °C
• Appearance: /
• Density: 1.011 g/cm³
• Vapor Pressure: 0.0115mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1-(2,6-Dimethylphenoxy)propan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-Dimethylphenoxy)propan-2-one(53012-41-2)
• EPA Substance Registry System: 1-(2,6-Dimethylphenoxy)propan-2-one(53012-41-2)

Safety Data

• Hazardous Substances Data: 53012-41-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Mexiletine (M340800) metabolite.

InChI:InChI=1/C11H14O2/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6H,7H2,1-3H3

Upstream product

• 31828-71-4 RS-mexiletine 
• 15261-41-3 1-allyloxy-2,6-dimethylbenzene 
• 94991-72-7 (S)-mexiletine 
• 576-26-1 2.6-dimethylphenol 
• 598-31-2 1-bromoacetone 
• 21078-03-5 1,3-dimethyl-2-(prop-2-yn-1-yloxy)benzene 
• 78-95-5 chloroacetone 
• 5370-01-4 (rac)-mexiletine hydrochloride 
• 16081-16-6 sodium 2,6-dimethylphenolate 

Downstream Products

• 1051392-53-0 (E)-1-(2,6-dimethyl-phenoxy)-propan-2-one oxime 
• 31828-71-4 RS-mexiletine 
• 128942-28-9 1-(2,6-dimethylphenoxy)-N-methylpropan-2-amine 
• 194027-20-8 1-(2,6-dimethylphenoxy)-N-ethylpropan-2-amine 
• 5370-01-4 (rac)-mexiletine hydrochloride 
• 81771-85-9 (+)-Mexiletine hydrochloride 
• 81771-86-0 (2R)-1-(2',6'-dimethylphenoxy)-2-aminopropane hydrochloride 
• 61102-09-8 (RS)-1-(2,6-dimethylphenoxy)propan-2-ol 
• 31828-71-4 (R)-mexiletine 

Relevant articles and documents

Inhibition of hERG potassium channel by the antiarrhythmic agent mexiletine and its metabolite m-hydroxymexiletine

Mexiletine is a sodium channel blocker, primarily used in the treatment of ventricular arrhythmias. Moreover, recent studies have demonstrated its therapeutic value to treat myotonic syndromes and to relieve neuropathic pain. The present study aims at investigating the direct blockade of hERG potassium channel by mexiletine and its metabolite m-hydroxymexiletine (MHM). Our data show that mexiletine inhibits hERG in a time- and voltage-dependent manner, with an IC50 of 3.7 ± 0.7 lmol/L. Analysis of the initial onset of current inhibition during a depolarizing test pulse indicates mexiletine binds preferentially to the open state of the hERG channel. Looking for a possible mexiletine alternative, we show that m-hydroxymexiletine (MHM), a minor mexiletine metabolite recently reported to be as active as the parent compound in an arrhythmia animal model, is a weaker hERG channel blocker, compared to mexiletine (IC50 = 22.4 ± 1.2 lmol/L). The hERG aromatic residues located in the S6 helix (Tyr652 and Phe656) are crucial in the binding of mexiletine and the different affinities of mexiletine and MHM with hERG channel are interpreted by modeling their corresponding binding interactions through ab initio calculations. The simulations demonstrate that the introduction of a hydroxyl group on the meta-position of the aromatic portion of mexiletine weakens the interaction of the drug xylyloxy moiety with Tyr652. These results provide further insights into the molecular basis of drug/hERG interactions and, in agreement with previously reported results on clofilium and ibutilide analogs, support the possibility of reducing hERG potency and related toxicity by modifying the aromatic pattern of substitution of clinically relevant compounds.

Human iPSC-derived cardiomyocytes and pyridyl-phenyl mexiletine analogs

In the United States, approximately one million individuals are hospitalized every year for arrhythmias, making arrhythmias one of the top causes of healthcare expenditures. Mexiletine is currently used as an antiarrhythmic drug but has limitations. The purpose of this work was to use normal and Long QT syndrome Type 3 (LQTS3) patient-derived human induced pluripotent stem cell (iPSC)-derived cardiomyocytes to identify an analog of mexiletine with superior drug-like properties. Compared to racemic mexiletine, medicinal chemistry optimization of substituted racemic pyridyl phenyl mexiletine analogs resulted in a more potent sodium channel inhibitor with greater selectivity for the sodium over the potassium channel and for late over peak sodium current.

Synthetic method for antiarrhythmic drug intermediate 1-(2,6-dimethoxy)-2-propanone

The invention discloses a synthetic method for the antiarrhythmic drug intermediate 1-(2,6-dimethoxy)-2-propanone. The synthetic method comprises the following steps: adding 1-(2,6-dimethyl-3-hydroxy-phenoxy)-2-aminopropane and a potassium nitrate solution into a reaction vessel, controlling a stirring speed, raising a solution temperature, adding a butyl benzyl phthalate solution, and continuinga reaction; and adding vananocene dichloride and a sodium sulfate solution, lowering the temperature, carrying out standing to realize the layering of the solution, separating an oil layer, washing the oil layer with a sulfur hexafluoride solution, then washing the oil layer with a 2-chlorophenol solution, carrying out recrystallization in a methyl chloride solution, and then carrying out dehydration with a dehydrating agent to obtain the finished 1-(2,6-dimethoxy)-2-propanone.