M2727
Mexiletine hydrochloride
≥98% (GC), powder, sodium channel blocker
Synonym(s):
1-(2,6-Dimethylphenoxy)-2-propanamine hydrochloride, 1-(2,6-Xylyloxy)-2-aminopropane hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C11H17NO · HCl
CAS Number:
Molecular Weight:
215.72
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
Mexiletine hydrochloride, powder
Assay
≥98% (GC)
Quality Level
form
powder
color
white to off-white
solubility
methanol: 50 mg/mL
originator
Boehringer Ingelheim
storage temp.
2-8°C
SMILES string
Cl[H].CC(N)COc1c(C)cccc1C
InChI
1S/C11H17NO.ClH/c1-8-5-4-6-9(2)11(8)13-7-10(3)12;/h4-6,10H,7,12H2,1-3H3;1H
InChI key
NFEIBWMZVIVJLQ-UHFFFAOYSA-N
Gene Information
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General description
Mexiletine is a class I B antiarrhythmic and an analog of lidocaine. It has shelf life of 10-12 hours and is metabolized in liver and eliminated post reduction, oxidation deamination or conjugation.
Application
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
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.
Features and Benefits
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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J F Desaphy et al.
Neuromuscular disorders : NMD, 9(3), 182-189 (1999-06-26)
The sea anemone toxin ATX II impairs skeletal muscle sodium channel inactivation, mimicking the persistent inward current observed in patients suffering from sodium channel myotonia. Mexiletine has beneficial effects on myotonia. To verify the efficiency of the drug on persistent
E L Logigian et al.
Neurology, 74(18), 1441-1448 (2010-05-05)
To determine if mexiletine is safe and effective in reducing myotonia in myotonic dystrophy type 1 (DM1). Myotonia is an early, prominent symptom in DM1 and contributes to decreased dexterity, gait instability, difficulty with speech/swallowing, and muscle pain. A few
Arnold E Pfahnl et al.
Heart rhythm, 4(1), 46-53 (2007-01-03)
Brugada and long QT type 3 syndromes are linked to sodium channel mutations and clinically cause arrhythmias that lead to sudden death. We have identified a novel threonine-to-isoleucine missense mutation at position 353 (T353I) adjacent to the pore-lining region of
Michela De Bellis et al.
Biophysical journal, 104(2), 344-354 (2013-02-28)
Previously identified potent and/or use-dependent mexiletine (Mex) analogs were used as template for the rational design of new Na(v)-channel blockers. The effects of the novel analogs were tested on sodium currents of native myofibers. Data and molecular modeling show that
Min-Tzu Wu et al.
PloS one, 8(1), e55212-e55212 (2013-02-06)
Primary erythromelalgia (PE) is an autosomal dominant neurological disorder characterized by severe burning pain and erythema in the extremities upon heat stimuli or exercise. Mutations in human SCN9A gene, encoding the α-subunit of the voltage-gated sodium channel, Na(v)1.7, were found
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