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M2727

Sigma-Aldrich

Mexiletine hydrochloride

powder

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Synonym(s):
1-(2,6-Dimethylphenoxy)-2-propanamine hydrochloride, 1-(2,6-Xylyloxy)-2-aminopropane hydrochloride
Empirical Formula (Hill Notation):
C11H17NO · HCl
CAS Number:
5370-01-4
Molecular Weight:
215.72
EC Number:
250-825-7
MDL number:
MFCD00216024
UNSPSC Code:
12352200
PubChem Substance ID:
24278542
NACRES:
NA.77

Assay

≥98% (GC)

Quality Level

200

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

human ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Erythromelagia: a rare and hard-to-treat condition: a 9-year-old boy responsive to intravenous lidocaine and oral mexilitene.
Francisca Elgueta et al.
Pain medicine (Malden, Mass.), 14(2), 311-312 (2013-02-02)
Tomoyuki Suzuki et al.
Cardiovascular research, 98(1), 136-144 (2013-01-24)
Na(+) channel blockers are often used to treat atrial fibrillation (AF), but may sometimes cause ventricular contractile dysfunction. However, amiodarone, a multi-channel blocker with Na(+) channel block, causes less contractile dysfunction. In this study, we tested the hypothesis that Na(+)
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