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Merck
CN

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:
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

Key Documents

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Product Name

Mexiletine hydrochloride, powder

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB6374
BCBL6076V
BCBL6076
BCBL3766
011M1248V

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Adam Romman et al.
Pain physician, 21(5), E573-E579 (2018-10-05)
Intravenous lidocaine has multiple applications in the management of acute and chronic pain. Mexiletine, an oral lidocaine analogue, has been used in a number of chronic pain conditions although its use is not well characterized. To report our experience using
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
Mexiletine
Monk, Jon P and Brogden, Rex N
Drugs, 40(3), 374-411 (1990)
K Mori et al.
Naunyn-Schmiedeberg's archives of pharmacology, 358(6), 641-648 (1999-01-08)
Recently we have reported that class III antiarrhythmic drugs including amiodarone inhibit the Na+-activated K+ (KNa) channels in isolated cardiac cells. In this study effects of antiarrhythmic drugs having class I and/or IV properties on the single KNa channel current
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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