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T0202

Sigma-Aldrich

Tocainide hydrochloride

≥98% (HPLC), solid

Synonym(s):

2-Amino-N-(2,6-dimethylphenyl)propanamide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H16N2O · HCl
CAS Number:
71395-14-7
Molecular Weight:
228.72
EC Number:
275-361-2
MDL number:
MFCD00941502
UNSPSC Code:
12352200
PubChem Substance ID:
24724626
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

storage condition

desiccated
under inert gas

color

white

solubility

DMSO: >20 mg/mL
H2O: ≥5 mg/mL

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

Cl[H].CC(N)C(=O)Nc1c(C)cccc1C

InChI

1S/C11H16N2O.ClH/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12;/h4-6,9H,12H2,1-3H3,(H,13,14);1H

InChI key

AMZACPWEJDQXGW-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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Application

Tocainide hydrochloride may be used in cell signaling studies.

Biochem/physiol Actions

Tocainide hydrochloride is a primary amine analog of lidocaine (lignocaine), used for the treatment of tinnitus. It blocks the sodium channels in the pain-producing foci in the nerve membranes and renders an analgesic effect in trigeminal neuralgia.
Tocainide hydrochloride is a sodium channel blocker; Class IB antiarrhythmic.

Features and Benefits

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Tocainide is voltage-dependent and use-dependent sodium channel blocker (class IB type antiarrhythmic); Ki = 115 μM in blockade of inactivated-state sodium channels; IC50 = 985μM in blockade of Na+ currents at a holding potential (HP) of -140 mV; IC50 = 254 μM in blockade of Na+ currents at HP -70 mV; IC50 = 523 μM in blockade of Na+ currents at tonic block (-100 mV); IC50 = 248 μM for use-dependent block at 10 Hz.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Helle Kirstein Erichsen et al.
European journal of pharmacology, 458(3), 275-282 (2002-12-31)
The pain-relieving effects of various voltage-activated Na(+) channel blockers have been evaluated in two rat models of neuropathic pain; the photochemically induced nerve injury model (Gazelius) and spared nerve injury model. Lidocaine (up to 40 mg/kg, i.p.) and lamotrigine (up
John C L Erve
Current drug metabolism, 9(2), 175-188 (2008-02-22)
Metabolism of xenobiotics can sometimes generate cyclic metabolites. Such metabolites are usually the result of intramolecular reactions occurring within a primary or secondary metabolite and this chemistry may lead to unexpected structures. Intramolecular chemistry is often driven by nucleophilic groups
Annamaria De Luca et al.
Molecular pharmacology, 64(4), 932-945 (2003-09-23)
Newly synthesized tocainide analogs were tested for their state-dependent affinity and use-dependent behavior on sodium currents (INa) of adult skeletal muscle fibers by means of the Vaseline-gap voltage clamp method. The drugs had the pharmacophore amino group constrained in position
Hassan Y Aboul-Enein et al.
Journal of biochemical and biophysical methods, 54(1-3), 407-413 (2003-01-25)
Enantiomeric resolution of thyroxine and tocainide was achieved on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid column. The mobile phases were methanol/water (4:1, v/v) and methanol/water containing 5 mM sulfuric acid (4:1, v/v) for tocainide and thyroxine respectively. The flow rate was 0.5 ml/min.
[Na channel myotonia].
H Nemoto et al.
Ryoikibetsu shokogun shirizu, (35)(35), 140-143 (2001-09-15)
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Articles

Sodium Channels

Voltage-gated sodium channels are present in most excitable cell membranes and play an important role in generating action potentials.

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