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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

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

Storage Class

11 - Combustible Solids

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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L He et al.
The Cochrane database of systematic reviews, (3)(3), CD004029-CD004029 (2006-07-21)
Non-antiepileptic drugs have been used in trigeminal neuralgia management since the 1970s. The objective was to review systematically the efficacy of non-antiepileptic drugs for trigeminal neuralgia. We searched the Cochrane Neuromuscular Disease Group Register, MEDLINE, EMBASE, and LILACS (all to
Alessia Catalano et al.
European journal of medicinal chemistry, 43(11), 2535-2540 (2008-03-18)
1-Benzyl-N-(2,6-dimethylphenyl)piperidine-3-carboxamide and 4-benzyl-N-(2,6-dimethylphenyl)piperazine-2-carboxamide, two conformationally restricted analogues of tocainide, were designed and synthesized as voltage-gated skeletal muscle sodium channel blockers. They showed, with respect to tocainide, a marked increase in both potency and use-dependent block.
C Ghelardini et al.
Neuroscience, 169(2), 863-873 (2010-06-29)
The role of voltage-gated sodium channels in the transmission of neuropathic pain is well recognized. For instance, genetic evidence recently indicate that the human Nav1.7 sodium channel subtype plays a crucial role in the ability to perceive pain sensation and
Antonio Carrieri et al.
European journal of medicinal chemistry, 44(4), 1477-1485 (2008-11-26)
Enantiomeric forms of Tocainide, Mexiletine, and structurally related local anaesthetic compounds, were analyzed with respect to their potency in blocking Na(v)1.4 channel. Structure-activity relationships based on in vitro pharmacological assays, suggested that an increase in terms of lipophilicity and/or molecular
Annamaria De Luca et al.
Neuromuscular disorders : NMD, 22(1), 56-65 (2011-08-02)
Drug screening on sodium currents of native myofibers by means of voltage-clamp recordings is predictive of pre-clinical anti-myotonic activity in vivo and ex vivo. By this approach we identified the N-benzylated beta-proline derivative of tocainide (To10) as the most potent
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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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