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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

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

Personal Protective Equipment

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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P Lindström et al.
Pain, 28(1), 45-50 (1987-01-01)
Tocainide is a derivative of lidocaine with anti-arrhythmic action and, unlike lidocaine, can be used for oral treatment. Tocainide was alternatively with carbamazepine given to 12 patients with trigeminal neuralgia in a double-blind cross-over study for 2 weeks. The analgesic
V Challapalli et al.
The Cochrane database of systematic reviews, (4)(4), CD003345-CD003345 (2005-10-20)
Lidocaine, mexiletine, tocainide, and flecainide are local anesthetics which give an analgesic effect when administered orally or parenterally. Early reports described the use of intravenous lidocaine or procaine to relieve cancer and postoperative pain (Keats 1951; Gilbert 1951; De Clive-Lowe
[Na channel myotonia].
H Nemoto et al.
Ryoikibetsu shokogun shirizu, (35)(35), 140-143 (2001-09-15)
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.
J R Emmett et al.
Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery, 88(4), 442-446 (1980-07-01)
Intravenous (IV) injection of lidocaine was used in patients with tinnitus for combined treatment with oral anticonvulsants carbamazepine (Tegretol) and primidone (Mysoline). In most cases, the high complication rate with these drugs precluded their long-term use. Tocainide hydrochloride (HCl), a
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