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T0202

Sigma-Aldrich

Tocainide hydrochloride

≥98% (HPLC), solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H16N2O · HCl
Numéro CAS:
Poids moléculaire :
228.72
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Conditions de stockage

desiccated
under inert gas

Couleur

white

Solubilité

DMSO: >20 mg/mL
H2O: ≥5 mg/mL

Auteur

AstraZeneca

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

AMZACPWEJDQXGW-UHFFFAOYSA-N

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Application

Tocainide hydrochloride may be used in cell signaling studies.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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
Marco Pistolozzi et al.
Journal of pharmaceutical and biomedical analysis, 53(2), 179-185 (2010-04-03)
A series of synthesised tocainide analogues were characterized for their human serum albumin (HSA) binding, using high-performance liquid affinity chromatography (HPLAC) and circular dichroism (CD). The synthesis and physico-chemical characterization of compounds 7a-7d is reported here. For the HPLAC investigation

Articles

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

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