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

• ChemBase ID: 153903
• Molecular Formular: C11H17ClN2O
• Molecular Mass: 228.71848
• Monoisotopic Mass: 228.10294085
• SMILES: Cc1cccc(c1NC(=O)C(C)N)C.Cl
• Canonical SMILES: CC(C(=O)Nc1c(C)cccc1C)N.Cl
• InChI: 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
• InChIKey: AMZACPWEJDQXGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N-(2,6-dimethylphenyl)propanamide hydrochloride
• IUPAC Traditional name: tocainide hydrochloride
• Synonyms: 2-Amino-N-(2,6-dimethylphenyl)propanamide hydrochloride; Tocainide hydrochloride; 2-Amino-N-(2,6-dimethylphenyl)propanamide 盐酸盐; Tocainide 盐酸盐

Database IDs

• CAS Number: 71395-14-7
• EC Number: 275-361-2
• MDL Number: MFCD00941502
• PubChem SID: 162248042; 24724626
• PubChem CID: 108173

CALCULATED PROPERTIES

• Acid pKa: 13.653854
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.6713139
• LogD (pH = 7.4): 0.9973883
• Log P: 1.8824334
• Molar Refractivity: 58.857 cm^3
• Polarizability: 22.107647 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: ≥5 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: desiccated; under inert gas
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H16N2O · HCl

DETAILS

Sigma Aldrich - T0202

Biochem/physiol Actions
Tocainide hydrochloride is a sodium channel blocker; Class IB antiarrhythmic.
Features and Benefits
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.