2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrate hydrochloride

• ChemBase ID: 131439
• Molecular Formular: C14H25ClN2O2
• Molecular Mass: 288.8135
• Monoisotopic Mass: 288.16045573
• SMILES: CCN(CC)CC(=O)Nc1c(cccc1C)C.O.Cl
• Canonical SMILES: CCN(CC(=O)Nc1c(C)cccc1C)CC.O.Cl
• InChI: InChI=1S/C14H22N2O.ClH.H2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4;;/h7-9H,5-6,10H2,1-4H3,(H,15,17);1H;1H2
• InChIKey: YECIFGHRMFEPJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide hydrate hydrochloride
• IUPAC Traditional name: lignocaine hydrate hydrochloride
• Synonyms: 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide hydrochloride monohydrate; Lignocaine hydrochloride monohydrate; Xylocaine hydrochloride monohydrate; Lidocaine hydrochloride monohydrate; 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide Hydrochloride Monohydrate; Basicaina Monohydrate; Batixim Monohydrate; Dynexan Monohydrate; Heweneural Monohydrate; Licain Monohydrate; Lidocaine Hydrochloride Monohydrate

Database IDs

• CAS Number: 6108-05-0
• EC Number: 200-803-8
• MDL Number: MFCD00150329
• PubChem SID: 24277718; 162225717
• PubChem CID: 16219577

CALCULATED PROPERTIES

• Acid pKa: 13.775423
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6099084
• LogD (pH = 7.4): 2.329713
• Log P: 2.8429134
• Molar Refractivity: 73.9296 cm^3
• Polarizability: 27.641424 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: soluble
• Apperance: white solid; White to Off-White Solid
• Melting Point: 80-82°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: AN7700000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

DETAILS

Sigma Aldrich - L5647

Biochem/physiol Actions
Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration

Toronto Research Chemicals - L397800

Anesthetic (local); antiarrhythmic (class IB). Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic.

REFERENCES

• Duce, R., et al.: J. Pharmacol. Exp. Ther., 179, 580 (1971)
• Kronberg, G.H., et al.: J. Med. Chem., 16, 739 (1971)
• Groningsson, K., et al.: Anal. Profiles Drug Subs., 14, 207 (1971)
• Davies, P.S., et al.: Drugs, 64, 937 (1971)