N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide

• ChemBase ID: 153262
• Molecular Formular: C12H18N2O
• Molecular Mass: 206.28412
• Monoisotopic Mass: 206.14191321
• SMILES: CCNCC(=O)Nc1c(cccc1C)C
• Canonical SMILES: CCNCC(=O)Nc1c(C)cccc1C
• InChI: InChI=1S/C12H18N2O/c1-4-13-8-11(15)14-12-9(2)6-5-7-10(12)3/h5-7,13H,4,8H2,1-3H3,(H,14,15)
• InChIKey: WRMRXPASUROZGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide
• IUPAC Traditional name: monoethylglycinexylidide
• Synonyms: N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide; 2-(Ethylamino)-2',6'-acetoxylidide; L 86; MEGX; Monoethylglycylxylidide; N-(N-Ethylglycyl)-2,6-xylidine; N-Ethylglycinexylidide; ω-Ethylamino-2',6'-dimethyl-acetanilide; N-Desethyl Lidocaine; Nor Lidocaine; Monoethylglycinexylidide; N-(2,6-dimethylphenyl)-2-(ethylamino)acetamide; Norlidocaine; MEGX

Database IDs

• CAS Number: 7728-40-7
• MDL Number: MFCD00098991
• PubChem SID: 162247401
• PubChem CID: 24415

CALCULATED PROPERTIES

• Acid pKa: 13.785018
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.7506011
• LogD (pH = 7.4): 0.89771
• Log P: 2.1030574
• Molar Refractivity: 63.8863 cm^3
• Polarizability: 23.951906 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥16 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 242-245°C; 45 - 47°C
• Hydrophobicity(logP): 0.818

Safety Information

• Storage Condition: -20°C Freezer
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C12H18N2O

DETAILS

Sigma Aldrich - SML0087

Biochem/physiol Actions
Monoethylglycinexylidide (MEGX) is an active metabolite of lidocaine.

Toronto Research Chemicals - N713500

A metabolite of Lidocaine (L397800).

REFERENCES

• Fukuda, S., et al.: Anesthesiology, 53, 106 (1980)