2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide

• ChemBase ID: 170702
• Molecular Formular: C12H18N2O2
• Molecular Mass: 222.28352
• Monoisotopic Mass: 222.13682783
• SMILES: c1cc(c(c(c1C)NC(=O)CNCC)C)O
• Canonical SMILES: CCNCC(=O)Nc1c(C)ccc(c1C)O
• InChI: InChI=1S/C12H18N2O2/c1-4-13-7-11(16)14-12-8(2)5-6-10(15)9(12)3/h5-6,13,15H,4,7H2,1-3H3,(H,14,16)
• InChIKey: YITCMQBVWIHTTA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
• IUPAC Traditional name: 2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
• Synonyms: 3-Hydroxymonoethylglycylxylidide; SNX 483; 3-Hydroxy-N-desethyl Lidocaine; 2-(Ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide; 3-Hydroxy-N-(N-ethylglycyl)-2,6-xylidine; 3-Hydroxy-ω-ethylamino-2,6-dimethylacetanilide

Database IDs

• CAS Number: 34604-56-3
• PubChem SID: 164226612
• PubChem CID: 3015693

CALCULATED PROPERTIES

• Acid pKa: 10.052576
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.0460888
• LogD (pH = 7.4): 0.6058278
• Log P: 1.6254328
• Molar Refractivity: 65.8672 cm^3
• Polarizability: 24.55011 Å^3
• Polar Surface Area: 61.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943800

A metabolite of Lidocaine (L397800).

REFERENCES

• Benowitz, N., et al.: Clin. Pharmacokinet., 3, 177 (1978)
• Bargetzi, M., et al.: Clin. Pharmacol. Ther., 46, 521 (1978)
• Newton, D., et al.: Drug Metab. Dispos., 23, 154 (1978)
• Venkatakrishnan, K., et al.: J. Clin. Pharmacol., 39, 567 (1978)
• Wang, J., e