2-(2-oxopyrrolidin-1-yl)butanamide

• ChemBase ID: 168796
• Molecular Formular: C8H14N2O2
• Molecular Mass: 170.20896
• Monoisotopic Mass: 170.1055277
• SMILES: C1CN(C(=O)C1)C(C(=O)N)CC
• Canonical SMILES: CCC(N1CCCC1=O)C(=O)N
• InChI: InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)
• InChIKey: HPHUVLMMVZITSG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-oxopyrrolidin-1-yl)butanamide
• IUPAC Traditional name: etiracetam
• Synonyms: α-Ethyl-2-oxo-1-pyrrolidineacetamide; UCB 6474; Etiracetam

Database IDs

• CAS Number: 33996-58-6
• PubChem SID: 162262928
• PubChem CID: 59708

CALCULATED PROPERTIES

• Acid pKa: 16.088663
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.59360605
• LogD (pH = 7.4): -0.5936059
• Log P: -0.5936059
• Molar Refractivity: 44.0793 cm^3
• Polarizability: 17.197067 Å^3
• Polar Surface Area: 63.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 115-118°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E932970

A nootropic drug that produced a significant increase in β-wave activity and stimulated α-wave activity dose-dependently. It has been used in studies to alleviate the effects of memory retrieval deficits in rats.

REFERENCES

• Sara, S.J.: Psychopharmacology, 68, 235 (1980)
• Wolthuis, O.L.: Pharamacol. Biochem. Behav., 15, 247 (1980)
• Saletu, B. et al.: Prog. Neuro-Psychopharmacol., 4, 469 (1980)