(2S)-2-[2-oxo(2H6)pyrrolidin-1-yl]butanamide

• ChemBase ID: 172275
• Molecular Formular: C8H14N2O2
• Molecular Mass: 170.20896
• Monoisotopic Mass: 170.1055277
• SMILES: C1CN(C(=O)C1)[C@H](C(=O)N)CC
• Canonical SMILES: CC[C@H](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)/t6-/m0/s1
• InChIKey: HPHUVLMMVZITSG-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[2-oxo(^2H₆)pyrrolidin-1-yl]butanamide
• IUPAC Traditional name: (2S)-2-[2-oxo(^2H₆)pyrrolidin-1-yl]butanamide
• Synonyms: (αS)-α-Ethyl-2-oxo-1-pyrrolidineacetamide-d6; (-)-Levetiracetam-d6; Keppra-d6; Levesam 500-d6; UCB-L 059-d6; Levetiracetam-d6See L331502

Database IDs

• CAS Number: 1133229-30-7
• PubChem SID: 164228185
• PubChem CID: 25231140

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

DETAILS

Toronto Research Chemicals - L331503

The labelled (S)-enantiomer of the ethyl analog of Piracetam. Used as an anticonvulsant.

REFERENCES

• Gower, A.J., et al.: Eur. J. Pharmacol., 222, 193 (1992)
• Kasteleijn-Noist Trenite, D.G.A., et al.: Epilepsy Res., 25, 225 (1992)
• Patsalos, P.N., et al.: Pharmacol. Ther., 85, 77 (1992)