(2S)-2-(2-oxopyrrolidin-1-yl)(4,4,4-2H3)butanamide

• ChemBase ID: 172274
• 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-oxopyrrolidin-1-yl)(4,4,4-^2H₃)butanamide
• IUPAC Traditional name: (2S)-2-(2-oxopyrrolidin-1-yl)(4,4,4-^2H₃)butanamide
• Synonyms: (αS)-α-(Ethyl-d3)-2-oxo-1-pyrrolidineacetamide; (-)-Levetiracetam-d3; Keppra-d3; Levesam 500-d3; UCB-L 059-d3; Levetiracetam-d3

Database IDs

• PubChem SID: 164228184
• PubChem CID: 45039653

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: Acetone; Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L331502

The labelled (S)-enantiomer of Etiracetam (E932970) and the ethyl analog of Piracetam (P500800). 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)