2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide

• ChemBase ID: 131243
• Molecular Formular: C6H10N2O3
• Molecular Mass: 158.1552
• Monoisotopic Mass: 158.06914219
• SMILES: C1C(CN(C1=O)CC(=O)N)O
• Canonical SMILES: NC(=O)CN1CC(CC1=O)O
• InChI: InChI=1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)
• InChIKey: IHLAQQPQKRMGSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide
• IUPAC Traditional name: oxiracetam
• Synonyms: 4-Hydroxy-2-oxopyrrolidine-N-acetamide; Oxiracetam; 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide; 4-Hydroxy-2-oxo-1-pyrrolidineacetamide; Hydroxypiracetam; 2-(4-Hydroxy-2-oxopyrrolidin-1-yl)acetamide; CGP 21690; CGP 21690E; CT 848; 4-Hydroxypyrrolidone-2-acetamide; ISF 2522; Neuractiv; Neuromet; Oxiracetam

Database IDs

• CAS Number: 62613-82-5
• MDL Number: MFCD00242951
• PubChem SID: 24278609; 162225521
• PubChem CID: 4626

CALCULATED PROPERTIES

• Acid pKa: 14.608332
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.6038888
• LogD (pH = 7.4): -2.6038888
• Log P: -2.6038888
• Molar Refractivity: 36.2689 cm^3
• Polarizability: 14.242021 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Whie Solid
• Melting Point: 133 - 135°C; 161-163°C
• Hydrophobicity(logP): -1.199

Safety Information

• Storage Condition: Refrigerator
• RTECS: UX9656638
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

Sigma Aldrich - O3011

Biochem/physiol Actions
Nootropic agent, improves learning and memory, and prevents impairment of cognitive functions. Its mechanism of action in not yet known, but it is suggested to modulate glutamatergic and cholinergic neurotransmission. Protein kinase C may be involved.

Toronto Research Chemicals - O846905

Nootropic. Analog of Piracetam with psychostimulant activity.

REFERENCES

• Son, J., et al.: J. Pharm. Biomed. Anal., 36, 657 (2004)
• Hlinak, Z., et al.: Behaviour. Brain Res., 161, 213 (2004)