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

• ChemBase ID: 104531
• Molecular Formular: C6H10N2O2
• Molecular Mass: 142.1558
• Monoisotopic Mass: 142.07422757
• SMILES: NC(=O)CN1CCCC1=O
• Canonical SMILES: NC(=O)CN1CCCC1=O
• InChI: InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
• InChIKey: GMZVRMREEHBGGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-oxopyrrolidin-1-yl)acetamide
• IUPAC Traditional name: 2-oxo-1-pyrrolidineacetamide; 2-oxo-pyrrolidine acetamide
• Brand Name: Breinox, Dinagen, Lucetam, Nootropil, Nootropyl, Oikamid, and many others
• Synonyms: 2-(2-oxopyrrolidin-1-yl)acetamide; 2-(2-Oxopyrrolidino)acetamide; (2-Oxopyrrolidino)acetamide; Avigilen; Axonyl; Cerebroforte; Piramem; Pyracetam; UCB 6215; 2-Oxo-1-pyrrolidineacetamide; PIRACETAM; Piracetam; 2-(2-oxopyrrolidin-1-yl)acetamide; 2-氧代-1-吡咯烷乙酰胺; 吡拉西坦; 吡乙酰胺

Database IDs

• CAS Number: 7491-74-9
• EC Number: 231-312-7
• MDL Number: MFCD00079246
• PubChem SID: 24278639; 24860593; 162092750
• PubChem CID: 4843
• ATC CODE: N06BX03
• CHEMBL: 36715
• Chemspider ID: 4677
• KEGG ID: D01914
• Unique Ingredient Identifier: ZH516LNZ10
• Wikipedia Title: Piracetam

CALCULATED PROPERTIES

• Acid pKa: 15.934727
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.6848925
• LogD (pH = 7.4): -1.6848925
• Log P: -1.6848925
• Molar Refractivity: 35.0614 cm^3
• Polarizability: 13.547892 Å^3
• Polar Surface Area: 63.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: UX9660500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Admin Routes: Oral and parenteral
• Bioavailability: ~100%
• Excretion: Urinary
• Half Life: 4–5 hr
• Legal Status: POM (UK)
• Gene Information: human ... GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)rat ... Gria1(50592); rat ... Gria1(50592)

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C6H10N2O2

DETAILS

MP Biomedicals - 02156275

(2-Oxo-1-pyrrolidineacetamide)

Sigma Aldrich - P5295

Biochem/physiol Actions
Prototypical nootropic with mechanism of action similar to that of aniracetam and oxiracetam; modulates Na+-flux at AMPA receptors.

Sigma Aldrich - 33895

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P500800

Nootropic.

REFERENCES

• Gobert, J., et al.: J. Pharm. Belg., 27, 281 (1972)
• Oosterveld, W.J., et al.: Arzneim.-Forsch., 30, 1947 (1972)
• Chouinard, G., et al.: Psychopharmacol. Bull., 17, 129 (1972)