3-carbamoylpyridin-1-ium-1-olate

• ChemBase ID: 78880
• Molecular Formular: C6H6N2O2
• Molecular Mass: 138.12404
• Monoisotopic Mass: 138.04292744
• SMILES: [n+]1(cc(ccc1)C(=O)N)[O-]
• Canonical SMILES: [O-][n+]1cccc(c1)C(=O)N
• InChI: InChI=1S/C6H6N2O2/c7-6(9)5-2-1-3-8(10)4-5/h1-4H,(H2,7,9)
• InChIKey: USSFUVKEHXDAPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoylpyridin-1-ium-1-olate
• IUPAC Traditional name: 3-carbamoylpyridin-1-ium-1-olate; 3-pyridinecarboxamide, 1-oxide
• Synonyms: Nicotinamide N-oxide; 3-Pyridinecarboxamide; Oxynicotinamide; Nicotinamide N-oxide; 1-Oxide 3-Pyridinecarboxamide; Nicotinamide 1-Oxide; NSC 168416; NSC 30531; Niacinamide N-Oxide; Pyridine-3-carboxamide 1-Oxide; 烟酰胺N-氧化物

Database IDs

• CAS Number: 1986-81-8
• EC Number: 217-859-4
• MDL Number: MFCD00006202
• PubChem SID: 24897634; 162043643
• PubChem CID: 72661

CALCULATED PROPERTIES

• Acid pKa: 12.763094
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.6539445
• LogD (pH = 7.4): -1.6539416
• Log P: -1.6539433
• Molar Refractivity: 36.669 cm^3
• Polarizability: 12.798193 Å^3
• Polar Surface Area: 68.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSo
• Apperance: White Solid
• Melting Point: 291-293 °C (dec.)(lit.); 291-293°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97%; ≥98%; 98%
• Empirical Formula (Hill Notation): C6H6N2O2

DETAILS

MP Biomedicals - 02155828

Purity: ≥97% Crystalline

Sigma Aldrich - N3258

Biochem/physiol Actions
Nicotinamide N-oxide is a niacin-related compound used in studies of mechanisms of niacin-related granulocyte differentiation of cells such as human promyelocytic leukemia cells (HL-60). Nicotinamide N-oxide reduced expression of c-myc in HL-60 cell line.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N3258.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - N407760

A metabolite of Nicotinamide.

REFERENCES

• Musfeld, C., et al.: J. Pharm. Biomed. Anal., 24, 391 (2001)
• Sakakibara, Y., et al.: Brain Res., 931, 68 (2001)
• Zielonka, J., et al.: Chem. Res. Toxicol., 19, 668 (2001)
• Wieczorkowska, M., et al.: Pharmacol. Rep., 59, 216 (2001)