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Safety Information

N3258

Sigma-Aldrich

Nicotinamide N-oxide

≥98%

Synonym(s):

3-Pyridinecarboxamide, Oxynicotinamide

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About This Item

Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
1986-81-8
Molecular Weight:
138.12
EC Number:
217-859-4
MDL number:
MFCD00006202
UNSPSC Code:
41106305
PubChem Substance ID:
24897634

Assay

≥98%

mp

291-293 °C (dec.) (lit.)

SMILES string

NC(=O)c1ccc[n+]([O-])c1

InChI

1S/C6H6N2O2/c7-6(9)5-2-1-3-8(10)4-5/h1-4H,(H2,7,9)

InChI key

USSFUVKEHXDAPM-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
047F3696
077F3681
073K3442

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P Dostert et al.
Xenobiotica; the fate of foreign compounds in biological systems, 15(10), 799-803 (1985-10-01)
Using the N-oxide derivative of niaprazine, a nicotinamide-based drug, as substrate, the possibility of a 1,2-oxygen shift from N to adjacent C occurring in vivo has been investigated. By comparison of the percentage of the 6-pyridone derivative formed after administration
N S Cutshall et al.
Bioorganic & medicinal chemistry letters, 11(14), 1951-1954 (2001-07-19)
A series of nicotinamide N-oxides was synthesized and shown to be novel, potent, and selective antagonists of the CXCR2 receptor. Furthermore, these compounds showed significant functional activity against GRO-alpha-driven human neutrophil chemotaxis. Compounds of this class may be useful for
Mark W Ruddock et al.
Oncology research, 16(12), 569-574 (2008-03-21)
Nicotinamide is a potent radiosensitizer currently employed in the treatment of cancer of the bladder, head, and neck. Unfortunately, nicotinamide is also a potent emetic at the concentrations required for radiosensitization. Previously, we have demonstrated that nicotinamide-induced emesis is the
J Bernier et al.
Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology, 48(2), 123-133 (1998-10-23)
The EORTC has initiated studies to combine nicotinamide with carbogen in accelerated fractionation schedules (ARCON), since for some tumour types, acute and chronic hypoxia as well as treatment protraction may prejudice the outcome of radiotherapy. The tolerable dose of nicotinamide
M R Stratford et al.
Cancer chemotherapy and pharmacology, 34(5), 399-404 (1994-01-01)
Nicotinamide sensitizes murine tumours to the effect of radiation, but the pharmacokinetics are not well characterized at doses that are achievable in humans. In the mouse, nicotinamide given i.p. at doses of 100-500 mg/kg showed biphasic elimination with dose-dependent changes
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