N3258
Nicotinamide N-oxide
≥98%
Synonym(s):
3-Pyridinecarboxamide, Oxynicotinamide
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About This Item
Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
UNSPSC Code:
41106305
PubChem Substance ID:
EC Number:
217-859-4
MDL number:
InChI key
USSFUVKEHXDAPM-UHFFFAOYSA-N
InChI
1S/C6H6N2O2/c7-6(9)5-2-1-3-8(10)4-5/h1-4H,(H2,7,9)
SMILES string
NC(=O)c1ccc[n+]([O-])c1
assay
≥98%
mp
291-293 °C (dec.) (lit.)
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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K Takekawa et al.
Xenobiotica; the fate of foreign compounds in biological systems, 31(1), 11-23 (2001-05-04)
1. The mechanism of reduction of aliphatic tertiary amine N-oxides to tertiary amines in liver microsomes was examined and a novel type of reduction by cytochrome P450 was found. 2. Rat liver microsomes exhibited a significant N-oxide reductase activity toward
S Shimada et al.
Investigative ophthalmology & visual science, 28(7), 1204-1206 (1987-07-01)
The nicotinamide N-oxide reductase activity of a variety of ocular tissues was investigated. The 9,000g supernatant of ciliary body, retinal pigment epithelium-choroid, iris, retina and cornea, but not lens, exhibited reductase activity under anaerobic conditions when supplemented with 2-hydroxypyrimidine, an
Spectroscopic (NMR, UV, FT-IR and FT-Raman) analysis and theoretical investigation of nicotinamide N-oxide with density functional theory.
Atac A, Karabacak M, Kose E, Karaca C.
Spectrochimica Acta Part A: Molecular Spectroscopy, 83(1), 250-258 (2011)
Nicotinamide N-oxide formation by rat liver microsomes.
K Nomura et al.
Biochemical pharmacology, 32(5), 934-936 (1983-03-01)
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
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