1986-81-8

Basic information

• Product Name: Nicotinamide-N-oxide
• Synonyms: 1-OXY-NICOTINAMIDE;3-(AMINOCARBONYL)PYRIDINIUM-1-OLATE;AKOS 94294;NICOTINAMIDE 1-OXIDE;NICOTINAMIDE N-OXIDE;TIMTEC-BB SBB004187;3-Pyridinecarboxamide, 1-oxide;3-Pyridinecarboxamide,1-oxide(9CI)
• CAS NO: 1986-81-8
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• EINECS: 217-859-4
• Product Categories: AMIDE;Biochemicals and Reagents;NAD and Analogs;Nucleosides, Nucleotides, Oligonucleotides;Amines;Bases & Related Reagents;Heterocycles;Metabolites & Impurities;Nicotine Derivatives;Nucleotides;Amines, Heterocycles, Metabolites & Impurities, Nicotine Derivatives, Nucleotides, Bases & Related Reagents
• Mol File: 1986-81-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 291-293 °C (dec.)(lit.)
• Boiling Point: 253.51°C (rough estimate)
• Flash Point: 265.1 °C
• Appearance: /
• Density: 1.3471 (rough estimate)
• Vapor Pressure: 1.05E-10mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 14.38±0.50(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: Nicotinamide-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Nicotinamide-N-oxide(1986-81-8)
• EPA Substance Registry System: Nicotinamide-N-oxide(1986-81-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1986-81-8(Hazardous Substances Data)

Usage

Description

Nicotinamide N-oxide, a metabolite of nicotinamide, is formed through the oxidation process by the cytochrome P450 (CYP) isoform CYP2E1. It exhibits properties that inhibit cell proliferation and promote cell differentiation, as observed in HL-60 promyelocytic leukemia cells. Additionally, it is associated with elevated urine levels in a mouse model of high-fat diet-induced obesity. Nicotinamide N-oxide is characterized by its white to slightly yellow fluffy crystalline or needle-like appearance.

Uses

1. Used in Pharmaceutical Applications:
Nicotinamide N-oxide is used as a therapeutic agent for promoting cell differentiation and inhibiting cell proliferation, particularly in the context of leukemia and other cancer-related conditions. Its ability to modulate cellular processes makes it a potential candidate for cancer treatment and research.
2. Used in Obesity Research:
Nicotinamide N-oxide is utilized as a biomarker in the study of obesity, particularly in mouse models induced by a high-fat diet. The elevated levels of this metabolite in urine can provide insights into the metabolic changes associated with obesity and potentially guide the development of targeted interventions.
3. Used in Metabolic Studies:
As a metabolite of nicotinamide, Nicotinamide N-oxide is employed in research aimed at understanding the complex metabolic pathways involving nicotinamide and its derivatives. This can contribute to the broader understanding of cellular metabolism and the role of nicotinamide in various physiological processes.
4. Used in Chemical Synthesis:
The unique chemical properties of Nicotinamide N-oxide, including its white to slightly yellow fluffy crystalline or needle-like appearance, make it a valuable compound in the synthesis of other related molecules for various applications in the chemical and pharmaceutical industries.

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

Upstream product

• 15905-18-7 1-oxy-nicotinic acid methyl ester 
• 108-99-6 3-Methylpyridine 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 98-92-0 nicotinamide 
• 14906-63-9 1-oxy-nicotinic acid ethyl ester 
• 6456-44-6 N-methylnicotineamide iodide 
• 1004-16-6 3-cyano-1-methylpyridinium iodide 

Downstream Products

• 89959-07-9 MoO₂(2,6-bis(2,2'-diphenyl-2-thioethyl)pyridinate) 
• 108272-32-8 4-(3-nitro-phenyl)-1-(1-oxy-nicotinoyl)-thiosemicarbazide 
• 96583-36-7 (3-nitro-phenyl)-[(1-oxy-[3]pyridyl)-[1,3,4]thiadiazol-2-yl]-amine 
• 101677-19-4 4-(3-nitro-phenyl)-5-(1-oxy-[3]pyridyl)-2,4-dihydro-[1,2,4]triazole-3-thione 
• 108245-73-4 4-benzyl-1-(1-oxy-nicotinoyl)-thiosemicarbazide 
• 108245-74-5 1-(1-oxy-nicotinoyl)-4-p-tolyl thiosemicarbazide 
• 109941-25-5 1-(1-oxy-nicotinoyl)-4-phenyl thiosemicarbazide 
• 108246-11-3 5-(1-oxy-[3]pyridyl)-4-p-tolyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 108850-56-2 1-oxy-nicotinic acid-(4-dimethylamino-benzylidenehydrazide) 
• 100728-38-9 1-oxy-nicotinic acid salicylidenehydrazide 
• 100728-23-2 1-oxy-nicotinic acid benzylidenehydrazide 
• 13438-65-8 2-aminopyridine-3-carboxamide 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 609-71-2 2-hydroxy-3-carboxypyridine 

Relevant articles and documents

Synthetic method for drug intermediate nicotinamide-N-oxide

The invention discloses a synthetic method for the drug intermediate nicotinamide-N-oxide. The synthetic method comprises the following steps: adding 3-methylpyridine and a potassium chloride solutioninto a reaction vessel, controlling a stirring speed to be 150-180 rpm, controlling a solution temperature to be 40-45 DEG C, adding a diethyl fumarate solution and a 1,3-propanediamine solution, adding N-chloroacetamide in batches within 30-50 min, and continuing a reaction for 80-100 min; and adding manganese chloride powder, controlling the stirring speed to be 230-250 rpm, continuing the reaction for 3-5 h, adding a sodium sulfate solution, subjecting the obtained solution to layering, separating an oil layer, washing the oil layer with a potassium bromide solution for 30-50 min, then washing the oil layer with a chloroprene solution for 20-40 min, carrying out recrystallization in a glycol monomethyl ether solution and then carrying out dehydration with a dehydrating agent so as to obtain the finished nicotinamide-N-oxide.

Renewable waste rice husk grafted oxo-vanadium catalyst for oxidation of tertiary amines to N-oxides

Low cost renewable waste rice husks (RH) have been used as a support for grafting of an oxo-vanadium Schiff base via covalent attachment for the oxidation of tertiary amines to N-oxide. The synthesis of the desired RH grafted oxo-vanadium complex involves prior functionalization of the RH support with amino-propyltrimethoxysilane (APTMS) followed by its reaction with salicylaldehyde to get an RH-functionalized Schiff base which subsequently reacted with vanadyl sulphate to get the targeted oxo-vanadium catalyst. The synthesized catalyst was found to be an efficient heterogeneous catalyst and afforded an excellent yield of corresponding N-oxides via oxidation of tertiary amines with hydrogen peroxide as an oxidant. Furthermore, the synthesized catalyst was found to be quite stable and showed consistent activity for five runs without any loss in activity.

Trichloroacetonitrile-hydrogen peroxide: A simple and efficient system for the selective oxidation of tertiary and secondary amines

A variety of tertiary and secondary amines were efficiently oxidized to their corresponding N-oxides and nitrones, respectively, using the trichloroacetonitrile-hydrogen peroxide system. The in situ generated trichloromethylperoxyimidic acid is the active reagent for the oxidation processes.