1986-81-8

Usage

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

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

Downstream Products

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 85320-76-9 1-oxy-thionicotinic acid amide 
• 609-71-2 1,2-dihydro-2-oxonicotinic acid 
• 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 

Relevant academic research and scientific papers

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.

Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane

The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.

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.

2,2,2-Trifluoroacetophenone as an organocatalyst for the oxidation of tertiary amines and azines to N-oxides

A cheap, mild and environmentally friendly oxidation of tertiary amines and azines to the corresponding Noxides is reported by using polyfluoroalkyl ketones as efficient organocatalysts. 2,2,2-Trifluoroacetophenone was identified as the optimum catalyst for the oxidation of aliphatic tertiary amines and azines. This oxidation is chemoselective and proceeds in high-to-quantitative yields utilizing 10 mol% of the catalyst and H2O2 as the oxidant.

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.

A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water

A simple and convenient protocol for deoxygenation of aliphatic and aromatic N-oxides to the corresponding amines in good to excellent yield using sodium borohydride-Raney nickel in water is reported. Other functional moieties such as alkenes, halides, ethers, and amides are unaffected under the present reaction condition.

Comparative rate study on the oxidation of nicotinamide and isonicotinamide by permanganate in acidic medium

A comparative rate study on the oxidation of nicotinamide and isonicotinamide by potassium permanganate has been carried out in acidic solutions over an extended [H+]·range (1 × 10 -5-1.0 mol L-1). Under the similar reaction conditions, the oxidation of pyridine is imperceptible. Further, In the absence of acid none of the two amides is oxidised and in both cases, the N-protonated amide species appears to be reactive. For nicotinamide, the results are in agreement with the two-term rate law (A). The oxidation product was corresponding N oxide. -d[MnO4 -Ydt = (k0K + k1KK 1 [H+]) [S]0, [MnO4 -]t [H+Y(1 + K [H+)]) (A) On the other hand, the oxidation of isonicotinamide follows a simpler rate law (B). -d[MnO4-Ydt = k0K [S]0 [MnO 4-]1 [H+Y(1 + K. [H+]) (B) The values of k0, K. and k1K1 for nicotinamide were round to be 5.5 × 10-3 L. mol-1 s-1, 1.8 × 104 and 1.0 × 10-2 L. mol-1 s-1, respectively at 35 °C. And for isonicotinamide, the k0, and K. values were 4.4 × 10 -3 L. mol-1 s-1 and 5.6 × 103 respectively at 35 °C. The oxidation of nicotinamide is faster than the oxidation of isonicotinamide. It appears that the presence of -CONH2 group at position 3 activates the ring nitrogen more for oxidation than the presence of this group at position 4.

Rhenium-catalyzed highly efficient oxidations of tertiary nitrogen compounds to N-oxides using sodium percarbonate as oxygen source

Sodium percarbonate was found to be an ideal and efficient oxygen source for the oxidation of tertiary nitrogen compounds to N-oxides in excellent yields in presence of various rhenium-based catalysts under mild reaction conditions. Georg Thieme Verlag Stuttgart.

Silica-supported vanadium-catalyzed N-oxidation of tertiary amines with aqueous hydrogen peroxide

A recyclable silica supported vanadium 1 catalyzes the oxidation of tertiray amines to the corresponding N-oxides with 30% H2O 2 in high yield.