519-65-3

Basic information

• Product Name: N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide
• Synonyms: N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide;1-(1-Phenyl-2-acetyl-2-methylhydrazino)-2-(dimethylamino)-1,2-ethanedione;N,N-Dimethyl-2-oxo-2-(1-phenyl-2-acetyl-2-methylhydrazino)acetamide;N'-Acetyl-N'-methyl-2-(dimethylamino)-2-oxo-N-phenylacetohydrazide;N-Methyl-N'-phenyl-N'-(N,N-dimethyloxamoyl)acetohydrazide;2-(N-[acetyl(methyl)amino]anilino)-2-keto-N,N-dimethyl-acetamide;2-(N-[acetyl(methyl)amino]anilino)-N,N-dimethyl-2-oxoacetamide;2-[[ethanoyl(methyl)amino]-phenyl-amino]-N,N-dimethyl-2-oxo-ethanamide
• CAS NO: 519-65-3
• Molecular Formula: C₁₃H₁₇N₃O₃
• Molecular Weight: 263.29238
• EINECS: 208-274-5
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 519-65-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 105.5° (softens at 96°)
• Boiling Point: bp2 194-201°
• Flash Point: 146.3°C
• Appearance: /
• Density: 1.1651 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• PKA: -0.84±0.50(Predicted)
• CAS DataBase Reference: N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide(519-65-3)
• EPA Substance Registry System: N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide(519-65-3)

Safety Data

• Hazardous Substances Data: 519-65-3(Hazardous Substances Data)

Usage

Description

N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide is a monocarboxylic acid amide that features a 2-acetyl-2-methyl-1-phenylhydrazinyl group substitution at the 2nd position. It is a metabolite of the drug aminopyrine, which is known for its antipyretic and analgesic properties.

Uses

1. Pharmaceutical Industry:
N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide is used as an intermediate compound for the synthesis of various pharmaceuticals due to its unique chemical structure and properties.
2. Metabolite Research:
In the field of metabolomics, N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide is used as a reference metabolite for studying the metabolism of 4-Dimethylaminoantipyrine (D460890), an antipyretic and analgesic drug. This helps in understanding the metabolic pathways and potential side effects of the drug.
3. Drug Development:
N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide can be utilized in drug development as a starting material or a structural component for designing new pharmaceuticals with improved efficacy and reduced side effects.
4. Analytical Chemistry:
N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide can be employed as a reference substance in analytical chemistry for the development and validation of analytical methods, such as high-performance liquid chromatography (HPLC) or mass spectrometry (MS), for the detection and quantification of related compounds in biological samples.
5. Toxicology Studies:
N'-acetyl-2-(dimethylamino)-N'-methyl-2-oxo-N-phenylacetohydrazide may be used in toxicology studies to investigate the potential toxic effects of aminopyrine and its metabolites, contributing to the safety assessment of the drug.
6. Quality Control:
In the pharmaceutical industry, this compound can be used for quality control purposes to ensure the purity and potency of aminopyrine and its related products by serving as a reference standard in various analytical tests.

Upstream product

• 50680-54-1 dimethylcarbamoylformylchloride 
• 38604-70-5 1-acetyl-1-methyl-2-phenylhydrazine 
• 58-15-1 aminopyrine 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 38604-70-5 1-acetyl-1-methyl-2-phenylhydrazine 
• 144-62-7 oxalic acid 
• 622-36-6 1-methyl-2-phenylhydrazine 
• 64-19-7 acetic acid 
• 124-40-3 dimethyl amine 
• 82943-67-7 dimethyloxalamide acid-(N'-methyl-N-phenyl)-hydrazide 

Relevant articles and documents

Oxidation of Aminopyrine by Hypochlorite to a Reactive Dication: Possible Implications for Aminopyrine-Induced Agranulocytosis

Aminopyrine is associated with a high incidence of agranulocytosis. It is known to be oxidized by peroxidases and hypochlorous acid to a blue cation radical. It has been proposed that the mechanism by which hypochlorous acid oxidizes aminopyrine to a cation radical involves N-chlorination followed by loss of a chlorine radical. Another possible mechanism is loss of HCl to form an iminium ion and subsequent reaction with another molecule of aminopyrine and a hydrogen ion to form two radical cations. This mechanism would lead to incorporation of a hydrogen from water; however, using a deuterated analog, we found no hydrogen incorporation, thus providing strong evidence against this mechanism. Using a stopped-flow diode array spectrophotometer to study the reaction between aminopyrine and hypochlorous acid, an intermediate with a λmax at ca. 420 nm was observed in the formation of the cation radical. We propose that this represents a dication formed by the loss of chloride ion from N-chloroaminopyrine. This intermediate is very reactive, with a half-life of approximately 15 ms, and in addition to being the precursor of the cation radical, it also appears to react with two molecules of water to form several other products that were observed and are consistent with the proposed dication intermediate. Similar stable products were formed when aminopyrine was oxidized by the combination of myeloperoxidase, hydrogen peroxide, and chloride or activated neutrophils. The reactive dication formed by neutrophil-derived hypochlorous acid could be responsible for aminopyrine-induced agranulocytosis.

Ring Opening of 3(2H)-Pyrazolones by Oxidation with Periodate

In contrast to the aminopyrazolones 1 the pyrazolones 3 and 5 are stable against singlet oxygen.However, no difference is observed in reaction of the title compounds 1, 3 and 5 with sodium metaperiodate forming the oxidation products 2, 4 and 6, respectively.The (1)H- and (13)C-nmr-spectra of 4 as well as those of 2 are complex due to the existence of rotameric isomers at room temperature.

Photochemical decomposition of phenazone derivatives. Part 7: Mechanism of decomposition in aqueous solutions

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