59875-58-0

Basic information

• Product Name: 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• Synonyms: 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate;2,6-Dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 2-[Methyl(phenylmethyl)amino]ethyl Ester Hydrochloride;Dehydro Nicardipine Hydrochloride;Dehydro Nicardipine (Freebase);Nicardipine USP Pyridine Analog (as dihydrochloride)
• CAS NO: 59875-58-0
• Molecular Formula: C₂₆H₂₇N₃O₆
• Molecular Weight: 477.51
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 59875-58-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 154-156°C
• Boiling Point: 583.1°C at 760 mmHg
• Flash Point: 306.4°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 1.39E-13mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate(59875-58-0)
• EPA Substance Registry System: 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate(59875-58-0)

Safety Data

• Hazardous Substances Data: 59875-58-0(Hazardous Substances Data)

Usage

Description

2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate is a complex organic compound with a molecular structure that features a pyridine ring, a nitrophenyl group, and an N-benzyl-N-methylaminoethyl methyl group. It is characterized by its pale yellow solid appearance and is a pyridine metabolite of Nicardipine, which is a dihydropyridine calcium channel blocker.

Uses

Used in Pharmaceutical Applications:
2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate is used as an active pharmaceutical ingredient (API) for the development of drugs targeting cardiovascular conditions. Its role as a metabolite of Nicardipine indicates its potential in antianginal and antihypertensive therapies, helping to manage and treat conditions such as angina and hypertension.
Used in Neuroprotective Applications:
In the field of neuroresearch, 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate is used as a neuroprotective agent. It contributes to the development of therapies aimed at protecting the nervous system and preserving brain function, which can be beneficial in treating various neurological disorders and conditions.
Used in Phototodegradation Studies:
As a phototodegradation product of Nicardipine, this compound is also utilized in research studies to understand the degradation processes of pharmaceuticals under light exposure. This knowledge can be crucial in optimizing drug stability and shelf life, as well as in the development of new drugs with improved photostability.
Used in Chemical Research:
2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate serves as a valuable compound in chemical research, particularly in the synthesis of new molecules and the study of reaction mechanisms involving pyridine and nitrophenyl groups. Its unique structure makes it a useful building block for the development of novel chemical entities with potential applications in various industries.

InChI:InChI=1/C26H27N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15H,13-14,16H2,1-4H3

Upstream product

• 55985-32-5 Nicardipine 

Downstream Products

• 59875-60-4 methyl 2-(N-methylamino)ethyl 4-(m-aminophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate 

Relevant articles and documents

Intramolecular electron transfer in the photochemistry of some nitrophenyldihydropyridines

4-Phenyl-1,4-dihydropyridine-3,5-dicarboxylates contain two π chromophores separated by an sp3 carbon. The lowest singlet is localized on the dihydropyridine moiety (1PyH2-Ph) and emits a blue fluorescence (with close to unitary efficiency in glass at 77 K). In 3-nitrophenyl derivatives (PyH2-PhNO2, some of which are photolabile drugs) the fluorescence is completely quenched. Reasonably, this is due to intramolecular electron transfer between the close-lying donor and acceptor moieties to give the charge-separated species (PyH2 .+-PhNO2.-). In EPA glass at 77 K, back-electron transfer gives the dihydropyridine-localized triplet ( 3PyH2-PhNO2), which emits a yellow phosphorescence. In solution, deprotonation from the radical cation on the dihydropyridine moiety initiates rearomatization, finally giving Py-PhNO 2 with low quantum yield (5 × 10-4 to 5 × 10-3, increasing up to 0.013 by irradiation at 254 nm, where direct excitation of the nitrophenyl chromophore contributes). In the presence of triethylamine, the reaction changes to neat reduction of the nitro group. When a tethered alkylamino group is present, oxidative degradation of that moiety occurs, again via an electron-transfer intramolecular process. This has been found with the drug nicardipine, where photodegration is more efficient (Φ 0.02 to 0.1). Donor-acceptor dyads of this type, easily available through the Hantzsch synthesis, may be useful for building new photoinduced electron-transfer systems.

Pyridyl compounds and pharmaceutical compositions containing them

The present invention is concerned with new pyridine double esters of formula (I), their acids, and pharmaceutically acceptable salts. These compounds can be obtained by oxydation of the corresponding 1,4-dihydropyridines, and they are useful as cardioprotective agents in pharmaceutical compositions.

Synthesis of the metabolites of 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride (nicardipine hydrochloride, YC-93)

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