50428-14-3

Usage

Uses

Used in Pharmaceutical Applications:
2,6-Ntp is used as a vasorelaxant agent for the treatment of cardiovascular diseases. It has been shown to relax contractions of the rat aortic strip induced by norepinephrine and other agonists, making it a potential candidate for the management of hypertension and other related conditions.
Used in Research and Development:
2,6-Ntp is utilized as a research compound in the study of photodegradation processes and the development of new pharmaceutical agents. Its photochemical properties and effects on vascular relaxation provide valuable insights into the design and synthesis of novel therapeutic agents with improved efficacy and safety profiles.

InChI:InChI=1/C17H16N2O5/c1-9-13(16(20)23-3)15(11-7-5-6-8-12(11)19-22)14(10(2)18-9)17(21)24-4/h5-8H,1-4H3

Upstream product

• 43114-08-5 methyl 1-(ethoxymethyl)-2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 21829-25-4 nifedipine 
• 105-45-3 acetoacetic acid methyl ester 
• 119777-23-0 C₁₇H₁₈N₂O₆*C₄₂H₇₀O₃₅ 
• 21731-17-9 methyl 3-aminocrotonate 
• 552-89-6 2-nitro-benzaldehyde 

Relevant academic research and scientific papers

Irradiated Nifedipine - a Nitroso Spin Trap

Irradiation of nifedipine yields a new nitroso spin trap which traps carbon-centred radicals and also forms relatively stable alkoxyl radical adducts.In addition, the reaction with unsaturated lipids yield highly stable covalent nitroxide radicals. - Keyw

Formation of substituted 6-hydroxy-5-oxo-5,6-dihydrobenzo[c][2,7] naphthyridine upon photochemical transformation of nifedipine

Long-term exposure of nifedipine to daylight in ethanol gives 2,2′-bis[3,5-bis(methoxycarbonyl)-2,6-dimethylpyridin-4-yl]azoxybenzene and 6-hydroxy-1-methoxycarbonyl-2,4-dimethyl-5-oxo-5,6-dihydrobenzo[c] [2,7]naphthyridine as the major products.

Newly discovered photodegradation products of nifedipine in hospital prescriptions

New photodegradation products of nifedipine (1) have been isolated. They were found in tablets dispensed in the pulverized form by hospitals. 1 decomposed concurrently into six components after storage of 30 days under exposure to normal room light. The main photoproduct was a nitroso derivative (2) and others were minor. Preparative thin-layer chromatography has been used to isolate the six photodegradation products. The chemical structures of these isolated compounds were identified or estimated by comparison with authentic samples and/or using UV, IR, 1H NMR, mass spectroscopy, melting point determination, and elementary analysis. From these analyses, it was found that 1 was converted into a cis-azoxy derivative (4), a trans-azoxy derivative (5), a N,N'-dioxide derivative (6) and a lactam derivative (7) in addition to 2 and a nitro derivative (3). Furthermore, it is proposed that 2 is mainly responsible for the formation of these new products (4-7) by photochemical condensation.

Photochemistry of 4-(2-Nitrophenyl)-1,4-dihydropyridines. Evidence for electron transfer and formation of an intermediate

New evidence about the path followed in the photochemical reaction of 4-(2-nitrophenyl)-1,4-dihydropyridines such as the drugs nifedipine (Compound 1) and nisoldipine (Compound 2) to give the corresponding nitrosophenylpyridines has been found through determination of the steady-state photochemical parameters and a comparison of the photoreactions in solution and in matrix at 90 K. Additional support is given by comparison with the isomeric 4-(3-nitrophenyl)dihydropyridine as well as with simpler derivatives, such as the corresponding 4-methyldihydropyridine. In Compounds 1 and 2, the lowest lying singlet, localized on the dihydropyridine chromophore, is deactivated by (largely exothermic) electron transfer to the nitrobenzene moiety, as evidenced by the complete quenching of the blue fluorescence observed in analogues not containing the electron-accepting group. Intramolecular proton transfer ensues in the 2-nitrophenyl derivatives with a relatively medium-independent quantum yield of ～0.3 and leads to an aromatic zwitterion, which is detected in matrix at 90 K (photoionization of this intermediate takes place in 2-methyltetrahydrofuran secondary). The intermediate is smoothly converted into the end product upon melting the glass. The 3-nitrophenyl analog, for which such a path is not available, is less reactive by about three orders of magnitude at 366 nm, although the quantum yield arrives at ～0.01 by irradiation at 254 nm in MeOH, reasonably via the nitrophenyl localized triplet.

Mediation of iron uptake and release in erythroid cells by photodegradation products of nifedipine

The effects of five Ca2+ channel antagonists on iron uptake by erythroid cells were investigated using rabbit reticulocytes and erythrocytes, and transferrin-bound iron and non-transferrin-bound iron (Fe(II)). All of the antagonists except nife

Antioxidant effects of photodegradation product of nifedipine

Recently, increasing evidence suggests that the antihypertensive drug nifedipine acts as a protective agent for endothelial cells, and that the activity is unrelated to its calcium channel blocking. Nifedipine is unstable under light and reportedly decomp

The protection of nifedipin from photodegradation due to complex formation with β-cyclodextrin

The inclusion complex β-cyclodextrin:nifedipin was prepared in solid state by coprecipitation with 1:1 mol ratio. The structure of the obtained complex and nifedipin was characterized by use of X-ray diffraction (XR), infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and differential scanning calorimetry (DSC) methods. The photodegradation of nifedipin and the β-cyclodextrin:nifedipin inclusion complex in solid state was monitored under natural daylight by infrared spectroscopy, whereby the free nifedipin degraded four to five times faster than the complexed nifedipin. The photodegradation products of both free and complexed nifedipin, formed during irradiation at 350 nm (with corresponding energy flux of 18 W m-2) were monitored by liquid chromatography during various time intervals. The speed of formation of nitroso- and nitro-phenyl derivatives by nifedipin irradiation was significantly higher than those of complexed nifedipin irradiation, which indicates its increased photostability in the inclusion complex. The effect on this property is significant because it contributes both to the improvement of the therapeutic effect of nifedipin and to the safer application thereof.

Spectrophotometric study of the photodecomposition kinetics of nifedipine

Nifedipine is a photosensitive compound. Irradiation for 4 h under a fluorescent lamp placed 30 cm from a solution of nifedipine in 95% ethanol leads to complete photo-oxidation as determined spectrophotometrically. The disappearance of the reduced form a

Nitro group photoreduction of 4-(2-nitrophenyl)- and 4-(3-nitrophenyl)-1,4- dihydropyridines

The photoprocesses of nifedipine, a 4-(2-nitrophenyl)-1,4-dihydropyridine, and nimodipine and nitrendipine, two 3-nitrophenyl Hantzsch-type analogues, were studied by steady-state and time-resolved methods. The intramolecular photoreduction of nifedipine

Photoinduced Aromatization of Dihydropyridines

The combination of tris(bipyridine)ruthenium(II)/visible light/air is found to be effective for the aromatization of many dihydropyridines. A low catalyst loading of just 0.02 mol% is required.