504-88-1

Usage

Uses

Used in Pharmaceutical Industry:
3-Nitropropionic acid is used as an antineoplastic agent for its potential role in cancer treatment. It has been found to have effects on various types of cancer, making it a valuable compound for pharmaceutical research and development.
Used in Neuroscience Research:
3-Nitropropionic acid is used as a tool to generate multiple system atrophy-parkinsonism (MSA-P) models in rats. This helps researchers evaluate the effects of 3-NPA on embryonic striatal and mesencephalic grafts, which are crucial for understanding the underlying mechanisms of neurodegenerative diseases.
Used in Neurochemical Studies:
3-Nitropropionic acid is used to inject into the nigrostriatal dopaminergic pathway in rats. This application allows researchers to examine the specific effects of 3-NPA on the dopamine system, which is essential for studying the role of dopamine in various neurological conditions.
Used in Cellular and Molecular Biology:
3-Nitropropionic acid serves as a succinate dehydrogenase (SDH) inhibitor for LUHMES neurons and cell lines. This application is vital for understanding the role of SDH in cellular respiration and energy production, as well as its potential implications in various diseases and disorders.

Air & Water Reactions

Water soluble.

Reactivity Profile

3-NITROPROPIONIC ACID is incompatible with bases, oxidizing agents and reducing agents.

Fire Hazard

Flash point data for 3-NITROPROPIONIC ACID are not available; however, 3-NITROPROPIONIC ACID is probably combustible.

Biological Activity

3-nitropropionic acid is an irreversible inhibitor of mitochondrial respiratory complex ii (succinate dehydrogenase), which impairs cellular energy metabolism by inhibiting succinate dehydrogenase and reducing atp production. also, 3-nitropropionic acid can cause the generation and release of reactive oxygen species (ros) from mitochondria (the main source of cellular oxidative stress), mitochondrial dna damage, as well as loss of mitochondrial function.1. huang ls, sun g, cobessi d, et al. 3-nitropropionic acid is a suicide inhibitor of mitochondrial respiration that, upon oxidation by complex ii, forms a covalent adduct with a catalytic base arginine in the active site of the enzyme. journal of biological chemistry, 2006, 281(9): 5965-5972.2. zhang jq, shen m, zhu cc, et al. 3-nitropropionic acid induces ovarian oxidative stress and impairs follicle in mouse. plos one, 2014, 9(2): e86589.3. mandavilli bs, boldogh i, van houten b. 3-nitropropionic acid-induced hydrogen peroxide, mitochondrial dna damage, and cell death are attenuated by bcl-2 overexpression in pc12 cells. brain research. molecular brain research, 2005, 133(2): 215-223.

Biochem/physiol Actions

Excitotoxin shown to cause brain lesions similar to those of Huntington′s disease.

Safety Profile

Poison by intravenous andintraperitoneal routes. Questionable carcinogen withexperimental neoplastigenic data. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

InChI:InChI=1/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)/p-1

Upstream product

• 57-57-8 β-Propiolactone 
• 802294-64-0 propionic acid 
• 70683-11-3 diethyl (RS)-nitrosuccinate 
• 7697-37-2 nitric acid 
• 141-76-4 3-iodopropanoic acid 
• 58657-26-4 3-nitropropionaldehyde 
• 590-92-1 3-Bromopropionic acid 
• 930-21-2 2-azetidinone 

Downstream Products

• 75640-08-3 2,3-bis-phenylhydrazono-propionic acid 
• 20497-95-4 methyl 3-nitropropionate 
• 690-39-1 1,1,1,3,3,3-hexafluoropropane 
• 25182-84-7 3-nitropropan-1-ol 
• 27850-46-0 phenyl 3-nitropropanoate 
• 107-95-9 3-amino propanoic acid 
• 62171-55-5 3-Nitro-selenopropionic acid Se-p-tolyl ester 
• 3590-37-2 ethyl 3-nitropropanoate 
• 1333341-12-0 C₁₇H₁₈N₂O₃ 
• 51833-96-6 C₉H₉BrN₂O₃ 
• 51833-89-7 C₉H₉FN₂O₃ 
• 51833-95-5 C₁₁H₁₄N₂O₃ 
• 1333341-15-3 C₁₄H₁₆F₃N₃O₃ 
• 51833-79-5 C₉H₁₀N₂O₃ 

Relevant academic research and scientific papers

Pyrrolo[2,1-c][1,4]naphthodiazepine Linked Piperazine Compounds and a Process for the Preparation Thereof

The present invention provides a compound of general formula A, useful as potential antitumour agents against five human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]naphthodiazepine linked substituted piperazine conjugates attached through different alkane spacers of general formula A. (Formula I) General formula A. Where R=R′=(Formula II). n=1-9 and R″=methyl, ethyl, acetyl, benzyl, piperinoyl, 4-fluorophenyl, 4-chlorophenyl, 4-methoxyphenyl, pyridyl, pyrimidyl

Oxidative cleavage of lactams in water using dioxiranes: An expedient and environmentally-safe route to ω-nitro acids

By taking advantage of the appreciable stability of dioxiranes in water, a safe yet efficient route to ω-nitro acids by oxidation of lactams of various ring sizes under mild conditions has been reported. In essentially all the cases examined, reactions proceed selectively to afford products in remarkably high yields (up to 99%) and with high purity (94-99%). Also, an interesting example of higher reaction selectivity in water than in organic solvent (acetonitrile) is discussed.

PYRROLO [2,1-C]1,4]NAPHTHODIAZEPINE LINKED PIPERAZINE COMPOUNDS AND A PROCESS FOR THE PREPARATION THEREOF

The present invention provides a compound of general formula A, useful as potential antitumour agents against five human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]naphthodiazepine linked substituted piperazine conjugates attached through different alkane spacers of general formula A. (Formula I) General formula A. Where R= R'= (Formula II). n=1-9 and R''= methyl, ethyl, acetyl, benzyl, piperinoyl, 4-fluorophenyl, 4-chlorophenyl, 4-methoxyphenyl, pyridyl, pyrimidyl

NUCLEIC ACID BINDING COMPOUNDS, METHODS OF MAKING, AND USE THEREOF

The present invention relates to oligomer compounds, including dimers and trimers, formed by a disulfide, sulfinyl thio, olefin or hydrocarbon bond, or a hydrazone exchange bond between two or more monomers. Methods of making the monomers and the oligomers is also disclosed. Use of the compounds for inhibiting the activity of target RNA molecules, particularly those having a secondary structure that include a stem or stem-loop formation. Dimer compounds capable of inhibiting the activity of an HIV-1 RNA frameshifting stem-loop and a (CUG)n expanded repeat stem- loop are disclosed, as are methods of treating diseases associated with these target RNA molecules.

Synthesis of 3-nitropropanol homologues

Several high yielding routes to oxygenated nitropropanes have been developed that include a palladium catalyzed nitro allylation of allylic carbonates, nitration of brominated compounds and a nitro aldol condensation/hydrogenation sequence. Georg Thieme Verlag Stuttgart.

Arylmethyl radicals from arylmethoxybromodiazirines

(Chemical Equation Presented) Photolytic decompositions of 3-arylmethoxy-3-bromodiazirines afford arylmethyl radicals by homolyses of the diazirines' excited states.

An expeditious synthesis of 3-nitropropionic acid and its ethyl and methyl esters

The synthesis to 3-nitropropionic acid 1 was easily accomplished, in two steps, from commercially available acrolein in 60% yield. The ethyl and methyl esters of 1 were also obtained.

The Fungal Biosynthesos of 3-Nitropropionic Acid: Is the Decarboxylation of L-Nitrosuccinate an Enzymatic Reaction?

In vitro enzymatic hydrolysis of diethyl (RS)-nitrosuccinate 2c by pig liver esterase at pH 7.8 affords 3-nitropropionic acid 1 indicating that the decarboxylation of (RS)-nitrosuccinate 2b is spontaneous under physiological conditions.In the in vivo synthesis of 1 from L-aspartate by cells of Penicillium atrovenetum, which involves oxidation of L-aspartate to nitrosuccinic acid, the decarboxylation of the nitrosuccinate may not require a specific biological catalyst.