3-Nitropropionic acid

Chemical Properties

gold crystalline solid

Uses

antineoplastic

Uses

3-Nitropropionic acid has been used:

• to generate multiple system atropy-parkinsoniam (MSA-P) model in rat to evaluate its effect on embryonic striatal and mesencephalic grafts
• to inject into the nigrostriatal dopaminergic pathway in rats in order to examine its specific effects on the dopamine system
• as succinate dehydrogenase (SDH) inhibitor for LUHMES neurons and cell lines

Definition

ChEBI: 3-nitropropanoic acid is a C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group. It has a role as a neurotoxin, an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor, an antimycobacterial drug and a mycotoxin. It is functionally related to a propionic acid. It is a conjugate acid of a 3-nitropropanoate. It is a tautomer of a 3-aci-nitropropanoic acid.

General Description

Golden crystals (from chloroform).

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.