Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C3H5NO4 |
| Molecular Weight | 119.0761 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC[N+]([O-])=O
InChI
InChIKey=WBLZUCOIBUDNBV-UHFFFAOYSA-N
InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)
| Molecular Formula | C3H5NO4 |
| Molecular Weight | 119.0761 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
3-Nitropropionic Acid (aka beta-Nitropropionic acid) is a mycotoxin and potent mitochondrial inhibitor. It is produced by a number of fungi and found widely in food, in sugar cane, and in Japanese fungally fermented staples such as miso, soy sauce, and katsuobushi. beta-Nitropropionic acid is also present in some traditional Chinese medicines. beta-Nitropropionic Acid can be systematically administered to produce localized striatal neurodegeneration mimicking the pathological features of Huntington's disease.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Neuropathological and behavioral changes induced by various treatment paradigms with MPTP and 3-nitropropionic acid in mice: towards a model of striatonigral degeneration (multiple system atrophy). | 2003-08 |
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| Influence of cytosolic and mitochondrial Ca2+, ATP, mitochondrial membrane potential, and calpain activity on the mechanism of neuron death induced by 3-nitropropionic acid. | 2003-07 |
|
| GFAP knockout mice have increased levels of GDNF that protect striatal neurons from metabolic and excitotoxic insults. | 2003-06-30 |
|
| Essential role of complex II of the respiratory chain in hypoxia-induced ROS generation in the pulmonary vasculature. | 2003-05 |
|
| Neuroprotective effects of (+/-)-huprine Y on in vitro and in vivo models of excitoxicity damage. | 2003-04 |
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| Quantitative on-line monitoring of hippocampus glucose and lactate metabolism in organotypic cultures using biosensor technology. | 2003-04 |
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| Opening of mitochondrial ATP-sensitive potassium channels is a trigger of 3-nitropropionic acid-induced tolerance to transient focal cerebral ischemia in rats. | 2003-04 |
|
| Differential regulation of 5' splice variants of the glutamate transporter EAAT2 in an in vivo model of chemical hypoxia induced by 3-nitropropionic acid. | 2003-03-15 |
|
| Specific progressive cAMP reduction implicates energy deficit in presymptomatic Huntington's disease knock-in mice. | 2003-03-01 |
|
| Microglial activation and cell death induced by the mitochondrial toxin 3-nitropropionic acid: in vitro and in vivo studies. | 2003-03 |
|
| Compounds acting at the endocannabinoid and/or endovanilloid systems reduce hyperkinesia in a rat model of Huntington's disease. | 2003-03 |
|
| Polycyclic phenols, estrogens and neuroprotection: a proposed mitochondrial mechanism. | 2003-01-25 |
|
| Mitochondrial complex inhibitors preferentially damage substantia nigra dopamine neurons in rat brain slices. | 2003-01 |
|
| Dystonia is predictive of subsequent altered dopaminergic responsiveness in a chronic 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine+3-nitropropionic acid model of striatonigral degeneration in monkeys. | 2002-12-19 |
|
| Estrogen blocks 3-nitropropionic acid-induced Ca2+i increase and cell damage in cultured rat cerebral endothelial cells. | 2002-11-22 |
|
| Calcium-dependent cleavage of endogenous wild-type huntingtin in primary cortical neurons. | 2002-10-18 |
|
| The adenosine A1 receptor agonist adenosine amine congener exerts a neuroprotective effect against the development of striatal lesions and motor impairments in the 3-nitropropionic acid model of neurotoxicity. | 2002-10-15 |
|
| 1-Methyl-4-phenylpyridinium and 3-nitropropionic acid diminish cortical synthesis of kynurenic acid via interference with kynurenine aminotransferases in rats. | 2002-09-13 |
|
| Analysis of mitochondrial free radical generation in animal models of neuronal disease. | 2002-09-01 |
|
| Effect of 3-nitropropionic acid on kynurenine aminotransferase in the rat brain. | 2002-09 |
|
| The effect of aging on p38 signaling pathway activity in the mouse liver and in response to ROS generated by 3-nitropropionic acid. | 2002-09 |
|
| 3-Nitropropionic acid induces cell death and mitochondrial dysfunction in rat corticostriatal slice cultures. | 2002-08-23 |
|
| Neuroprotection by hypoxic preconditioning requires sequential activation of vascular endothelial growth factor receptor and Akt. | 2002-08-01 |
|
| Decreased TCA cycle rate in the rat brain after acute 3-NP treatment measured by in vivo 1H-[13C] NMR spectroscopy. | 2002-08 |
|
| Striatal and cortical neurochemical changes induced by chronic metabolic compromise in the 3-nitropropionic model of Huntington's disease. | 2002-08 |
|
| Involvement of superoxide in excitotoxicity and DNA fragmentation in striatal vulnerability in mice after treatment with the mitochondrial toxin, 3-nitropropionic acid. | 2002-07 |
|
| Mice overexpressing 70-kDa heat shock protein show increased resistance to malonate and 3-nitropropionic acid. | 2002-07 |
|
| 3-Nitropropionic acid neurotoxicity in hippocampal slice cultures: developmental and regional vulnerability and dependency on glucose. | 2002-07 |
|
| beta-Amyloid neurotoxicity is exacerbated during glycolysis inhibition and mitochondrial impairment in the rat hippocampus in vivo and in isolated nerve terminals: implications for Alzheimer's disease. | 2002-07 |
|
| The differential vulnerability of striatal projection neurons in 3-nitropropionic acid-treated rats does not match that typical of adult-onset Huntington's disease. | 2002-07 |
|
| Corticostriatopallidal neuroprotection by adenovirus-mediated ciliary neurotrophic factor gene transfer in a rat model of progressive striatal degeneration. | 2002-06-01 |
|
| 3-nitropropionic acid-induced changes in bilayer fluidity in synaptosomal membranes: implications for Huntington's disease. | 2002-06 |
|
| A method to assay glyoxylate cycle inhibitors for antifungals. | 2002-06 |
|
| Dopamine transporter knock-out mice are hypersensitive to 3-nitropropionic acid-induced striatal damage. | 2002-06 |
|
| Chemical preconditioning with 3-nitropropionic acid: lack of induction of neuronal tolerance in gerbil hippocampus subjected to transient forebrain ischemia. | 2002-05 |
|
| Mitochondrial toxin inhibition of [(3)H]dopamine uptake into rat striatal synaptosomes. | 2002-04-15 |
|
| Gender-dependent hypoxic tolerance mediated via gender-specific mechanisms. | 2002-04-01 |
|
| Coenzyme Q10 as a possible treatment for neurodegenerative diseases. | 2002-04 |
|
| [Huntington disease]. | 2002-04 |
|
| Evaluation of 3-nitrotyrosine as a marker for 3-nitropropionic acid-induced oxidative stress in Lewis and Wistar rats and strain-specific whole brain spheroid cultures. | 2002-03-22 |
|
| Excitotoxic and metabolic damage to the rodent striatum: role of the P75 neurotrophin receptor and glial progenitors. | 2002-03-18 |
|
| Modulation of apoptotic regulatory proteins and early activation of cytochrome C following systemic 3-nitropropionic acid administration. | 2002-03-15 |
|
| The mitochondrial toxin 3-nitropropionic acid induces striatal neurodegeneration via a c-Jun N-terminal kinase/c-Jun module. | 2002-03-15 |
|
| Evaluation of neuronal cell death by laser scanning cytometry. | 2002-02 |
|
| Increased neuronal hypoxic tolerance induced by repetitive chemical hypoxia. | 2002 |
|
| Subacute systemic 3-nitropropionic acid intoxication induces a distinct motor disorder in adult C57Bl/6 mice: behavioural and histopathological characterisation. | 2002 |
|
| Impaired hypoxic tolerance and altered protein binding of NADH in presymptomatic APP23 transgenic mice. | 2002 |
|
| Acute and chronic alterations in calcium homeostasis in 3-nitropropionic acid-treated human NT2-N neurons. | 2002 |
|
| The mechanisms of neuronal death produced by mitochondrial toxin 3-nitropropionic acid: the roles of N-methyl-D-aspartate glutamate receptors and mitochondrial calcium overload. | 2002 |
|
| Concentrations of different sterols in the striatum and serum of 3-nitropropionic acid-treated Wistar and Lewis rats. | 2001-11 |
Patents
Sample Use Guides
To simulate the neuro-degenerative effects of Huntington's Disease adult (9months) and old (24 months) albino Wistar female rats were administered 10 mg/kg bw 3-Nitropropionic Acid twice daily by intraperitoneal injection for four days.
Route of Administration:
Intraperitoneal
Near pure cortical neuronal cell cultures were prepared from E15 Swiss-Webster, C57/Bl6J, ZnT3–/–, MT3–/–, or Wallerian degeneration-slow (Wld^s) mice. Slow toxicity was initiated after 8 days in vitro, by exposure to 100 - 1,000 M 3-Nitropropionic Acid. After 3 or 8 hours exposure of striatal/midbrain or cortical neuronal
cultures to toxic levels of 3-NP, [Zn 2+ ]_i levels are optimally increased as measured using Fluo-Zin3 fluorescence dye microscopy. The increase observed in cortical neurons is equal to, or for 3-NPA greater than, the strong ROS generators, H2O2, or ethacrynic acid.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:25:55 GMT 2025
by
admin
on
Mon Mar 31 19:25:55 GMT 2025
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| Record UNII |
QY4L0FOX0D
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| Record Status |
Validated (UNII)
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| Record Version |
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3-Nitropropionic acid
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C015392
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