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Merck
CN

N5636

3-Nitropropionic acid

≥97% (HPLC), powder or crystals, mitochondrial complex II inhibitor

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About This Item

Linear Formula:
O2N(CH2)2CO2H
CAS Number:
504-88-1
Molecular Weight:
119.08
Beilstein:
1759889
EC Number:
208-003-0
MDL number:
MFCD00007406
UNSPSC Code:
12352200
PubChem Substance ID:
24278593
NACRES:
NA.77

Key Documents

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Product Name

3-Nitropropionic acid, ≥97%

biological source

synthetic

Quality Level

100

Assay

≥97%

form

powder or crystals

color

white to light yellow

mp

68-70 °C (lit.)

solubility

alcohol: may be light yellow 100 mg/mL

storage temp.

2-8°C

SMILES string

OC(CC[N+]([O-])=O)=O

InChI

1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)

InChI key

WBLZUCOIBUDNBV-UHFFFAOYSA-N

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Application

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

Biochem/physiol Actions

Administering 3-nitropropionic acid (3-NP) to the inner ear can stimulate sensorineural hearing loss. It serves as an irreversible inhibitor of mitochondrial complex II.
Excitotoxin shown to cause brain lesions similar to those of Huntington′s disease.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK2461
BCCJ8391
STBG3966V
STBF0866V
STBC6258V

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Mouse Models of Dystonia
Animal Models of Movement Disorders (2005)
No functional effects of embryonic neuronal grafts on motor deficits in a 3-nitropropionic acid rat model of advanced striatonigral degeneration (multiple system atrophy)
Waldner R, et al.
Neuroscience, 102(3), 581-592 (2001)
Dual loss of succinate dehydrogenase (SDH) and complex I activity is necessary to recapitulate the metabolic phenotype of SDH mutant tumors
Lorendeau D, et al.
Metabolic engineering, 43, 187-197 (2017)
Specific lesions in the extrapyramidal system of the rat brain induced by 3-nitropropionic acid (3-NPA)
Pei G and Ebendal T
Experimental Neurology, 132(1), 105-115 (1995)
The protective effect of Egb 761 against 3-nitropropionic acid-induced hearing loss: the role of sirtuin 1
Chang M Y, et al.
Clinical and Experimental Otorhinolaryngology, 11(1), 9-9 (2018)
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