3-Nitropropionic acid

β-Nitropropionic acid

Names
Preferred IUPAC name 3-Nitropropanoic acid
Other names 3-NPA β-Nitropropionic acid Hiptagenic acid Bovinocidin
Identifiers
CAS Number	504-88-1 checkY
3D model (JSmol)	Interactive image
ChemSpider	1615
ECHA InfoCard
E number
PubChem CID	1678
UNII	QY4L0FOX0D checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C3H5NO4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6) Key: WBLZUCOIBUDNBV-UHFFFAOYSA-N
SMILES C(C[N+](=O)[O-])C(=O)O
Properties
Chemical formula	C3H5NO4
Molar mass	119.076 g·mol−1
Melting point	65–67 °C (149–153 °F; 338–340 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Nitropropionic acid (3-NPA) is a mycotoxin, a potent mitochondrial inhibitor, which is toxic to humans. It is produced by a number of fungi, and may be found in food such as in sugar cane as well as Japanese fungally fermented staples, including miso, soy sauce, katsuobushi, coconuts and some traditional Chinese medicines.

It can be caused by extreme weather, stressed crop growth conditions, as well as storage conditions (like moisture), which can give a further rise under global warming conditions. Fungi of the genus Arthrinium are known to produce 3-nitropropanoic acid.

Fatal 3-NPA poisoning as a result of drinking coconut water has been reported in a case where a coconut had been processed and stored at room temperature for a month, instead of being refrigerated.

It is found that 3-nitropropionic acid is a mitochondrial toxin and produces striatal alterations in rats similar to those observed in the brain of Huntington's disease patients, and administration of the cannabinoid receptor agonist WIN55212-2 to rats for six consecutive days, before the 3-NPA injection, displayed preventative effects on all alterations elicited by the toxin, like mitochondrial dysfunction and lipid peroxidation, by activation of the CB1 receptor.