3-Nitropropionic acid

3-Nitropropionic acid (3-NPA) is a mycotoxin, a potent mitochondrial inhibitor,^[1] 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,^[2] coconuts^[3] and some traditional Chinese medicines.^[4]

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 Y
3D model (JSmol)	Interactive image
ChemSpider	1615
ECHA InfoCard	100.007.276
PubChem CID	1678
UNII	QY4L0FOX0D Y
CompTox Dashboard (EPA)	DTXSID1020982
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

It can be caused by extreme weather, stressed crop growth conditions, as well as storage conditions (like moisture),^[5] which can give a further rise under global warming conditions.^[6] Fungi of the genus Arthrinium are known to produce 3-nitropropanoic acid.^[7]

Fatal 3-NPA poisoning as a result of drinking coconut water has been reported in a case where a pre-prepared coconut had been stored at room temperature for a month, instead of being refrigerated.^[8]

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, exerted preventive effects on all alterations elicited by the toxin, like mitochondrial dysfunction and lipid peroxidation, by activation of the CB1 receptor.^[9]