beta-nitropropionic acid

β-Nitropropionic acid (3-nitropropanoic acid, BPA, 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 widely 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.

β-Nitropropionic acid
Names
Preferred IUPAC name
3-Nitropropanoic acid
Other names
3-Nitropropionic acid; β-Nitropropanoic acid; BPA; 3-NPA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.276
PubChem CID
UNII
  • 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
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), which can give a further rise under global warming conditions. Fungi of the genus Arthrinium are known to produce 3-nitropropanoic acid.

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.

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