beta-Nitropropionic acid (3-nitropropanoic acid, BPA, 3-NPA) is a mycotoxin, a potent mitochondrial inhibitor, toxic to humans. It is produced by a number of fungi, and found widely in food, in sugar cane, as well as Japanese fungally fermented staples miso, soy sauce, katsuobushi, and some traditional Chinese medicines.
3-Nitropropionic acid; β-Nitropropanoic acid; BPA; 3-NPA
3D model (JSmol)
CompTox Dashboard (EPA)
|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).
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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