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).
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.
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.
- Roberts, Toby John (2004). "3-Nitropropionic Acid Model of Metabolic Stress: Assessment by Magnetic Resonance Imaging". Stroke Genomics. 104: 203. doi:10.1385/1-59259-836-6:203. ISBN 1-59259-836-6.
- Advances in Food Mycology
- Wang, X.P.; Yang, R.M. (2003). "Movement Disorders Possibly Induced by Traditional Chinese Herbs". European Neurology. 50 (3): 153. doi:10.1159/000073056. PMID 14530621.
- Jensen, Ole (Jun 13, 2016). "Management of mycotoxin risk in pig production" (PDF). Powerpoint by Ole Jensen.
- Norbäck, Dan; Hashim, Jamal Hisham; Cai, Gui-Hong; Hashim, Zailina; Ali, Faridah; Bloom, Erica; Larsson, Lennart (2016-02-01). "Rhinitis, Ocular, Throat and Dermal Symptoms, Headache and Tiredness among Students in Schools from Johor Bahru, Malaysia: Associations with Fungal DNA and Mycotoxins in Classroom Dust". PLoS ONE. 11 (2). doi:10.1371/journal.pone.0147996. ISSN 1932-6203. PMC 4734676. PMID 26829324.
- Maya-López, Marisol; Colín-González, Ana Laura; Aguilera, Gabriela; de Lima, María Eduarda; Colpo-Ceolin, Ana; Rangel-López, Edgar; Villeda-Hernández, Juana; Rembao-Bojórquez, Daniel; Túnez, Isaac (2017-02-15). "Neuroprotective effect of WIN55,212-2 against 3-nitropropionic acid-induced toxicity in the rat brain: involvement of CB1 and NMDA receptors". American Journal of Translational Research. 9 (2): 261–274. ISSN 1943-8141. PMC 5340665. PMID 28337258.