3-Nitropropionic acid

β-Nitropropionic acid
Names
	Preferred IUPAC name 3-Nitropropanoic acid
	Other names 3-Nitropropionic acid; β-Nitropropanoic acid; BPA; 3-NPA
Identifiers
CAS Number	504-88-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	1615;
ECHA InfoCard	100.007.276
PubChem CID	1678;
UNII	QY4L0FOX0D ;
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

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

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]

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.^[8]

References

^ Roberts, Toby John (2004). "3-Nitropropionic Acid Model of Metabolic Stress: Assessment by Magnetic Resonance Imaging". Stroke Genomics. 104: 203–220. doi:10.1385/1-59259-836-6:203. ISBN 1-59259-836-6. PMID 15454669.
^ Hocking, Ailsa D.; Pitt, John I.; Samson, Robert A.; Thrane, Ulf (29 August 2006). Advances in Food Mycology. ISBN 9780387283913.
^ Birkelund, T.; Johansen, R. F.; Illum, D. G.; Dyrskog, S. E.; Østergaard, J. A.; Falconer, T. M.; Andersen, C.; Fridholm, H.; Overballe-Petersen, S.; Jensen, J. S. (2021). "Fatal 3-Nitropropionic Acid Poisoning after Consuming Coconut Water". Emerging Infectious Diseases. 27 (1): 278–280. doi:10.3201/eid2701.202222. PMC 7774558. PMID 33350928.
^ Wang, X.P.; Yang, R.M. (2003). "Movement Disorders Possibly Induced by Traditional Chinese Herbs". European Neurology. 50 (3): 153–159. doi:10.1159/000073056. PMID 14530621. S2CID 43878555.
^ 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): e0147996. Bibcode:2016PLoSO..1147996N. doi:10.1371/journal.pone.0147996. ISSN 1932-6203. PMC 4734676. PMID 26829324.
^ Wei, D. L.; Chang, S. C.; Lin, S. C.; Doong, M. L.; Jong, S. C. (1994). "Production of 3-nitropropionic acid by Arthrinium species". Current Microbiology (USA). 28: 1–5. doi:10.1007/BF01575978. ISSN 0343-8651. S2CID 41489212.
^ 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.

References

Further reading