Furoxan

Furoxan
Names
	IUPAC name 1,2,5-Oxadiazole 2-oxide
	Other names Furazan N-oxide; Furazan 2-oxide
Identifiers
CAS Number	497-27-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	4482868 ;
MeSH	C528141
PubChem CID	5325374;
CompTox Dashboard (EPA)	DTXSID80416009 ;
	InChI InChI=1S/C2H2N2O2/c5-4-2-1-3-6-4/h1-2H Key: KCMCIQNPQUSQKQ-UHFFFAOYSA-N ; InChI=1/C2H2N2O2/c5-4-2-1-3-6-4/h1-2H Key: KCMCIQNPQUSQKQ-UHFFFAOYAH;
	SMILES [O-][N+]1=CC=NO1;
Properties
Chemical formula	C2H2N2O2
Molar mass	86.050 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Furoxan or 1,2,5-oxadiazole 2-oxide is a heterocycle of the isoxazole family and an amine oxide derivative of furazan. It is a nitric oxide donor.[1] As such, furoxan and its derivatives are actively researched as potential new drugs and insensitive high density explosives. Ipramidil is an example.

Furoxanes can be formed by dimerization of nitrile oxides.

References

Clara Cena; Massimo Bertinaria; Donatella Boschi; Marta Giorgis; Alberto Gasco (2006). "Use of the furoxan (1,2,5-oxadiazole 2-oxide) system in the design of new NO-donor antioxidant hybrids" (PDF). Arkivoc (HL-1787GR): 301–309.

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[1] Clara Cena; Massimo Bertinaria; Donatella Boschi; Marta Giorgis; Alberto Gasco (2006). "Use of the furoxan (1,2,5-oxadiazole 2-oxide) system in the design of new NO-donor antioxidant hybrids" (PDF). Arkivoc (HL-1787GR): 301–309.