Furoxan (1,2,5-oxadiazole 2-oxide) is a

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

of the

isoxazole Isoxazole is an electron-rich azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the Valence (chemistry), univalent functional group derived from isoxazole. Occurrence Isoxazole ri ...

family and an

amine oxide In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that has the chemical formula . It contains a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substitue ...

derivative of

furazan Furazan, or 1,2,5-oxadiazole, is a heterocyclic aromatic organic compound consisting of a five-atom ring containing 1 oxygen and 2 nitrogen atoms. The furazan ring system is also found in the steroid furazabol. Furazan and its derivatives are ob ...

. It is a

nitric oxide Nitric oxide (nitrogen oxide, nitrogen monooxide, or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes den ...

donor. As such, furoxan and its derivatives, such as ipramidil, are being actively studied as potential new

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

s and insensitive high density explosives (

4,4’-dinitro-3,3’-diazenofuroxan 4,4’-Dinitro-3,3’-diazenofuroxan (DDF) is a powerful experimental high explosive, with performance comparable to that of other high-density high-explosives such as octanitrocubane. It is synthesised by oxidative coupling of 4-amino-3-(azidoca ...

). Furoxanes can be formed by dimerization of

nitrile oxide In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

References

Amine oxides Oxadiazoles {{heterocyclic-stub