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Ball and stick model of nitroxyl
CAS number 14332-28-6
PubChem 945
ChemSpider 920 YesY
MeSH Nitroxyl
Jmol-3D images Image 1
Molecular formula HNO
Molar mass 31.01 g mol−1
log P 0.74
Molecular shape Dihedral
heat capacity
33.88 J K-1 mol-1
Std molar
220.91 J K-1 mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Nitroxyl is the common chemical name for HNO, being azanone its IUPAC name.[1] It is well known in the gas phase.[2] In aqueous solution it acts as an acid with the conjugate base NO, (pKa = 11.4).[3] NO is the reduced form of nitric oxide (NO) and is isoelectronic with dioxygen. Nitroxyl can be formed as a reaction intermediate.
Nitroxyl is very reactive towards nucleophiles (especially thiols) and quickly dimerizes to hyponitrous acid, H2N2O2, which is then dehydrated to nitrous oxide N2O. Therefore, HNO is generally prepared in situ for example with the compounds such as Angeli’s salt (Na2N2O3) and Piloty’s acid (PhSO2NHOH) when it is needed.

Nitroxyl shows potential in the treatment of heart failure and ongoing research is focused on finding new nitroxyl donors. In one study [4] such donor is prepared by organic oxidation of cyclohexanone oxime with lead tetraacetate to 1-nitrosocyclohexyl acetate:

Nitrosocyclohexyl acetate

This compound can be hydrolyzed under basic conditions in a phosphate buffer to nitroxyl HNO, acetic acid and cyclohexanone.

Other studies that have been conducted on HNO precursors include those from Nagasawa et al.[5] in which Piloty's acid is derivatized and produces HNO upon thermal decomposition. Other notable studies on the production of HNO come from Toscano et al.[6] in which cycloadducts of acyl nitroso species (which are known to decompose via hydrolysis to HNO and acyl acid) are synthesized. Upon photolysis these compounds release the acyl nitroso species which then further decomposes.


  1. ^ Nitroxyl (azanone) trapping by metalloporphyrinsDoctorovich, F., Bikiel, D., Pellegrino, J., Suárez, S.A., Larsen, A., Martí, M.A.2011Coordination Chemistry Reviews255(23-24), pp. 2764-2784
  2. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0080379419. 
  3. ^ Egon Wiberg, Arnold Frederick Holleman (2001) Inorganic Chemistry, Elsevier ISBN 0-12-352651-5
  4. ^ Hydrolysis of Acyloxy Nitroso Compounds Yields Nitroxyl (HNO) Xin Sha, T. Scott Isbell, Rakesh P. Patel, Cynthia S. Day, and S. Bruce King J. Am. Chem. Soc.; 2006; 128(30) pp 9687 - 9692; (Article) doi: 10.1021/ja062365a
  5. ^ Prodrugs of Nitroxyl as Potential Aldehyde Dehydrogenase Inhibitors vis-a-vis Vascular Smooth Muscle Relaxants Nagasawa, H. T.; Kawle, S. P.; Elberling, J. A.; DeMaster, E. G.; Fukuto, J. M. J. Med. Chem., 38, 1865-1871. doi:10.1021/jm00011a005
  6. ^ Cohen, A. D.; Zeng, B.-B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.doi:10.1021/ja028978e

Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Nitroxyl — Please support Wikipedia.
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DocCheck News

DocCheck News
Wed, 16 Jul 2014 06:18:45 -0700

Bessere Durchblutung, ein niedriger Blutdruck und ein kräftiges Herz – diese Effekte wiesen Wissenschaftler nun bei der Erforschung des bisher wenig beachteten Wirkstoffes Nitroxyl nach. Gleichzeitig zeigten sie dessen Grenzen auf: Nitroxyl kann auch ...
PR Newswire (press release)
Thu, 20 Nov 2014 06:15:00 -0800

Nitroxyl, the chemical name for HNO, has been studied for its potential as a treatment for heart failure; it acts to dilate blood vessels and works directly on the heart through a unique mechanism to enhance both systolic and diastolic cardiac function.
PR Newswire (press release)
Wed, 18 Sep 2013 11:43:26 -0700

18, 2013 /PRNewswire-iReach/ -- Nitro Solution, a website that offers high quality and all-natural nitric oxide supplements, has just launched its brand new and user-friendly site. In addition to featuring the safe and innovative supplement called ...
Mon, 28 Jul 2014 06:07:30 -0700

Nitroxyl, the chemical name for HNO, has been studied for its potential as a treatment for heart failure. HNO dilates blood vessels and acts directly on the heart through a unique mechanism to safely enhance both systolic and diastolic function ...
Tue, 16 Sep 2014 11:00:33 -0700

CXL-1036, like other experimental compounds under development at Cardioxyl, is a prodrug that releases HNO in the bloodstream following administration. Nitroxyl, the chemical name for HNO, has been studied for its potential as a treatment for heart ...


Wed, 30 Apr 2014 04:50:08 -0700

New method for detecting nitroxyl will boost cardiac drug research. Jul 06, 2009. Wake Forest University scientists have developed a new research tool in the pursuit of heart medications based on the compound nitroxyl by identifying unique chemical ...
UC Los Angeles
Fri, 28 Feb 2014 00:26:15 -0800

Both work synergistically to catalyze the production of nitroxyl, which can be used inside the blood like nitric oxide, although it contains one less electron. Nitroxyl has been reported as being analogous to nitric oxide in its clot-preventing ...
Tue, 18 Feb 2014 05:30:06 -0800

They propose coating implants with a catalyst that uses the patient's own blood to make an anticoagulant called nitroxyl. The coating catalyses – speeds up without participating in – two reactions in the blood near the implant. The catalysts are ...

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