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Compound Information

Compound Name: 1-[N-(2-Aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate

Compound

Figure: DETA/NO (also NOC-18) Structure

  1. Category Information
  2. Nickname: DETA/NO (also NOC-18)
  3. CAS Registry Number: 146724-94-9
  4. Molecular Formula: C4H13N5O2
  5. Molecular Weight: 163
  6. Half-life at pH 7.4 and 37oC: 20 h
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: > 0.1 M Phosphate pH 7.4
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    252 in 0.01 M NaOH

    7.6
  10. X-Ray Crystallographic Data:
  11. Special Comments: Very widely used to produce steady fluxes of NO in culture media and other aqueous solutions. With its 20-h half-life, its NO generation rate after a day is about half of what it was when first dissolved. DETA/NO has shown promise in animal models of human disease as a possible treatment for such clinical disorders as cerebral vasospasm and pulmonary hypertension. This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
BiologicalAntifung McElhaney-Feser G.E.; Raulli R.E.; Cihlar R.L. Synergy of nitric oxide and azoles against Candida species in vitro. Antimicrob. Agents Chemother. 1998, 42, 2342-2346. Pubmed Abstract
BiologicalAntioxidant Goss S. P.; Hogg N.; Kalyanaraman B. The effect of nitric oxide release rates on the oxidation of human low density lipoprotein. J. Biol. Chem. 1997, 272, 21647-21653. Pubmed Abstract
BiologicalAntiparasitic Ahmed, S. F.; Oswald, I. P.; Caspar, P., Hieny; S., Keefer; L., Sher; A., James, S. L. Developmental differences determine larval susceptibility to nitric oxide-mediated killing in a murine model of vaccination against Schistosoma mansoni. Infect. Immun. 1997, 65, 219-226. Pubmed Abstract
BiologicalCytostasis Mooradian, D. L.; Hutsell, T. C.; Keefer, L. K. Nitric oxide (NO) donor molecules: effect of NO release rate on vascular smooth muscle cell proliferation in vitro. J. Cardiovasc. Pharmacol. 1995, 25, 674-678. Pubmed Abstract
BiologicalCytostasis Varu, V. N.; Ahanchi, S. S.; Hogg, M. E.; Bhikhapurwala, H. A.; Chen, A.; Popowich, D. A.; Vavra, A. K.; Martinez, J.; Jiang, Q.; Saavedra, J. E.; Hrabie, J. A.; Keefer L. K.; Kibbe, M. R. Insulinenhances the effect of nitric oxide at inhibiting neointimal hyperplasia in a ratmodel of type 1 diabetes. Am. J. Physiol.: Heart Circ. Physiol. 2010, 299 (3), H772-H779. Pubmed Abstract
BiologicalInhalational Therapy Cornfield, D. N.; Martin, E. B.; Hampl, V.; Archer, S. L. Aerosol delivery of diethylenetriamine/nitric oxide, a nitric oxide adduct, causes selective pulmonary vasodilation in perinatal lambs. J. Lab. Clin. Med. 1999, 134, 419-425. Pubmed Abstract
BiologicalMechanism of Action Vavra, A. K.; Havelka, G. E.; Martinez, J.; Lee, V. R.; Fu, B.; Jiang, Q.; Keefer, L. K.; Kibbe, M. R. Insights into the effect of nitric oxide and its metabolites nitrite and nitrate at inhibiting neointimal hyperplasia. Nitric Oxide 2011, 25 (1), 22-30. Pubmed Abstract
BiologicalNeuroprotection Zhang R.; Zhang L.; Zhang Z.; Wang Y.; Lu M.; Lapointe M.; Chopp M. A nitric oxide donor induces neurogenesis and reduces functional deficits after stroke in rats. Ann Neurol. 50, 602-611. Pubmed Abstract
BiologicalStroke Wolf, E. W.; Banerjee, A.; Soble-Smith, J.; Dohan, F. C. Jr.; White, R. P.; Robertson, J. T. Reversal of cerebral vasospasm using an intrathecally administered nitric oxide donor. J. Neurosurg. 1998, 89, 279-288. Pubmed Abstract
BiologicalVasospasm Tierney, T. S.; Clatterbuck, R. E.; Lawson, C.; Thai, Q. A.; Rhines, L. D.; Tamargo, R. J. Prevention and reversal of experimental posthemorrhagic vasospasm by the periadventitial administration of nitric oxide from a controlled-release polymer. Neurosurgery 2001, 49, 945-953. Pubmed Abstract
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