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Compound Information

Compound Name: (Z)-1-{N-Methyl-N-[6-(N-methylammoniohexyl)amino]}diazen-1-ium-1,2-diolate

Compound

Figure: MAHMA/NO (also NOC-9) Structure

  1. Category Information
  2. Nickname: MAHMA/NO (also NOC-9)
  3. CAS Registry Number: 146724-86-9
  4. Molecular Formula: C8H20N4O2
  5. Molecular Weight: 204
  6. Half-life at pH 7.4 and 37oC: 1 min
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: In base
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    250

    7.3
  10. X-Ray Crystallographic Data:
  11. Special Comments: A commercially available reagent for producing reliable fluxes of NO in aqueous solutions or culture media with a short half-life (about 1 min). This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
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
BiologicalAntioxidant Korytowski, W.; Zareba, M.; Girotti, A. W. Inhibition of Free Radical-Mediated Cholesterol Peroxidation by Diazeniumdiolate-Derived Nitric Oxide: Effect of Release Rate on Mechanism of Action in a Membrane System. Chem. Res. Toxicol. 2000, 13, 1265-1274. Pubmed Abstract
BiologicalAntioxidant Seccia, M.; Perugini, C.; Albano, E.; Bellomo, G. Inhibition of Cu2+-Induced LDL Oxidation by Nitric Oxide: a Study Using Donors with Different Half-Time of NO Release. Biochem. Biophys. Res. Commun. 1996, 220, 306-309. Pubmed Abstract
BiologicalAntiplatelet Mowery, K. A.; Schoenfisch, M. H.; Baliga, N.; Wahr, J. A.; Meyerhoff, M. E. More biocompatible electrochemical sensors using nitric oxide release polymers. Electroanalysis 1999, 11, 681-686.
BiologicalAntiplatelet Annich, G. M.; Meinhardt, J. P.; Mowery, K. A.; Ashton, B. A.; Merz, S. I.; Hirschl, R. B.; Meyerhoff, M. E.; Bartlett, R. H. Reduced platelet activation and thrombosis in extracorporeal circuits coated with nitric oxide release polymers. Crit. Care Med. 2000, 28, 915-920. Pubmed Abstract
BiologicalErectile Function Champion, H. C.; Bivalacqua, T. J.; Wang, R.; Kadowitz, P. J.; Keefer, L. K.; Saavedra, J. E.; Hrabie, J. A.; Doherty, P. C.; Hellstrom, W. J. G. Induction of penile erection by intracavernosal and transurethral administration of novel nitric oxide donors in the cat. J. Urol. 1999, 161, 2013-2019. Pubmed Abstract
Chemical  Hrabie, J. A.; Klose, J. R.; Wink, D. A.; Keefer, L. K. New nitric oxide-releasing zwitterions derived from polyamines. J. Org. Chem. 1993, 58, 1472-1476.
Chemical  Keefer, L. K.; Nims, R. W.; Davies, K. M.; Wink, D. A. "NONOates" (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: Convenient nitric oxide dosage forms. Methods Enzymol. 1996, 268, 281-293. Pubmed Abstract
Chemical  Davies, K. M.; Wink, D. A.; Saavedra, J. E.; Keefer, L. K. Chemistry of the diazeniumdiolates. 2. Kinetics and mechanisms of dissociation in aqueous solution. J. Am. Chem. Soc. 2001, 123, 5473-5481. Pubmed Abstract
Patent  Keefer, L. K.; Hrabie, J. A. Complexes of nitric oxide with polyamines. U.S. Patent 5,155,137, October 13, 1992. Patent 5155137 Full Text
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