Molecular structure of 3-Morpholinosydnonimine, CAS Number: 16142-27-1
3-Morpholinosydnonimine (CAS 16142-27-1)
See product citations (10)
Alternate Names:
3-Morpholinosydnonimine is also known as SIN-1.
Application:
3-Morpholinosydnonimine is a potent vasodilator that inhibits platelet aggregation and cysteine proteases.
CAS Number:
16142-27-1
Purity:
≥98%
Molecular Weight:
206.63
Molecular Formula:
C6H10N4O2•HCl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
3-Morpholinosydnonimine (SIN-1) is a metabolite of molsidomine (sc-200337) which may act to decompose spontaneously in solution in the presence of oxygen. This reaction with 3-Morpholinosydnonimine releases nitric oxide (NO) and a superoxide anion, which under physiological conditions, reacts to produce peroxynitrite. 3-Morpholinosydnonimine is a potent vasodilator, inhibitor of platelet aggregation, general cysteine protease inhibitor. 3-Morpholinosydnonimine may act to produce significant protective effects in myocardial ischemia-reperfusion. Some of the effects of 3-Morpholinosydnonimine can be attenuated by nitroglycerin-induced tolerance.
3-Morpholinosydnonimine (CAS 16142-27-1) References
- Inhibition of cysteine protease activity by NO-donors. | Ascenzi, P., et al. 2001. Curr Protein Pept Sci. 2: 137-53. PMID: 12370021
- Metallothionein attenuates 3-morpholinosydnonimine (SIN-1)-induced oxidative stress in dopaminergic neurons. | Sharma, SK. and Ebadi, M. 2003. Antioxid Redox Signal. 5: 251-64. PMID: 12880480
- Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. | Hogg, N., et al. 1992. Biochem J. 281 (Pt 2): 419-24. PMID: 1310595
- Protective effect of 1-methylated beta-carbolines against 3-morpholinosydnonimine-induced mitochondrial damage and cell viability loss in PC12 cells. | Choi, WT., et al. 2004. Neurochem Res. 29: 1807-16. PMID: 15532535
- Cardioprotection and attenuation of endothelial dysfunction by organic nitric oxide donors in myocardial ischemia-reperfusion. | Siegfried, MR., et al. 1992. J Pharmacol Exp Ther. 260: 668-75. PMID: 1738117
- The peroxynitrite donor 3-morpholinosydnonimine induces reversible changes in electrophysiological properties of neurons of the guinea-pig spinal cord. | Ashki, N., et al. 2008. Neuroscience. 156: 107-17. PMID: 18662749
- 3-morpholinosydnonimine participates in the attenuation of neointima formation via inhibition of annexin A2-mediated vascular smooth muscle cell migration. | Won, KJ., et al. 2011. Proteomics. 11: 193-201. PMID: 21204247
- The peroxynitrite donor 3-morpholinosydnonimine activates Nrf2 and the UPR leading to a cytoprotective response in endothelial cells. | Mattart, L., et al. 2012. Cell Signal. 24: 199-213. PMID: 21945407
- Nitroglycerin-induced tolerance affects multiple sites in the organic nitrate bioconversion cascade. | Henry, PJ., et al. 1989. J Pharmacol Exp Ther. 248: 762-8. PMID: 2563771
- 3-morpholinosydnonimine (SIN-1)-induced oxidative stress leads to necrosis in hypertrophic chondrocytes in vitro. | He, Y., et al. 2018. Biomed Pharmacother. 106: 1696-1704. PMID: 30119244
- Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites. | Nishikawa, M., et al. 1982. J Pharmacol Exp Ther. 220: 183-90. PMID: 6118429
- Increased cytotoxicity of 3-morpholinosydnonimine to HepG2 cells in the presence of superoxide dismutase. Role of hydrogen peroxide and iron. | Gergel, D., et al. 1995. J Biol Chem. 270: 20922-9. PMID: 7673115
- Spin-trapping studies of peroxynitrite decomposition and of 3-morpholinosydnonimine N-ethylcarbamide autooxidation: direct evidence for metal-independent formation of free radical intermediates. | Augusto, O., et al. 1994. Arch Biochem Biophys. 310: 118-25. PMID: 8161194
- A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. | Lipton, SA., et al. 1993. Nature. 364: 626-32. PMID: 8394509
- Activation of soluble guanylyl cyclase by the nitrovasodilator 3-morpholinosydnonimine involves formation of S-nitrosoglutathione. | Schrammel, A., et al. 1998. Mol Pharmacol. 54: 207-12. PMID: 9658207
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GCS.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
3-Morpholinosydnonimine, 20 mg | sc-200339 | 20 mg | $89.00 | |||
3-Morpholinosydnonimine, 100 mg | sc-200339A | 100 mg | $369.00 |