3-MorpholinosydnonimineA potent vasodilator that inhibits platelet aggregation and cysteine proteases

3-Morpholinosydnonimine (CAS 16142-27-1)

3-Morpholinosydnonimine | CAS 33876-97-0 is rated 5.0 out of 5 by 1.
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Synonym: SIN-1, Hydrochloride;Linsidomine hydrochloride
Application: 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
* Refer to Certificate of Analysis for lot specific data (including water content).
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3-Morpholinosydnonimine (SIN-1) is a metabolite of molsidomine (sc-200337) which has been shown to decompose spontaneously in solution in the presence of oxygen. This reaction releases nitric oxide (NO) and superoxide anion, which under physiological conditions, react to produce peroxynitrite. SIN-1 is a potent vasodilator, activator of GCS (guanylyl cyclase), inhibitor of platelet aggregation, general cysteine protease inhibitor, and has been shown to produce significant protective effects in myocardial ischemia-reperfusion. Some of the effects of SIN-1 can be attenuated by nitroglycerin-induced tolerance.


References

1. Hogg, N., et al., 1992. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. The Biochemical journal. 281 ( Pt 2)(): 419-24. PMID: 1310595
2. Siegfried, M R., et al., 1992. Cardioprotection and attenuation of endothelial dysfunction by organic nitric oxide donors in myocardial ischemia-reperfusion. The Journal of pharmacology and experimental therapeutics. 260(2): 668-75. PMID: 1738117
3. Henry, P J., et al., 1989. Nitroglycerin-induced tolerance affects multiple sites in the organic nitrate bioconversion cascade. The Journal of pharmacology and experimental therapeutics. 248(2): 762-8. PMID: 2563771
4. Nishikawa, M., et al., 1982. Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites. The Journal of pharmacology and experimental therapeutics. 220(1): 183-90. PMID: 6118429
5. Lipton, S A., et al., 1993. A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature. 364(6438): 626-32. PMID: 8394509
6. Ascenzi, P., et al., 2001. Inhibition of cysteine protease activity by NO-donors. Current protein & peptide science. 2(2): 137-53. PMID: 12370021

Physical State :
Solid
Solubility :
Soluble in water (25 mg/ml), ethanol (10 mg/ml), and DMSO (10 mg/ml).
Storage :
Store at -20° C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
WU7687800
PubChem CID :
9859122
MDL Number :
MFCD00214332
SMILES :
C1COCCN1[N+]2=CC(=N)O[N-]2.Cl

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Certificate of Analysis

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3-Morpholinosydnonimine  Product Citations

See how others have used 3-Morpholinosydnonimine. Click on the entry to view the PubMed entry .

Citations 1 to 8 of 8 total

PMID: # 27010352  Silina, YE. et al. 2016. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 1020: 6-13.

PMID: # 27158388  Xu, Z. et al. 2016. Am J Transl Res. 8: 1027-36.

PMID: # 24804999  Kinoshita, C. et al. 2014. Nat Commun. 5: 3823.

PMID: # 22210510  Aoyama, K. et al. 2012. Neurobiol. Dis. 45: 973-82.

PMID: # 21371533  Aoyama, K. et al. 2011. Neuroscience. 181: 206-15.

PMID: # 14742271  Kang, DH et al. 2004. Am. J. Pathology. 164: 679-688.

PMID: # 11352817  Banan, A. et al. 2001. Am. J. Physiol. Gastrointest. Liver Physiol. 280: G1234-G1246.

PMID: # 9388195  Narayan, S. et al. 1997. J. Biol. Chem. 272: 30619-30622.

Citations 1 to 8 of 8 total

What is the half life of this chemical?

Asked by: Io5ay
Thank you for your question. We have not determined the half life of 3-morpholinosydnonimine, hydrochloride (SIN-1), BML-CN245. As per an article in Clinical Pharmokinetics, the half life of BML-CN245-0020 is 1- 2 hour.
Answered by: Technical Support
Date published: 2017-03-09

Can solutions be prepared in advance or should they be prepared prior to use?

Asked by: Io5ay
Thank you for your question. We recommend dissolving the product freshly each time before use.
Answered by: Technical Support
Date published: 2017-03-09

What is the stability of this compound in water?

Asked by: Io5ay
Thank you for your question. This compound is soluble in water to 100 mM and in DMSO to 10 mM. The product can be stored for up to 12 months, providing storage is as stated on the product vial and the vial is kept tightly sealed. Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
Answered by: Technical Support
Date published: 2017-03-09
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Rated 5 out of 5 by from Kang et al Kang et al. (PubMed ID 14742271) used 3-Morpholinosydnonimine (SIN-1) to generate nitric oxide and found this to inhibit VEGF expression in rat proximal tubule (NRK52E) cells.
Date published: 2015-06-10
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