3-Morpholinosydnonimine hydrochloride

Description

As the active metabolite of molsidomine, SIN-1 (chloride) is a potent vasorelaxant and inhibitor of platelet aggregation. It produces both NO and superoxide and can therefore be used to generate peroxynitrite under physiological conditions.

Chemical Properties

White Crystalline Solid

Uses

SIN-1 is a metabolite of the vasodilator molsidomine and is considered to be a peroxynitrite releasing compound

Uses

3-Morpholinosydnonimine hydrochloride is a metabolite of the vasodilator Molsidomine (M488002) and is considered to be a peroxynitrite releasing compound. Molsidomine Impurity A.

Uses

3-Morpholinosydnonimine hydrochloride has been used:

• as a peroxynitrite donor standard to study the accumulation of peroxynitriteinArabidopsis thaliana
• to study its effects on nitrosative stress in human brain vascular pericytes and human embryonic kidney cells
• as a ROS to study its effects on mouse embryonic fibroblasts

Indications

Linsidomine (SIN-1) is an active metabolite of the antianginal drug molsidomine. Its mechanism of action upon the corpus cavernosum involves the release of nitric oxide. Injected intracavernosally it can produce penile erections, but its clinical usefulness has not been fully established.

Biological Activity

This compound (the active product of the prodrug SIN-10, molsidomine) acts as a vasodilator and inhibitor of platelet aggregation; longer acting than nitroprusside or nitroglycerin. Decreases myocardial necrosis and reperfusion-induced endothelial dysfunction in models of myocardial ischemia-reperfusion.

Biochem/physiol Actions

3-Morpholinosydnonimine participates in the inhibition of cysteine proteases.

storage

Store at +4°C

References

[1] M NISHIKAWA  H H  M Kanamori. Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites.[J]. Journal of Pharmacology and Experimental Therapeutics, 1982, 220 1: 183-190.
[2] N HOGG. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide.[J]. Biochemical Journal, 1992, 281 ( Pt 2): 419-424. DOI:10.1042/bj2810419
[3] M KIRSCH. Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines. Implications for a general mechanism.[J]. The Journal of Biological Chemistry, 1998, 273 21: 12716-12724. DOI:10.1074/jbc.273.21.12716
[4] RAFFAELLA PRIORA . In vitro inhibition of human and rat platelets by NO donors, nitrosoglutathione, sodium nitroprusside and SIN-1, through activation of cGMP-independent pathways[J]. Pharmacological research, 2011, 64 3: Pages 289-297. DOI:10.1016/j.phrs.2011.03.014
[5] BAIPING REN. Identification of a New Function of Cardiovascular Disease Drug 3-Morpholinosydnonimine Hydrochloride as an Amyloid-β Aggregation Inhibitor[J]. ACS Omega, 2017, 2 1: 243-250. DOI:10.1021/acsomega.6b00397