3-Morpholinosydnonimine hydrochloride Chemical Properties

Melting point:

186 °C

Density 

1.303 at 20℃

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to 35 mg/ml) or in Water (up to 65 mg/ml)

form 

White solid

color 

White

Water Solubility 

soluble

Stability:

Stable for 1 year from date of purchase as supplied. Solutions must be prepared fresh and cannot be stored.

LogP

-6.28 at 25℃

CAS DataBase Reference

16142-27-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

WU7687800

HS Code 

29349990

MSDS

• Language:English Provider:SIN-1 hydrochloride
• Language:English Provider:ACROS

3-Morpholinosydnonimine hydrochloride Usage And Synthesis

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 has been used:

• as a peroxynitrite donor standard to study the accumulation of peroxynitrite?in?Arabidopsis 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

Uses

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

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) Nishikawa?et al.?(1982)?Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites;?J. Pharmacol. Exp. Ther.?220?183 2) Hogg?et al.?(1992)?Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide; Biochem. J.?281?419 3) Kirsch?et al.?(1998)?Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines. Implications for a general mechanism.; J. Biol. Chem.?273?12716 4) Priora?et al.?(2011)?In vitro inhibition of human and rat platelets by NO donors nitrosoglutathione sodium nitroprusside and SIN-1 through activation of cGMP independent pathways; Pharmacol. Res.?64?289 5) Ren?et al.?(2017)?Identification of a New Function of Cardiovascular Disease Drug 3-Morpholinosydnonimine Hydrochloride as an Amyloid-β Aggregation Inhibitor;?ACS Omega.?2?243

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