| Identification | More | [Name]
3-Morpholinosydnonimine hydrochloride | [CAS]
16142-27-1 | [Synonyms]
3-(4-MORPHOLINYL)-SYDNONE IMINE HYDROCHLORIDE
3-MORPHOLINOSYDNOIMINE HCL
3-MORPHOLINOSYDNOIMINE HYDROCHLORIDE
3-MORPHOLINOSYDNONIMINE CHLORIDE
3-MORPHOLINOSYDNONIMINE HCL
3-MORPHOLINOSYDNONIMINE HYDROCHLORIDE
3-MORPHOLINOSYDNONIMIN HYDROCHLORIDE
5-AMINO-3-(4-MORPHOLINYL)-1,2,3-OXADIAZOLIUM CHLORIDE
5-AMINO-3-MORPHOLIN-4-YL-[1,2,3]OXADIAZOL-3-IUM, CHLORIDE
5-AMINO-3-MORPHOLINYL-1,2,3-OXADIAZOLIUM CHLORIDE
LINSIDOMINE
LINSIDOMINE HCL
LINSIDOMINE HYDROCHLORIDE
SIN-1
SIN-1 CHLORIDE
SIN-1 HCL
SIN-1 HYDROCHLORIDE
SIN-I HYDROCHLORIDE
3-morpholinosydnoneiminehydrochloride
3-morpholino-sydnoneiminmonohydrochloride | [EINECS(EC#)]
247-207-4 | [Molecular Formula]
C6H11ClN4O2 | [MDL Number]
MFCD00221615 | [Molecular Weight]
206.63 | [MOL File]
16142-27-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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 | [Usage]
SIN-1 is a metabolite of the vasodilator molsidomine and is considered to be a peroxynitrite releasing compound | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions must be prepared fresh and cannot be stored. | [InChI]
1S/C6H10N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5,7H,1-4H2;1H | [InChIKey]
NCGICGYLBXGBGN-UHFFFAOYSA-N | [SMILES]
Cl[H].[NH-]c1c[n+](no1)N2CCOCC2 | [LogP]
-6.28 at 25℃ | [CAS DataBase Reference]
16142-27-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3 | [RTECS ]
WU7687800 | [REACH Registrations]
Active | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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.1,2,3 | [Chemical Properties]
White Crystalline Solid | [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. | [Uses]
SIN-1 is a metabolite of the vasodilator molsidomine and is considered to be a peroxynitrite releasing compound | [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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