M184

Sigma-Aldrich

3-Morpholinosydnonimine hydrochloride

solid

Synonym(s):
SIN-1 hydrochloride, 3-(4-Morpholinyl)sydnone imine hydrochloride, Linsidomine hydrochloride
Empirical Formula (Hill Notation):
C6H10N4O2 · HCl
CAS Number:
Molecular Weight:
206.63
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

form

solid

color

off-white

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

ClH.NH-c1cn+(no1)N2CCOCC2

InChI

1S/C6H10N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5,7H,1-4H2;1H

InChI key

NCGICGYLBXGBGN-UHFFFAOYSA-N

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Biochem/physiol Actions

Liberates nitric oxide (NO) spontaneously when in solution, activating guanylyl cyclase and causing an increase in cyclic-GMP. This product is a vasodilator and inhibits platelet aggregation. Using molecular oxygen, it generates both superoxide anion and nitric oxide that spontaneously form peroxynitrite.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Caution

Hygroscopic, photosensitive

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

3

Tangying Lu et al.
The Journal of clinical investigation, 121(10), 4015-4029 (2011-09-14)
Cancer immunotherapeutic approaches induce tumor-specific immune responses, in particular CTL responses, in many patients treated. However, such approaches are clinically beneficial to only a few patients. We set out to investigate one possible explanation for the failure of CTLs to...
S Chandra et al.
British journal of pharmacology, 165(2), 506-519 (2011-07-12)
NO produced by endothelial NOS is needed for normal vascular function. During diabetes, aging and hypertension, elevated levels of arginase can compete with NOS for available l-arginine, reducing NO and increasing superoxide (O(2) (.-)) production via NOS uncoupling. Elevated O(2)...
K I Thelen et al.
Naunyn-Schmiedeberg's archives of pharmacology, 345(1), 93-99 (1992-01-01)
The modulating effects of exogenous and endogenous nitric oxide (NO) on the cardiac anaphylactic reaction and eicosanoid release were investigated in isolated perfused sensitized guinea-pig hearts using 3-morpholinosydnonimine (SIN-1), the active metabolite of molsidomine, as NO-donor and NG-nitro-L-arginine (NNA) as...
K A Jones et al.
The American journal of physiology, 266(1 Pt 1), L9-16 (1994-01-01)
Nitrovasodilators relax airway smooth muscle by both guanosine 3',5'-cyclic monophosphate (cGMP)-dependent and cGMP-independent mechanisms and by mechanisms that reduce cytosolic calcium concentration ([Ca2+]i). This study was conducted to determine the relative importance of these mechanisms in relaxation of canine tracheal...
Mushfiquddin Khan et al.
Journal of neuroinflammation, 8, 78-78 (2011-07-08)
Traumatic brain injury (TBI) induces primary and secondary damage in both the endothelium and the brain parenchyma, collectively termed the neurovascular unit. While neurons die quickly by necrosis, a vicious cycle of secondary injury in endothelial cells exacerbates the initial...

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