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M5793

Sigma-Aldrich

3-Morpholinosydnonimine hydrochloride

(consistent with structure, NMR)

Synonym(s):

3-(4-Morpholinyl)sydnone imine hydrochloride, Linsidomine hydrochloride, SIN-1 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H10N4O2 · HCl
CAS Number:
16142-27-1
Molecular Weight:
206.63
MDL number:
MFCD00214332
UNSPSC Code:
12352200
PubChem Substance ID:
24897048
NACRES:
NA.77

Quality Level

200

storage temp.

−20°C

SMILES string

Cl[H].[NH-]c1c[n+](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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Application

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

Biochem/physiol Actions

3-Morpholinosydnonimine participates in the inhibition of cysteine proteases.
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H de Groot et al.
FEBS letters, 315(2), 139-142 (1993-01-04)
SIN-1 which spontaneously decomposes to yield nitric oxide (NO.) and superoxide anion (O2.-) radicals caused a loss of microsomal alpha-tocopherol paralleled by the formation of alpha-tocopheryl quinone. The loss was partially prevented by superoxide dismutase but not by catalase. The
P Ascenzi et al.
Current protein & peptide science, 2(2), 137-153 (2002-10-09)
Cysteine proteases represent a broad class of proteolytic enzymes widely distributed among living organisms. Although well known as typical lysosomal enzymes, cysteine proteases are actually recognized as multi-function enzymes, being involved in antigen processing and presentation, in membrane-bound protein cleavage
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
Fabiana Blanco et al.
Diabetes & vascular disease research, 15(4), 302-313 (2018-03-04)
Despite vast clinical experience linking diabetes and atherosclerosis, the molecular mechanisms leading to accelerated vascular damage are still unclear. Here, we investigated the effects of nuclear factor of activated T-cells inhibition on plaque burden in a novel mouse model of
Kareem Clark et al.
ASN neuro, 9(6), 1759091417745426-1759091417745426 (2017-12-13)
The axon initial segment (AIS), the domain responsible for action potential initiation and maintenance of neuronal polarity, is targeted for disruption in a variety of central nervous system pathological insults. Previous work in our laboratory implicates oxidative stress as a
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