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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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Frank Gaupels et al.
Nitric oxide : biology and chemistry, 25(2), 222-228 (2011-02-08)
Nitric oxide (NO) is synthesized in plants in response to stress, and its role in signaling is well-documented. In contrast, very little is known about the physiological role of its derivate peroxynitrite (ONOO(-)), which forms when NO reacts with O(2)(-)
Keren Zohar et al.
Biomedicines, 9(9) (2021-09-29)
A hallmark of the aging brain is the robust inflammation mediated by microglial activation. Pathophysiology of common neurodegenerative diseases involves oxidative stress and neuroinflammation. Chronic treatment of aging rats by ladostigil, a compound with antioxidant and anti-inflammatory function, prevented microglial
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
Kittipot Sirichaiwetchakoon et al.
BioMed research international, 2020, 4183643-4183643 (2020-10-09)
Tea is one of the most popular beverages in the world. Camellia sinensis tea (CST) or green tea is widely regarded as a potent antioxidant. In Thailand, Pluchea indica (L.) Less. tea (PIT) has been commercially available as a health-promoting
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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