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Merck
CN

M5793

3-Morpholinosydnonimine hydrochloride

guanylyl cyclase activator

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
UNSPSC Code:
12352200
PubChem Substance ID:
24897048
NACRES:
NA.77
MDL number:
MFCD00214332

Key Documents

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Product Name

3-Morpholinosydnonimine hydrochloride, (consistent with structure, NMR)

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

storage temp.

−20°C

Quality Level

200

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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.
Liberates nitric oxide (NO) spontaneously when in solution, activating guanylyl cyclase and causing an increase in cyclic-GMP; vasodilator.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000458780
0000458780
0000404431
0000404431
0000389762

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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
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
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)(-)
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
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感应染料

一氧化氮 (NO) 是神经元、内皮细胞和免疫系统中的信号转运分子。

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