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N3398

Sigma-Aldrich

S-Nitroso-N-acetyl-DL-penicillamine

≥97%, powder

Synonym(s):

N-Acetyl-3-(nitrosothio)-DL-valine, S-Nitroso-N-acetylpenicillamine, SNAP

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About This Item

Empirical Formula (Hill Notation):
C7H12N2O4S
CAS Number:
67776-06-1
Molecular Weight:
220.25
MDL number:
MFCD00272624
UNSPSC Code:
12352116
PubChem Substance ID:
24278584
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

300

Assay

≥97%

form

powder

color

faint green to very dark green

solubility

H2O: ≥2 mg/mL
DMSO: ≥20 mg/mL, clear (faint green to very dark green)

storage temp.

−20°C

SMILES string

CC(=O)NC(C(O)=O)C(C)(C)SN=O

InChI

1S/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)

InChI key

ZIIQCSMRQKCOCT-UHFFFAOYSA-N

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Application

S-Nitroso-N-acetyl-DL-penicillamine (SNAP) has been used:
  • as a positive control in nitrite generation assay.[1]
  • to block the activity of endogenous transglutaminase (TG2).[2]
  • in proliferation assays to generate nitric oxide (NO) in cell cultures.[3]

Biochem/physiol Actions

NO donor; vasodilator, smooth muscle relaxant, lymphocyte activator. Activates soluble guanylyl cyclase.
SNAP, a nitrosothiol derivative, releases nitric oxide (NO.) under physiological conditions thus making it a useful tool for studying pharmacological and physiological actions of NO. Because of its NO releasing properties SNAP is a potent vasodilator in vitro and in vivo and is less prone to produce pharmacological tolerance.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000374442
0000305891
0000298336
0000151288
0000192521

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Sigma-Aldrich

495320

ODQ

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Australian veterinary journal, 95(12), 462-468 (2017-12-16)
To determine the prevalence of selected canine vector-borne diseases (Leishmania infantum, Anaplasma spp., Ehrlichia canis, Borrelia burgdorferi and Dirofilaria immitis) and endo- and ectoparasites in Samoan dogs presenting for surgical sterilisation and to report on the general health management of
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The intrinsic similarity shared between the members of the complement factor H family, which comprises complement factor H and five complement factor H-related (CFHR) genes, leads to various recombination events. In turn these events lead to deletions of some genes
The redox state of transglutaminase 2 controls arterial remodeling.
van den Akker J
PLoS ONE, 6(8), e23067-e23067 (2011)
Sophiya Garasia et al.
Scientific reports, 7(1), 1629-1629 (2017-05-11)
We assessed the association between depression status and prevalent and incident type 2 diabetes (T2D) as well as the interaction between depression and a genetic risk score (GS) based on 20 T2D single-nucleotide polymorphisms (SNPs) in a multi-ethnic longitudinal study.
Immunomodulatory activities of chitin microparticles on Leishmania major-infected murine macrophages.
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Articles

Sensor Dyes

Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.

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