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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

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.
  • to block the activity of endogenous transglutaminase (TG2).
  • in proliferation assays to generate nitric oxide (NO) in cell cultures.

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

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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Sigma-Aldrich

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Lethal autoimmune myocarditis in interferon-gamma receptor-deficient mice: enhanced disease severity by impaired inducible nitric oxide synthase induction.
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Circulation, 103(1), 18-21 (2001)
Akshata R Naik et al.
The journal of physical chemistry. B, 123(32), 6997-7005 (2019-07-20)
The cell plasma membrane is a highly dynamic organelle governing a wide range of cellular activities including ion transport, secretion, cell division, growth, and development. The fundamental process involved in the addition of new membranes to pre-existing plasma membranes, however
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R J Carslake et al.
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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