N3398

Sigma-Aldrich

S-Nitroso-N-acetyl-DL-penicillamine

≥97%, powder

Synonym(s):
S-Nitroso-N-acetylpenicillamine, SNAP, N-Acetyl-3-(nitrosothio)-DL-valine
Empirical Formula (Hill Notation):
C7H12N2O4S
CAS Number:
Molecular Weight:
220.25
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

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.

Packaging

25 mg in poly bottle
50 mg in glass bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Zorana Milanović et al.
Journal of veterinary internal medicine, 33(4), 1686-1694 (2019-06-09)
Babesia canis infection induces a marked acute phase response (APR) that might be associated with alteration in lipid and lipoprotein metabolism and disease prognosis. Dogs with B. canis-induced APR develop dyslipidemia with altered lipoprotein concentration and morphology. Twenty-nine client-owned dogs...
Sophie Nicole et al.
Brain : a journal of neurology, 137(Pt 9), 2429-2443 (2014-06-22)
Congenital myasthenic syndromes are a clinically and genetically heterogeneous group of rare diseases resulting from impaired neuromuscular transmission. Their clinical hallmark is fatigable muscle weakness associated with a decremental muscle response to repetitive nerve stimulation and frequently related to postsynaptic...
Lethal autoimmune myocarditis in interferon-gamma receptor-deficient mice: enhanced disease severity by impaired inducible nitric oxide synthase induction.
Eriksson U
Circulation, 103(1), 18-21 (2001)
Jodie D Anderson et al.
Journal of veterinary internal medicine, 33(4), 1593-1601 (2019-05-28)
Intravenous continuous rate infusion (IVCRI) of lispro at a starting dose of 0.09 U/kg/h and the use of 0.9% sodium chloride (NaCl) for fluid resuscitation in cats with diabetic ketoacidosis (DKA) have not been reported. Protocols for correction of electrolyte deficiencies...
Articles
Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.
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