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SNAP

Cayman Chemical Item Number 82250

S-Nitroso-N-Acetyl-D,L-Penicillamine (CAS 67776-06-1)

SNAP (CAS 67776-06-1)

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Description

SNAP is an S-nitrosothiol which serves as a NO donor and a potent vasodilator. Its stability in solution varies from seconds to hours depending on temperature, buffer composition and metal content.1,2,3,4 At pH 6-8 and 37°C, the half-life of SNAP is approximately six hours in the presence of transition metal ion chelators.5,4

1 Butler, A.R., and Rhodes, P. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal Biochem 249 1-9 (1997).

2 Gasco, A., Fruttero, R., and Sorba, G. NO-donors: An emerging class of compounds in medicinal chemistry. Farmaco 51 617-635 (1996).

3 Cook, J.A., Kim, S.Y., Teague, D., et al. Convenient colorimetric and fluorometric assays for S-nitrosothiols. Anal Biochem 238 150-158 (1996).

4 Roy, B., d'Hardemare, A.M., and Fontecave, M. New thionitrites: Synthesis, stability, and nitric oxide generation. J Org Chem 59 7019-7026 (1994).

5 Singh, R.J., Hogg, N., Joseph, J., et al. Mechanism of nitric oxide release from S-nitrosothiols. J Biol Chem 271 18596-18603 (1996).

Synonyms
  • S-Nitroso-N-Acetyl-D,L-Penicillamine
Formal Name N-​(acetyloxy)-​3-​nitrosothiovaline
CAS Number 67776-06-1
Molecular Formula C7H12N2O4S
Formula Weight 220.2
Formulation A crystalline solid
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=NSC(C)​(C)​C(NC(=O)​C)​C(=O)​O

Background Reading

Gasco, A., Fruttero, R., and Sorba, G. NO-donors: An emerging class of compounds in medicinal chemistry. Farmaco 51 617-635 (1996).

Gibson, A., Babbedge, R., Brave, S.R., et al. An investigation of some S-nitrosothiols, and of hydroxy-arginine, on the mouse anococcygeus. Br J Pharmacol 107 715-721 (1992).

Cook, J.A., Kim, S.Y., Teague, D., et al. Convenient colorimetric and fluorometric assays for S-nitrosothiols. Anal Biochem 238 150-158 (1996).

Butler, A.R., and Rhodes, P. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal Biochem 249 1-9 (1997).

Singh, R.J., Hogg, N., Joseph, J., et al. Mechanism of nitric oxide release from S-nitrosothiols. J Biol Chem 271 18596-18603 (1996).

Roy, B., d'Hardemare, A.M., and Fontecave, M. New thionitrites: Synthesis, stability, and nitric oxide generation. J Org Chem 59 7019-7026 (1994).

Askew, S.C., Barnett, D.J., McAninly, J., et al. Catalysis by Cu2+ of nitric oxide release from S-nitrosothiols (RSNO). J Chem Soc Perkin Trans II 2 741-745 (1995).

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