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(±)-S-Nitroso-N-acetylpenicillamine (CAS 79032-48-7)

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Alternate Names:
(±)-S-Nitroso-N-acetylpenicillamine also known as S-Nitroso-N-acetyl-DL-penicillamine; SNAP;N-Acetyl-3-(nitrosothio)-DL-valine; (±)-S-nitroso-N-acetylpenicillamine; C7-H12-N2-O4-S; penicillamine, (±)-S-nitroso-N-acetyl-
Application:
(±)-S-Nitroso-N-acetylpenicillamine is a cysteine protease inhibitor and spontaneous NO donor in physiological conditions
CAS Number:
79032-48-7
Purity:
≥98%
Molecular Weight:
220.25
Molecular Formula:
C7H12N2O4S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(±)-S-Nitroso-N-acetylpenicillamine is a research chemical of interest due to its role as a nitric oxide (NO) donor. In biochemical studies, it is used to mimic the effects of endogenous NO, enabling researchers to investigate the diverse physiological roles of this gaseous signaling molecule. (±)-S-Nitroso-N-acetylpenicillamine is utilized in the examination of signal transduction pathways that are modulated by NO, such as those affecting platelet function and neurotransmission. The compound′s ability to release NO in a controlled manner makes it valuable in understanding the mechanisms of NO-related cellular processes and in the study of the molecular basis of conditions where NO signaling is disrupted.


(±)-S-Nitroso-N-acetylpenicillamine (CAS 79032-48-7) References

  1. Synthesis and cytotoxicities of mannose conjugated S-nitroso-N-acetylpenicillamine (SNAP).  |  Wu, X., et al. 2002. Bioorg Med Chem. 10: 2303-7. PMID: 11983528
  2. Inhibition of cysteine protease activity by NO-donors.  |  Ascenzi, P., et al. 2001. Curr Protein Pept Sci. 2: 137-53. PMID: 12370021
  3. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide.  |  Hogg, N., et al. 1992. Biochem J. 281 (Pt 2): 419-24. PMID: 1310595
  4. Lack of tolerance to a 24-hour infusion of S-nitroso N-acetylpenicillamine (SNAP) in conscious rabbits.  |  Shaffer, JE., et al. 1992. J Pharmacol Exp Ther. 260: 286-93. PMID: 1731043
  5. Nitric oxide donor, (+/-)-S-nitroso-N-acetylpenicillamine, stabilizes transactive hypoxia-inducible factor-1alpha by inhibiting von Hippel-Lindau recruitment and asparagine hydroxylation.  |  Park, YK., et al. 2008. Mol Pharmacol. 74: 236-45. PMID: 18426857
  6. Nitric oxide-generating vasodilators and 8-bromo-cyclic guanosine monophosphate inhibit mitogenesis and proliferation of cultured rat vascular smooth muscle cells.  |  Garg, UC. and Hassid, A. 1989. J Clin Invest. 83: 1774-7. PMID: 2540223
  7. Nitroglycerin-induced tolerance affects multiple sites in the organic nitrate bioconversion cascade.  |  Henry, PJ., et al. 1989. J Pharmacol Exp Ther. 248: 762-8. PMID: 2563771
  8. Moderate-Intensity Physical Exercise Protects Against Experimental 6-Hydroxydopamine-Induced Hemiparkinsonism Through Nrf2-Antioxidant Response Element Pathway.  |  Aguiar, AS., et al. 2016. Neurochem Res. 41: 64-72. PMID: 26323504
  9. Tolerance to relaxation in rat aorta: comparison of an S-nitrosothiol with nitroglycerin.  |  Kowaluk, EA., et al. 1987. Eur J Pharmacol. 144: 379-83. PMID: 3126076
  10. S-Nitroso-N-acetylpenicillamine impregnated endotracheal tubes for prevention of ventilator-associated pneumonia.  |  Homeyer, KH., et al. 2020. Biotechnol Bioeng. 117: 2237-2246. PMID: 32215917
  11. Covalently Bound S-Nitroso-N-Acetylpenicillamine to Electrospun Polyacrylonitrile Nanofibers for Multifunctional Tissue Engineering Applications.  |  Workman, CD., et al. 2021. ACS Biomater Sci Eng. 7: 5279-5287. PMID: 34695358
  12. Intrastriatal infusion of (+/-)-S-nitroso-N-acetylpenicillamine releases vesicular dopamine via an ionotropic glutamate receptor-mediated mechanism: an in vivo microdialysis study in chloral hydrate-anesthetized rats.  |  West, AR. and Galloway, MP. 1996. J Neurochem. 66: 1971-80. PMID: 8780025
  13. Intrabulbar infusions of (+/-)S-nitroso-N-acetylpenicillamine and L-arginine induce functional plasticity in the accessory olfactory bulb of female mice.  |  Okere, CO., et al. 1996. Neurosci Lett. 217: 197-9. PMID: 8916106

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(±)-S-Nitroso-N-acetylpenicillamine, 10 mg

sc-200319B
10 mg
$73.00

(±)-S-Nitroso-N-acetylpenicillamine, 20 mg

sc-200319
20 mg
$112.00

(±)-S-Nitroso-N-acetylpenicillamine, 100 mg

sc-200319A
100 mg
$367.00

Hello, is this product sterile or do I need to sterilize it myself prior to use? I cannot seem to find this information in the data sheet. Thank you, Anne

Asked by: AnneDK
Thank you for your question. This product is not sterile.
Answered by: Technical Support
Date published: 2017-11-09

Hello, How long would SNAP dissolved in 100% DMSO last in -20C? By "prepare solutions daily", does this mean that I have to measure out the tiny amount of the powder every time, as opposed to storing it dissolved in DMSO? Thanks, Peter

Asked by: Pmin91
Thank you for your question. You correct, due to the products instability in solution, we recommend reconstituting just prior to use.
Answered by: Technical Support
Date published: 2017-01-16
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Rated 5 out of 5 by from Très efficaceLe produit est satisfaisant, les chercheurs enseignants y travaillent;
Date published: 2020-11-14
Rated 5 out of 5 by from Worked well!We used this reagent to treat cell at 100 uM, which wrok well.
Date published: 2018-02-05
Rated 5 out of 5 by from Megson et alMegson et al. (PubMed ID 10188974) found that the slow decomposition of ( )-S-Nitroso-N-acetylpenicillamine (SNAP) within arterial endothelium generated enough nitric oxide to prolong vasodilation. -SCBT Publication Review
Date published: 2015-05-19
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(±)-S-Nitroso-N-acetylpenicillamine is rated 5.0 out of 5 by 3.
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