S-Nitroso-N-acetylpenicillamine
Skeletal formula of SNAP
Ball-and-stick model of SNAP
Names
IUPAC name
S-Nitroso-N-acetylpenicillamine
Other names
N-Acetyl-3-(nitrosothio)-DL-valine
S-Nitroso-N-acetylpenicillamine
Identifiers
3D model (JSmol)
Abbreviations SNAP
ChEBI
ChEMBL
ChemSpider
UNII
  • 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)/t5-/m0/s1 checkY
    Key: ZIIQCSMRQKCOCT-YFKPBYRVSA-N checkY
  • InChI=1/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)/t5-/m0/s1
    Key: ZIIQCSMRQKCOCT-YFKPBYRVBE
  • O=C(N[C@@H](C(=O)O)C(SN=O)(C)C)C
Properties
C7H12N2O4S
Molar mass 220.25 g/mol
Appearance green solid
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

S-Nitroso-N-acetylpenicillamine (SNAP) is the organosulfur compound with the formula ONSC(CH3)2CH(NHAc)CO2H. It is a green solid.[2]

SNAP is an S-nitrosothiol and is used as a model for the general class of S-nitrosothiols which have received much attention in biochemistry because nitric oxide and some organic nitroso derivatives serve as signaling molecules in living systems, especially related to vasodilation.[3] SNAP is derived from the amino acid penicillamine. S-Nitrosoglutathione is a related agent.

References

  1. ↑ "N3398 h S-Nitroso-N-acetyl-DL-penicillamine". Sigma-Aldric. Retrieved 13 December 2021.
  2. ↑ Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between Conformational Dynamics and the Redox Chemistry of S-Nitrosothiols". Journal of the American Chemical Society. 121 (30): 7115–7123. doi:10.1021/ja9901314.
  3. ↑ Zhang Y.; Hogg, N. (2005). "S-Nitrosothiols: Cellular Formation and Transport". Free Radical Biology and Medicine. 38 (7): 831–838. doi:10.1016/j.freeradbiomed.2004.12.016. PMID 15749378.
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