S-Nitroso-N-acetylpenicillamine

S-Nitroso-N-acetylpenicillamine
Names
	IUPAC name S-Nitroso-N-acetylpenicillamine
	Other names N-Acetyl-3-(nitrosothio)-DL-valine; S-Nitroso-N-acetylpenicillamine
Identifiers
CAS Number	79032-48-7 ;
3D model (JSmol)	Interactive image;
Abbreviations	SNAP
ChEBI	CHEBI:77702 ;
ChEMBL	ChEMBL73188 ;
ChemSpider	5036251 ;
PubChem CID	6603945;
UNII	6E47VKF8B8 ;
CompTox Dashboard (EPA)	DTXSID80897531 ;
	InChI 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 Key: ZIIQCSMRQKCOCT-YFKPBYRVSA-N ; 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;
	SMILES O=C(N[C@@H](C(=O)O)C(SN=O)(C)C)C;
Properties
Chemical formula	C7H12N2O4S
Molar mass	220.25 g/mol
Appearance	green solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). verify (what is ?) Infobox references

S-Nitroso-N-acetylpenicillamine (SNAP) is the organosulfur compound with the formula ON S C(CH₃)₂C H(N H Ac)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

^ "N3398 h S-Nitroso-N-acetyl-DL-penicillamine". Sigma-Aldric. Retrieved 13 December 2021.
^ 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.
^ 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.