S-Nitroso-N-acetylpenicillamine

S-Nitroso-N-acetylpenicillamine (SNAP) is the chemical compound with the formula ONSC(CH₃)₂CH(NHAc)CO₂H. 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.[1] SNAP is derived from the amino acid penicillamine. S-Nitrosoglutathione is a related agent.

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	67776-06-1
3D model (JSmol)	Interactive image
Abbreviations	SNAP
ChEBI	CHEBI:77702
ChEMBL	ChEMBL73188
ChemSpider	5036251
PubChem CID	6603945
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
Hazards
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26 S36
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

References

1. 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.