S-Nitroso-N-acetylpenicillamine

S-Nitroso-N-acetylpenicillamine
IUPAC name S-Nitroso-N-acetylpenicillamine
Other names N-Acetyl-3-(nitrosothio)-DL-valine S-Nitroso-N-acetylpenicillamine
Identifiers
Abbreviations	SNAP
CAS number	67776-06-1
PubChem	6603945
ChemSpider	5036251 Y
ChEMBL	CHEMBL73188 Y
Jmol-3D images	Image 1
SMILES O=C(N[C@@H](C(=O)O)C(SN=O)(C)C)C
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 Y Key: ZIIQCSMRQKCOCT-YFKPBYRVSA-N Y
Properties
Molecular formula	C7H12N2O4S
Molar mass	220.25 g/mol
Hazards
R-phrases	R36/37/38
S-phrases	S26 S36
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

References

1. ^ Zhang Y.; Hogg, N. “S-Nitrosothiols: cellular formation and transport” Free Radical Biology and Medicine 2005, volume 38, pp. 831-838. doi:10.1016/j.freeradbiomed.2004.12.016