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^Y
3D model (JSmol)	Interactive image
Abbreviations	SNAP
ChEBI	CHEBI:77702^Y
ChEMBL	ChEMBL73188^Y
ChemSpider	5036251^Y
PubChem CID	6603945
UNII	6E47VKF8B8^Y
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^Y Key: ZIIQCSMRQKCOCT-YFKPBYRVSA-N^Y 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:^[1]
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). N verify (what is ^YN ?) 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.

sGC	Activators/stimulators: Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat Inhibitors: ODQ

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N<sup>5</sup>-(1-Iminoethyl)-L-ornithine (<small>L</small>-NIO) N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA) N<sup>ω</sup>-Propyl-<small>L</small>-arginine (<small>L</small>-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO) N<sup>6</sup>-(1-Iminoethyl)-<small>L</small>-lysine (<small>L</small>-NIL) N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA) Ronopterin (VAS-203) TRIM
eNOS	Aminoguanidine (pimagedine) N<sup>5</sup>-(1-Iminoethyl)-<small>L</small>-ornithine (<small>L</small>-NIO) N<sup>ω</sup>-Methyl-<small>L</small>-arginine (<small>L</small>-NMA) Nitroarginine (NNA, NOARG)
Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381

Others

Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
ET_B receptor antagonists (e.g., bosentan)
L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
Nebivolol (beta blocker)
PDE5 inhibitors (e.g., sildenafil)
non-selective PDE inhibitors (e.g., caffeine)
PDE9 inhibitors (e.g., paraxanthine)
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
Statins (e.g., simvastatin)

See also: Receptor/signaling modulators

This page was last edited on 17 September 2023, at 21:27