Description
S-Nitroso-N-acetylpenicillamine (±) (CAS No. 67776-06-1) is a nitrosothiol compound widely utilized in biochemical and physiological research as a nitric oxide (NO) donor. With the molecular formula C7H12N2O4S and IUPAC name 2-acetamido-3-methyl-3-nitrososulfanylbutanoic acid, this compound offers controlled release of nitric oxide, making it invaluable for studying NO-mediated signaling pathways. It is supplied as a racemic mixture (±) to ensure broad applicability in experimental models. S-Nitroso-N-acetylpenicillamine is highly soluble in aqueous buffers and organic solvents, facilitating its use in in vitro and in vivo studies. Store at -20°C under inert conditions to maintain stability and prevent degradation.
Properties
- CAS Number: 67776-06-1
- Complexity: 254
- IUPAC Name: 2-acetamido-3-methyl-3-nitrososulfanyl-butanoic acid
- 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)
- InChI Key: ZIIQCSMRQKCOCT-UHFFFAOYSA-N
- Exact Mass: 220.05177804
- Molecular Formula: C7H12N2O4S
- Molecular Weight: 220.25
- SMILES: CC(=O)NC(C(=O)O)C(C)(C)SN=O
- Topological: 121
- Monoisotopic Mass: 220.05177804
- Synonyms: 67776-06-1, S-Nitroso-N-acetyl-DL-penicillamine, SNAP (amino acid), N-Acetyl-S-nitroso-DL-penicillamine, C4AX527AX8, SNAP (+-), S-Nitroso-N-acetylpenicillamine, (+-), 636-172-4, snap, Valine,N-acetyl-3-(nitrosothio)-, S-Nitroso-N-acetyl-D,L-penicillamine, 2-acetamido-3-methyl-3-(nitrososulfanyl)butanoic acid, 152971-80-7, DL-Valine, N-acetyl-3-(nitrosothio)-, 2-Acetamido-3-methyl-3-nitrososulfanylbutanoic acid, (+/-)-S-Nitroso-N-acetylpenicillamine, SNAP (S-NITROSO-N-ACETYLPENICILLAMINE), MFCD00272624, N-Acetyl-3-(nitrosothio)-DL-valine, 2-acetamido-3-methyl-3-nitrososulfanyl-butanoic acid, NSC312630, 2-ACETAMIDO-3-METHYL-3-(NITROSOTHIO)BUTANOIC ACID, S-Nitrosoacetylpenicillamine, (R)-2-Acetamido-3-methyl-3-(nitrosothio)butanoic acid, Valine, N-acetyl-3-(nitrosothio)-, SNAP [S-Nitroso-N-acetylpenicillamine], Spectrum_001453, SpecPlus_000805, Spectrum2_001466, Spectrum3_000773, Spectrum4_001043, Spectrum5_001916, UNII-C4AX527AX8, BSPBio_002446, KBioGR_001306, KBioSS_001933, CHEMBL27308, DivK1c_006901, SCHEMBL139789, SPECTRUM1502060, SPBio_001391, KBio1_001845, KBio2_001933, KBio2_004501, KBio2_007069, KBio3_001666, S-nitroso-N-Acetyl-penicillamine, DTXSID70987112, ZIIQCSMRQKCOCT-UHFFFAOYSA-N, HMS1923O15, BCP21207, SNAP (+/-)-, CCG-39274, HSCI1_000047, AKOS024458576, FS46817, N-ACETYL-3-(NITROSOTHIO)VALINE, SB13130, NCGC00015734-03, NCGC00015734-04, NCGC00024673-02, NCGC00024673-03, AS-60790, S-Nitroso-N-acetylpenicillamine, (+/-), SY099074, SNAP;N-Acetyl-3-(nitrosothio)-DL-valine, HY-121526, CS-0082469, P19575, S-NITROSO-N-ACETYL-DL-PENICILLAMINE 98%, N-(1-Hydroxyethylidene)-3-(nitrososulfanyl)valine, S-NITROSO-N-ACETYLPENICILLAMINE, (+/-)-, SR-01000597612, SR-01000597612-1, S-Nitroso-N-acetyl-DL-penicillamine, >=97%, powder, 2-Acetamido-3-methyl-3-(nitrososulfanyl)butanoic acid (Ac-DL-Pen(NO)-OH)
Application
S-Nitroso-N-acetylpenicillamine (±) is extensively used to investigate the role of nitric oxide in vasodilation, neurotransmission, and immune response modulation. Researchers employ it to simulate endogenous NO release in cell cultures and tissue preparations, aiding in the study of cardiovascular and neurological systems. Its reliable NO-donating properties make it a staple in pharmacological and toxicological assays.
Safety and Hazards
GHS Hazard Statements
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statements
- P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Skin Irrit. 2 (100%)
- Eye Irrit. 2 (100%)
- STOT SE 3 (100%)
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