S-Nitroso-N-acetyl-DL-penicillamine

Base Information

• Chemical Name: S-Nitroso-N-acetyl-DL-penicillamine
• CAS No.: 67776-06-1
• Deprecated CAS: 81739-40-4
• Molecular Formula: C7H12N2O4S
• Molecular Weight: 220.249
• European Community (EC) Number: 636-172-4
• NSC Number: 312630
• UNII: C4AX527AX8
• DSSTox Substance ID: DTXSID70987112
• Nikkaji Number: J379.550K
• Wikipedia: S-Nitroso-N-acetylpenicillamine
• ChEMBL ID: CHEMBL27308
• Mol file: 67776-06-1.mol

Synonyms:N-Acetyl-S-Nitrosopenicillamine;N2-Acetyl-S-Nitroso-D,L-Penicillinaminamide;S-Nitroso-N-Acetylpenicillamine;S-Nitrosylacetylpenicillamine;S-NONAP;SNAP (NO donor)

Chemical Property of S-Nitroso-N-acetyl-DL-penicillamine

Chemical Property:

• Appearance/Colour: green crystalline solid
• Melting Point: 151oC
• Refractive Index: 1.5400 (estimate)
• PKA: 3.06±0.10(Predicted)
• PSA: 121.13000
• Density: 1.36 g/cm³
• LogP: 1.15980
• Storage Temp.: −20°C
• Solubility.: H2O: ≥2 mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 220.05177804
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

98%,99%, ^*data from raw suppliers

S-Nitroso-N-acetyl-D,L-penicillamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(C(=O)O)C(C)(C)SN=O
• Description: SNAP is an S-nitrosothiol which serves as a NO donor and a potent vasodilator. Its stability in solution varies from seconds to hours depending on temperature, buffer composition and metal content. At pH 6-8 and 37°C, the half-life of SNAP is approximately six hours in the presence of transition metal ion chelators.

Technology Process of S-Nitroso-N-acetyl-DL-penicillamine

There total 13 articles about S-Nitroso-N-acetyl-DL-penicillamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

NAP (59-53-0) → S-nitroso-N-acetyl-DL-penicillamine (67776-06-1,81739-40-4)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 4 ℃; for 0.166667h;

DOI:10.1016/S0045-2068(02)00509-6

Reference yield: 73.0%

NAP (59-53-0) → 1-(2-chloroethyl)-3-(3-pyridylmethyl)urea Narom-oxide (70015-88-2) + S-nitroso-N-acetyl-DL-penicillamine (67776-06-1,81739-40-4)

Guidance literature:

With hydrogenchloride; sulfuric acid; 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N_arom-oxide; In methanol; at 25 ℃; for 8h;

DOI:10.1248/cpb.33.5557

Reference yield: 42.0%

NAP (59-53-0) + 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N-oxide (70015-86-0) → 1-(2-chloroethyl)-3-(3-pyridylmethyl)urea Narom-oxide (70015-88-2) + S-nitroso-N-acetyl-DL-penicillamine (67776-06-1,81739-40-4)

Guidance literature:

With hydrogenchloride; sulfuric acid; In methanol; at 25 ℃; for 8h;

DOI:10.1248/cpb.33.5557

upstream raw materials:

NAP

N,N'-diphenyl-N-nitroso-urea

1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N-oxide

2-hydroxy-S-nitrosoethanethiol

Downstream raw materials:

NAP

N-acetyl-D,L-penicillamine disulfide

(S)-nitroso-L-cysteine ethyl ester

S-nitroso-N-acetylpenicillamine

Refernces

• 1、 Lu, Tsai-Te,Chen, Chih-Hao,Liaw, Wen-Feng. "Formation of the distinct redox-interrelated forms of nitric oxide from reaction of dinitrosyl iron complexes (DNICs) and substitution ligands". . p. 8088 - 8095. Retrieved 2010.
• 2、 He, Weilue,Frost, Megan C.. "Direct measurement of actual levels of nitric oxide (NO) in cell culture conditions using soluble NO donors". . p. 1 - 14. Retrieved 2016.
• 3、 -. "THROMBORESISTANT/BACTERICIDAL S-NITROSO-N-ACETYLPENICILLAMINE (SNAP)-DOPED NITRIC OXIDE RELEASE POLYMERS WITH ENHANCED STABILITY". Paragraph 0100; 0101. . Retrieved 2015/09/23.