A0737

N-acetylcysteine amide

≥98% (HPLC), lyophilized powder, antioxidant

• Synonym(s): (R)- 2-(Acetylamino)-3-mercapto-Propanamide, AD4, N-Acetyl-L-cysteinamide, NACA, acetylcysteinamide
• Empirical Formula (Hill Notation): C₅H₁₀N₂O₂S
• CAS Number: 38520-57-9
• Molecular Weight: 162.21
• MDL number: MFCD01696115
• UNSPSC Code: 12352209
• PubChem Substance ID: 329770626
• NACRES: NA.25

Properties

• Product Name: N-acetylcysteine amide, ≥98% (HPLC)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: lyophilized powder
• storage condition: desiccated
• color: white to off-white
• solubility: H₂O: ≥20 mg/mL; DMSO: >40 mg/mL
• storage temp.: 2-8°C
• SMILES string: CC(=O)N[C@@H](CS)C(N)=O
• InChI: 1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
• InChI key: UJCHIZDEQZMODR-BYPYZUCNSA-N

Description

Application

N-acetylcysteine amide has been used:

• to protect retinal pigment epithelium (RPE) from oxidative stress
• to show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelination
• to protect cells from apoptosis induced by shikonin plus erlotinib/gefitinib
• as a component in various culture media

as an antioxidant to reduce oxidative stress in brains of homozygous Drosophila spermine synthase (dSms e/e) mutant flies and melanoma cells.

Biochem/physiol Actions

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.

Other Notes

This product is hydroscopic and air sensitive.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable