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A0737

N-acetylcysteine amide

Name: N-acetylcysteine amide
Brand: SIGMA

≥98% (HPLC), lyophilized powder, antioxidant

Synonyme(s) :

(R)- 2-(Acetylamino)-3-mercapto-Propanamide, AD4, N-Acetyl-L-cysteinamide, NACA, acetylcysteinamide

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Conditionnement	Référence	Disponibilité	Prix

A propos de cet article

Formule empirique (notation de Hill) :

C₅H₁₀N₂O₂S

Numéro CAS:

38520-57-9

Poids moléculaire :

162.21

UNSPSC Code:

12352209

PubChem Substance ID:

329770626

NACRES:

NA.25

MDL number:

MFCD01696115

Assay:

≥98% (HPLC)

Form:

lyophilized powder

Storage condition:

desiccated

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Propriétés

Nom du produit

N-acetylcysteine amide, ≥98% (HPLC)

Quality Segment

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.

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.

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Cet article	S8825	S9318	SML1065
Sigma-Aldrich A0737 N-acetylcysteine amide	Sigma-Aldrich S8825 Salermide	Sigma-Aldrich S9318 Sandoz 58-035	Sigma-Aldrich SML1065 TR100
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay >98% (HPLC)	assay ≥98% (HPLC)
form lyophilized powder	form powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility H₂O: ≥20 mg/mL, DMSO: >40 mg/mL	solubility DMSO: >10 mg/mL	solubility DMSO: 16 mg/mL, H₂O: insoluble	solubility DMSO: 5 mg/mL, clear (warmed)
storage condition desiccated	storage condition desiccated	storage condition -	storage condition -