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Merck

D3648

Diamide

Synonym(s):

1,1′-Azobis(N,N-dimethylformamide), N,N,N′,N′-Tetramethylazodicarboxamide, Azodicarboxylic acid bis(dimethylamide), Diazenedicarboxylic acid bis(N,N-dimethylamide), TMAD

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About This Item

Linear Formula:
(CH3)2NCON=NCON(CH3)2
CAS Number:
10465-78-8
Molecular Weight:
172.19
UNSPSC Code:
12352102
NACRES:
NA.22
PubChem Substance ID:
24278365
EC Number:
233-951-7
Beilstein/REAXYS Number:
1910409
MDL number:
MFCD00008318

Key Documents

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InChI key

VLSDXINSOMDCBK-BQYQJAHWSA-N

InChI

1S/C6H12N4O2/c1-9(2)5(11)7-8-6(12)10(3)4/h1-4H3/b8-7+

SMILES string

CN(C)C(=O)\N=N\C(=O)N(C)C

assay

≥98% (TLC)

form

powder

mp

113-115 °C

solubility

water: 19.60-21.00 mg/mL, clear to slightly hazy, orange

storage temp.

−20°C

Quality Level

200

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Application

Reported to be of use as a thiol oxidizing agent. Diamide has been used to titrate protein glutathiolation to discriminate from other oxidative protein modifications. Treatment increased protein glutathiolation in a concentration-dependent manner and had comparably little effect on protein-protein disulfide formation.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000492900
0000492901
0000492901
0000492900
0000458107

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Yumei He et al.
Nucleic acids research, 45(1), 106-114 (2016-09-25)
We describe a Pap1-Oxs1 pathway for diamide-induced disulfide stress in Schizosaccharomyces pombe, where the nucleocytoplasmic HMG protein Oxs1 acts cooperatively with Pap1 to regulate transcription. Oxs1 and Pap1 form a complex when cells are exposed to diamide or Cd that
Carlos A Sorgi et al.
Scientific reports, 7(1), 10981-10981 (2017-09-10)
The differentiation of resident tissue macrophages from embryonic precursors and that of inflammatory macrophages from bone marrow cells leads to macrophage heterogeneity. Further plasticity is displayed through their ability to be polarized as subtypes M1 and M2 in a cell
Bradford G Hill et al.
Biochimica et biophysica acta, 1797(2), 285-295 (2009-11-21)
Protein thiolation by glutathione is a reversible and regulated post-translational modification that is increased in response to oxidants and nitric oxide. Because many mitochondrial enzymes contain critical thiol residues, it has been hypothesized that thiolation reactions regulate cell metabolism and
Yong Tao et al.
Insect biochemistry and molecular biology, 43(9), 820-828 (2013-06-29)
Anthranilic diamides, which include the new commercial insecticide, chlorantraniliprole, are an exciting new class of chemistry that target insect ryanodine receptors. These receptors regulate release of stored intracellular calcium and play a critical role in muscle contraction. As with insects
Ilse A E Bollen et al.
The American journal of pathology, 187(12), 2645-2658 (2017-09-25)
Peripartum cardiomyopathy (PPCM) and dilated cardiomyopathy (DCM) show similarities in clinical presentation. However, although DCM patients do not recover and slowly deteriorate further, PPCM patients show either a fast cardiac deterioration or complete recovery. The aim of this study was
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