Iodoacetamide

Iodoacetamide (IAA) is an organic compound with the chemical formula ICH2CONH2. It is an alkylating agent used for peptide mapping purposes. Its actions are similar to those of iodoacetate. It is commonly used to bind covalently with the thiol group of cysteine so the protein cannot form disulfide bonds. It is also used in ubiquitin studies as an inhibitor of deubiquitinase enzymes (DUBs) because it alkylates the cysteine residues at the DUB active site.

Iodoacetamide
Names
Preferred IUPAC name
2-Iodoacetamide
Other names
IAA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.119
EC Number
  • 205-630-1
PubChem CID
RTECS number
  • AC4200000
UNII
  • InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5) Y
    Key: PGLTVOMIXTUURA-UHFFFAOYSA-N Y
  • InChI=1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
    Key: PGLTVOMIXTUURA-UHFFFAOYAE
SMILES
  • C(C(=O)N)I
Properties
ICH2CONH2
Molar mass 184.964 g·mol−1
Appearance white crystals (yellow colouration indicates the presence of iodine)
Melting point 94 °C (201 °F; 367 K)
Hazards
NFPA 704 (fire diamond)
3
0
1
Safety data sheet (SDS) MSDS 1, MSDS 2
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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