I6125

Iodoacetamide

≥99% (NMR), crystalline

• Synonym(s): α-Iodoacetamide, 2-Iodoacetamide
• Linear Formula: ICH₂CONH₂
• CAS Number: 144-48-9
• Molecular Weight: 184.96
• UNSPSC Code: 12352202
• NACRES: NA.77
• PubChem Substance ID: 24896083
• EC Number: 205-630-1
• Beilstein/REAXYS Number: 1739080
• MDL number: MFCD00008028

Properties

• biological source: synthetic (organic)
• Quality Level: 300
• assay: ≥99% (NMR)
• form: crystalline
• mp: 92-95 °C (lit.)
• solubility: H₂O: soluble 0.5 M, clear, colorless
• storage temp.: 2-8°C
• SMILES string: NC(=O)CI
• InChI: 1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
• InChI key: PGLTVOMIXTUURA-UHFFFAOYSA-N

Description

Application

• A Mass Spectrometry Strategy for Protein Quantification Based on the Differential Alkylation of Cysteines Using Iodoacetamide and Acrylamide.: This study presents a novel mass spectrometry method for quantifying proteins by differentially alkylating cysteines with iodoacetamide and acrylamide, enhancing the accuracy of protein quantification in complex samples. (Virág et al., 2024).


• Laminarin ameliorates iodoacetamide-induced functional dyspepsia via modulation of 5-HT(3) receptors and the gut microbiota.: Research demonstrates that laminarin can mitigate functional dyspepsia induced by iodoacetamide through modulating 5-HT(3) receptors and altering gut microbiota composition, offering potential therapeutic benefits. (Liu et al., 2024).


• Redox proteomics in melanoma cells: An optimized protocol.: This paper describes an optimized redox proteomics protocol using iodoacetamide, which facilitates the identification of redox-sensitive proteins in melanoma cells, aiding in the understanding of redox regulation in cancer. (Cunha et al., 2024).


• Molecular targets of cisplatin in HeLa cells explored through competitive activity-based protein profiling strategy.: Utilizing iodoacetamide in competitive activity-based protein profiling, this study identifies molecular targets of cisplatin in HeLa cells, providing insights into the drug′s mechanisms. (Chen et al., 2024).


• Development and Comparison of 4-Thiouridine to Cytidine Base Conversion Reaction.: This research compares base conversion reactions involving 4-thiouridine and cytidine, with iodoacetamide playing a crucial role in the reaction mechanism, contributing to advancements in nucleotide chemistry. (Ohashi et al., 2024).

Biochem/physiol Actions

Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. It is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibiting ribonuclease.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H317,H334,H413
• pcodes: P261 - P264 - P273 - P280 - P301 + P310 - P302 + P352
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 4 - Resp. Sens. 1 - Skin Sens. 1
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges