2-Iodoacetamide (Iodoacetamide) is a commonly used alkylating agent that is used to alkylate cysteine in the process of preparing proteomics samples.

Physicochemical Properties

Molecular Formula	C2H4INO
Molecular Weight	184.96
Exact Mass	184.933
CAS #	144-48-9
Related CAS #	2-Iodoacetamide-d4;1219802-64-8
PubChem CID	3727
Appearance	White to yellow solid powder
Density	2.3±0.1 g/cm3
Boiling Point	297.1±23.0 °C at 760 mmHg
Melting Point	92-95 °C(lit.)
Flash Point	133.5±22.6 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.602
LogP	-0.19
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Heavy Atom Count	5
Complexity	44.9
Defined Atom Stereocenter Count	0
InChi Key	PGLTVOMIXTUURA-UHFFFAOYSA-N
InChi Code	InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
Chemical Name	2-iodoacetamide
Synonyms	Iodoacetamide; 2-Iodoacetamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	The production of viral structural proteins involves a partial cleavage cascade mechanism. The largest virally induced protein found in infected cells has a molecular weight of 144,000. Two polypeptides with molecular weights of 205,000 and 180,000 emerge when the infected cells are pretreated with iodoacetamide before being pulsed with 35S-methionine. When iodoacetamide is present, additional modifications take place in the viral protein precursors.[2]
ln Vivo	2-Iodoacetamide (2.0–10 mg; 20–93 days; drinking; daily) In the secretory portion of the rat stomach, feeding invariably results in long-term, deep ulcers[2].
Cell Assay	After being pretreated for 15 minutes with 2 mM iodoaeetamide, infected cells were pulsed for 30 minutes with 500 μCi of 35S-methionine. By directly comparing the corresponding autoradiogram and the stained dried slab gel, the molecular weights are determined.
Animal Protocol	Animal/Disease Models: SD (Sprague-Dawley) rats[2] Doses: 2.0-10 mg Route of Administration: Drinking water, daily, for periods of 20 to 93 days Experimental Results: Produced gastritis which was further complicated by chronic ulceration in many of the test rats .
References	[1]. The Impact of Commonly Used Alkylating Agents on Artifactual Peptide Modification. J Proteome Resq. 2017 Sep 1;16(9):3443-3447. [2]. J J LALICH. Iodoacetamide induced gastric ulcers in rats. Proc Soc Exp Biol Med. 1962 Apr;109:905-8.
Additional Infomation	Iodoacetamide is a sulfhydryl alkylating reagent that forms covalent bonds with the thiol group of cysteines so the protein or peptide no longer forms disulfide bonds. An alkylating sulfhydryl reagent. Its actions are similar to those of iodoacetate.

Solubility Data

Solubility (In Vitro)

DMSO : 40~100 mg/mL (216.3~540.7 mM) H2O : ~100 mg/mL (~540.7 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (13.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 100 mg/mL (540.66 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.4066 mL	27.0329 mL	54.0657 mL
	5 mM	1.0813 mL	5.4066 mL	10.8131 mL
	10 mM	0.5407 mL	2.7033 mL	5.4066 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.