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| Other Sizes |
| Targets |
The primary targets of 2-bromoacetamide include liver alcohol dehydrogenase (LADH), which it can inactivate. The compound also interferes with microtubule and actin cytoskeletal function. As an alkylating agent, it reacts with nucleophiles such as thiol groups in cysteine residues, effectively blocking disulfide bond formation by alkylating free thiols.
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| ln Vitro |
In vitro studies demonstrate that 2-bromoacetamide is a potent alkylating agent for a range of nucleophiles. It is highly effective for cysteine alkylation with a reduced propensity for side reactions compared to other alkylating agents. The compound can inactivate liver alcohol dehydrogenase and interfere with microtubule and actin cytoskeletal function in cell-free systems.
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| ln Vivo |
In vivo activity data for 2-bromoacetamide are primarily related to its toxicity as a disinfection byproduct. The compound is a potent developmental toxicant in animals. Its ability to inactivate liver alcohol dehydrogenase and interfere with cytoskeletal function suggests potential for systemic toxicity. However, specific in vivo pharmacological studies are limited.
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| Enzyme Assay |
Non-cellular assays for 2-bromoacetamide typically involve characterizing its alkylating activity. The compound's reactivity with thiol-containing compounds can be monitored using spectrophotometric methods with Ellman's reagent or other thiol-detecting probes. Enzyme inactivation assays using purified liver alcohol dehydrogenase measure the compound's ability to inhibit enzyme activity. These cell-free systems allow for precise characterization of the compound's chemical reactivity.
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| Cell Assay |
Cellular assays for 2-bromoacetamide are conducted using various cell lines to assess its effects on cytoskeletal function and cell viability. Cells are treated with the compound, and microtubule and actin cytoskeletal integrity is assessed by immunofluorescence microscopy. Cell viability is measured using MTT or similar assays. These studies demonstrate the compound's interference with cytoskeletal function at the cellular level.
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| Animal Protocol |
In vivo animal experiments for 2-bromoacetamide are typically conducted in developmental toxicity studies. The compound is administered to pregnant animals, and developmental outcomes are assessed in the offspring. These studies have shown that 2-bromoacetamide is a potent developmental toxicant. Other in vivo studies may assess the compound's effects on liver function and alcohol dehydrogenase activity.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-bromoacetamide are not well-characterized. As a small, polar molecule (MW 137.96 g/mol), it is likely absorbed following oral or inhalation exposure. The compound may be metabolized and excreted in urine. Its stability in biological fluids and its distribution in vivo have not been extensively studied. The compound is sensitive to light and heat.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-bromoacetamide indicate that it is a potent developmental toxicant in animals. As a disinfection byproduct, it is a concern for human health through exposure to chlorinated drinking water. The compound can inactivate liver alcohol dehydrogenase and interfere with cytoskeletal function, suggesting potential for hepatotoxicity and other systemic effects. Standard laboratory safety precautions should be followed when handling the compound.
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| References |
[1]. Fries RW, et al. Activation of liver alcohol dehydrogenases by imidoesters generated in solution. Biochemistry. 1975;14(23):5233‐5238.
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| Additional Infomation |
Other information includes 2-bromoacetamide's use as a versatile intermediate in pharmaceutical synthesis. It is a disinfection byproduct formed during water treatment. The compound is a precursor to dehydropeptidase I inactivator. It is available with ≥98% purity and should be stored protected from light and heat due to its instability. The compound is also known as bromoacetamide and has a faint odor.
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| Molecular Formula |
C2H4BRNO
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|---|---|
| Molecular Weight |
137.96
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| Exact Mass |
136.947
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| CAS # |
683-57-8
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| PubChem CID |
69632
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| Appearance |
White to off-white solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
271.6±23.0 °C at 760 mmHg
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| Melting Point |
87-91 °C(lit.)
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| Flash Point |
118.1±22.6 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.511
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| LogP |
-0.52
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
5
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| Complexity |
44.9
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| Defined Atom Stereocenter Count |
0
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| SMILES |
BrC([H])([H])C(N([H])[H])=O
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| InChi Key |
JUIKUQOUMZUFQT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C2H4BrNO/c3-1-2(4)5/h1H2,(H2,4,5)
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| Chemical Name |
2-bromoacetamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (724.85 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.12 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 (18.12 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (18.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.2485 mL | 36.2424 mL | 72.4848 mL | |
| 5 mM | 1.4497 mL | 7.2485 mL | 14.4970 mL | |
| 10 mM | 0.7248 mL | 3.6242 mL | 7.2485 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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