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Bis(2-chloroethyl)amine hydrochloride is a nitrogen mustard derivative that can alkylate DNA and other biomolecules through the formation of reactive aziridinium intermediates. The compound's biological target is DNA, where it forms crosslinks that interfere with DNA replication and transcription. This mechanism is the basis for the anticancer activity of nitrogen mustard compounds. The compound itself is a synthetic intermediate and a precursor to various anticancer drugs. When incorporated into pharmaceutical compounds, the bis(2-chloroethyl)amine moiety can alkylate nucleophilic sites in DNA.
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| ln Vitro |
Hydrochloride of bis(2-chloroethyl)amine is employed as a pharmaceutical intermediate.
In vitro, bis(2-chloroethyl)amine hydrochloride exhibits alkylating activity that can crosslink DNA and inhibit cell proliferation. The compound is a precursor to various nitrogen mustard anticancer drugs. In cell-based assays, nitrogen mustard derivatives show concentration-dependent cytotoxicity against cancer cell lines through DNA crosslinking and induction of apoptosis. The compound itself is not typically used as a therapeutic agent but as an intermediate in the synthesis of more complex anticancer drugs. Its utility is demonstrated in the preparation of various pharmaceutical compounds. |
| ln Vivo |
Bis(2-chloroethyl)amine hydrochloride is not a pharmacologically approved drug itself, but it is a key intermediate in the synthesis of nitrogen mustard anticancer agents. These agents have been used in the treatment of various cancers including Hodgkin's lymphoma and other hematological malignancies. The compound's in vivo activity would be associated with the final drug products synthesized from this intermediate, not with the intermediate itself. The compound is not administered to animals in pharmacological studies as a test article.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays are not applicable to bis(2-chloroethyl)amine hydrochloride as it is a synthetic intermediate rather than a biologically active test compound. Standard characterization protocols for this reagent include nuclear magnetic resonance (¹H NMR, ¹³C NMR) and mass spectrometry to confirm structure and purity. Melting point determination and HPLC analysis are used for quality control. For synthetic applications, typical reactions include the use of the compound as a building block for the synthesis of nitrogen mustard anticancer agents and other pharmaceutical compounds.
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| Cell Assay |
Cell-based experiments are not performed with bis(2-chloroethyl)amine hydrochloride itself, as it is a chemical intermediate rather than a test compound for biological activity. When the compound is used to synthesize anticancer drug candidates, those products may be tested in cell culture using standard protocols. Typically, final compounds are dissolved in DMSO and diluted in culture medium to achieve desired concentrations (typically 0.1-100 µM). Cells are incubated for 24-72 hours, and effects on cell viability, proliferation, or DNA damage are measured using appropriate assays. The intermediate itself is not evaluated in cellular systems.
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| Animal Protocol |
In vivo animal studies are not conducted with bis(2-chloroethyl)amine hydrochloride, as it is a research reagent for chemical synthesis. When the compound is used to synthesize anticancer drug candidates, those final products undergo standard preclinical evaluation. Typical protocols for anticancer candidates include xenograft studies in immunodeficient mice, pharmacokinetic studies in rodents, and toxicology studies. These studies evaluate the safety and efficacy of the final drug molecules, not the synthetic intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of bis(2-chloroethyl)amine hydrochloride are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 178.49, hydrochloride salt, high water solubility), the compound would be expected to have low oral bioavailability due to poor membrane permeability. It would likely be rapidly metabolized and cleared. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For anticancer drug candidates synthesized from this intermediate, pharmacokinetic properties are determined as part of drug development.
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| Toxicity/Toxicokinetics |
Toxicity Data
LCLo (mice) = 1,000 mg/m³/10 minutes Bis(2-chloroethyl)amine hydrochloride is a corrosive compound that causes severe skin burns and eye damage. It is a potential carcinogen due to its DNA-alkylating properties. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored in a cool, dry place away from moisture and strong oxidizing agents. Special precautions are required due to its mutagenic and carcinogenic potential. |
| Additional Infomation |
Bis(2-chloroethyl)amine hydrochloride is a key intermediate in the synthesis of nitrogen mustard anticancer agents. It is also known as nor-nitrogen mustard hydrochloride. The compound has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is chemical—serving as a precursor for the synthesis of DNA-alkylating anticancer agents.
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| Molecular Formula |
C4H10CL3N
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| Molecular Weight |
178.49
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| Exact Mass |
176.987
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| CAS # |
821-48-7
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| Related CAS # |
Bis(2-chloroethyl)amine-1,1,2,2-d4 hydrochloride;352431-06-2;Bis(2-Chloroethyl)amine hydrochloride-d8;102092-04-6
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| PubChem CID |
522769
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| Appearance |
White to off-white solid powder
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| Density |
1.125 g/cm3
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| Boiling Point |
204.2ºC at 760 mmHg
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| Melting Point |
212-214 °C(lit.)
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| Flash Point |
77.3ºC
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| LogP |
2.246
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
8
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| Complexity |
28.9
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl.ClCCNCCCl
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| InChi Key |
YMDZDFSUDFLGMX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H9Cl2N.ClH/c5-1-3-7-4-2-6;/h7H,1-4H2;1H
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| Chemical Name |
2-chloro-N-(2-chloroethyl)ethanamine;hydrochloride
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6026 mL | 28.0128 mL | 56.0255 mL | |
| 5 mM | 1.1205 mL | 5.6026 mL | 11.2051 mL | |
| 10 mM | 0.5603 mL | 2.8013 mL | 5.6026 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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