| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
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| Other Sizes |
| Targets |
IC50: Adrenergic receptor[1]
Dibenamine hydrochloride targets α-adrenoceptors. It is a non-selective, irreversible antagonist that alkylates the receptor, leading to a long-lasting blockade. The compound forms an ethyleneimonium ion which reacts covalently with the α-adrenoceptor. By blocking α-adrenoceptors, it inhibits the effects of endogenous catecholamines like norepinephrine and epinephrine at these receptors, leading to vasodilation and decreased peripheral resistance. |
|---|---|
| ln Vitro |
In the isolated vas deferens of guinea pigs, dibenamine (100 nM–10 μM) attenuates the degree of cocaine-induced increase in acetylcholine sensitivity while having no effect on cholinergic contraction. Furthermore, the degree of dibenamine-induced inhibition is negatively correlated with cocaine concentration and depends on dibenamine concentration[3].
In vitro, Dibenamine hydrochloride acts as a non-selective, irreversible α-adrenoceptor antagonist. Its activity is typically assessed by measuring its ability to inhibit agonist-induced contraction of isolated smooth muscle preparations, such as rat aorta. The irreversible nature of its blockade is confirmed by demonstrating that the inhibition cannot be reversed by washing. The compound is used as a tool to study the role of α-adrenoceptors in various physiological processes. |
| ln Vivo |
Subcutaneous injection of 25 mg/kg dibenamine hydrochloride 48 and 24 hours prior to CCl4 administration reduces CHCl3 levels by 30–50% at 2 and 6 hours, but has no discernible effect on the half-life of CHCl3 in the liver. The conversion of Ccl4 to CHCL3 appears to be slowed down by pretreatment with dibenzamine[1].
In vivo, Dibenamine hydrochloride produces effects consistent with α-adrenoceptor blockade, including vasodilation and decreased blood pressure. Its irreversible nature results in a long-lasting effect. However, due to its non-selectivity and potential for significant side effects, it is not used clinically. It is primarily used as a research tool to study the physiological and pathological roles of α-adrenoceptors. |
| Enzyme Assay |
For non-cell-based receptor binding assays, Dibenamine hydrochloride can be evaluated using membrane preparations from tissues expressing α-adrenoceptors. Radioligand binding displacement experiments are performed using a suitable radiolabeled ligand such as [3H]-prazosin for α1 or [3H]-yohimbine for α2. Membrane homogenates are incubated with increasing concentrations of the test compound and a fixed concentration of the radioligand. However, due to the irreversible nature of its binding, standard displacement assays may not be suitable, and the compound's effect is typically assessed by its ability to reduce the maximal binding capacity (Bmax) rather than by displacement.
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| Cell Assay |
For in vitro cellular assays, cells expressing α-adrenoceptors are cultured in appropriate media. For functional assays, the compound's ability to inhibit agonist-induced calcium mobilization or contraction is assessed. Cells are pre-incubated with various concentrations of Dibenamine hydrochloride, washed to remove unbound compound, and then stimulated with an agonist. The reduction in response compared to control indicates irreversible antagonist activity. The compound's effects are typically long-lasting due to the covalent modification of the receptor.
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| Animal Protocol |
For in vivo animal studies, Dibenamine hydrochloride can be administered to rodents via intravenous or intraperitoneal injection. In cardiovascular studies, blood pressure and heart rate are monitored following compound administration. The compound's effects on vascular tone and sympathetic nervous system function are assessed. Dosing regimens vary depending on the specific model and desired exposure levels.
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| ADME/Pharmacokinetics |
Dibenamine hydrochloride has a molecular weight of 296.24 and a molecular formula of C16H19Cl2N. It is a haloalkylamine compound. The compound is typically stored under desiccated conditions. It is soluble in appropriate solvents for research use. It is for research use only and is not intended for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of Dibenamine hydrochloride includes potential for significant cardiovascular effects due to its non-selective α-adrenoceptor blockade. High doses may cause profound hypotension and reflex tachycardia. The compound is for research use only and is not intended for human consumption. Standard safety precautions should be observed when handling the compound.
|
| References |
[1]. Effect of dibenamine (N-(2-chloroethyl) dibenzylamine) on the metabolism of radioactive epinephrine.J Biol Chem. 1953 May;202(1):39-43.
[2]. Nature of the protection against carbon tetrachloride-induced hepatotoxicity produced by pretreatment with dibenamine (N-(2-chloroethyl)dibenzylamine). Biochem Pharmacol. 1974 May 15;23(10):1479-91. [3]. K Araki, et al. Pharmacological studies on supersensitization. VII. Inhibitory effect of dibenamine on cocaine-induced supersensitivity of isolated vas deferens of guinea pig. J Pharmacobiodyn. 1982 Oct;5(10):789-95. |
| Additional Infomation |
Dibenamine hydrochloride (N-(2-Chloroethyl)dibenzylamine hydrochloride) is a classical, non-selective, irreversible α-adrenoceptor antagonist. It forms an ethyleneimonium ion which alkylates the α-adrenoceptor, leading to irreversible blockade. It is used in research to study adrenergic receptor function and sympathetic nervous system physiology. It is available for research purposes only.
|
| Molecular Formula |
C16H19CL2N
|
|---|---|
| Molecular Weight |
296.23
|
| Exact Mass |
295.089
|
| CAS # |
55-43-6
|
| Related CAS # |
51-50-3; 55-43-6
|
| PubChem CID |
5925
|
| Appearance |
White to light yellow solid powder
|
| Density |
1.107g/cm3
|
| Boiling Point |
320ºC at 760mmHg
|
| Melting Point |
190-193 °C(lit.)
|
| Flash Point |
147.3ºC
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| LogP |
4.729
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
6
|
| Heavy Atom Count |
19
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| Complexity |
187
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C(C=C1)CN(CCCl)CC2=CC=CC=C2.Cl
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| InChi Key |
LZXCEBPGNFLHEQ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C16H18ClN.ClH/c17-11-12-18(13-15-7-3-1-4-8-15)14-16-9-5-2-6-10-16;/h1-10H,11-14H2;1H
|
| Chemical Name |
N,N-dibenzyl-2-chloroethanamine;hydrochloride
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| Synonyms |
55-43-6; Dibenamine hydrochloride; N-(2-Chloroethyl)dibenzylamine hydrochloride; Dibenzylchlorethamine hydrochloride; Dibenamine HCl;
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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) |
DMSO: 125 mg/mL (421.97 mM)
H2O: 33.33 mg/mL (112.51 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.02 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 20.8 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: ≥ 2.08 mg/mL (7.02 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 20.8 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: ≥ 2.08 mg/mL (7.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 9.09 mg/mL (30.69 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3758 mL | 16.8788 mL | 33.7576 mL | |
| 5 mM | 0.6752 mL | 3.3758 mL | 6.7515 mL | |
| 10 mM | 0.3376 mL | 1.6879 mL | 3.3758 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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