| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| Targets |
Dimethindene targets the histamine H1 receptor as a potent and selective antagonist. By binding to the H1 receptor, it blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. This inhibition prevents the vasodilation, increased vascular permeability, and smooth muscle contraction that are characteristic of allergic responses. The compound also has anticholinergic activity, with the (S)-(+)-enantiomer being a potent M2-selective muscarinic receptor antagonist. The (R)-(-)-enantiomer is the eutomer responsible for bioactivity at the histamine H1 receptor. Dimethindene can also block K+ currents.
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| ln Vitro |
At an IC50 value of 29.5 μM, dimethindene (5-500 μM) decreases the K+ current produced by Cromakalim in vesicle-sealed Xenopus laevis oocytes [2].
In vitro, dimethindene has been shown to be a potent antagonist of the histamine H1 receptor. In cell-based assays using cells expressing the H1 receptor, the compound inhibits histamine-induced calcium mobilization and other downstream signaling events. Its anticholinergic activity has been confirmed in assays using muscarinic receptors. At an IC50 value of 29.5 μM, dimethindene (5-500 μM) decreases the K+ current produced by Cromakalim in vesicle-sealed Xenopus laevis oocytes. These in vitro activities are consistent with its clinical efficacy in treating allergic conditions. |
| ln Vivo |
Dimethylindene (0.25 mg; intraperitoneal; once; C57BL/6 mice with cutaneous WH) inhibits WH and postpones the closure of cutaneous wounds [1].
In vivo, dimethindene is effective in alleviating symptoms such as itching, swelling, and redness associated with conditions like allergic rhinitis, urticaria, and atopic dermatitis. It is used for the symptomatic treatment of allergic reactions, including urticaria, allergies of the upper respiratory tract such as hay fever and perennial rhinitis, food and drug allergies, and pruritus of various origins. In animal models, dimethindene (0.25 mg; intraperitoneal; once; C57BL/6 mice) inhibits wound healing and postpones the closure of cutaneous wounds. Skin wound closure was delayed compared with vehicle-treated mice. |
| Enzyme Assay |
In vitro enzyme or receptor binding (non-cell) assays for dimethindene involve studying its binding affinity for the histamine H1 receptor. Radioligand binding assays are performed using membrane preparations from cells expressing the H1 receptor. The compound is incubated with a radiolabeled ligand, such as [3H]mepyramine, and the displacement of the ligand is measured to determine the Ki or IC50. These assays confirm the compound's affinity for the H1 receptor. Selectivity is assessed by testing the compound against other histamine receptors and muscarinic receptors.
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| Cell Assay |
In vitro cell-based assays for dimethindene are performed using cells that express the histamine H1 receptor, such as HeLa cells or CHO cells transfected with the receptor. Cells are loaded with a calcium-sensitive fluorescent dye and stimulated with histamine. The inhibition of the calcium response by dimethindene is measured as a functional readout of receptor antagonism. The compound's effects on cell proliferation and other signaling pathways can also be assessed. Its effects on K+ currents can be studied using electrophysiological techniques.
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| Animal Protocol |
Animal/Disease Models: C57BL/6 mice with skinned WH[1]
Doses: 0.25 mg Route of Administration: intraperitoneal (ip) injection; Experimental Results: Skin wound closure was delayed compared with vehicle-treated mice. In vivo animal experiments for dimethindene are conducted using rodent models of allergy and inflammation. The compound is administered orally or intraperitoneally. Models of passive cutaneous anaphylaxis (PCA) or histamine-induced skin reactions are used to evaluate the compound's antihistaminic activity. The compound's effects on pruritus (itching) are assessed using models of scratching behavior. In C57BL/6 mice with skin wounds, intraperitoneal injection of 0.25 mg dimethindene resulted in delayed skin wound closure compared with vehicle-treated mice. |
| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of dimethindene indicate that it is well-absorbed after oral administration. The compound has a molecular weight of 292.418 and a molecular formula of C20H24N2. It has a melting point of 50-53°C and a boiling point of 416.3°C. The LogP is 4.146, indicating moderate lipophilicity. The compound is typically administered orally or topically. It is metabolized in the liver, and its half-life is relatively short. It is excreted renally. The compound can cross the blood-brain barrier, which may contribute to its central nervous system side effects, such as drowsiness.
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| Toxicity/Toxicokinetics |
Toxicology (toxicology) data for dimethindene indicate that it is generally well-tolerated. Common side effects include drowsiness, dizziness, and dry mouth, which are typical of first-generation antihistamines. The compound may also cause gastrointestinal disturbances. As an anticholinergic agent, it should be used with caution in patients with glaucoma, prostatic hypertrophy, or other conditions that may be exacerbated by anticholinergic effects. It may cause sedation and should be used with caution when driving or operating machinery. Dimethindene impairs cutaneous wound healing.
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| References | |
| Additional Infomation |
Dimethyl indene is an indene compound. Dimethyl indene (fenisol) is an antihistamine/anticholinergic drug that can be taken orally or topically for the relief of itching. It is a histamine H1 receptor antagonist. It is used to treat allergic reactions, rhinitis, pruritus, and some common cold medications. Indications: Suitable for the symptomatic treatment of allergic reactions: urticaria, upper respiratory tract allergies (such as hay fever and perennial rhinitis), food and drug allergies; pruritus of various causes (except cholestatic pruritus); insect bites. Dimethyl indene is also suitable for treating pruritus caused by fulminant skin diseases such as chickenpox. Dimethyl indene can also be used as an adjunct therapy for the treatment of eczema and other allergic pruritus. Mechanism of Action: Dimethyl indene is a selective histamine H1 receptor antagonist that binds to histamine H1 receptors. This blocks the action of endogenous histamine, thereby temporarily relieving the adverse symptoms caused by histamine.
Pharmacodynamics Dimethylindene exists as a racemic mixture. (S)-(+)-dimethylindene is a potent M2-selective muscarinic receptor antagonist (with lower affinity for M1, M3, and M4 muscarinic receptors). The (R)-(-)-enantiomer is the histamine H1 receptor-binding enantiomer (which is biologically active). Other information: Dimethindene is a first-generation antihistamine used for the symptomatic treatment of allergic conditions. It is also known as Fenistil. The compound is available in various formulations, including oral drops, tablets, and topical gels. Its CAS number is 5636-83-9. The (S)-(+)-dimethindene maleate has CAS number 136152-65-3, and dimethindene maleate has CAS number 3614-69-5. |
| Molecular Formula |
C20H24N2
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|---|---|
| Molecular Weight |
292.418
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| Exact Mass |
292.194
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| CAS # |
5636-83-9
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| Related CAS # |
(S)-(+)-Dimethindene maleate;136152-65-3;Dimethindene maleate;3614-69-5
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| PubChem CID |
21855
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.065 g/cm3
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| Boiling Point |
416.3ºC at 760 mmHg
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| Melting Point |
50 - 53 °C
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| Flash Point |
205.6ºC
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| Index of Refraction |
1.587
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| LogP |
4.146
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
22
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| Complexity |
399
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN(CCC1CC2=CC=CC=C2C=1C(C1=CC=CC=N1)C)C
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| InChi Key |
MVMQESMQSYOVGV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3
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| Chemical Name |
N,N-dimethyl-2-[3-(1-pyridin-2-ylethyl)-1H-inden-2-yl]ethanamine
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| Synonyms |
Z-2001; Z2001; Z 2001
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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) |
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 | 3.4197 mL | 17.0987 mL | 34.1974 mL | |
| 5 mM | 0.6839 mL | 3.4197 mL | 6.8395 mL | |
| 10 mM | 0.3420 mL | 1.7099 mL | 3.4197 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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