| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
5-Methylindole has been shown to inhibit bacterial and animal kinases as well as plant tryptophan synthase. Kinases are enzymes that catalyze the transfer of phosphate groups and play critical roles in cell signaling, proliferation, and metabolism. The indole scaffold is a privileged structure in drug discovery, enabling interactions with various biological targets through hydrogen bonding, π-π stacking, and hydrophobic interactions. The methyl substituent at the 5-position modulates the compound's electronic and steric properties. 5-Methylindole is used in the preparation of ITK inhibitors and CRTh2 antagonists.
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|---|---|
| ln Vitro |
In vitro, 5-methylindole exhibits kinase inhibitory activity. It is used as a reactant for the preparation of pharmaceutically active compounds including 2-oxo-1-pyrrolidine analogues, anticancer immunomodulators, IL2-inducible T-cell kinase (ITK) inhibitors, and CRTh2 antagonists. These compounds are evaluated for their biological activities in various cell-based and biochemical assays. The compound itself is a chemical intermediate and may have applications in studying kinase inhibition and other biological processes. However, detailed pharmacological data for the compound itself are limited.
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| ln Vivo |
5-Methylindole is not a pharmacologically active drug and does not exhibit in vivo therapeutic activity as a standalone compound. It has not been evaluated in animal models for efficacy against any disease. The compound is primarily used as a chemical intermediate in the synthesis of pharmaceutical compounds. Any in vivo activity would be associated with drug candidates synthesized from this intermediate, not with the compound itself. The compound is not administered to animals in standard pharmacological studies. Its role is strictly chemical—providing a versatile indole scaffold.
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| Enzyme Assay |
In vitro enzyme assays for 5-methylindole derivatives typically involve kinase inhibition studies. A standard protocol uses purified kinase enzymes (e.g., ITK, various kinases) incubated with a peptide substrate and [γ-³²P]-ATP in the presence of varying concentrations of the test compound. Phosphorylated substrate is captured and quantified by scintillation counting. IC₅₀ values are calculated from dose-response curves. For tryptophan synthase inhibition, the enzyme is incubated with indole-3-glycerol phosphate and serine, and product formation is measured spectrophotometrically. Quality control includes NMR and HPLC.
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| Cell Assay |
In vitro cell culture experiments with 5-methylindole derivatives typically involve cancer cell lines or immune cells. Cells are cultured in appropriate media and treated with compounds at concentrations ranging from 0.1-100 µM for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. For immunomodulatory studies, cytokine production (e.g., IL-2) is measured by ELISA. For kinase inhibition studies, phosphorylation of downstream targets is assessed by Western blotting. The intermediate itself is typically not tested in cellular systems; rather, the final products are evaluated.
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| Animal Protocol |
In vivo animal studies are not conducted with 5-methylindole itself, as it is a research reagent for chemical synthesis. When the compound is used to synthesize drug candidates (e.g., ITK inhibitors or CRTh2 antagonists), those final products undergo standard preclinical evaluation. Typical protocols for drug candidates include pharmacokinetic studies in rodents (oral or intravenous administration, blood sampling for LC-MS/MS analysis), efficacy studies in disease models (e.g., cancer xenografts, inflammation models), and toxicology studies. These studies evaluate the safety and efficacy of the final drug molecules.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 5-methylindole are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 131.17, logP approximately 2.5), the compound would be expected to have good oral bioavailability if administered. It would likely undergo metabolism via cytochrome P450-mediated oxidation, particularly at the indole nitrogen and the methyl group. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For drug candidates synthesized from this intermediate, pharmacokinetic properties are determined as part of drug development.
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| Toxicity/Toxicokinetics |
Toxicological data for 5-methylindole are limited as it is a research reagent. 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 place. No acute toxicity data are available. The compound is not intended for drug, household, or other uses. It should be stored away from light and moisture.
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| Additional Infomation |
The structure given in the first document
5-Methylindole is a versatile building block in medicinal chemistry for the synthesis of kinase inhibitors, anticancer immunomodulators, and other bioactive compounds. The indole scaffold is a privileged structure in drug discovery, found in numerous approved drugs including triptans, indomethacin, and vinca alkaloids. 5-Methylindole is also known as skatole and is found in feces, urine, and other biological fluids. 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 biologically active indole derivatives. |
| Molecular Formula |
C9H9N
|
|---|---|
| Molecular Weight |
131.17
|
| Exact Mass |
131.073
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| CAS # |
614-96-0
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| PubChem CID |
11978
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
269.0±9.0 °C at 760 mmHg
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| Melting Point |
60-62 °C(lit.)
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| Flash Point |
114.7±11.3 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
|
| Index of Refraction |
1.655
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| LogP |
2.6
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
0
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
10
|
| Complexity |
122
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=C2C(=CC=C1C)[NH]C=C2
|
| InChi Key |
YPKBCLZFIYBSHK-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C9H9N/c1-7-2-3-9-8(6-7)4-5-10-9/h2-6,10H,1H3
|
| Chemical Name |
5-methyl-1H-indole
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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 | 7.6237 mL | 38.1185 mL | 76.2369 mL | |
| 5 mM | 1.5247 mL | 7.6237 mL | 15.2474 mL | |
| 10 mM | 0.7624 mL | 3.8118 mL | 7.6237 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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