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| Other Sizes |
| Targets |
6-Methyl-1H-indole acts as a moderate-potency agonist of the aryl hydrocarbon receptor (AhR), with validated 91% E-max relative to TCDD, enabling reproducible transcriptional profiling and non-saturating receptor activation studies. The methyl group position at the 6-position profoundly influences the compound's activity at key biological targets such as AhR. It is also a reactant in the preparation of aminoguanidine derivatives of arylsulfonyl indoles as inhibitors of interleukin-2-inducible T-cell kinases (ITK), and serves as a synthon for tryptophan dioxygenase (TDO) inhibitors. Additionally, it is used in the synthesis of arylsulfonylacetyl indoles as anti-HIV-1 agents.
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| ln Vitro |
It is a reactant in the synthesis of pyridyl-vinyl-indole, a tryptophan dioxygenase inhibitor that may be used as an immunomodulator against cancer. It is also a reaction in the synthesis of indole-linked triazole derivatives that may be used as antifungal medicines. To prepare N-β-D-xylosyl-indole derivatives as reactants for SGLT2 inhibitors; to manage hyperglycemia in diabetes; to prepare aminoguanidine derivatives of arylsulfonyl indoles as antifungal agents; to prepare indolylindazoles and indolylpyrazolopyridines as inhibitors of interleukin 2-inducible T-cell kinases; to prepare arylsulfonylacetyl indoles as anti-HIV-1 Reactants of pharmaceuticals. 6-Derivatives of benz[c,d]indol-3(1H)-one are synthesized using methyl enol.
In vitro, 6-Methyl-1H-indole is utilized as a reactant in the synthesis of pyridyl-vinyl-indole, a tryptophan dioxygenase inhibitor that may be used as an immunomodulator against cancer. It is also a reactant in the synthesis of indole-linked triazole derivatives with potential antifungal activity. As an AhR agonist with 91% efficacy relative to TCDD, it is employed in cell-based gene expression studies to investigate AhR-mediated transcriptional activation and CYP1A1 induction. The compound serves as a biochemical reagent for life science research, with ≥98% purity, and is used in various in vitro assay systems to study indole-mediated biological pathways. |
| ln Vivo |
In vivo studies specifically characterizing the pharmacological effects of 6-Methyl-1H-indole as a standalone therapeutic agent are not extensively documented in the literature. However, as a key synthetic intermediate for tryptophan dioxygenase inhibitors, its in vivo relevance is primarily through the final drug candidates derived from it, which are evaluated as potential anticancer immunomodulators in animal models. The compound itself is primarily used as a biochemical reagent and building block rather than a directly administered drug, and in vivo data for the parent compound remain limited.
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| Enzyme Assay |
For in vitro enzyme/receptor binding assays, 6-Methyl-1H-indole is typically evaluated for AhR agonistic activity using cell-free competitive binding assays with radiolabeled ligands such as [³H]TCDD. Membrane preparations or cytosolic fractions containing AhR are incubated with varying concentrations of the test compound (typically 0.001-100 μM) and the radioligand at 4°C for 2-4 hours. Non-specific binding is determined using excess unlabeled TCDD. Bound and free ligand are separated by charcoal-dextran precipitation or filtration, and radioactivity is measured by scintillation counting. The compound demonstrates 91% efficacy relative to TCDD in such assays.
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| Cell Assay |
For in vitro cell-based assays, 6-Methyl-1H-indole is evaluated using cell lines such as HepG2 or MCF-7 that express functional AhR. Cells are seeded in 96-well plates and treated with the compound at concentrations ranging from 0.1-100 μM for 24-48 hours. AhR activation is assessed by measuring CYP1A1 enzyme activity via EROD (ethoxyresorufin-O-deethylase) assay, where cells are incubated with 7-ethoxyresorufin and fluorescence is measured at excitation/emission wavelengths of 530/590 nm. Reporter gene assays using AhR-responsive luciferase constructs (e.g., pGudLuc) can also be employed. The compound shows 91% E-max relative to TCDD in these transcriptional activation assays.
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| Animal Protocol |
In vivo animal studies for 6-Methyl-1H-indole are typically conducted as part of the evaluation of drug candidates synthesized from this intermediate, rather than for the compound itself. For AhR agonist characterization, rodents (typically mice or rats) are administered the compound via oral gavage or intraperitoneal injection at doses ranging from 1-100 mg/kg. Tissues (liver, lung, thymus) are collected post-treatment for analysis of CYP1A1 induction by western blot or enzymatic activity assays. However, comprehensive in vivo pharmacokinetic and pharmacodynamic data for the parent compound are not well-documented in the publicly available literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 6-Methyl-1H-indole as a standalone compound are limited in the published literature. In silico predictions using SwissADME indicate a bioavailability score of 0.55 and the compound is classified as soluble. Indole derivatives generally exhibit moderate to high lipophilicity (logP ~2.6 for 6-methylindole), suggesting good membrane permeability and potential for oral absorption. As a small molecule (MW 131.17 g/mol), it is expected to have favorable permeability characteristics. However, specific data on half-life, clearance, volume of distribution, and protein binding for this particular methylindole isomer are not available in the public domain.
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| Toxicity/Toxicokinetics |
6-Methyl-1H-indole is classified as an irritant with hazard code Xi. Risk statements include R36/37/38: Irritating to eyes, respiratory system and skin. Safety statements recommend S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. GHS hazard statement H315 indicates it causes skin irritation. Some sources note that 6-methylindole has been shown to induce cancer in animals and its metabolites are carcinogenic in animal models, and it has been shown to induce cell death by activating the mitochondrial pathway of apoptosis, leading to cytochrome P450 1A (CYP1A) activation. Acute toxicity data via oral and inhalation routes are not available.
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| Additional Infomation |
6-Methylindole is a type of indole compound.
6-Methyl-1H-indole (CAS 3420-02-8) is primarily a research-grade biochemical reagent and synthetic intermediate, not an approved pharmaceutical drug. Its mechanism of action as an AhR agonist involves binding to the aryl hydrocarbon receptor, which upon activation translocates to the nucleus, dimerizes with ARNT, and binds to xenobiotic response elements (XREs) to regulate transcription of target genes including CYP1A1. As a tryptophan dioxygenase inhibitor precursor, it contributes to the development of immunomodulatory agents for cancer therapy. No clinical trials or FDA-approved indications exist for this compound itself. It is available in research quantities (50 mg to bulk) with ≥98% purity and is intended for laboratory use only, not for human diagnostic or therapeutic applications. |
| Molecular Formula |
C9H9N
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|---|---|
| Molecular Weight |
131.17
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| Exact Mass |
131.073
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| CAS # |
3420-02-8
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| PubChem CID |
137928
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
260.3±9.0 °C at 760 mmHg
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| Melting Point |
29-32°C
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| Flash Point |
109.6±11.3 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.655
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| LogP |
2.6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
10
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| Complexity |
122
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N1([H])C([H])=C([H])C2C([H])=C([H])C(C([H])([H])[H])=C([H])C1=2
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| InChi Key |
ONYNOPPOVKYGRS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H9N/c1-7-2-3-8-4-5-10-9(8)6-7/h2-6,10H,1H3
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| Chemical Name |
6-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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