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| Other Sizes |
| Targets |
5-Methoxyindole targets the 5-HT3A receptor as a partial agonist and exhibits dual agonist/inverse agonist activity at the 5-HT3B receptor. It may also be an endogenous ligand for PPARγ. The compound's mechanism of action involves modulation of serotonin receptor signaling and potential activation of PPARγ-mediated pathways. Its diverse biological activities make it relevant for research in oncology, inflammation, and neurology.
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| ln Vitro |
In vitro, 5-methoxyindole exhibits significant anti-cancer and anti-inflammatory activities. It shows strong adverse activity against the phytopathogenic fungus Fusarium graminearum, effectively inhibiting its growth, formation, and conidia germination. The compound is used as a drug intermediate and as a research tool to study serotonin receptor pharmacology and PPARγ signaling.
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| ln Vivo |
In vivo data for 5-methoxyindole as a therapeutic agent are limited. As an endogenous compound and melatonin precursor, it may have physiological roles in sleep regulation and circadian rhythms. However, specific in vivo pharmacokinetic and pharmacodynamic data for the compound itself are not well-documented. Its in vivo relevance is primarily through its role as a melatonin precursor and its potential anti-cancer and anti-inflammatory activities.
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| Enzyme Assay |
For in vitro receptor binding assays, 5-methoxyindole is evaluated for 5-HT3 receptor activity. Standard protocols involve incubating the compound with cells expressing 5-HT3A or 5-HT3B receptors and measuring receptor activation using calcium flux assays or electrophysiology. For PPARγ binding, standard radioligand displacement assays are used with [³H]-rosiglitazone. The compound shows partial agonist activity at 5-HT3A receptors and dual activity at 5-HT3B receptors.
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| Cell Assay |
For in vitro cell-based experiments, 5-methoxyindole is evaluated for anti-cancer and anti-inflammatory activities. Cancer cells or immune cells are treated with the compound at various concentrations (typically 1-100 µM) for 24-72 hours. Cell viability is assessed using MTT or resazurin-based assays. Anti-inflammatory activity is measured by cytokine production (e.g., TNF-α, IL-6) using ELISA. Antifungal activity is assessed using broth microdilution methods against Fusarium graminearum.
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| Animal Protocol |
In vivo animal studies using 5-methoxyindole are limited. For anti-cancer or anti-inflammatory candidates derived from this scaffold, efficacy studies would typically be performed in mouse models of cancer or inflammation. Standard in vivo protocols involve administration to rodents via oral gavage or intraperitoneal injection, with appropriate pharmacokinetic and pharmacodynamic endpoints. Specific protocols for this compound are not well-documented.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 5-methoxyindole are not extensively characterized. The compound has a molecular weight of 147.17 g/mol, which is favorable for oral bioavailability. As an endogenous compound, it is expected to be metabolized through normal pathways. The methoxy group may be subject to O-demethylation. Empirical pharmacokinetic data such as half-life, clearance, and volume of distribution are not available in the public literature.
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| Toxicity/Toxicokinetics |
5-Methoxyindole is a research chemical and should be handled with appropriate laboratory safety precautions. As an indole derivative, it may cause skin and eye irritation. The compound is for research use only and not for human therapeutic or diagnostic applications. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. Standard safety practices include the use of personal protective equipment and working in a fume hood.
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| Additional Infomation |
5-Methoxyindole is a type of indole compound.
5-Methoxyindole (CAS 1006-94-6) is primarily a research-grade biochemical reagent and drug intermediate, not an FDA-approved pharmaceutical drug. Its primary applications are as a drug intermediate for melatonin synthesis, as a 5-HT3 receptor modulator, and as an anti-cancer and anti-inflammatory research tool. No clinical trials or approved therapeutic indications exist for this compound. |
| Molecular Formula |
C9H9NO
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|---|---|
| Molecular Weight |
147.17
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| Exact Mass |
147.068
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| CAS # |
1006-94-6
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| PubChem CID |
13872
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| Appearance |
White to yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
311.9±0.0 °C at 760 mmHg
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| Melting Point |
52-55 °C(lit.)
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| Flash Point |
109.2±10.1 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
|
| Index of Refraction |
1.637
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| LogP |
2.06
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
|
| Heavy Atom Count |
11
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| Complexity |
138
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C([H])([H])[H])C1C([H])=C([H])C2=C(C([H])=C([H])N2[H])C=1[H]
|
| InChi Key |
DWAQDRSOVMLGRQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H9NO/c1-11-8-2-3-9-7(6-8)4-5-10-9/h2-6,10H,1H3
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| Chemical Name |
5-methoxy-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) |
DMSO: 100 mg/mL (679.49 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.99 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 25.0 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: ≥ 2.5 mg/mL (16.99 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 25.0 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: ≥ 2.5 mg/mL (16.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7949 mL | 33.9743 mL | 67.9486 mL | |
| 5 mM | 1.3590 mL | 6.7949 mL | 13.5897 mL | |
| 10 mM | 0.6795 mL | 3.3974 mL | 6.7949 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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