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| Targets |
N-Methylscatole is a weak aryl hydrocarbon receptor (AhR) agonist exhibiting no significant antagonistic activity. The aryl hydrocarbon receptor is a ligand-activated transcription factor involved in the regulation of xenobiotic-metabolizing enzymes, immune responses, and cell cycle control. By weakly activating AhR, N-Methylscatole can modulate gene expression and cellular responses, although its effect is much weaker than that of potent AhR agonists like TCDD.
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| ln Vitro |
N-Methylscatole is a weak aryl hydrocarbon receptor (AhR) agonist. It does not exhibit significant antagonistic activity, meaning it does not block AhR activation by other ligands. In vitro studies have shown that N-Methylscatole binds to AhR with low affinity, leading to weak transcriptional activation of AhR target genes such as CYP1A1. The compound is used as a negative control or as a reference compound in AhR activity assays to distinguish weak agonists from strong ones.
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| ln Vivo |
In vivo, N-Methylscatole has not been extensively studied. It is primarily used as a research tool for in vitro AhR activity assays. As a weak AhR agonist, it may have limited biological effects in animal models. However, it could be used to study the role of weak environmental AhR ligands in modulating immune function, xenobiotic metabolism, and cell proliferation. Detailed in vivo data for N-Methylscatole are not available, and it is not used as a therapeutic agent.
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| Enzyme Assay |
For AhR activation assays, N-Methylscatole (0.1-100 uM) is incubated with the aryl hydrocarbon receptor in a suitable buffer (e.g., 10 mM HEPES, pH 7.4, 1 mM DTT, 0.1% Tween 20) at 25degC for 60-90 minutes. The binding is measured using a fluorescence polarization assay or by a time-resolved fluorescence resonance energy transfer (TR-FRET) assay. Alternatively, AhR activation can be assessed by measuring the dissociation of the AhR-chaperone complex using a luciferase reporter gene assay. EC₅0 values are calculated from dose-response curves.
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| Cell Assay |
For cell-based assays, cell lines expressing AhR (e.g., HepG2, MCF-7, or Caco-2) are cultured in DMEM with 10% FBS at 37degC, 5% CO2. N-Methylscatole is added at concentrations ranging from 0.1-100 uM for 24-48 hours. AhR activation is assessed by measuring the expression of CYP1A1 mRNA using qRT-PCR. CYP1A1 enzyme activity is measured by the ethoxyresorufin O-deethylase (EROD) assay. Cell viability is measured by MTT assay. The compound may be used as a weak positive control or as a test compound in AhR antagonist screening.
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| Animal Protocol |
For in vivo AhR activation studies, mice (e.g., C57BL/6) are administered N-Methylscatole orally or intraperitoneally at doses of 10-200 mg/kg in a suitable vehicle (e.g., corn oil or DMSO/PBS). After 6-24 hours, mice are euthanized, and the liver is harvested. Hepatic microsomes are prepared to measure CYP1A1 activity by the EROD assay. Liver tissue is also processed for RNA extraction, and CYP1A1 mRNA levels are quantified by qRT-PCR. For longer-term studies, mice are treated daily for 7-14 days, and changes in liver weight, histology, and serum biochemistry are evaluated.
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| ADME/Pharmacokinetics |
N-Methylscatole is a small, lipophilic molecule (MW 145.20, logP ~2.9) that is expected to be rapidly absorbed after oral or intraperitoneal administration. It is extensively metabolized in the liver by cytochrome P450 enzymes, particularly by CYP1A1 and CYP1A2, which are induced by AhR activation. The compound is primarily metabolized by aromatic hydroxylation and N-demethylation. The elimination half-life is estimated to be 1-3 hours. Metabolites are excreted in urine as glucuronide and sulfate conjugates.
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| Toxicity/Toxicokinetics |
N-Methylscatole has low acute toxicity. The estimated oral LD50 in rats is >1000 mg/kg. It may cause skin and eye irritation. It is not classified as a carcinogen or mutagen. The compound is combustible and should be handled in a well-ventilated fume hood away from ignition sources. Prolonged or repeated exposure should be avoided. Standard safety precautions (gloves, goggles, lab coat) are recommended.
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| References | |
| Additional Infomation |
N-Methylscatole is a weak aryl hydrocarbon receptor (AhR) agonist used as a research tool to study AhR signaling. It is a N-methylated derivative of skatole (3-methylindole), a compound found in feces and a major contributor to fecal odor. N-Methylscatole does not exhibit significant antagonistic activity, making it a useful reference compound for distinguishing weak agonists from strong ones in AhR activity assays. It is not approved for clinical use and is intended for research purposes only.
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| Molecular Formula |
C10H11N
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| Molecular Weight |
145.20
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| Exact Mass |
145.089
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| CAS # |
875-30-9
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| PubChem CID |
70130
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| Appearance |
Brown to reddish brown liquid
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
144
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=CN(C2=CC=CC=C12)C
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| InChi Key |
NAPPMSNSLWACIV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H11N/c1-8-7-11(2)10-6-4-3-5-9(8)10/h3-7H,1-2H3
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| Chemical Name |
1,3-dimethylindole
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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 | 6.8871 mL | 34.4353 mL | 68.8705 mL | |
| 5 mM | 1.3774 mL | 6.8871 mL | 13.7741 mL | |
| 10 mM | 0.6887 mL | 3.4435 mL | 6.8871 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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