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| Other Sizes |
| Targets |
3-Indoleacetonitrile does not have a well-defined pharmacological target. It acts as an auxin-inhibitory substance in plants and has a role as a plant hormone, a plant metabolite, and a human xenobiotic metabolite. In bacteria, it has been shown to reduce biofilm formation by E. coli and P. aeruginosa, suggesting it may interact with bacterial quorum sensing or biofilm-related pathways. However, its specific molecular targets in these contexts have not been fully characterized.
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| ln Vitro |
3-Indoleacetonitrile demonstrates antibacterial activity in vitro. It reduces biofilm formation by E. coli and P. aeruginosa when used at a concentration of 100 µg/ml. The compound's activity is related to its indole alkaloid structure, which is common among plant-derived antimicrobial agents. The levels of indole-3-acetonitrile are increased in P. brassicae-infected cabbage roots, indicating its role in plant defense responses. However, detailed in vitro activity data beyond its antibacterial effects are limited.
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| ln Vivo |
In vivo activity of 3-Indoleacetonitrile is related to its role as a plant metabolite and plant hormone. It functions as a light-induced auxin-inhibitory substance in plants, regulating growth and development. The compound is also a human xenobiotic metabolite, indicating it can be metabolized in humans after exposure. However, comprehensive in vivo studies evaluating its pharmacokinetic properties, efficacy, and safety in animal models have not been extensively reported.
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| Enzyme Assay |
In vitro enzyme/receptor binding experiments for 3-Indoleacetonitrile are not typical, as it is a natural plant metabolite rather than a well-defined pharmacologically active compound. Studies may involve measuring its antibacterial activity using broth microdilution or biofilm formation assays. Its chemical properties are characterized using standard analytical methods such as GC, HPLC, and mass spectrometry. The compound can also be used as a reference standard in analytical chemistry for the identification of indole alkaloids.
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| Cell Assay |
In vitro cellular experiments for 3-Indoleacetonitrile typically involve studying its antibacterial effects on bacterial cultures. Biofilm formation assays are performed by incubating bacteria with the compound at various concentrations and measuring the amount of biofilm formed using crystal violet staining or other methods. The compound's effects on bacterial growth and viability are also assessed. Cytotoxicity assays may be performed to determine if the compound affects mammalian cell viability.
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| Animal Protocol |
In vivo animal experiments for 3-Indoleacetonitrile are not typical, as it is a plant metabolite rather than a drug candidate. However, studies may involve administering the compound to animals to study its metabolism or to evaluate its effects as a xenobiotic metabolite. The compound's role in plant defense could be studied in plant models. Comprehensive in vivo studies in animal models have not been extensively reported.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3-Indoleacetonitrile have not been extensively characterized. With a molecular weight of 156.18, the compound is expected to have moderate lipophilicity. It is slightly soluble in water and soluble in organic solvents such as chloroform, DMSO, and methanol. The compound has a melting point of 33-36°C and a boiling point of 157-160°C at 0.2 mm Hg. Detailed studies on its absorption, distribution, metabolism, and excretion in humans are limited.
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| Toxicity/Toxicokinetics |
Toxicological data for 3-Indoleacetonitrile indicate that it is a hazardous substance. It has GHS hazard statements H301+H311+H331-H302-H312-H332, indicating toxicity if swallowed, in contact with skin, or if inhaled. The signal word is "Danger". The compound is harmful and requires precautionary measures when handling. Researchers should follow standard safety protocols for handling nitriles and indole compounds.
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| Additional Infomation |
Indole-3-acetonitrile is a nitrile compound with the structure acetonitrile molecule, in which one methyl hydrogen atom is replaced by a 1H-indole-3-yl group. It has multiple functions, including acting as an auxin, plant hormone, plant metabolite, and exogenous metabolite in humans. It belongs to the nitrile class and is one of the indole classes. Its function is related to acetonitrile. 3-Indoleacetonitrile has been reported to exist in sow thistle (Rorippa dubia), cabbage (Brassica oleracea), and other organisms with relevant data.
3-Indoleacetonitrile is a research compound that has not entered clinical trials or received regulatory approval for therapeutic use. It is primarily used as a research tool to study plant hormone signaling, auxin inhibition, and antibacterial mechanisms. The compound is also used as a reference standard in analytical chemistry. Its antibacterial activity against biofilm formation makes it a compound of interest for studying bacterial pathogenesis and developing new antimicrobial strategies. It is also known as Indolylacetonitrile or IAN. |
| Molecular Formula |
C₁₀H₈N₂
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|---|---|
| Molecular Weight |
156.18
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| Exact Mass |
156.068
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| CAS # |
771-51-7
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| PubChem CID |
351795
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| Appearance |
Light yellow to light brown solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
374.1±17.0 °C at 760 mmHg
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| Melting Point |
33-36 °C(lit.)
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| Flash Point |
127.6±6.1 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.673
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| LogP |
1.37
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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
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| Heavy Atom Count |
12
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| Complexity |
203
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
DMCPFOBLJMLSNX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
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| Chemical Name |
2-(1H-indol-3-yl)acetonitrile
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| Synonyms |
3Indoleacetonitrile; 3 Indoleacetonitrile
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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 (~640.29 mM)
H2O : ~1 mg/mL (~6.40 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.01 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 (16.01 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (16.01 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 | 6.4029 mL | 32.0143 mL | 64.0287 mL | |
| 5 mM | 1.2806 mL | 6.4029 mL | 12.8057 mL | |
| 10 mM | 0.6403 mL | 3.2014 mL | 6.4029 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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