| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
IAM targets specific amidohydrolase enzymes (IAM hydrolases, IAMH1 and IAMH2 in Arabidopsis) that convert IAM into the active auxin IAA. In bacteria, the target is the iaaH protein. In plant research, its primary biological target is the auxin signaling pathway (TIR1/AFB receptors) indirectly via its conversion to IAA. Exogenous application of IAM aims to increase free IAA levels, thereby activating auxin-responsive gene expression. |
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| ln Vitro |
In vitro, IAM exhibits auxin-like activity in bioassays after conversion to IAA. It promotes hypocotyl elongation and root growth inhibition in Arabidopsis seedlings when added to growth media. It induces the expression of auxin-responsive reporter genes (e.g., DR5:GUS). The potency of IAM is significantly lower than IAA itself, requiring micromolar to millimolar concentrations to achieve effects similar to nanomolar IAA, due to the enzymatic conversion step being rate-limiting.
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| ln Vivo |
In vivo, IAM activity is demonstrated through bacterial iaaM gene overexpression studies. Transgenic plants (Arabidopsis, tobacco, petunia) overexpressing the bacterial iaaM gene accumulate high levels of IAM, which is subsequently hydrolyzed to IAA by endogenous plant hydrolases. This leads to auxin overproduction phenotypes including epinasty, adventitious root formation, increased vascular branching, and parthenocarpic fruit development. IAM feeding experiments in whole plants confirm its conversion to IAA.
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| Enzyme Assay |
Protocols for IAM hydrolase assays involve incubating recombinant IAMH protein (e.g., from Arabidopsis or bacteria) with IAM substrate (typically 0.5-2 mM) in Tris-HCl buffer (pH 7.5) at 30degC for 30-120 minutes. The reaction is terminated by adding acid (HCl). The product (IAA) is extracted with ethyl acetate, dried, resuspended in methanol, and quantified by HPLC-UV or LC-MS/MS. Control reactions without enzyme or with heat-inactivated enzyme are included.
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| Cell Assay |
A common protocol involves surface-sterilizing Arabidopsis seeds, vernalizing them at 4degC for 2-3 days, and plating them on half-strength Murashige and Skoog (MS) agar plates supplemented with various concentrations of IAM (0, 10, 50, 100 uM). Plates are placed vertically in a growth chamber (22degC, 16h light/8h dark) for 5-7 days. Root length and hypocotyl length are measured. Alternatively, DR5:GUS reporter seedlings are treated with IAM, followed by histochemical GUS staining to visualize auxin response.
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| Animal Protocol |
For animal models, IAM is not typically used in drug development. However, in plant research, Arabidopsis mutants (iamh1 iamh2 double mutants) are used to study IAM physiology. Plants are grown under standard long-day conditions (16h light/8h dark) at 22degC. IAM is applied by spraying a solution (e.g., 100 uM IAM + 0.01% Silwet L-77) onto 2-week-old soil-grown plants, or by adding to hydroponic solution. Tissues are harvested 1-24 hours post-treatment for IAA quantification or RNA extraction for qPCR analysis.
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| ADME/Pharmacokinetics |
IAM itself is an intermediate, not a drug; PK data is limited to plant physiology. In plants, exogenous IAM is taken up by roots or leaves and rapidly converted to IAA. The half-life of IAM in plant tissues is typically short (minutes to hours). In bacteria, IAM is actively exported. In mammalian systems, there is limited data, but IAM is generally considered to have low bioavailability and is rapidly metabolized.
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| Toxicity/Toxicokinetics |
Regarding toxicity, IAM is not considered a potent mammalian toxin. It has low acute oral toxicity (LD50 > 2000 mg/kg in rats predicted). However, as a precursor to IAA (auxin), high doses can cause cholinergic effects in animals due to structural similarity to indole derivatives. Skin and eye irritation potential is low. Standard laboratory safety precautions (gloves, goggles) should be used. It is not classified as a carcinogen.
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| References | |
| Additional Infomation |
Indole-3-acetamide is an indole compound with acetamide replaced by a 1H-indole-3-yl group at the 2-position. It is an intermediate in the synthesis of the plant hormone indoleacetic acid (IAA). It is a metabolite of fungi, bacteria, and plants. It is an N-acylamine, belonging to the monocarboxylic acid amide class, and is also an indole compound. Its function is similar to acetamide. Indole-3-acetamide has been reported in Balansia epichloe, Solanum tuberosum, and other organisms with relevant data.
IAM is not a pharmaceutical drug; it is a research biochemical for plant biology. It plays a crucial role in the study of auxin biosynthesis. The bacterial iaaM gene (converts Trp to IAM) is widely used as a selectable marker in plant genetic engineering and in studies of plant-pathogen interactions. Historically, IAM was a key discovery in understanding crown gall disease caused by Agrobacterium. There is no clinical trial status or approved drug indication for IAM in humans. |
| Molecular Formula |
C10H10N2O
|
|---|---|
| Molecular Weight |
174.20
|
| Exact Mass |
174.079
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| Elemental Analysis |
C, 68.95; H, 5.79; N, 16.08; O, 9.18
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| CAS # |
879-37-8
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| Related CAS # |
Indole-3-acetamide-d5; 1204700-53-7
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| PubChem CID |
397
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
407.1±47.0 °C at 760 mmHg
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| Melting Point |
150 - 151 °C
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| Flash Point |
200.0±29.3 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.650
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| LogP |
0.79
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
205
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C(CC1C2C(=CC=CC=2)NC=1)N
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| InChi Key |
ZOAMBXDOGPRZLP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
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| Chemical Name |
2-(1H-indol-3-yl)acetamide
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| Synonyms |
IAM; Indole-3-acetamide; NSC 1969; NSC-1969; NSC1969
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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 (~574.05 mM)
H2O :~1.3 mg/mL (~7.46 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. Solubility in Formulation 2: 2.5 mg/mL (14.35 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7405 mL | 28.7026 mL | 57.4053 mL | |
| 5 mM | 1.1481 mL | 5.7405 mL | 11.4811 mL | |
| 10 mM | 0.5741 mL | 2.8703 mL | 5.7405 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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