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Indole-3-acetamide-d5 (3-indoleacetamide-d5; indole-3-acetamide-d5)

Cat No.:V72605 Purity: ≥98%
Indole-3-acetamide-d5 is the deuterated form of Indole-3-acetamide.
Indole-3-acetamide-d5 (3-indoleacetamide-d5; indole-3-acetamide-d5)
Indole-3-acetamide-d5 (3-indoleacetamide-d5; indole-3-acetamide-d5) Chemical Structure CAS No.: 1204700-53-7
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes

Other Forms of Indole-3-acetamide-d5 (3-indoleacetamide-d5; indole-3-acetamide-d5):

  • Indole-3-acetamide
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Indole-3-acetamide-d5 is the deuterated form of Indole-3-acetamide. Indole-3-acetamide is a biosynthetic intermediate of indole-3-acetic acid. Indole-3-acetic acid is the most common natural plant growth hormone in the auxin class.
Indole-3-acetamide-d5 (CAS: 1204700-53-7) is the deuterium-labeled form of indole-3-acetamide, a biosynthetic intermediate of indole-3-acetic acid (the most common natural plant growth hormone of the auxin class). Five hydrogen atoms are replaced with deuterium, making it suitable for use as an analytical standard and tracer in mass spectrometry and metabolic studies.
Biological Activity I Assay Protocols (From Reference)
Targets
Indole-3-acetamide-d5 has no pharmacological target in mammalian systems as it is primarily a plant hormone intermediate. Its non-labeled parent compound is an intermediate in the biosynthesis of indole-3-acetic acid (auxin), a plant growth regulator that acts through TIR1/AFB auxin receptor proteins in plants. In plant biology, the indole-3-acetamide pathway represents an alternative auxin biosynthesis route.
ln Vitro
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
As a stable isotope-labeled compound, Indole-3-acetamide-d5 is not tested for in vitro pharmacological activity in mammalian cells. In plant cell systems, it is used to trace the conversion of indole-3-acetamide to indole-3-acetic acid by amidohydrolase enzymes. The non-labeled indole-3-acetamide is a plant hormone intermediate with no defined activity in mammalian pharmacological assays.
ln Vivo
Indole-3-acetamide-d5 has no in vivo activity in animals as it is a deuterium-labeled plant biochemical intermediate. In plant studies, it can be administered to plant tissues to trace auxin biosynthesis via the indole-3-acetamide pathway. The compound is used exclusively as an analytical standard and tracer and is not intended for therapeutic applications.
Enzyme Assay
For in vitro enzyme assays using Indole-3-acetamide-d5 as a tracer, the compound is dissolved in an appropriate solvent such as DMSO or methanol to prepare a stock solution. The tracer is then added to plant enzyme extracts containing amidohydrolase activity. The reaction mixture (e.g., 100 microL total volume) is incubated at room temperature or 30degC for 0-60 minutes. The reaction is stopped by adding organic solvent, and products are analyzed by LC-MS to detect the conversion of labeled indole-3-acetamide to indole-3-acetic acid-d.
Cell Assay
For cell-based studies, plant tissues (e.g., Arabidopsis seedlings) are incubated in medium containing Indole-3-acetamide-d5 at defined concentrations (e.g., 1-50 microM). After incubation periods (e.g., 0, 1, 2, 4, 8, 12, 24 hours), tissues are harvested and homogenized in extraction buffer (e.g., methanol containing 0.1% formic acid). The extracts are centrifuged and analyzed by LC-MS/MS to quantify the uptake of labeled compound and its conversion to indole-3-acetic acid-d.
Animal Protocol
In vivo tracer studies are primarily conducted in plants, not in animals. For plant studies, Indole-3-acetamide-d5 is applied to plant tissues via root uptake from hydroponic medium or direct injection into stems/shoots. Plants are maintained under controlled growth conditions (light/dark cycle, temperature 22degC). After treatment periods of 0-24 hours, plant tissues are harvested, frozen in liquid nitrogen, and extracted for LC-MS/MS analysis to trace auxin biosynthesis.
ADME/Pharmacokinetics
Indole-3-acetamide-d5 is an analytical standard and stable isotope tracer, not a therapeutic drug. No pharmacokinetic parameters have been established for this compound. When used in plant studies, uptake and metabolism follow the plant-specific pathways for indole-3-acetamide, with conversion to indole-3-acetic acid occurring via amidohydrolase activity. In mammalian systems, this compound is not expected to be systemically absorbed or metabolized to active products.
Toxicity/Toxicokinetics
Indole-3-acetamide-d5 has low toxicity as it is used at microgram to milligram quantities for research purposes. The non-labeled indole-3-acetamide is a plant metabolite with no significant known toxicity in mammals. Standard laboratory safety precautions for handling organic compounds apply. The compound is not intended for human or veterinary consumption, and no formal toxicological studies have been conducted for this deuterium-labeled material.
References

[1]. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.

[2]. Indole-3-acetamide-dependent auxin biosynthesis: a widely distributed way of indole-3-acetic acid production? Eur J Cell Biol. 2010 Dec;89(12):895-905.

Additional Infomation
Indole-3-acetamide-d5 is not a drug but a deuterium-labeled research reagent. It has no approved drug status, no clinical trial history, and is not intended for human use. The compound is used exclusively as an analytical standard and tracer in plant biology and biochemistry studies, particularly in research related to plant hormones (auxins). It is also employed as an internal standard for accurate quantification of indole-3-acetic acid and related metabolites by mass spectrometry. Available in high isotopic purity (99.99%).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H5D5N2O
Molecular Weight
179.23
Exact Mass
174.079
CAS #
1204700-53-7
Related CAS #
Indole-3-acetamide;879-37-8
PubChem CID
131668185
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
407.1±47.0 °C at 760 mmHg
Flash Point
200.0±29.3 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.650
LogP
0.79
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Heavy Atom Count
13
Complexity
205
Defined Atom Stereocenter Count
0
SMILES
[2H]C1=C(C(=C2C(=C1[2H])C(=C(N2)[2H])CC(=O)N)[2H])[2H]
InChi Key
ZOAMBXDOGPRZLP-SNOLXCFTSA-N
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)/i1D,2D,3D,4D,6D
Chemical Name
2-(2,4,5,6,7-pentadeuterio-1H-indol-3-yl)acetamide
HS Tariff Code
2934.99.9001
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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.5794 mL 27.8971 mL 55.7942 mL
5 mM 1.1159 mL 5.5794 mL 11.1588 mL
10 mM 0.5579 mL 2.7897 mL 5.5794 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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