An endogenous metabolite of tryptophan in phytopathogenic bacteria
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Indole-3-acetamide

Item No. 34374

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-indole-3-acetamide
CAS Number
879-37-8
Synonyms
  • IAM
  • NSC 1969
Molecular Formula
C10H10N2O
Formula Weight
174.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml
λmax
220 nm
SMILES
O=C(CC1=CNC2=C1C=CC=C2)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)
InChi Key
ZOAMBXDOGPRZLP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $36

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    25 g

    $81

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    50 g

    $153

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    100 g

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    Product Description

    Indole-3-acetamide is an endogenous metabolite of tryptophan and intermediate in the biosynthesis of the major plant, fungal, and bacterial auxin hormone, indole-3-acetic acid (IAA; Item No. 16954), in phytopathogenic bacteria.1 It is formed directly from tryptophan in plants by tryptophan monooxygenase or, indirectly, through indole-3-acetonitrile or indole-3-acetaldoxime intermediates. Exogenous application of indole-3-acetamide (20 µM) increases the expression of ami1, the gene encoding amidase 1, the enzyme that catalyzes the synthesis of indole-3-acetic acid from indole-3-acetamide, in Arabidopsis.2 It reduces relative primary root elongation in Arabidopsis mutants that have increased amidase activity and lower indole-3-acetamide levels, but not in wild-type Arabidopsis, when used at concentrations of 1 and 10 µM. Indole-3-acetamide (2mM) inhibits mouse and rat liver, as well as P. fluorescens, tryptophan 2,3-dioxygenase, but not rabbit intestine or mouse epididymis indoleamine 2,3-dioxygenase.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duca, D., Lorv, J., Patten, C.L., et al. Indole-3-acetic acid in plant-microbe interactions. Anton. Van. Lee. J. M. S. 106(1), 85-125 (2014).

    2. Pérez-Alonso, M.-M., Ortiz-García, P., Moya-Cuevas, J., et al. Endogenous indole-3-acetamide levels contribute to the crosstalk between auxin and abscisic acid, and trigger plant stress responses in Arabidopsis. J. Exp. Bot. 72(2), 459-475 (2021).

    3. Eguchi, N., Watanabe, Y., Kawanishi, K., et al. Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by β-carboline and indole derivatives. Arch. Biochem. Biophys. 232(2), 602-609 (1984).