Indole-3-acetamide

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, Cay-16954), in phytopathogenic bacteria. 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. 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 inhibits mouse and rat liver, as well as P. fluorescens and tryptophan 2,3-dioxygenase but not rabbit intestine or mouse epididymis indoleamine 2,3-dioxygenase.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: DMF: 30 mg/ml, DMSO: 30 mg/ml, DMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml. lambdamax: 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.