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286281

Sigma-Aldrich

Indole-3-acetamide

98%

Synonym(s):
3-Indolylacetamide, NSC 1969
Empirical Formula (Hill Notation):
C10H10N2O
CAS Number:
Molecular Weight:
174.20
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

148-150 °C (lit.)

SMILES string

NC(=O)Cc1c[nH]c2ccccc12

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

General description

Indole-3-acetamide is an auxin precursor.

Application

Indole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid.
Reactant for the synthesis of:
  • PET agent for imaging of protein kinase C
  • A potential agent against Prion Disease
  • Protein kinase C (PKC) inhibitor bisindolylmaleimide IV
  • Glycogen synthase kinase-3ß (GSK-3ß) inhibitors
  • Inhibitors of CaMKIId
  • A VEGF inhibitor
  • JAK3 inhibitors
  • Inhibitors of NAD+-Dependent Histone Deacetylases
  • Inhibitors of human adipocyte fatty acid-binding protein
  • Cyclin-dependent kinase inhibitors

Packaging

1, 5 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 286281.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Stephan Pollmann et al.
Phytochemistry, 62(3), 293-300 (2003-03-07)
Acylamidohydrolases from higher plants have not been characterized or cloned so far. AtAMI1 is the first member of this enzyme family from a higher plant and was identified in the genome of Arabidopsis thaliana based on sequence homology with the
Christian O Dimkpa et al.
Applied and environmental microbiology, 78(5), 1404-1410 (2012-01-03)
The beneficial bacterium Pseudomonas chlororaphis O6 produces indole-3-acetic acid (IAA), a plant growth regulator. However, the pathway involved in IAA production in this bacterium has not been reported. In this paper we describe the involvement of the indole-3-acetamide (IAM) pathway
Chuntao Yin et al.
Molecular plant-microbe interactions : MPMI, 27(3), 227-235 (2013-12-20)
The plant hormone indole-3-acetic acid (IAA) is best known as a regulator of plant growth and development but its production can also affect plant-microbe interactions. Microorganisms, including numerous plant-associated bacteria and several fungi, are also capable of producing IAA. The
Rudy Maor et al.
Applied and environmental microbiology, 70(3), 1852-1854 (2004-03-10)
The plant pathogenic fungus Colletotrichum gloeosporioides f. sp. aeschynomene utilizes external tryptophan to produce indole-3-acetic acid (IAA) through the intermediate indole-3-acetamide (IAM). We studied the effects of tryptophan, IAA, and IAM on IAA biosynthesis in fungal axenic cultures and on
Elena Tsavkelova et al.
Fungal genetics and biology : FG & B, 49(1), 48-57 (2011-11-15)
The plant hormone indole-3-acetic acid (IAA) can be synthesized from tryptophan via the intermediate indole-3-acetamide (IAM). The two genes, IaaM (encoding tryptophan monooxygenase) and IaaH (encoding indole-3-acetamide hydrolase) that constitute the IAM pathway have been described in plant-associated bacteria. We

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