286281
Indole-3-acetamide
98%
Synonym(s):
3-Indolylacetamide, NSC 1969
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About This Item
Empirical Formula (Hill Notation):
C10H10N2O
CAS Number:
Molecular Weight:
174.20
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
212-904-4
MDL number:
Assay:
98%
Product Name
Indole-3-acetamide, 98%
InChI key
ZOAMBXDOGPRZLP-UHFFFAOYSA-N
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)
SMILES string
NC(=O)Cc1c[nH]c2ccccc12
assay
98%
mp
148-150 °C (lit.)
functional group
amide
Quality Level
Related Categories
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
General description
Indole-3-acetamide is an auxin precursor.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
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
Daiana Duca et al.
Antonie van Leeuwenhoek, 106(1), 85-125 (2014-01-22)
Indole-3-acetic acid (IAA) is an important phytohormone with the capacity to control plant development in both beneficial and deleterious ways. The ability to synthesize IAA is an attribute that many bacteria including both plant growth-promoters and phytopathogens possess. There are
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