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Sigma-Aldrich

Indole-3-acetamide

98%

Synonym(s):

3-Indolylacetamide, NSC 1969

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About This Item

Empirical Formula (Hill Notation):
C10H10N2O
CAS Number:
879-37-8
Molecular Weight:
174.20
EC Number:
212-904-4
MDL number:
MFCD00005641
UNSPSC Code:
12352100
PubChem Substance ID:
24857238
NACRES:
NA.22

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

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
S Taliani et al.
Current medicinal chemistry, 16(26), 3359-3380 (2009-06-25)
The Translocator protein (TSPO), formerly known as the peripheral-type benzodiazepine receptor, is an 18 kDa mitochondrial protein primarily involved in steroid biosynthesis in both peripheral and glial cells. It has been extensively reported that TSPO regulates the rate-limiting translocation of
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
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