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Key Documents

286281

Sigma-Aldrich

Indole-3-acetamide

98%

Synonyme(s) :

3-Indolylacetamide, NSC 1969

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About This Item

Formule empirique (notation de Hill):
C10H10N2O
Numéro CAS:
Poids moléculaire :
174.20
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

98%

Pf

148-150 °C (lit.)

Chaîne SMILES 

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)

Clé InChI

ZOAMBXDOGPRZLP-UHFFFAOYSA-N

Description générale

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

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
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
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

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