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286281

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

Quality Level

100

Assay

98%

mp

148-150 °C (lit.)

functional group

amide

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

286281-1G:
286281-250MG:
286281-BULK:
286281-5G:
286281-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9636
MKCN3866
MKCJ3703
MKCL3104
MKCD5475

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Stephan Pollmann et al.
Phytochemistry, 70(4), 523-531 (2009-03-10)
Plants are suggested to produce their major growth promoting phytohormone, indole-3-acetic acid (IAA), via multiple redundantly operating pathways. Although great effort has been made and plenty of possible routes have been proposed based on experimental evidence, a complete pathway for
Casandra K Gutierrez et al.
Applied and environmental microbiology, 75(8), 2253-2258 (2009-02-17)
Strains of Vibrio spp. isolated from roots of the estuarine grasses Spartina alterniflora and Juncus roemerianus produce the phytohormone indole-3-acetic acid (IAA). The colorimetric Salkowski assay was used for initial screening of IAA production. Gas chromatography-mass spectroscopy (GC-MS) was then
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
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
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