Indole-3-acetamide - 10mM in DMSO , CAS No.879-37-8

CAS: 879-37-8 Cat. No.: I426645 Molecular Weight: 174.2 Beilstein Registry Number: 22(5)370 EC Number: 212-904-4

GRADE & PURITY 10mM in DMSO

Synonyms

AKOS001129741 | bmse000696 | I0668 | InChI=1/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13) | 2-(3-Indolyl)acetamide | 3-Indoleacetamide | SB15031 | SY014237 | (1H-indol-3-yl)acetamide | AM1212 | C10H10N2O | Indole-3-acetamide (8CI

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Product Description:

Indole-3-acetamide is an auxin precursor.

Product 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

Specifications

Synonyms

AKOS001129741 | bmse000696 | I0668 | InChI=1/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4, 6, 12H, 5H2, (H2, 11, 13) | 2-(3-Indolyl)acetamide | 3-Indoleacetamide | SB15031 | SY014237 | (1H-indol-3-yl)acetamide | AM1212 | C10H10N2O | Indole-3-acetamide (8CI

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1=CC=C2C(=C1)C(=CN2)CC(=O)N
• IUPAC Name: 2-(1H-indol-3-yl)acetamide
• InChIKey: 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)
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)N
• WGK Germany: 3
• Molecular Weight: 174.2
• Beilstein: 22(5)370
• Reaxy-Rn: 143368
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=143368&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indoles
• Intermediate Tree Nodes: Not available
• Direct Parent: 3-alkylindoles
• Alternative Parents: Substituted pyrroles Benzenoids Heteroaromatic compounds Carboximidic acids Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3-alkylindole - Benzenoid - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Azacycle - Carboximidic acid derivative - Carboximidic acid - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: light & air sensitive
• Melt Point(°C): 153°C
• Molecular Weight: 174.200 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.079 Da
• Monoisotopic Mass: 174.079 Da
• Topological Polar Surface Area: 58.900 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 205.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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4. Han Ziyi, Fu Jian, Gong Aiyan, Ren Wenkai.  (2025)  Bacterial indole-3-propionic acid inhibits macrophage IL-1β production through targeting methionine metabolism.  Science China-Life Sciences,      [PMID:39825207] [10.1007/s11427-024-2789-1]

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7. Xianqiang Zeng, Chen Liu, Xue Wang, Yan Cao, Peng He, Huiquan Li, Liguo Wang.  (2024)  Versatile Underwater Pressure Sensitive Adhesive: UV Curing Synthesis and Substrate-Independent Adhesion.  ACS Applied Materials & Interfaces,      [PMID:39049199] [10.1021/acsami.4c06163]

8. Su Xiaoran, Wang Xinliu, Zhang Xin, Sun Yajie, Jia Yugai.  (2024)  β-Indole-3-acetic acid attenuated collagen-induced arthritis through reducing the ubiquitination of Foxp3 via the AhR-TAZ-Tip60 pathway.  IMMUNOLOGIC RESEARCH,      [PMID:38630408] [10.1007/s12026-024-09480-x]

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