Indole-3-acetamide
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Basic information
- CAS
879-37-8- Standard SMILES
NC(=O)Cc1c[nH]c2ccccc12- InChIKey
ZOAMBXDOGPRZLP-UHFFFAOYSA-N- Molecular formula
- C10H10N2O
- Average molar mass
- 174.2 g/mol
- Monoisotopic mass
- 174.07931294
Overview
Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a plant metabolite, a fungal metabolite and a bacterial metabolite. It is a member of indoles, a monocarboxylic acid amide and a N-acylammonia. It is functionally related to an acetamide.
Names & identifiers
- Preferred name
- Indole-3-acetamide
- IUPAC
- 2-(1H-indol-3-yl)acetamide
- English name
- 3-Indoleacetamide
- Molecular formula
- C10H10N2O
- Molecular weight
- 174.2
Names & synonyms
indole-3-acetamide879-37-82-(1H-Indol-3-yl)acetamide3-IndoleacetamideIndoleacetamide(indol-3-yl)acetamideO9SEW65XW3DTXSID60236686NSC-1969CHEBI:16031RefChem:148193DTXCID90159177
Show more names
BRN08735433-IndoleaceBRN 0873543BRN-0873543ACETAMIDOINDOZE
212-904-41H-Indole-3-acetamide3-IndolylacetamideMFCD000056411H-Indol-3-ylacetamide2-(3-Indolyl)acetamide1-Indole-3-acetamideNSC 1969
Database identifiers
- CAS
879-37-8- PubChem CID
- 397
- DTXSID
DTXSID60236686- ChEBI
CHEBI:16031- UNII
- O9SEW65XW3
- EC Number
- 212-904-4
- Nikkaji
- J128.124K
Properties
Computed structural propertiesFilling in
- XLogP
- 0.8
- Topological polar surface area
- 58.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 205
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point150 - 151 °C
Physical DescriptionSolid
Collision Cross Section
135.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
136.2 Ų [M+H]+
Physicochemical properties
- Melting point
- 148 · 148-150 °C(lit.)
- Boiling point
- 469.7 · 469.7±28.0 °C(Predicted)
- Density
- 1.285 · 1.285±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly)
- form
- Solid
- pka
- 16.37 · 16.37±0.40(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (37 of 37) of all reports.
Not Classified
Aggregated GHS information provided per 37 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2933990099
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesIndole-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 CA potential agent against Prion DiseaseProtein kinase C (PKC) inhibitor bisindolylmaleimide IVGlycogen synthase kinase-3 (GSK-3) inhibitorsInhibitors of CaMKIIdA VEGF inhibitorJAK3 inhibitorsInhibitors of NAD+-Dependent Histone DeacetylasesInhibitors of human adipocyte fatty acid-binding proteinCyclin-dependent kinase inhibitors
General DescriptionIndole-3-acetamide is an auxin precursor.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a fungal metabolite, a bacterial metabolite and a plant metabolite. It is a N-acylammonia, a monocarboxylic acid amide and a member of indoles. It is functionally related to an acetamide.
Related reactions
40 records
Compound notes
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