57280
3-Indoleacetonitrile
purum, ≥96.0% (GC)
Synonym(s):
(3-Indolyl)acetonitrile, 3-(Cyanomethyl)indole, IAN, Indolylacetonitrile, NSC 523272
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About This Item
Empirical Formula (Hill Notation):
C10H8N2
CAS Number:
Molecular Weight:
156.18
EC Number:
212-232-1
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
125488
MDL number:
grade
purum
assay
≥96.0% (GC)
bp
157-160 °C/0.2 mmHg (lit.)
mp
33-36 °C
storage temp.
2-8°C
SMILES string
N#CCc1c[nH]c2ccccc12
InChI
1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
InChI key
DMCPFOBLJMLSNX-UHFFFAOYSA-N
Application
Reactant for preparation of:
- Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Histone deacetylase inhibitors
- Potential kinase inhibitors
- Kv7/KCNQ potassium channel activators
- Kinesin-Specific MKLP-2 Inhibitor
- Pesticides
- Potential PET cancer imaging agents
- Agonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatment
- Butyrylcholinesterase inhibitors
- Necroptosis inhibitors
Other Notes
Plant growth activator. Promotes callus growth and shoot formation in tobacco callus
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
233.6 °F - closed cup
flash_point_c
112 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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E. Maeda et al.
Phytomorphology, 29, 146-146 (1979)
A B Renwick et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 37(6), 609-618 (1999-09-09)
In this study the effect of some indole derivatives on xenobiotic metabolizing enzymes and xenobiotic-induced toxicity has been examined in cultured precision-cut liver slices from male Sprague-Dawley rats. While treatment of rat liver slices for 72 hours with 2-200 microM
Tongbing Su et al.
The Plant cell, 23(1), 364-380 (2011-01-18)
Camalexin, a major phytoalexin in Arabidopsis thaliana, consists of an indole ring and a thiazole ring. The indole ring is produced from Trp, which is converted to indole-3-acetonitrile (IAN) by CYP79B2/CYP79B3 and CYP71A13. Conversion of Cys(IAN) to dihydrocamalexic acid and