176688-98-5

Basic information

• Product Name: (5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE
• Synonyms: (5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE;2-(5-Methoxy-1-Methyl-1H-indol-3-yl)acetonitrile
• CAS NO: 176688-98-5
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.23648
• Mol File: 176688-98-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE(176688-98-5)
• EPA Substance Registry System: (5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE(176688-98-5)

Safety Data

• Hazardous Substances Data: 176688-98-5(Hazardous Substances Data)

Usage

Description

(5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE is a chemical compound belonging to the indole family, characterized by the molecular formula C11H11N2O. It features a nitrile group, a methoxy group, and a methyl group attached to the indole ring, making it a versatile building block in medicinal chemistry.
Used in Pharmaceutical Industry:
(5-METHOXY-1-METHYL-1H-INDOL-3-YL)ACETONITRILE is used as a synthetic intermediate for the development of various bioactive molecules, particularly in the creation of pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of potential drug candidates, contributing to the advancement of medicinal chemistry.

Upstream product

• 2436-17-1 5-methoxyindole-3-acetonitrile 
• 74-88-4 methyl iodide 
• 1006-94-6 5-methoxylindole 
• 10601-19-1 5-methoxyindole-3-carboxaldehyde 

Relevant articles and documents

Mapping the melatonin receptor. 7. Subtype selective ligands based on β-substituted N-acyl-5-methoxytryptamines and β-Substituted N-acyl-5-methoxy-1-methyltryptamines

A series of β-substituted and β,β-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxytryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT1 and MT2 receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores, β-Methylmelatonin (17a) and β,β-dimethylmelatonin (17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus, N-Butanoyl 5-methoxy-1-methyl-β,β-trimethylenetryptamine (12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-β,β-tetramethylenetryptamine (13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

New indole derivatives as ACAT inhibitors: Synthesis and structure-activity relationships

A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED25 less than 0.1 mg/kg po.