39760-01-5

Usage

Uses

Used in Pharmaceutical Research:
N-[2-(2-Methyl-1H-indol-3-yl)ethyl]acetamide is used as a research compound for exploring its potential as a ligand for serotonin receptors. Its interaction with these receptors can provide insights into the development of new drugs targeting the serotonin system, which is implicated in various neurological and psychiatric disorders.
Used in Drug Development:
As a compound with potential pharmacological properties, N-[2-(2-Methyl-1H-indol-3-yl)ethyl]acetamide is utilized in the development of new drug candidates. Its structure and activity can be optimized to create more effective and selective medications for treating a range of conditions.
Used in Chemical Synthesis:
N-[2-(2-Methyl-1H-indol-3-yl)ethyl]acetamide can also be used as a building block or intermediate in the synthesis of more complex molecules with specific biological activities. Its indole ring and acetamide group provide a versatile platform for further chemical modifications and the creation of novel compounds with tailored properties.

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 142-26-7 2-acetylaminoethanol 
• 62005-48-5 N-acetylaminoacetaldehyde dimethyl acetal 
• 267899-36-5 1-(5-methyl-2,3-dihydro-pyrrol-1-yl)-ethanone 
• 872-32-2 2-methyl-1H-pyrroline 
• 7546-14-7 N-acetylpyridinium chloride 
• 17636-95-2 N-<(4-oxo)-1-pentyl>acetamide 
• 100-63-0 phenylhydrazine 

Downstream Products

• 2731-06-8 2-methyltryptamine 

Relevant academic research and scientific papers

Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: Exploiting N-protected β-amino alcohols as alkylating agents

The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

A one-pot three-component reaction for the preparation of highly functionalized tryptamines

We have developed a general one-pot method to provide highly functionalized tryptamine derivatives, via a Fischer indole type pathway. In this article, we demonstrate optimal conditions for a one-pot indole synthesis, allowing for the synthesis of a broad scope of 2-methyl tryptamine derivatives and a precursor for the synthesis of the core structure of some akuammiline alkaloids. Additionally, further modification of the indole products is described.

Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles

An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.

Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines

A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines create the desired substituents in the carbocycle of indolylalkylamides and suitable choice of amidoketone can direct the amidoalkyl chain to the 2- or 3-position of the indole. Graphical Abstract