1203-95-8

Basic information

• Product Name: 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine
• Synonyms: 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine;Albb-006626;2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine(SALTDATA: HCl 0.5H2O);5-Chloro-2-MethyltriptaMine;2-(5-Chloro-2-methyl-1H-indol-3-yl)-ethylamine hydrochloride
• CAS NO: 1203-95-8
• Molecular Formula: C₁₁H₁₃ClN₂
• Molecular Weight: 208.69
• Mol File: 1203-95-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 385.2°C at 760 mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 3.86E-06mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine(1203-95-8)
• EPA Substance Registry System: 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine(1203-95-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1203-95-8(Hazardous Substances Data)

Usage

Description

2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine, also known as 5-chloro-2-methyltriptamine, is a derivative of tryptamine, a naturally occurring compound found in the plant and animal kingdoms. It is characterized by its indole structure with a chloro and methyl group substitution, which contributes to its unique properties and potential applications.

Uses

Used in Pharmaceutical Industry:
2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine is used as a pharmaceutical compound for its ability to inhibit the NMDA receptor in a voltage-dependent manner. This makes it a potential candidate for the development of treatments targeting neurological disorders and conditions related to the overstimulation of the NMDA receptor, such as Alzheimer's disease, Parkinson's disease, and neuropathic pain.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine is utilized as a key intermediate in the development of novel pim-1 kinase competitive inhibitors. These inhibitors are designed to target fluorescently labeled substrate peptides, which can be crucial in the study and development of new therapeutic strategies for various diseases, including cancer.
Used in Research Applications:
2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine is also employed in research settings as a tool to investigate the role of the NMDA receptor in various physiological and pathological processes. Its ability to modulate the receptor's activity can provide valuable insights into the underlying mechanisms of receptor function and contribute to the development of more effective therapeutic agents.

InChI:InChI=1/C11H13ClN2/c1-7-9(4-5-13)10-6-8(12)2-3-11(10)14-7/h2-3,6,14H,4-5,13H2,1H3

Upstream product

• 1075-35-0 5-chloro-2-methylindole 
• 57335-86-1 5-Chloro-2-methyl-1H-indole-3-carboxaldehyde 
• 2731-06-8 2-methyltryptamine 
• 5891-21-4 5-chloro-2-pentanone 
• 1073-69-4 N-4-chlorophenylhydrazine 

Downstream Products

• 1392268-34-6 3-chloro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 
• 1392268-33-5 2-chloro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide 

Relevant articles and documents

Directed evolution of RebH for catalyst-controlled halogenation of indole C-H bonds

RebH variants capable of chlorinating substituted indoles ortho-, meta-, and para-to the indole nitrogen were evolved by directly screening for altered selectivity on deuterium-substituted probe substrates using mass spectrometry. This systematic approach allowed for rapid accumulation of beneficial mutations using simple adaptive walks and should prove generally useful for altering and optimizing the selectivity of C-H functionalization catalysts. Analysis of the beneficial mutations showed that structure-guided selection of active site residues for targeted mutagenesis can be complicated either by activity/selectivity tradeoffs that reduce the possibility of detecting such mutations or by epistatic effects that actually eliminate the benefits of a mutation in certain contexts. As a corollary to this finding, the precise manner in which the beneficial mutations identified led to the observed changes in RebH selectivity is not clear. Docking simulations suggest that tryptamine binds to these variants as tryptophan does to native halogenases, but structural studies will be required to confirm these models and shed light on how particular mutations impact tryptamine binding. Similar directed evolution efforts on other enzymes or artificial metalloenzymes could enable a wide range of C-H functionalization reactions.

Structural Characterization and Computer-Aided Optimization of a Small-Molecule Inhibitor of the Arp2/3 Complex, a Key Regulator of the Actin Cytoskeleton

CK-666 (1) is a recently discovered small-molecule inhibitor of the actin-related protein 2/3 (Arp2/3) complex, a key actin cytoskeleton regulator with roles in bacterial pathogenesis and cancer cell motility. Although 1 is commercially available, the crystal structure of Arp2/3 complex with 1 bound has not been reported, making its mechanism of action uncertain. Furthermore, its relatively low potency increases its potential for off-target effects invivo, complicating interpretation of its influence in cell biological studies and precluding its clinical use. Herein we report the crystal structure of 1 bound to Arp2/3 complex, which reveals that 1 binds between the Arp2 and Arp3 subunits to stabilize the inactive conformation of the complex. Based on the crystal structure, we used computational docking and free-energy perturbation calculations of monosubstituted derivatives of 1 to guide optimization efforts. Biochemical assays of ten newly synthesized compounds led to the identification of compound 2, which exhibits a threefold increase in inhibitory activity invitro relative to 1. In addition, our computational analyses unveiled a surface groove at the interface of the Arp2 and Arp3 subunits that can be exploited for additional structure-based optimization.