1013-47-4

Basic information

• Product Name: 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE
• Synonyms: 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE;RARECHEM AN KC 1419;1-(7-methyl-1H-indol-3-yl)propan-2-amine hydrochloride;1-(7-methyl-1H-indol-3-yl)propan-2-amine
• CAS NO: 1013-47-4
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27
• Mol File: 1013-47-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE(1013-47-4)
• EPA Substance Registry System: 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE(1013-47-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 1013-47-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE is used as a key intermediate in the synthesis of alpha-methyltryptamine (AMT) inhibitors. These inhibitors are important in the development of medications targeting the serotonergic system, which plays a crucial role in various physiological processes, including mood regulation, appetite control, and cognitive function.
In the synthesis of AMT inhibitors, 1-METHYL-2-(7-METHYL-1H-INDOL-3-YL)-ETHYLAMINE serves as a building block, contributing to the formation of the final compound with desired pharmacological properties. The development of such inhibitors can lead to novel therapeutic agents for the treatment of various disorders associated with the dysregulation of serotonin levels, such as depression, anxiety, and certain neurological conditions.

Upstream product

• 4771-50-0 7-methyl-1H-indole-3-carbaldehyde 
• 91392-37-9 7-methyl-3-(2-nitro-propenyl)-1H-indole 

Relevant articles and documents

α-Methyltryptamine sulfonamide derivatives as novel glucocorticoid receptor ligands

α-Methyltryptamine sulfonamides were identified as human glucocorticoid receptor (hGR) ligands in an ultra high throughput screening (UHTS) campaign. Described will be the hit-to-lead activities, including parallel and single point analog synthesis to map the scaffold. Ligands were identified that exhibited 30 nM binding to hGR. The SAR and selectivity of these compounds will be discussed.

Discovery of a novel and potent human and rat β3-adrenergic receptor agonist, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl] -1H-indol-7-yloxy]acetic acid

In search for potent and selective β3-adrenergic receptor (β3-AR) agonists as potential drugs for the treatment of type II diabetes and obesity, a novel series of 1-(3-chlorophenyl)-2-aminoethanol derivatives were prepared and evaluated for their biological activity at human β1-, β2-, and β3-ARs and rat β3-AR expressed in Chinese hamster ovary (CHO) cells. Replacement of the right-hand side (RHS, benzene ring) in the 'first generation' β3-AR agonists BRL 37344 and CL 316243 with a 1H-indole ring gave compound 31 with unique pharmacological properties among β3-AR agonists. Initial in vitro assays showed that 31 possesses modest rat and human β3-ARs agonistic activity. Introduction of various substituent into the indole nucleus of 31 afforded a number of compounds with good β3-ARs agonistic activity. In particular, 90 having a carboxylic acid functionality at the 7-position of the indole nucleus showed the most potent human β3-AR agonistic activity. Finally, optical resolution of 90 led to the identification of the most promising compound, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H- indol-7-yloxy]acetic acid (96, AJ-9677). This compound exhibited potent human β3-AR agonistic activity (EC50 = 0.062 nM, IA = 116%) with 210- and 103-fold selectivity over human β2-AR and β1-AR, respectively. Compound 96 also exhibited potent rat β3-AR agonistic activity (EC50 = 0.016 nM, IA = 110%). Moreover, repeated oral administration of 96 inhibited body weight gain and significantly decreased glucose, insulin, free fatty acid, and triglyceride concentrations in plasma in KK-Ay/Ta mice. On the basis of this pharmacological profile, 96 entered clinical development as a drug for the treatment of type II diabetes and obesity.