20127-61-1

Basic information

• Product Name: 1-ethyl-9H-beta-carboline
• Synonyms: 1-Ethyl-9H-beta-carboline; 1-Ethyl-9H-pyrido(3,4-b)indole; 9H-Pyrido(3,4-b)indole, 1-ethyl-; 9H-pyrido[3,4-b]indole, 1-ethyl-
• CAS NO: 20127-61-1
• Molecular Formula: C₁₃H₁₂N₂
• Molecular Weight: 196.2478
• Mol File: 20127-61-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 390.2°C at 760 mmHg
• Flash Point: 174.9°C
• Density: 1.211g/cm³
• Vapor Pressure: 6.05E-06mmHg at 25°C
• Refractive Index: 1.72
• CAS DataBase Reference: 1-ethyl-9H-beta-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethyl-9H-beta-carboline(20127-61-1)
• EPA Substance Registry System: 1-ethyl-9H-beta-carboline(20127-61-1)

Safety Data

• Hazardous Substances Data: 20127-61-1(Hazardous Substances Data)

Usage

Chemical structure

Resembling indole, a naturally occurring beta-carboline alkaloid.

Occurrence

Found in various plants and foods, and generated as a byproduct of bacterial and fungal metabolism.

Psychoactive properties

Some studies suggest its potential role in modulating the central nervous system and neurotransmitter activity.

Pharmaceutical and medicinal applications

Investigated for potential use, particularly in the fields of neurology and neuropsychiatry.

Role in neurodegenerative diseases

Studied for its potential involvement in neurodegenerative processes.

Antioxidant and anti-inflammatory agent

Possesses potential antioxidant and anti-inflammatory properties.

Upstream product

• 65601-07-2 1-Ethyl-4,9-dihydro-3H-pyrido<3,4-b>indole 
• 123-38-6 propionaldehyde 
• 54-12-6 Trp 
• 97-94-9 triethyl borane 
• 102337-43-9 1-Chlor-9H-pyrido<3,4-b>indol 
• 75304-06-2 1-ethyl-2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 75304-03-9 methyl 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 90686-26-3 1-ethyl-β-carboline-2N-oxide 
• 98258-89-0 3,4-dihydro-1-ethyl-9-methoxy-β-carboline 
• 61-54-1 tryptamine 
• 925-90-6 ethylmagnesium bromide 
• 146141-07-3 2,2-dimethyl-N-(2-(3-fluoro-4-pyridyl)phenyl)propanamide 
• 69111-76-8 1-methoxy-3-(2-nitrovinyl)indole 
• 54698-11-2 1-methoxyindole 

Downstream Products

• 50892-83-6 1-(9H-β-carbolin-1-yl)-ethanone 

Relevant articles and documents

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Synthesis and antitumor activity of javacarboline derivatives

Syntheses of 12H-pyrido[2,1-a]-[β-carbolin-5-ium bromides (15-27) and 11H-pyrrolo[2,1-a]-β-carbolines (32-35), structurally related to the tetracyclic alkaloid javacarboline (1) have been achieved via 2 steps routes starting from the respective β-carbolines. Their synthetic compounds showed potent antitumor activities against P-388 murine leukemia cells and PC-6 human lung carcinoma cells.

Direct Biomimetic Synthesis of β-Carboline Alkaloids from Two Amino Acids

The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet-Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.

Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines

A microwave-mediated Pictet-Spengler procedure utilizing 1,2-dichloroethane (DCE) and trifluoroacetic acid (TFA) was developed to provide tetrahydro-β-carboline salts in high yields. Reactions are complete in 20 minutes or less and the product precipitates from solution in high yields and purity, negating the need for liquid-liquid extraction or column chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro-β-carbolines to β-carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification. A microwave-assisted Pictet-Spengler procedure was developed to afford tetrahydro-β-carboline salts in high yields with no liquid-liquid extraction or chromatography required. A subsequent microwave-assisted aromatization procedure was also developed to provide β-carbolines in high yields requiring limited purification.