9-Methyl-9H-pyrido[3,4-b]indole
[CAS# 2521-07-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 9-Methyl-9H-pyrido[3,4-b]indole
• Synonyms: 9-Methyl-beta-carboline; 9-Methylnorharman; 9-Methylnorharmane; N-Methylnorharman
• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 182.22
• CAS Registry Number: 2521-07-5
• SMILES: CN1C2=CC=CC=C2C3=C1C=NC=C3

Properties

• Solubility: Very slightly soluble (0.2 g/L) (25 ºC), Calc.^*
• Density: 1.17±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 109 ºC^**
• Index of Refraction: 1.658, Calc.^*
• Boiling Point: 367.3±24.0 ºC (760 mmHg), Calc.^*
• Flash Point: 175.9±22.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

^** Henecka, H.; Med. Chem., Abhandl. Med.-Chem. Forschungsstaetten Farbenfabriken Bayer A.-G. 1963, V7, P277-86.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Discovory and Applicatios

9-Methyl-9H-pyrido[3,4-b]indole is an organic compound that belongs to the class of heterocyclic aromatic compounds, specifically the indole derivatives. It is characterized by a pyridine fused to an indole structure, making it an important molecule in the field of medicinal chemistry and material science. The compound has attracted attention for its unique chemical properties, including its ability to interact with biological systems, and its potential applications in the development of new therapeutic agents.

The discovery of 9-methyl-9H-pyrido[3,4-b]indole dates back to research exploring the properties of heterocyclic compounds, particularly those containing fused ring systems, which are often found in biologically active molecules. As a derivative of the indole and pyridine family, 9-methyl-9H-pyrido[3,4-b]indole exhibits the typical features of such structures, which include the potential for nucleophilic substitution reactions, electronic interactions, and its role as a ligand in coordination chemistry. The introduction of a methyl group at the 9-position further modifies the compound's electronic characteristics, enhancing its reactivity and affinity for certain receptors.

One of the most significant applications of 9-methyl-9H-pyrido[3,4-b]indole is in the field of medicinal chemistry. It has shown potential as a lead compound in the development of drugs targeting various enzymes and receptors, particularly those involved in cancer, neurodegenerative diseases, and inflammation. Studies have demonstrated its activity as a selective inhibitor of specific protein kinases and as a modulator of certain pathways that play key roles in cell signaling, making it a promising candidate for drug development.

Moreover, 9-methyl-9H-pyrido[3,4-b]indole has been investigated for its potential in the treatment of neurological conditions, due to its ability to cross the blood-brain barrier and interact with receptors in the central nervous system. Its biological activity is believed to be partly attributed to its structure, which allows it to engage with a range of molecular targets involved in the regulation of neuronal function. Additionally, the compound's ability to influence oxidative stress and modulate inflammatory responses is of interest in the development of therapies for conditions like Alzheimer's disease and Parkinson's disease.

In material science, 9-methyl-9H-pyrido[3,4-b]indole has shown promise as a component in the development of organic electronic materials, such as organic semiconductors and photovoltaic devices. Its conjugated structure allows it to absorb light efficiently and conduct electricity, which is useful in the fabrication of organic light-emitting diodes (OLEDs) and organic solar cells. The compound's unique combination of electronic properties makes it a subject of interest for future research in the development of more efficient, low-cost, and environmentally friendly electronic devices.

The synthetic routes to 9-methyl-9H-pyrido[3,4-b]indole involve various cyclization methods, with the methylation step typically introduced to enhance the stability and reactivity of the molecule. Researchers are actively exploring ways to optimize its synthesis and improve its biological and material properties.