7076-11-1

Basic information

• Product Name: 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE
• Synonyms: 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE;5,6,7,8-Tetrahydro-9H-pyrido[2,3-b]indole
• CAS NO: 7076-11-1
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.23
• Mol File: 7076-11-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 150 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 0.000189mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE(7076-11-1)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE(7076-11-1)

Safety Data

• Hazardous Substances Data: 7076-11-1(Hazardous Substances Data)

Usage

Description

5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE, also known as norharmane, is a chemical compound characterized by a pyridine and indole ring structure. It is a naturally occurring substance found in tobacco smoke, as well as in various foods and beverages like coffee, beer, and roasted peanuts. Norharmane has been associated with genotoxic and carcinogenic properties, which may contribute to cancer development. Furthermore, it has been studied for its potential role in neurodegenerative diseases such as Parkinson's and Alzheimer's. Additionally, norharmane acts as an inhibitor of the enzyme monoamine oxidase, which is involved in the regulation of neurotransmitters in the brain.

Uses

Used in Pharmaceutical Research:
5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE is used as a research compound for investigating its genotoxic and carcinogenic effects, which can help in understanding its contribution to the development of cancer. This knowledge can aid in the development of potential therapeutic agents or preventive measures against cancer.
Used in Neurodegenerative Disease Research:
In the field of neurodegenerative disease research, 5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE is utilized as a subject of study to explore its role in conditions such as Parkinson's and Alzheimer's. Understanding its impact on these diseases can contribute to the advancement of treatments and interventions.
Used in Neurotransmitter Regulation Studies:
5,6,7,8-TETRAHYDRO-1H-PYRIDO[2,3-B]INDOLE is used as an inhibitor of the enzyme monoamine oxidase in studies focused on neurotransmitter regulation. This application can provide insights into the compound's effects on brain chemistry and potentially lead to the development of new approaches for managing neurological conditions related to neurotransmitter imbalances.

InChI:InChI=1/C11H12N2/c1-2-6-10-8(4-1)9-5-3-7-12-11(9)13-10/h3,5,7H,1-2,4,6H2,(H,12,13)

Upstream product

• 1135-36-0 cyclohexanone pyridin-2-ylhydrazone 
• 74803-20-6 9-acetyl-5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole 
• 86119-84-8 phosphoric acid 
• 13534-99-1 2-Amino-3-bromopyridine 
• 108-94-1 cyclohexanone 
• 35486-42-1 2-amino-3,5-dibromopyridine 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 54231-33-3 3-bromo-2-nitropyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 54230-88-5 8-bromotetrazolo[1,5-a]pyridine 
• 2942-59-8 2-chloronicotinic acid 
• 42330-59-6 (2-chloropyrid-3-yl)methanol 
• 111108-72-6 (2-chloro-3-pyridinyl)methyl bromide 
• 49609-84-9 2-Chloronicotinoyl chloride 

Downstream Products

• 244-76-8 α-carboline 

Relevant articles and documents

Iron-Catalyzed Radical Activation Mechanism for Denitrogenative Rearrangement Over C(sp3)–H Amination

An iron-catalyzed denitrogenative rearrangement of 1,2,3,4-tetrazole is developed over the competitive C(sp3)–H amination. This catalytic rearrangement reaction follows an unprecedented metalloradical activation mechanism. Employing the developed method, a wide number of complex-N-heterocyclic product classes have been accessed. The synthetic utility of this radical activation method is showcased with the short synthesis of a bioactive molecule. Collectively, this discovery underlines the progress of radical activation strategy that should find wide application in the perspective of medicinal chemistry, drug discovery and natural product synthesis research.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

Palladium-catalyzed one-pot synthesis of pyrrole-annulated coumarin, quinolone, and 7-aza-indole derivatives

An efficient one-pot approach for the synthesis of highly substituted pyrrolocoumarin, quinolone, and pyrrolopyridine derivatives has been achieved by palladium acetate catalyzed reaction in DMF through initially formed enamine from cyclic and acyclic ketones and 6-amino-5-bromocoumarin, 6-amino-5-bromo-1-methyl quinolone, and 2-amino-3,5-dibromopyridine, respectively. Georg Thieme Verlag Stuttgart - New York.