Structure via PubChem · Public domain (PubChem)
norharman
Sign in to saveAlso known as carbazoline, norharmane, beta-carboline, β-carboline, 9H-pyrido[3,4-b]indole, 2,9-Diazafluorene, 2-Azacarbazole, 9H-Pyrido(3,4-B)indole
β-Carboline, also known as norharman or as '9H-pyrido[3,4-b]indole', is a tricyclic chemical compound and alkaloid. It is the parent structure of the substituted β-carbolines, a large group of alkaloids and synthetic compounds. β-Carboline may be thought of as a cyclized tryptamine. The compound has been found to possess a variety of pharmacological activities, including DNA mutagenic effects, imidazoline receptor interactions, serotonin reuptake inhibition, monoamine oxidase inhibition, cytochrome P450 enzyme inhibition, and inhibition of other enzymes, among others.
Chemical data
- Formula
- C11H8N2
- Molecular weight
- 168.19 g/mol
- IUPAC name
- 9H-pyrido[3,4-b]indole
- SMILES
- C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
- InChIKey
- AIFRHYZBTHREPW-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 28.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
583 papers- β-Carboline (norharman).Acta crystallographica. Section C, Crystal structure communications · 2011
- Exposure to beta-carbolines norharman and harman.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2004
- Tryptophan metabolite norharman secreted by cultivated Lactobacillus attenuates acute pancreatitis as an antagonist of histone deacetylases.BMC medicine · 2023
- β-Carbolines norharman and harman change neurobehavior causing neurological damage in Caenorhabditis elegans.Food & function · 2023
- β-carbolines norharman and harman in vegetable oils in China.Food additives & contaminants. Part B, Surveillance · 2020
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 168.069
Show 7 more facts
- topic's main category
- Category:Beta-Carbolines
- chemical formula
- C₁₁H₈N₂
- canonical SMILES
- C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
- found in taxon
- Amanita exitialis
- subject has role
- biological pigment
- Commons category
- Carbolines
- physically interacts with
- Indoleamine 2,3-dioxygenase 1
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
β-Carboline, also known as norharman or as '9H-pyrido[3,4-b]indole', is a tricyclic chemical compound and alkaloid. It is the parent structure of the substituted β-carbolines, a large group of alkaloids and synthetic compounds. β-Carboline may be thought of as a cyclized tryptamine. The compound has been found to possess a variety of pharmacological activities, including DNA mutagenic effects, imidazoline receptor interactions, serotonin reuptake inhibition, monoamine oxidase inhibition, cytochrome P450 enzyme inhibition, and inhibition of other enzymes, among others.
==See also== Substituted β-carboline Tryptoline γ-Carboline
Excerpted from Wikipedia’s “norharman” article, available under the CC BY-SA 4.0 licence.