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β-Carboline

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(Redirected from Norharman)
Not to be confused with Substituted β-carboline.
β-Carboline
Chemical structure of β-carboline
Names
Preferred IUPAC name
9H-Pyrido[3,4-b]indole
Other names
  • Norharmane
  • Norharman
  • Carbazoline
  • 2-Azacarbazole
  • 2,9-Diazafluorene
Identifiers
3D model (JSmol)
128414
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.418 Edit this at Wikidata
EC Number
  • 205-959-0
KEGG
MeSH norharman
UNII
  • InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H checkY
    Key: AIFRHYZBTHREPW-UHFFFAOYSA-N checkY
  • InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
    Key: AIFRHYZBTHREPW-UHFFFAOYAG
  • c1ccc3c(c1)[nH]c2cnccc23
Properties
C11H8N2
Molar mass 168.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

β-Carboline, also known as norharman, norharmane, or 9H-pyrido[3,4-b]indole, is a tricyclic chemical compound and alkaloid.[1] It is the parent structure of the substituted β-carbolines, a large group of alkaloids and synthetic compounds.[1] β-Carboline may be thought of as a cyclized tryptamine.[1] 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.[1]

β-Carboline is a weak reversible inhibitor of monoamine oxidase A (RIMA), with an IC50Tooltip half-maximal inhibitory concentration of 1,700 nM.[2] It is also a weak dopamine reuptake inhibitor (DRI), with an IC50 of 3,040 nM at the dopamine transporter (DAT).[2] The drug shows weak affinity for the serotonin 5-HT2B and 5-HT2C receptors (Ki = 738 nM and 2,522 nM, respectively), but not for the serotonin 5-HT2A receptor (Ki = >10,000 nM).[3]

See also

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References

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  1. ^ a b c d Cao R, Peng W, Wang Z, Xu A (2007). "beta-Carboline alkaloids: biochemical and pharmacological functions". Curr Med Chem. 14 (4): 479–500. doi:10.2174/092986707779940998. PMID 17305548.
  2. ^ a b Saro G, Johne S, Latino DA, Moine F, van der Toorn M, Mathis C, Veljkovic E (March 2025). "Monoamine Oxidase Inhibitors Present in Tobacco Modulate Dopamine Balance Via the Dopamine Transporter". ACS Chem Neurosci. 16 (6): 1117–1131. doi:10.1021/acschemneuro.4c00789. PMC 11926787. PMID 40033845.
  3. ^ Foley, Caroline A.; Al-Issa, Yazan A.; Hiller, Kathryn P.; Mulcahy, Seann P. (30 June 2019). "Synthesis and Structure–Activity Relationships of 1-Aryl-β-carbolines as Affinity Probes for the 5-Hydroxytryptamine Receptor". ACS Omega. 4 (6): 9807–9812. doi:10.1021/acsomega.9b01111. ISSN 2470-1343.
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