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definition - Beta-carboline

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beta-Carboline

                   
β-Carboline
Identifiers
CAS number 244-63-3 YesY
PubChem 64961
ChemSpider 58486 YesY
MeSH norharman
ChEBI CHEBI:109895 YesY
ChEMBL CHEMBL275224 YesY
Jmol-3D images Image 1
Properties
Molecular formula C11H8N2
Molar mass 168.20 g/mol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

β-Carboline (9H-pyrido[3,4-b]indole) also known as norharmane is a nitrogen containing heterocycle. It is also the prototype of a class of compounds known as β-carbolines.

Contents

  Pharmacology

β-Carboline alkaloids are widespread in plants and animals, and frequently act as monoamine oxidase inhibitors (MAOI). As components of the liana Banisteriopsis caapi, the β-carbolines harmine, harmaline, and tetrahydroharmine play a pivotal role in the pharmacology of the indigenous hallucinogenic drug ayahuasca by preventing the breakdown of dimethyltryptamine in the gut by inhibiting monoamine oxidase, thus making it psychoactive upon oral administration. Some β-carbolines, notably tryptoline and pinoline, are formed naturally in the human body. The latter is implicated along with melatonin in the role of the pineal gland in regulating the sleep-wake cycle.[citation needed] The β-carboline can link to cerebral benzodiazepine receptors and induce inverse agonist effect.

  Structure

β-Carboline belongs to the group of indole alkaloids and consist of pyridine ring that is fused to an indole skeleton.[1] The structure of β-carboline is similar to that of tryptamine, with the ethylamine chain re-connected to the indole ring via an extra carbon atom, to produce a three-ringed structure. The biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines.[2] Different levels of saturation are possible in the third ring, which is indicated here in the structural formula by colouring the optionally double bonds red and blue:

Substituted beta-carbolines (structural formula)

  Examples of β-carbolines

Some of the more important β-carbolines are tabulated by structure below.

Short Name
Red Bond
Blue Bond
R1 R6 R7 Structure
β-Carboline
×
×
H
H
H
β-Carboline
Tryptoline    
H
H
H
Tryptoline
Pinoline    
H
OCH3
H
Pinoline
Harmane
×
 
CH3
H
H
Harmane
Harmine
×
×
CH3
H
OCH3
Harmine
Harmaline
×
 
CH3
H
OCH3
Harmaline
Tetrahydroharmine    
CH3
H
H
OCH3
Tetrahydroharmine

  Occurrence in nature

"There are presently 64 known β-carboline alkaloids dispersed throughout at least eight plant families." The seeds of Peganum harmala (Syrian Rue) are a good source of beta-carbolines. Estimates of the quantity of harmaline in P. harmala seeds range from 0.16% [3] to 5.9% [4]of the dried weight. (As for most plants, yields vary with factors such as sub-species, growing conditions and season of collection.)

As a result of the presence of β-carbolines in the cuticle of scorpions, their skin is known to fluoresce when exposed to certain wavelengths of ultraviolet light such as that produced by a blacklight.[5]

Several β-carbolines have actions opposite to those of benzodiazepines: convulsive, anxiogenic and memory enhancing.[6]

  See also

  References

  1. ^ The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications. Ratsch, Christian. Park Street Press c. 2005
  2. ^ Baiget, Jessica; Llona-Minguez, Sabin; Lang, Stuart; MacKay, Simon P; Suckling, Colin J; Sutcliffe, Oliver B (2011). "Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-bindole-1-carboxylate: Concise synthesis of alangiobussinine"]. Beilstein Journal of Organic Chemistry 7: 1407–11. DOI:10.3762/bjoc.7.164. PMC 3201054. PMID 22043251. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3201054. 
  3. ^ Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (Aug 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal Chim Acta 575 (2): 290–9. DOI:10.1016/j.aca.2006.05.093. PMID 17723604. 
  4. ^ Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. (2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)". Food Chem Toxicol. 48 (3): 839–43. DOI:10.1016/j.fct.2009.12.019. PMID 20036304. 
  5. ^ Stachel SJ, Stockwell SA, Van Vranken DL (August 1999). "The fluorescence of scorpions and cataractogenesis". Chem. Biol. 6 (8): 531–9. DOI:10.1016/S1074-5521(99)80085-4. PMID 10421760. 
  6. ^ Venault P, Chapouthier G (2007). "From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory". ScientificWorldJournal 7: 204–23. DOI:10.1100/tsw.2007.48. PMID 17334612. 

  External links

   
               

 

All translations of Beta-carboline


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