Tryptoline

Tryptoline
Names
Preferred IUPAC name
2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole
Other names
Noreleagnine
Tetrahydronorharman
2,3,4,9-Tetrahydro-1H-β-carboline
Identifiers
CAS Number
  • 16502-01-5 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL269236 checkY
ChemSpider
  • 96979 checkY
ECHA InfoCard 100.156.194 Edit this at Wikidata
PubChem CID
  • 107838
UNII
  • 65027TMI0H checkY
CompTox Dashboard (EPA)
  • DTXSID10167835 Edit this at Wikidata
InChI
  • InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 checkY
    Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N checkY
  • InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
    Key: CFTOTSJVQRFXOF-UHFFFAOYAW
  • c1ccc2c(c1)c3c([nH]2)CNCC3
Properties
Chemical formula
 C11H12N2
Molar mass 172.226 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of beta-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.[1]

Pharmacology

Tryptolines are competitive selective inhibitors of the enzyme monoamine oxidase type A (MAO-A). 5-Hydroxytryptoline and 5-methoxytryptoline (pinoline) are the most active monoamine oxidase inhibitors (MAOIs) with IC50s of 0.5 μM and 1.5 μM respectively.[2]

Tryptolines are also potent reuptake inhibitors of serotonin and epinephrine, with a significantly greater selectivity for serotonin.[2]

In vivo formation of tryptolines has been a matter of controversy.[2]

See also

References

  1. ^ "Tryptoline". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b c Youdim, N.B.H.; Oppenheim, B. (April 1981). "The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets". Neuroscience. 6 (4): 801–810. doi:10.1016/0306-4522(81)90163-9. PMID 7242917. S2CID 37681465.