Tryptoline

Chemical compound From Wikipedia, the free encyclopedia

Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of β-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]

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.156.194 Edit this at Wikidata
UNII
  • 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
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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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

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