Tryptoline

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.

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
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 Y
    Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N Y
  • 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).
N verify (what is YN ?)
Infobox references

Pharmacology

Many 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, using 5-hydroxytryptamine (serotonin) as substrate.

Tryptolines are also potent reuptake inhibitors of serotonin and epinephrine, with a significantly greater selectivity for serotonin. Comparison of the inhibition kinetics of tetrahydro-β-carbolines for serotonin and epinephrine reuptake to that of the platelet aggregation response to these amines has shown that 5-hydroxymethtryptoline, methtryptoline, and tryptoline are poor inhibitors of reuptake. In all respects 5-hydroxytryptoline and 5-methoxytryptoline showed greater pharmacological activity than the tryptoline and methtryptoline.

Although the in vivo formation of tryptolines has been a matter of controversy, they have profound pharmacological activity.

See also

References
    • H. Rommelspacher; H. Kauffmann; C. Heyck Cohnitz; H. Coper (1977). "Pharmacological properties of tetrahydronorharmane (Tryptoline)". Journal Naunyn-Schmiedeberg's Archives of Pharmacology. 298 (2): 83–91. doi:10.1007/BF00508615.
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