|Jmol-3D images||Image 1|
|Molar mass||172.226 g/mol|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
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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.
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.
There is evidence that tryptolines may be potent neurotoxins that may play a role in Parkinson's Disease
- H. Rommelspacher, H. Kauffmann, C. Heyck Cohnitz and H. Coper (1977). "Pharmacological properties of tetrahydronorharmane (Tryptoline)". Journal Naunyn-Schmiedeberg's Archives of Pharmacology 298 (2): 83–91. doi:10.1007/BF00508615.