Chemistry:Tryptoline
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| 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 | |
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3D model (JSmol)
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PubChem CID
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| 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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| Infobox references | |
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
- Norharmane
- Harmane
- beta-Carboline
- Harmala alkaloid
References
- ↑ "Tryptoline". https://pubchem.ncbi.nlm.nih.gov/compound/107838.
- ↑ 2.0 2.1 2.2 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. https://doi.org/10.1016/0306-4522(81)90163-9.
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