Tryptoline
From Wikipedia, the free encyclopedia
| Tryptoline | |
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| IUPAC name | 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole |
| Other names | Noreleagnine Tetrahydronorharman 2,3,4,9-Tetrahydro-1H-β-carboline |
| Identifiers | |
| CAS number | [16502-01-5] |
| PubChem | |
| SMILES | C1CNCC2=C1C3=CC=CC=C3N2 |
| Properties | |
| Molecular formula | C11H12N2 |
| Molar mass | 172.226 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Tryptoline is a natural organic amine. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.
[edit] Pharmacology
Many tryptolines are competitive selective inhibitors of monoamine oxidase type A (MAO-A). 5-Hydroxytryptoline and 5-methoxytryptoline are the most active monoamine oxidase inhibitors with IC50s of 0.5 μM and 1.5 μM respectively, using 5-hydroxytryptamine as substrate.
Tryptolines are also potent reuptake inhibitors of 5-hydroxytryptamine and epinephrine; a significantly greater uptake inhibitory selectivity being shown for 5-hydroxytryptamine than epinephrine. The comparison of the inhibition kinetics of tetrahydro-β-carbolines for 5-hydroxytryptamine and epinephrine uptake (with that of the platelet aggregation response to these amines) have shown that 5-hydroxymethtryptoline, methtryptoline, and tryptoline are poor inhibitors of uptake. 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.
[edit] See also
[edit] References
- 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:.
