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词条 Tryptoline
释义

  1. Pharmacology

  2. See also

  3. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470618432
| ImageFile = Tryptoline structure.png
| ImageSize =
| IUPACName = 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole
| OtherNames = Noreleagnine
Tetrahydronorharman
2,3,4,9-Tetrahydro-1H-β-carboline
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 96979
| 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
| InChIKey = CFTOTSJVQRFXOF-UHFFFAOYAW
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 269236
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CFTOTSJVQRFXOF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 16502-01-5
| PubChem = 107838
| SMILES = c1ccc2c(c1)c3c([nH]2)CNCC3
}}
|Section2={{Chembox Properties
| Formula = C11H12N2
| MolarMass = 172.226 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

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.

Pharmacology

{{unreferenced section|date=May 2018}}

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

  • Norharmane
  • harmane
  • beta-Carboline
  • Harmala alkaloid

References

  • {{cite journal | author1 =H. Rommelspacher | author2 =H. Kauffmann | author3 =C. Heyck Cohnitz |author4 = H. Coper | title =Pharmacological properties of tetrahydronorharmane (Tryptoline) | journal =Journal Naunyn-Schmiedeberg's Archives of Pharmacology | year =1977 | volume =298 | issue =2 | pages =83–91 | doi =10.1007/BF00508615 | url =http://www.springerlink.com/content/g264075045877742/ }}

4 : Alkaloids|Beta-Carbolines|Tryptamines|Monoamine oxidase inhibitors

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