Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H12N2 |
Molecular Weight | 172.2264 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CC2=C(CN1)NC3=CC=CC=C23
InChI
InChIKey=CFTOTSJVQRFXOF-UHFFFAOYSA-N
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
Tryptoline (also known as a tetrahydronorharmane), a metabolite of tryptamine, is an inhibitor of the reuptake of serotonin. Some in vitro experiments have shown that tryptoline prevents the lipid peroxidation induced by hydrogen peroxide and thus this compound can be further investigated as a neuroprotective agent.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/934360 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Behavioural and electrocortical power spectrum effects of 5-methoxytryptoline and other analogs after intraventricular administration in rats. | 1987 Oct 6 |
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Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. | 2002 |
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Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order haplosclerida: an inhibitor of cathepsin K. | 2002 Apr |
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L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-beta-carboline alkaloids: activity as antioxidants and free radical scavengers. | 2003 Apr 9 |
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Tetrahydro-beta-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. | 2003 Nov 19 |
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Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite. | 2004 Jan |
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Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004 Mar |
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Structure determination of a tetrahydro-beta-carboline of arthropod origin: a novel alkaloid-toxin subclass from the web of spider Nephila clavipes. | 2005 Apr |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Catalytic asymmetric Pictet-Spengler reaction. | 2006 Feb 1 |
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Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular N-carbamyliminium Pictet-Spengler reactions. | 2006 Oct 25 |
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Design, synthesis and cardioprotective effect of a new class of dual-acting agents: phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates. | 2007 Nov 15 |
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[Synthesis and biological evaluation of tetrahydro-beta-carline derivatives]. | 2008 Aug |
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A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum. | 2008 May 5 |
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DMD mediated formal synthesis of (+/-)-coerulescine. | 2009 Jun |
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Facile synthesis of 1,2,3,4-tetrahydro-beta-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization. | 2009 May 7 |
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Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media. | 2009 Nov 5 |
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Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles. | 2010 |
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Profiling of residue-level photo-oxidative damage in peptides. | 2010 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/560635
in rats: 98 mg/kg was calculated for i.p. injection
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7368949
Curator's Comment: Tetrahydro-beta-carboline (tryptoline) was more potent inhibitor than its 1-methylderivative, tetrahydroharmane (methtryptoline) or norharmane (beta-carboline) for the serotonin (5-HT) uptake in rat brain synaptosomes.
Unknown
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TRYPTOLINE
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C009804
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DTXSID10167835
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SUBSTANCE RECORD