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=C2C=CC=C3
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
| Molecular Formula | C11H12N2 |
| Molecular Weight | 172.2264 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Interaction of β-carboline alkaloids with RNA. | 2010-12 |
|
| Triazolyl tryptoline derivatives as β-secretase inhibitors. | 2010-11-15 |
|
| Beta-carboline alkaloids bind DNA. | 2010-08-02 |
|
| Discovery of tetrahydro-beta-carbolines as inhibitors of the mitotic kinesin KSP. | 2010-06-15 |
|
| Profiling of residue-level photo-oxidative damage in peptides. | 2010-06 |
|
| Direct and selective functionalization of a tetrahydro-beta-carboline at position 4. | 2010-03-19 |
|
| Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage. | 2010-01-21 |
|
| Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles. | 2010 |
|
| Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media. | 2009-11-05 |
|
| Monoamine oxidase inhibitory activities of indolylalkaloid toxins from the venom of the colonial spider Parawixia bistriata: functional characterization of PwTX-I. | 2009-11 |
|
| Alterations of nocturnal activity in rats following subchronic oral administration of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline. | 2009-10 |
|
| Molecular determinants of beta-carboline inhibition of the glycine receptor. | 2009-09 |
|
| The Methyltetrahydro-{beta}-Carbolines in Maca (Lepidium meyenii). | 2009-09 |
|
| Metaplasticity of hypothalamic synapses following in vivo challenge. | 2009-06-25 |
|
| DMD mediated formal synthesis of (+/-)-coerulescine. | 2009-06 |
|
| Synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines fused to pyrrolidines and solution-phase parallel acylation. | 2009-05-29 |
|
| Solution-phase parallel annulation of (thio)hydantoins to tetrahydroisoquinolines and tetrahydro-beta-carbolines containing the 2-arylethyl amine scaffold. | 2009-05-29 |
|
| Facile synthesis of 1,2,3,4-tetrahydro-beta-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization. | 2009-05-07 |
|
| Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1,2,3,4-9H-tetrahydro-beta-carboline-3-carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry. | 2009-04 |
|
| Syntheses of tetrahydro-beta-carbolines via a tandem hydroformylation-Pictet-Spengler reaction. Scope and limitations. | 2008-11-07 |
|
| Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils. | 2008-11-07 |
|
| Noradrenergic inputs to the paraventricular hypothalamus contribute to hypothalamic-pituitary-adrenal axis and central Fos activation in rats after acute systemic endotoxin exposure. | 2008-10-28 |
|
| A novel access to tetrahydro-beta-carbolines via one-pot hydroformylation/fischer indole synthesis: rearrangement of 3,3-spiroindoleninium cations. | 2008-08-21 |
|
| [Synthesis and biological evaluation of tetrahydro-beta-carline derivatives]. | 2008-08 |
|
| A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum. | 2008-05-05 |
|
| Design, synthesis and cardioprotective effect of a new class of dual-acting agents: phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates. | 2007-11-15 |
|
| Increased level of tetrahydro-beta-carboline derivatives in short-term fermented garlic. | 2006-12 |
|
| Cytotoxicity of chloral-derived beta-carbolines is not specific towards neuronal nor dopaminergic cells. | 2006-12 |
|
| Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular N-carbamyliminium Pictet-Spengler reactions. | 2006-10-25 |
|
| Dual-acting agents that possess free radical scavenging and antithrombotic activities: design, synthesis, and evaluation of phenolic tetrahydro-beta-carboline RGD peptide conjugates. | 2006-09-01 |
|
| Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity. | 2006-07-15 |
|
| Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by beta-carboline alkaloids occurring in foods and plants. | 2006-07-07 |
|
| Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-beta-carboline formation. | 2006-06-07 |
|
| Development of the Pictet-Spengler reaction catalyzed by AuCl3/AgOTf. | 2006-03-17 |
|
| Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation. | 2006-02-08 |
|
| Catalytic asymmetric Pictet-Spengler reaction. | 2006-02-01 |
|
| Sinoaortic denervation abolishes blood pressure-induced GABA release in the locus coeruleus of conscious rats. | 2006-01-30 |
|
| Synthesis and biological evaluation of new tetrahydro-beta-carbolines as inhibitors of the mitotic kinesin Eg5. | 2005-11-15 |
|
| Antimalarial constituents from Nauclea orientalis (L.) L. | 2005-10 |
|
| High-affinity binding of beta-carbolines to imidazoline I2B receptors and MAO-A in rat tissues: norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain. | 2005-08-22 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Structure determination of a tetrahydro-beta-carboline of arthropod origin: a novel alkaloid-toxin subclass from the web of spider Nephila clavipes. | 2005-04 |
|
| Chiral ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde. | 2005-01-07 |
|
| Sympathetic modulation of activity in Adelta- and C-primary nociceptive afferents after intradermal injection of capsaicin in rats. | 2005-01 |
|
| Impact of aerobic training on immune-endocrine parameters, neurotrophic factors, quality of life and coordinative function in multiple sclerosis. | 2004-10-15 |
|
| Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages. | 2004-05-05 |
|
| High-performance liquid chromatographic analysis of beta-carbolines in human scalp hair. | 2004-03-26 |
|
| Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004-03 |
|
| A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction. | 2004 |
|
| Behavioural and electrocortical power spectrum effects of 5-methoxytryptoline and other analogs after intraventricular administration in rats. | 1987-10-06 |
Sample Use Guides
in rats: 98 mg/kg was calculated for i.p. injection
Route of Administration:
Intraperitoneal
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:53:05 GMT 2025
by
admin
on
Mon Mar 31 19:53:05 GMT 2025
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| Record UNII |
65027TMI0H
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| Record Status |
Validated (UNII)
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| Record Version |
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TRYPTOLINE
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C009804
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SUB184032
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16502-01-5
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65027TMI0H
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100000170163
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DTXSID10167835
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