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
| 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 |
|---|---|---|
| Behavioural and electrocortical power spectrum effects of 5-methoxytryptoline and other analogs after intraventricular administration in rats. | 1987 Oct 6 |
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| Identification of potent non-peptide somatostatin antagonists with sst(3) selectivity. | 2001 Aug 30 |
|
| Quantitative structure-activity relationship study on tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus. | 2001 Dec |
|
| Reduction of rat brain levels of the endogenous dopaminergic proneurotoxins 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro-beta-carboline by cigarette smoke. | 2001 Feb 9 |
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| Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. | 2002 |
|
| Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order haplosclerida: an inhibitor of cathepsin K. | 2002 Apr |
|
| Tetrahydro-beta-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay. | 2002 Aug |
|
| Identification and occurrence of the novel alkaloid pentahydroxypentyl-tetrahydro-beta-carboline-3-carboxylic acid as a tryptophan glycoconjugate in fruit juices and jams. | 2002 Jul 31 |
|
| Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids. | 2002 Mar 1 |
|
| 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 |
|
| Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003 Jun |
|
| Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis. | 2003 Nov 14 |
|
| Tetrahydro-beta-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. | 2003 Nov 19 |
|
| New versatile route to the synthesis of tetrahydro-beta-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3. | 2003 Sep 5 |
|
| A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction. | 2004 |
|
| Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite. | 2004 Jan |
|
| Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004 Mar |
|
| The emergence of selective 5-HT 2B antagonists structures, activities and potential therapeutic applications. | 2004 Mar |
|
| High-performance liquid chromatographic analysis of beta-carbolines in human scalp hair. | 2004 Mar 26 |
|
| Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages. | 2004 May 5 |
|
| Impact of aerobic training on immune-endocrine parameters, neurotrophic factors, quality of life and coordinative function in multiple sclerosis. | 2004 Oct 15 |
|
| Structure determination of a tetrahydro-beta-carboline of arthropod origin: a novel alkaloid-toxin subclass from the web of spider Nephila clavipes. | 2005 Apr |
|
| 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 Aug 22 |
|
| Sympathetic modulation of activity in Adelta- and C-primary nociceptive afferents after intradermal injection of capsaicin in rats. | 2005 Jan |
|
| Chiral ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde. | 2005 Jan 7 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Synthesis and biological evaluation of new tetrahydro-beta-carbolines as inhibitors of the mitotic kinesin Eg5. | 2005 Nov 15 |
|
| Antimalarial constituents from Nauclea orientalis (L.) L. | 2005 Oct |
|
| Catalytic asymmetric Pictet-Spengler reaction. | 2006 Feb 1 |
|
| Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation. | 2006 Feb 8 |
|
| Sinoaortic denervation abolishes blood pressure-induced GABA release in the locus coeruleus of conscious rats. | 2006 Jan 30 |
|
| Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity. | 2006 Jul 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 Jul 7 |
|
| Design, synthesis and cardioprotective effect of a new class of dual-acting agents: phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates. | 2007 Nov 15 |
|
| [Synthesis and biological evaluation of tetrahydro-beta-carline derivatives]. | 2008 Aug |
|
| A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum. | 2008 May 5 |
|
| Syntheses of tetrahydro-beta-carbolines via a tandem hydroformylation-Pictet-Spengler reaction. Scope and limitations. | 2008 Nov 7 |
|
| Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils. | 2008 Nov 7 |
|
| Noradrenergic inputs to the paraventricular hypothalamus contribute to hypothalamic-pituitary-adrenal axis and central Fos activation in rats after acute systemic endotoxin exposure. | 2008 Oct 28 |
|
| Solution-phase parallel annulation of (thio)hydantoins to tetrahydroisoquinolines and tetrahydro-beta-carbolines containing the 2-arylethyl amine scaffold. | 2009 Jul-Aug |
|
| DMD mediated formal synthesis of (+/-)-coerulescine. | 2009 Jun |
|
| Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media. | 2009 Nov 5 |
|
| The Methyltetrahydro-{beta}-Carbolines in Maca (Lepidium meyenii). | 2009 Sep |
|
| Beta-carboline alkaloids bind DNA. | 2010 Aug 2 |
|
| Interaction of β-carboline alkaloids with RNA. | 2010 Dec |
|
| Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage. | 2010 Jan 21 |
|
| Profiling of residue-level photo-oxidative damage in peptides. | 2010 Jun |
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
Fri Dec 15 19:40:37 GMT 2023
by
admin
on
Fri Dec 15 19:40:37 GMT 2023
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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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65027TMI0H
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DTXSID10167835
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