TRYPTOLINE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/934360 | https://www.ncbi.nlm.nih.gov/pubmed/11044572

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
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/934360	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Behavioural and electrocortical power spectrum effects of 5-methoxytryptoline and other analogs after intraventricular administration in rats.	1987 Oct 6	3691630
Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract.	2002	14530594
Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order haplosclerida: an inhibitor of cathepsin K.	2002 Apr	11975521
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	12670151
Tetrahydro-beta-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers.	2003 Nov 19	14611187
Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite.	2004 Jan	14709885
Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay.	2004 Mar	15129740
Structure determination of a tetrahydro-beta-carboline of arthropod origin: a novel alkaloid-toxin subclass from the web of spider Nephila clavipes.	2005 Apr	17192002
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Catalytic asymmetric Pictet-Spengler reaction.	2006 Feb 1	16433519
Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular N-carbamyliminium Pictet-Spengler reactions.	2006 Oct 25	16881029
Design, synthesis and cardioprotective effect of a new class of dual-acting agents: phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates.	2007 Nov 15	17827017
[Synthesis and biological evaluation of tetrahydro-beta-carline derivatives].	2008 Aug	18956775
A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum.	2008 May 5	18329636
DMD mediated formal synthesis of (+/-)-coerulescine.	2009 Jun	19634325
Facile synthesis of 1,2,3,4-tetrahydro-beta-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization.	2009 May 7	19354232
Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media.	2009 Nov 5	19807116
Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles.	2010	21061230
Profiling of residue-level photo-oxidative damage in peptides.	2010 Jun	20091070

Patents

Sample Use Guides

In Vivo Use Guide

in rats: 98 mg/kg was calculated for i.p. injection

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Name

Type

Language

TRYPTOLINE

Systematic Name

English

TETRAHYDRO-.BETA.-CARBOLINE

Systematic Name

English

2,3,4,9-TETRAHYDRO-1H-.BETA.-CARBOLINE

Systematic Name

English

1,2,3,4-TETRAHYDRO-9H-PYRIDO(3,4-B)INDOLE

Systematic Name

English

TETRAHYDRONORHARMAN

Common Name

English

NORELEAGNINE

Common Name

English

Code System Code Type Description

WIKIPEDIA

TRYPTOLINE