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
Identification of potent non-peptide somatostatin antagonists with sst(3) selectivity.	2001 Aug 30	11520208
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	11165438
Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order haplosclerida: an inhibitor of cathepsin K.	2002 Apr	11975521
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
The emergence of selective 5-HT 2B antagonists structures, activities and potential therapeutic applications.	2004 Mar	15032678
High-performance liquid chromatographic analysis of beta-carbolines in human scalp hair.	2004 Mar 26	15058601
Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages.	2004 May 5	15113173
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
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	16061219
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	15624931
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Antimalarial constituents from Nauclea orientalis (L.) L.	2005 Oct	17191939
Increased level of tetrahydro-beta-carboline derivatives in short-term fermented garlic.	2006 Dec	17039401
Highly enantioselective synthesis of tetrahydro-beta-carbolines and tetrahydro-gamma-carbolines via Pd-catalyzed intramolecular allylic alkylation.	2006 Feb 8	16448093
Development of the Pictet-Spengler reaction catalyzed by AuCl3/AgOTf.	2006 Mar 17	16526809
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
A novel access to tetrahydro-beta-carbolines via one-pot hydroformylation/fischer indole synthesis: rearrangement of 3,3-spiroindoleninium cations.	2008 Aug 21	18642825
A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum.	2008 May 5	18329636
Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils.	2008 Nov 7	18823897
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	18773942
Synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines fused to pyrrolidines and solution-phase parallel acylation.	2009 Jul-Aug	19472986
DMD mediated formal synthesis of (+/-)-coerulescine.	2009 Jun	19634325
Metaplasticity of hypothalamic synapses following in vivo challenge.	2009 Jun 25	19555652
Alterations of nocturnal activity in rats following subchronic oral administration of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline.	2009 Oct	19609633
Molecular determinants of beta-carboline inhibition of the glycine receptor.	2009 Sep	19619142
Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles.	2010	21061230
Interaction of β-carboline alkaloids with RNA.	2010 Dec	20731607

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