CHEBI:2089 - 5-methoxytryptamine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 5-methoxytryptamine
ChEBI ID CHEBI:2089
Definition A member of the class of tryptamines that is the methyl ether derivative of serotonin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C11H14N2O
Net Charge 0
Average Mass 190.246
Monoisotopic Mass 190.11061
InChI InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
InChIKey JTEJPPKMYBDEMY-UHFFFAOYSA-N
SMILES COC1=CC2=C(NC=C2CCN)C=C1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Brassica napus (NCBI:txid3708) Found in leaf lamina (BTO:0000719). From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by Cornelius Lentner.
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
5-hydroxytryptamine 2A receptor agonist
An agonist at the 5-hydroxytryptamine 2A (5-HT2A) receptor.
5-hydroxytryptamine 2B receptor agonist
An agonist at the 5-hydroxytryptamine 2B (5-HT2B) receptor.
5-hydroxytryptamine 2C receptor agonist
An agonist at the 5-hydroxytryptamine 2B (5-HT2C) receptor.
Application(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
radiation protective agent
Any compound that is able to protect normal cells from the damage caused by radiation therapy.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-methoxytryptamine (CHEBI:2089) has functional parent serotonin (CHEBI:28790)
5-methoxytryptamine (CHEBI:2089) has role 5-hydroxytryptamine 2A receptor agonist (CHEBI:145982)
5-methoxytryptamine (CHEBI:2089) has role 5-hydroxytryptamine 2B receptor agonist (CHEBI:142184)
5-methoxytryptamine (CHEBI:2089) has role 5-hydroxytryptamine 2C receptor agonist (CHEBI:142185)
5-methoxytryptamine (CHEBI:2089) has role antioxidant (CHEBI:22586)
5-methoxytryptamine (CHEBI:2089) has role cardioprotective agent (CHEBI:77307)
5-methoxytryptamine (CHEBI:2089) has role human metabolite (CHEBI:77746)
5-methoxytryptamine (CHEBI:2089) has role mouse metabolite (CHEBI:75771)
5-methoxytryptamine (CHEBI:2089) has role neuroprotective agent (CHEBI:63726)
5-methoxytryptamine (CHEBI:2089) has role radiation protective agent (CHEBI:66987)
5-methoxytryptamine (CHEBI:2089) has role serotonergic agonist (CHEBI:35941)
5-methoxytryptamine (CHEBI:2089) is a aromatic ether (CHEBI:35618)
5-methoxytryptamine (CHEBI:2089) is a primary amino compound (CHEBI:50994)
5-methoxytryptamine (CHEBI:2089) is a tryptamines (CHEBI:27162)
5-methoxytryptamine (CHEBI:2089) is conjugate base of 5-methoxytryptamine(1+) (CHEBI:166874)
Incoming 5-methoxy-N,N-diisopropyltryptamine (CHEBI:48282) has functional parent 5-methoxytryptamine (CHEBI:2089)
5-methoxytryptamine(1+) (CHEBI:166874) is conjugate acid of 5-methoxytryptamine (CHEBI:2089)
IUPAC Name
2-(5-methoxy-1H-indol-3-yl)ethanamine
Synonyms Sources
2-(5-methoxyindol-3-yl)ethylamine ChemIDplus
3-(2-aminoethyl)-5-methoxyindole ChemIDplus
5-MeOT IUPHAR
5-MeOT KEGG COMPOUND
5-methoxy-1H-indole-3-ethanamine NIST Chemistry WebBook
5-Methoxytryptamine KEGG COMPOUND
5-Mot ChemIDplus
5-MT IUPHAR
5MOT ChemIDplus
mexamine NIST Chemistry WebBook
O-methylserotonin ChEBI
Manual Xrefs Databases
1767 ChemSpider
5-Methoxytryptamine Wikipedia
C00051985 KNApSAcK
C05659 KEGG COMPOUND
EP1653948 Patent
F5U PDBeChem
FDB023311 FooDB
HMDB0004095 HMDB
LSM-4582 LINCS
WO2005009419 Patent
View more database links
Registry Numbers Types Sources
1220927 Gmelin Registry Number Gmelin
145587 Reaxys Registry Number Reaxys
145587 Beilstein Registry Number Beilstein
608-07-1 CAS Registry Number ChemIDplus
608-07-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
10420441 PubMed citation Europe PMC
11270479 PubMed citation Europe PMC
12659894 PubMed citation Europe PMC
16007002 PubMed citation Europe PMC
16714247 PubMed citation Europe PMC
17451889 PubMed citation Europe PMC
17601618 PubMed citation Europe PMC
18318189 PubMed citation Europe PMC
22678752 PubMed citation Europe PMC
23098818 PubMed citation Europe PMC
23451999 PubMed citation Europe PMC
25863630 PubMed citation Europe PMC
27112772 PubMed citation Europe PMC
3919158 PubMed citation Europe PMC
9128844 PubMed citation Europe PMC
Last Modified
02 June 2021