CHEBI:2089 - 5-methoxytryptamine

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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 ChemicalBook:CB0676885, eMolecules:494805, ZINC000000057163
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5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the body in low levels, especially in the pineal gland. It is formed via O-methylation of serotonin or N-deacetylation of melatonin. 5-MT is a highly potent and non-selective serotonin receptor agonist and shows serotonergic psychedelic-like effects in animals. However, it is inactive in humans, at least orally, likely due to rapid metabolism by monoamine oxidase (MAO). The levels and effects of 5-MT are dramatically potentiated by monoamine oxidase inhibitors (MAOIs) in animals.
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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
608-07-1 CAS Registry Number ChemIDplus
608-07-1 CAS Registry Number NIST Chemistry WebBook
Citations
Tan DX, Hardeland R, Back K, Manchester LC, Alatorre-Jimenez MA, Reiter RJ (2016)
On the significance of an alternate pathway of melatonin synthesis via 5-methoxytryptamine: comparisons across species.
Journal of pineal research 61, 27-40 [PubMed:27112772]
[show Abstract]
Goh TB, Koh RY, Yam MF, Azhar ME, Mordi MN, Mansor SM (2015)
5-Methoxytryptamine reacts with natural food flavour to produce 6-methoxy tetrahydro-β-carbolines: in vitro investigation of their antioxidant and cytotoxicity properties.
Food chemistry 183, 208-216 [PubMed:25863630]
[show Abstract]
Haduch A, Bromek E, Sadakierska-Chudy A, Wójcikowski J, Daniel WA (2013)
The catalytic competence of cytochrome P450 in the synthesis of serotonin from 5-methoxytryptamine in the brain: an in vitro study.
Pharmacological research 67, 53-59 [PubMed:23098818]
[show Abstract]
Verma P, Mathur AK, Masood N, Luqman S, Shanker K (2013)
Tryptophan over-producing cell suspensions of Catharanthus roseus (L) G. Don and their up-scaling in stirred tank bioreactor: detection of a phenolic compound with antioxidant potential.
Protoplasma 250, 371-380 [PubMed:22678752]
[show Abstract]
Lissoni P, Messina G, Rovelli F (2012)
Cancer as the main aging factor for humans: the fundamental role of 5-methoxy-tryptamine in reversal of cancer-induced aging processes in metabolic and immune reactions by non-melatonin pineal hormones.
Current aging science 5, 231-235 [PubMed:23451999]
[show Abstract]
Gavrilov SS, Kulinskiĭ VI (2007)
[5-hydroxytryptamine and 5-methoxytryptamine increase tolerance to global cerebral ischemia].
Eksperimental'naia i klinicheskaia farmakologiia 70, 17-18 [PubMed:18318189]
[show Abstract]
Cannizzaro C, Plescia F, Gagliano M, Cannizzaro G, Provenzano G, Mantia G, Cannizzaro E (2007)
Effects of pre- and postnatal exposure to 5-methoxytryptamine and early handling on an object-place association learning task in adolescent rat offspring.
Neuroscience research 59, 74-80 [PubMed:17601618]
[show Abstract]
Lissoni P (2007)
Biochemotherapy with immunomodulating pineal hormones other than melatonin: 5-methoxytryptamine as a new oncostatic pineal agent.
Pathologie-biologie 55, 198-200 [PubMed:17451889]
[show Abstract]
Römsing S, Bökman F, Bergqvist Y (2006)
Determination of melatonin in saliva using automated solid-phase extraction, high-performance liquid chromatography and fluorescence detection.
Scandinavian journal of clinical and laboratory investigation 66, 181-190 [PubMed:16714247]
[show Abstract]
Kirchheiner J, Henckel HB, Franke L, Meineke I, Tzvetkov M, Uebelhack R, Roots I, Brockmöller J (2005)
Impact of the CYP2D6 ultra-rapid metabolizer genotype on doxepin pharmacokinetics and serotonin in platelets.
Pharmacogenetics and genomics 15, 579-587 [PubMed:16007002]
[show Abstract]
Bayari S, Ide S (2003)
Fourier transform infrared spectra and molecular structure of 5-methoxytryptamine, N-acetyl-5-methoxytryptamine and N-phenylsulfonamide-5-methoxytryptamine.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 59, 1255-1263 [PubMed:12659894]
[show Abstract]
Lissoni P, Bucovec R, Bonfanti A, Giani L, Mandelli A, Roselli MG, Rovelli F, Fumagalli L (2001)
Thrombopoietic properties of 5-methoxytryptamine plus melatonin versus melatonin alone in the treatment of cancer-related thrombocytopenia.
Journal of pineal research 30, 123-126 [PubMed:11270479]
[show Abstract]
Hardeland R (1999)
Melatonin and 5-methoxytryptamine in non-metazoans.
Reproduction, nutrition, development 39, 399-408 [PubMed:10420441]
[show Abstract]
Yamada J, Sugimoto Y, Yoshikawa T, Horisaka K (1997)
Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor.
European journal of pharmacology 323, 235-240 [PubMed:9128844]
[show Abstract]
Geffard M, Dulluc J, Rock AM (1985)
Antisera against the indolealkylamines: tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-methoxytryptophan, and 5-methoxytryptamine tested by an enzyme-linked immunosorbent assay method.
Journal of neurochemistry 44, 1221-1228 [PubMed:3919158]
[show Abstract]
Last Modified
02 June 2021