5-methoxytryptamine (CHEBI:2089)

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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	ZINC000085552494

Download	Molfile XML SDF

more structures >>

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F5U - Ideal conformer

Mrv1927 06022114093D

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Time for openFile(F5U - Ideal conformer

Mrv1927 06022114093D

28 29 0 0 0 0 999 V2000

-0.6540 -2.5340 -0.1210 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.1790 -0.3670 0.1950 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3810 -1.6220 -0.1030 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7520 -1.7300 -0.3120 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5510 -0.6120 -0.2260 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8350 -1.9010 0.1540 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.6560 0.4500 0.6800 C 0 0 1 0 0 0 0 0 0 0 0 0

4.2000 1.5250 -0.0770 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1110 1.1380 -0.6090 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0000 0.6330 0.0690 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6420 0.7600 0.2800 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6170 -0.5920 0.3540 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.1240 2.1530 -0.2910 N 0 0 1 0 0 0 0 0 0 0 0 0

2.8030 1.7270 0.1510 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5580 -3.4820 -0.3040 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1900 -2.6900 -0.5410 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6150 -0.7010 -0.3890 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8000 -2.3840 0.2020 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2290 1.1900 1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5120 -0.0270 1.1590 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5890 0.8200 0.6570 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3500 1.1260 -1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0

4.7240 2.4760 0.0180 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2560 1.6150 -1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5390 0.3970 -1.2840 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2150 1.7260 0.5080 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7730 2.8150 0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.4400 2.6220 -1.1260 H 0 0 0 0 0 0 0 0 0 0 0 0

1 6 1 0 0 0 0

1 3 1 0 0 0 0

4 3 2 0 0 0 0

4 5 1 0 0 0 0

6 12 2 0 0 0 0

3 2 1 0 0 0 0

5 10 2 0 0 0 0

12 2 1 0 0 0 0

12 7 1 0 0 0 0

2 11 2 0 0 0 0

10 11 1 0 0 0 0

10 14 1 0 0 0 0

7 9 1 0 0 0 0

8 14 1 0 0 0 0

9 13 1 0 0 0 0

1 15 1 0 0 0 0

4 16 1 0 0 0 0

5 17 1 0 0 0 0

6 18 1 0 0 0 0

7 19 1 0 0 0 0

7 20 1 0 0 0 0

8 21 1 0 0 0 0

8 22 1 0 0 0 0

8 23 1 0 0 0 0

9 24 1 0 0 0 0

9 25 1 0 0 0 0

11 26 1 0 0 0 0

13 27 1 0 0 0 0

13 28 1 0 0 0 0

M END): 18 ms

reading 28 atoms

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Wikipedia	License
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.
Read full article at Wikipedia

Formula

C11H14N2O

Net Charge

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

Last Modified

02 June 2021

CHEBI:2089 - 5-methoxytryptamine

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