CHEBI:64149 - 5-nonyloxytryptamine

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ChEBI Name 5-nonyloxytryptamine
ChEBI ID CHEBI:64149
Definition A tryptamine derivative that consists of serotonin bearing an additional O-nonyl substituent. 5-HT1B selective agonist, several times more potent than sumatriptan and inactive as a 5-HT1A agonist (Ki at 5-HT1B = 1 nM, selectivity over 5-HT1A > 300-fold).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C19H30N2O
Net Charge 0
Average Mass 302.45430
Monoisotopic Mass 302.23581
InChI InChI=1S/C19H30N2O/c1-2-3-4-5-6-7-8-13-22-17-9-10-19-18(14-17)16(11-12-20)15-21-19/h9-10,14-15,21H,2-8,11-13,20H2,1H3
InChIKey YHSMSRREJYOGQJ-UHFFFAOYSA-N
SMILES CCCCCCCCCOc1ccc2[nH]cc(CCN)c2c1
Roles Classification
Chemical Role(s): 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.
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.
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ChEBI Ontology
Outgoing 5-nonyloxytryptamine (CHEBI:64149) has functional parent serotonin (CHEBI:28790)
5-nonyloxytryptamine (CHEBI:64149) has role serotonergic agonist (CHEBI:35941)
5-nonyloxytryptamine (CHEBI:64149) is a aromatic ether (CHEBI:35618)
5-nonyloxytryptamine (CHEBI:64149) is a primary amino compound (CHEBI:50994)
5-nonyloxytryptamine (CHEBI:64149) is a tryptamines (CHEBI:27162)
5-nonyloxytryptamine (CHEBI:64149) is conjugate base of 5-nonyloxytryptaminium(1+) (CHEBI:64150)
Incoming 5-nonyloxytryptaminium(1+) (CHEBI:64150) is conjugate acid of 5-nonyloxytryptamine (CHEBI:64149)
IUPAC Name
2-[5-(nonyloxy)-1H-indol-3-yl]ethanamine
Synonyms Sources
3-(2-aminoethyl)-5-nonyloxyindole ChEBI
5-(Nonyloxy)-1H-indole-3-ethanamine ChemIDplus
5-(Nonyloxy)tryptamine ChemIDplus
O-nonylserotonin ChEBI
Manual Xrefs Databases
LSM-20005 LINCS
US5496957 Patent
View more database links
Registry Numbers Types Sources
157798-12-4 CAS Registry Number ChemIDplus
7077925 Reaxys Registry Number Reaxys
Last Modified
25 February 2016