CHEBI:5000 - fenfluramine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fenfluramine
ChEBI ID CHEBI:5000
Definition A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:239434
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C12H16F3N
Net Charge 0
Average Mass 231.25730
Monoisotopic Mass 231.123
InChI InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3
InChIKey DBGIVFWFUFKIQN-UHFFFAOYSA-N
SMILES CCNC(C)Cc1cccc(c1)C(F)(F)F
Roles Classification
Biological Role(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
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): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
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.
appetite depressant
Agent that is used to decrease appetite.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fenfluramine (CHEBI:5000) has role appetite depressant (CHEBI:50507)
fenfluramine (CHEBI:5000) has role serotonergic agonist (CHEBI:35941)
fenfluramine (CHEBI:5000) has role serotonin uptake inhibitor (CHEBI:50949)
fenfluramine (CHEBI:5000) is a (trifluoromethyl)benzenes (CHEBI:83565)
fenfluramine (CHEBI:5000) is a secondary amino compound (CHEBI:50995)
Incoming fenfluramine hydrochloride (CHEBI:59729) has part fenfluramine (CHEBI:5000)
(R)-fenfluramine (CHEBI:521051) is a fenfluramine (CHEBI:5000)
(S)-fenfluramine (CHEBI:439329) is a fenfluramine (CHEBI:5000)
IUPAC Name
N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
INNs Sources
fenfluramine ChemIDplus
fenfluraminum ChemIDplus
Synonyms Sources
(±)-fenfluramine ChEBI
1-(m-trifluoromethyl-phenyl)-2-ethylaminopropane ChemIDplus
2-ethylamino-1-(3-trifluoromethylphenyl)propane ChemIDplus
3-(trifluoromethyl)-N-ethyl-α-methylphenethylamine NIST Chemistry WebBook
Ethyl-[1-methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-amine ChEMBL
Fenfluramine KEGG COMPOUND
N-ethyl-1-(3-(trifluoromethyl)phenyl)propan-2-amine ChEMBL
N-ethyl-α-methyl-3-trifluoromethylphenethylamine NIST Chemistry WebBook
Database Links Databases
1150 DrugCentral
C06996 KEGG COMPOUND
D07945 KEGG DRUG
DB00574 DrugBank
Fenfluramine Wikipedia
HMDB0015322 HMDB
US3198833 Patent
View more database links
Registry Numbers Types Sources
2109374 Beilstein Registry Number Beilstein
2109374 Reaxys Registry Number Reaxys
458-24-2 CAS Registry Number ChemIDplus
458-24-2 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11716826 PubMed citation Europe PMC
15637164 PubMed citation Europe PMC
15677429 PubMed citation Europe PMC
Last Modified
22 February 2017