fenfluramine (CHEBI:5000)

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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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.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

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Formula

C12H16F3N

Net Charge

Average Mass

231.25730

Monoisotopic Mass

231.12348

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
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):	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 Any agent that is used to decrease appetite.

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

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

Last Modified

22 February 2017