Molecular Identity
Fenfluramine
N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
PubChem CID: 3337
Fenfluramine is 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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension. It has a role as a serotonergic agonist, an appetite depressant and a serotonin uptake inhibitor. It is a secondary amino compound and a member of (trifluoromethyl)benzenes.
2D Structure
Properties
C12H16F3N
Molecular Formula
231.26
Molecular Weight
g/mol
231.1235
Exact Mass
Da
3.4
XLogP
Drug-like (Lipinski: < 5)
12
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
4
H-Bond Acceptors
203
Complexity
SMILES
Canonical SMILES
SMILES: CCNC(C)CC1=CC(=CC=C1)C(F)(F)FIsomeric SMILES
SMILES: CCNC(C)CC1=CC(=CC=C1)C(F)(F)FSynonyms(20)
fenfluramineObedrexRotondinPesosDL-FenfluraminePonderax PA458-24-2FenfluraminaAcinoFenfluraminum(+-)-FenfluramineFenfluraminPhenfluramineBrabafenPonderax
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Fenfluramine
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