Fenfluramine

Chemical Information
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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.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.
| CAS Number | 458-24-2 |
| PubChem CID | 3337 |
| IUPAC Name | N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine |
| Molecular Formula | C12H16F3N |
| Molecular Weight | 231.26 |
| XLogP | 3.4 |
| Topological Polar Surface Area | 12 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Complexity | 203 |
| Property | Value |
|---|---|
| Molecular Weight | 231.26 |
| XLogP3 | 3.4 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Exact Mass | 231.12348400 |
| Monoisotopic Mass | 231.12348400 |
| Topological Polar Surface Area | 12 Ų |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Complexity | 203 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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