| Watchedfields: | changed |
| Verifiedrevid: | 422837453 |
| Cas Number: | 19036-73-8 |
| Pubchem: | 15897 |
| Iuphar Ligand: | 215 |
| Chemspiderid: | 15108 |
| Unii: | CLX07A6ZIY |
| Chebi: | 125411 |
| Chembl: | 1979333 |
| Synonyms: | 3-Trifluoromethylamphetamine; 3-TFMA; Desethylfenfluramine; JP-92 |
| Iupac Name: | 1-[3-(trifluoromethyl)phenyl]propan-2-amine |
| C: | 10 |
| H: | 12 |
| F: | 3 |
| N: | 1 |
| Smiles: | FC(F)(F)c1cccc(c1)CC(N)C |
| Stdinchi: | 1S/C10H12F3N/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7H,5,14H2,1H3 |
| Stdinchikey: | MLBHFBKZUPLWBD-UHFFFAOYSA-N |
Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family that behaves as a serotonin and norepinephrine releasing agent and potent 5-HT2A, 5-HT2B, and 5-HT2C agonist. The action of norfenfluramine on 5-HT2B receptors on heart valves leads to a characteristic pattern of heart failure following proliferation of cardiac fibroblasts on the tricuspid valve, known as cardiac fibrosis.[1] This side effect led to the withdrawal of fenfluramine as an anorectic agent worldwide, and to the withdrawal of benfluorex in Europe,[2] as both fenfluramine and benfluorex form norfenfluramine as an active metabolite. It is a human TAAR1 agonist.[3]
In spite of acting as a serotonin 5-HT2A receptor agonist, norfenfluramine is described as non-hallucinogenic.[4] However, hallucinations have occasionally been reported with large doses of fenfluramine, which itself is a much weaker serotonin 5-HT2A receptor agonist than norfenfluramine but produces norfenfluramine as a major active metabolite.