Norfenfluramine

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Norfenfluramine
Norfenfluramine.png
Ball-and-stick model of the norfenfluramine molecule
Names
IUPAC name
1-[3-(Trifluoromethyl)phenyl]propan-2-amine
Other names
3-Trifluoromethylamphetamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.866
Properties
C10H12F3N
Molar mass 203.21 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family which 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]

See also[edit]

References[edit]

  1. ^ Setola, V.; Dukat, M.; Glennon, R. A.; Roth, B. L. (2005). "Molecular Determinants for the Interaction of the Valvulopathic Anorexigen Norfenfluramine with the 5-HT2B Receptor" (pdf). Molecular Pharmacology. 68 (1): 20–33. doi:10.1124/mol.104.009266. PMID 15831837. 
  2. ^ "European Medicines Agency recommends withdrawal of benfluorex from the market in European Union" (PDF). European Medicines Agency. 2009-12-18. Archived from the original (pdf) on 2009-12-22. 
  3. ^ Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorg. Med. Chem. 19 (23): 7044–8. doi:10.1016/j.bmc.2011.10.007. PMC 3236098Freely accessible. PMID 22037049.