Norfenfluramine

Norfenfluramine
Identifiers
CAS number 19036-73-8 YesY
PubChem 15897
ChemSpider 15108 YesY
IUPHAR ligand 215
Jmol-3D images Image 1
Properties
Molecular formula C10H12F3N
Molar mass 203.2 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Norfenfluramine (3-trifluoromethylamphetamine) is a psychoactive drug which functions as a serotonin releasing agent and potent 5HT2B receptor agonist. The action of norfenfluramine on 5HT2B 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 drug worldwide, and to the withdrawal of benfluorex in Europe[2], as both fenfluramine and benfluorex form norfenfluramine as a metabolite.

Norfenfluramine has also been shown to be vasoactive in its own right, causing pulmonary hypertension.[3][4]

See also

References

  1. ^ Setola, V; Dukat, M; Glennon, RA; Roth, BL (2005). "Molecular determinants for the interaction of the valvulopathic anorexigen norfenfluramine with the 5-HT2B receptor". Molecular pharmacology 68 (1): 20–33. doi:10.1124/mol.104.009266. PMID 15831837. 
  2. ^ Press Release European Medicines Agency recommends withdrawal of benfluorex from the market in European Union [1]
  3. ^ Hong, Z; Olschewski, A; Reeve, HL; Nelson, DP; Hong, F; Weir, EK (2004). "Nordexfenfluramine causes more severe pulmonary vasoconstriction than dexfenfluramine". American journal of physiology. Lung cellular and molecular physiology 286 (3): L531–8. doi:10.1152/ajplung.00247.2003. PMID 14607779. 
  4. ^ Ni, W; Li, MW; Thakali, K; Fink, GD; Watts, SW (2004). "The fenfluramine metabolite (+)-norfenfluramine is vasoactive". The Journal of pharmacology and experimental therapeutics 309 (2): 845–52. doi:10.1124/jpet.103.060806. PMID 14752059.