Norfenfluramine

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-HT_2A, 5-HT_2B, and 5-HT_2C agonist. The action of norfenfluramine on 5-HT_2B 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]

Norfenfluramine

Names
Preferred IUPAC name 1-[3-(Trifluoromethyl)phenyl]propan-2-amine
Other names 3-Trifluoromethylamphetamine
Identifiers
CAS Number	19036-73-8 Y
3D model (JSmol)	Interactive image
ChemSpider	15108 Y
IUPHAR/BPS	215
PubChem CID	15897
UNII	CLX07A6ZIY Y
CompTox Dashboard (EPA)	DTXSID60904717
InChI InChI=1S/C10H12F3N/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7H,5,14H2,1H3 Y Key: MLBHFBKZUPLWBD-UHFFFAOYSA-N Y InChI=1/C10H12F3N/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7H,5,14H2,1H3 Key: MLBHFBKZUPLWBD-UHFFFAOYAR
SMILES FC(F)(F)c1cccc(c1)CC(N)C
Properties
Chemical formula	C10H12F3N
Molar mass	203.208 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

See also

• Fenfluramine
• Benfluorex
• Norfenfluramine is the precursor to flucetorex

References

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-HT_2B Receptor" (PDF). Molecular Pharmacology. 68 (1): 20–33. doi:10.1124/mol.104.009266. PMID 15831837. S2CID 30906680.
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 3236098. PMID 22037049.