1-Fluoro(18F)-1-deoxyephedrine

1-Fluoro(18F)-1-deoxyephedrine
Names
IUPAC name
(1R,2S)-1-(18F)fluoro-N-methyl-1-phenylpropan-2-amine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C10H14FN/c1-8(12-2)10(11)9-6-4-3-5-7-9/h3-8,10,12H,1-2H3/t8-,10-/m0/s1/i11-1
    Key: QHGKNGIWQABHRY-QJOTUPEMSA-N
  • C[C@@H]([C@@H](C1=CC=CC=C1)[18F])NC
Properties
C10H14FN
Molar mass 167.227 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1-Fluoro(18F)-1-deoxyephedrine (1-[¹⁸F]Fluoro-1-deoxyephedrine, [¹⁸F]FDE, FDE) is chemical compound, a radiotracer, used in positron emission tomography (PET) for in vivo imaging of biochemical processes in the brain. In its chemical structure, it is a fluorinated analogue of ephedrine, where the hydroxyl group in the beta position is replaced by the isotope fluorine-18.

It has high lipophilicity, allowing it to penetrate the blood-brain barrier without hindrance, which was accompanied by high, uniform uptake by the brain (approximately 8% of the administered dose), similar to that observed for the structurally related analogue [11C]methamphetamine. The ephedrine (1R,2S) isomer is three times more effective than the pseudoephedrine (1S,2S) isomer, it is a metabolically stable compound.[1][2][3]

References

  1. ↑ Van Dort, M. E.; Jung, Y. W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. (1995-03-03). "Fluorine for hydroxy substitution in biogenic amines: asymmetric synthesis and biological evaluation of fluorine-18-labeled beta-fluorophenylalkylamines as model systems". Journal of Medicinal Chemistry. 38 (5): 810–815. doi:10.1021/jm00005a008. ISSN 0022-2623. PMID 7877146.
  2. ↑ Dort, Marcian E. Van; Jung, Yong-Woon; Sherman, Philip S.; Kilbourn, Michael R.; Wieland, Donald M. (1995-03-01). "Fluorine for Hydroxy Substitution in Biogenic Amines: Asymmetric Synthesis and Biological Evaluation of Fluorine-18-Labeled .beta.-Fluorophenylalkylamines as Model Systems". Journal of Medicinal Chemistry. 38 (5): 810–815. doi:10.1021/jm00005a008. PMID 7877146. Retrieved 2026-03-20.
  3. ↑ Ross, T. L.; Wester, H. J. (2011), "18F: Labeling Chemistry and Labeled Compounds", Handbook of Nuclear Chemistry, Springer, Boston, MA, pp. 2021–2071, doi:10.1007/978-1-4419-0720-2_42, ISBN 978-1-4419-0720-2, retrieved 2026-03-20
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