4-Fluorodeprenyl

Last updated

4-Fluorodeprenyl
4-Fluorodeprenyl.svg
Clinical data
Other namesp-F-Depreny; Fludeprenyl; N-Methyl-N-propargyl-4-fluoroamphetamine; N-Propargyl-4-fluoromethamphetamine; N-Propargyl-4-FMA
Drug class Stimulant; Monoamine oxidase inhibitor; MAO-B inhibitor
ATC code
  • None
Identifiers
  • 1-(4-fluorophenyl)-N-methyl-N-prop-2-ynylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H16FN
Molar mass 205.276 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)F)N(C)CC#C
  • InChI=1S/C13H16FN/c1-4-9-15(3)11(2)10-12-5-7-13(14)8-6-12/h1,5-8,11H,9-10H2,2-3H3
  • Key:MUDUXRHPVDVWHU-UHFFFAOYSA-N

4-Fluorodeprenyl, or p-F-deprenyl, also known as fludeprenyl or as N-methyl-N-propargyl-4-fluoroamphetamine, is a stimulant and monoamine oxidase inhibitor (MAOI) of the amphetamine family. [1] [2] [3] [4] It is the 4-fluoro derivative of deprenyl and the racemic form of 4-fluoroselegiline. [3] [4] [2] The drug is metabolized into the stimulants 4-fluoroamphetamine (4-FA) and 4-fluoromethamphetamine (4-FMA) and hence acts in part as a prodrug of these metabolites. [3] [4] [1] [2] Accordingly, it produces methamphetamine-like effects in drug discrimination tests in squirrel monkeys. [1] [2] Like deprenyl and selegiline (L-deprenyl), 4-fluorodeprenyl is additionally a selective and irreversible inhibitor of monoamine oxidase B (MAO-B). [4] The drug was encountered as a novel designer drug in Germany in 2019. [4]

Contents

See also

References

  1. 1 2 3 Kirk KL, Yoshida S, Haufe G (2008). "Synthesis and Biochemical Evaluation of Fluorinated Monoamine Oxidase Inhibitors". Fluorine and Health. Elsevier. pp. 661–697. doi:10.1016/b978-0-444-53086-8.00015-1. ISBN   978-0-444-53086-8 . Retrieved 1 January 2026.
  2. 1 2 3 4 Yasar S, Gaal J, Justinova Z, Bergman J (October 2005). "Discriminative stimulus and reinforcing effects of p-fluoro-L-deprenyl in monkeys". Psychopharmacology. 182 (1): 95–103. doi:10.1007/s00213-005-0063-y. PMID   15990999. S2CID   444126.
  3. 1 2 3 "п-Фтордепренил (p-F-Deprenyl)". АИПСИН (in Russian). Retrieved 1 January 2026.
  4. 1 2 3 4 5 "п-Фтордепренил (4F-deprenyl)". АИПСИН (in Russian). Retrieved 1 January 2026.
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