4-Fluoroselegiline

Last updated

4-Fluoroselegiline
4-Fluoro-L-deprenyl.svg
Clinical data
Other namesChinoin-175; Fludepryl; SR-96516-A; p-Fluoro-L-deprenyl
Identifiers
  • (2R)-1-(4-Fluorophenyl)-N-methyl-N-prop-2-ynylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C13H16FN
Molar mass 205.276 g·mol−1
3D model (JSmol)
Density 1.024 ± 0.06 g/cm3[ citation needed ]
  • C[C@H](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/t11-/m1/s1
  • Key:MUDUXRHPVDVWHU-LLVKDONJSA-N

4-Fluoroselegiline, or p-fluoro-L-deprenyl, is a substituted amphetamine designer drug. It is the enantiopure L- enantiomer of 4-fluorodeprenyl and the 4-fluorinated derivative of selegiline (L-deprenyl).

Contents

Pharmacology

Pharmacodynamics

4-Fluoroselegiline is a selective and irreversible inhibitor of monoamine oxidase B and monoaminergic activity enhancer. [1] [2] [3]

A radiolabelled derivative incorporating 18F is used to study MAO-B inhibition in both in vivo and in vitro experiments. [4]

Pharmacokinetics

4-Fluorodeprenyl is metabolized to 4-fluoromethamphetamine and 4-fluoroamphetamine, both of which are active. The levels of substituted amphetamine metabolites in the brain is three times higher following 4-fluoroselegiline administration compared to an equivalent dose of selegiline. [2]

Society and culture

Names

Synonyms of 4-fluoroselegiline or 4-fluorodeprenyl (the racemic form) include Chinoin-175, Fludepryl, and SR-96516-A. [5]

See also

References

  1. ↑ Erdö F, Baranyi A, Takács J, Arányi P (August 2000). "Different neurorescue profiles of selegiline and p-fluoro-selegiline in gerbils". NeuroReport. 11 (11): 2597–2600. doi:10.1097/00001756-200008030-00049. PMID   10943729. S2CID   20944931.
  2. 1 2 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. ↑ Knoll J, Miklya I (1994). "Multiple, small dose administration of (-)deprenyl enhances catecholaminergic activity and diminishes serotoninergic activity in the brain and these effects are unrelated to MAO-B inhibition". Arch Int Pharmacodyn Ther. 328 (1): 1–15. PMID 7893186.
  4. ↑ Plenevaux A, Fowler JS, Dewey SL, Wolf AP, Guillaume M (January 1991). "The synthesis of no-carrier-added DL-4-[18F]fluorodeprenyl via the nucleophilic aromatic substitution reaction". International Journal of Radiation Applications and Instrumentation, Part A. 42 (2): 121–127. doi:10.1016/0883-2889(91)90060-E. PMID   1648033.
  5. ↑ Paul W, Szelenyi I (1993). "Appendix I: Chemical Structures and Pharmacological Features of MAO-B Inhibitors". In Szelenyi I (ed.). Inhibitors of Monoamine Oxidase B: Pharmacology and Clinical Use in Neurodegenerative Disorders. Milestones in Drug Therapy. Basel: Birkhäuser Basel. pp. 339–358. ISBN   978-3-0348-6349-0. ISSN   2296-6056.
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