4-Fluoroselegiline Explained

Drug Name:4-Fluoroselegiline
Tradename:Fludepryl
Cas Number:103596-43-6
Pubchem:128418
Chemspiderid:113833
Iupac Name:N-[1-(4-fluorophenyl)propan-2-yl]-N-methylprop-2-yn-1-amine
C:13
H:16
F:1
N:1
Smiles:CC(CC1=CC=C(F)C=C1)N(C)CC#C
Stdinchi: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
Stdinchikey:MUDUXRHPVDVWHU-UHFFFAOYSA-N
Density:1.024 ± 0.06
Boiling Point:276.2 ± 25

4-Fluoroselegiline or p-fluoro-L-deprenyl is a substituted amphetamine designer drug. It is the 4-fluorinated derivate of selegiline.

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

p-Fluoro-L-deprenyl is metabolized to p-fluoro-L-methamphetamine and p-fluoro-L-amphetamine, 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]

Notes and 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 . 10.1097/00001756-200008030-00049 . 10943729 . 20944931.
  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 . 10.1007/s00213-005-0063-y . 15990999 . 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 . 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 . January 1991 . 1648033 . 10.1016/0883-2889(91)90060-E .