4-Fluoroselegiline

Chemical compound

4-Fluoroselegiline
Clinical data
Trade namesFludepryl
Identifiers
  • N-[1-(4-fluorophenyl)propan-2-yl]-N-methylprop-2-yn-1-amine
CAS Number
  • 103596-43-6 checkY
PubChem CID
  • 128418
ChemSpider
  • 113833 ☒N
CompTox Dashboard (EPA)
  • DTXSID50874435 Edit this at Wikidata
Chemical and physical data
FormulaC13H16FN
Molar mass205.276 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.024 ± 0.06 g/cm3
Boiling point276.2 ± 25 °C (529.2 ± 45.0 °F)
  • CC(CC1=CC=C(F)C=C1)N(C)CC#C
InChI
  • 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-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

4-Fluoro-deprenyl 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]

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. ^ a b 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.


  • v
  • t
  • e
Monoamine metabolism modulators
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine, epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-monooxygenase
PNMTTooltip Phenylethanolamine N-methyltransferase
  • Inhibitors: CGS-19281A
  • SKF-64139
  • SKF-7698
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin, melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
  • Substrates→Products: L-Histidine→Histamine
HNMTTooltip Histamine N-methyltransferase
  • Substrates→Products: Histamine→N-Methylhistamine
DAOTooltip Diamine oxidase
  • Substrates→Products: Histamine→Imidazole acetic acid
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins
  • v
  • t
  • e
Endogenous
Synthetic
Antagonists
See also: Receptor/signaling modulators • Monoamine releasing agents • Monoamine reuptake inhibitors • Monoamine metabolism modulators • TAAR ligands