4-Fluoroselegiline

4-Fluoroselegiline

Clinical data
Other names	Chinoin-175; Fludepryl; SR-96516-A; p-Fluoro-L-deprenyl
Identifiers
IUPAC name N-[1-(4-fluorophenyl)propan-2-yl]-N-methylprop-2-yn-1-amine
CAS Number	103596-43-6^Y
PubChem CID	128418
ChemSpider	113833^N
CompTox Dashboard (EPA)	DTXSID50874435
Chemical and physical data
Formula	C13H16FN
Molar mass	205.276 g·mol^−1
3D model (JSmol)	Interactive image
Density	1.024 ± 0.06 g/cm^3
Boiling point	276.2 ± 25 °C (529.2 ± 45.0 °F)
SMILES 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]

Society and culture

Names

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

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. 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.