4-Fluoroselegiline

4-Fluoroselegiline
Clinical data
Trade names	Fludepryl
Identifiers
	IUPAC name N-[1-(4-fluorophenyl)propan-2-yl]-N-methylprop-2-yn-1-amine;
CAS Number	103596-43-6 ;
PubChem CID	128418;
ChemSpider	113833 ;
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/cm3
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. Much like its parent compount, selegiline, it is a selective and irreversible inhibitor of monoamine oxidase B.^[1]

Pharmacology[edit]

Pharmacodynamics[edit]

4-Fluoroselegiline has a similar pharmacological profile to its parent compound, selegiline.^[2]

A radiolabelled derivative incorporating ¹⁸F is used to study MAO-B inhibition in both in vivo and in vitro experiments.^[3]

Pharmacokinetics[edit]

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]

References[edit]

^ 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.
^ ^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.
^ 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, Applied Radiation and Isotopes. 42 (2): 121–127. doi:10.1016/0883-2889(91)90060-E. PMID 1648033.

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[Erdao_2000-1] 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.

[Yasar_2005-2] 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.

[Plenevaux_1991-3] 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, Applied Radiation and Isotopes. 42 (2): 121–127. doi:10.1016/0883-2889(91)90060-E. PMID 1648033.

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