Chemistry:4-Fluoroselegiline

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Short description: Chemical compound
4-Fluoroselegiline
4fluoroselegiline.svg
Clinical data
Trade namesFludepryl
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H16FN
Molar mass205.276 g·mol−1
3D model (JSmol)
Density1.024 ± 0.06 g/cm3
Boiling point276.2 ± 25 °C (529.2 ± 45.0 °F)

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

Pharmacodynamics

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

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

  1. Erdaö, Franciska; Baranyi, Attila; Takács, József; Arányi, Péter (3 August 2000). "Different neurorescue profiles of selegiline and p-fluoro-selegiline in gerbils". NeuroReport 11 (11): 2597–3100. doi:10.1097/00001756-200008030-00049. ISSN 0959-4965. PMID 10943729. https://journals.lww.com/neuroreport/abstract/2000/08030/different_neurorescue_profiles_of_selegiline_and.49.aspx. Retrieved 4 January 2024. 
  2. 2.0 2.1 Yasar, Sevil; Gaal, Jozsef; Justinova, Zuzana; Bergman, Jack (1 October 2005). "Discriminative stimulus and reinforcing effects of p-fluoro-l-deprenyl in monkeys" (in en). Psychopharmacology 182 (1): 95–103. doi:10.1007/s00213-005-0063-y. ISSN 1432-2072. PMID 15990999. https://link.springer.com/article/10.1007/s00213-005-0063-y. 
  3. Plenevaux, Alain; Fowler, Joanna S.; Dewey, Stephen L.; Wolf, Alfred P.; Guillaume, Marcel (January 1991). "The synthesis of no-c arrier-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.