Levophacetoperane (Lidépran, Phacétoperane) is a psychostimulant developed by Rhône-Poulenc in the 1950s.[2] The drug has been used as an antidepressant and anorectic.[3][4] It is the reverse ester of methylphenidate. Phacetoperane and levophacetoperane have been used as wakefulness-promoting agents in the treatment of narcolepsy.[5]

Levophacetoperane
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Identifiers
  • [(R)-phenyl-[(2R)-piperidin-2-yl]methyl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H19NO2
Molar mass233.311 g·mol−1
3D model (JSmol)
  • CC(=O)O[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2
  • InChI=1S/C14H19NO2/c1-11(16)17-14(12-7-3-2-4-8-12)13-9-5-6-10-15-13/h2-4,7-8,13-15H,5-6,9-10H2,1H3/t13-,14-/m1/s1
  • Key:BKPLVPRTTWIDNL-ZIAGYGMSSA-N
  (verify)

See also

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References

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  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ US 2928835, Marie JN, Michel JR, "New esters", published 15 March 1960, assigned to Rhône-Poulenc 
  3. ^ Delbeke FT, Debackere M (March 1975). "Isolation and detection of methylphenidate, phacetoperane and some other sympatomimetic central nervous stimulants with special reference to doping. I. Gas chromatographic detection procedure with electron capture detection for some secondary amines". Journal of Chromatography. 106 (2): 412–7. doi:10.1016/S0021-9673(00)93853-6. PMID 239015.
  4. ^ US 20150038533, Konofal E, Figadere B, "Phacetoperane for the treatment of attention-deficit hyperactivity disorder", published 5 February 2015, assigned to Assistance Publique – Hôpitaux de Paris 
  5. ^ Konofal E (August 2024). "From past to future: 50 years of pharmacological interventions to treat narcolepsy". Pharmacol Biochem Behav. 241: 173804. doi:10.1016/j.pbb.2024.173804. PMID 38852786.