Levophacetoperane

Levophacetoperane
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Identifiers
	IUPAC name [(R)-phenyl-[(2R)-piperidin-2-yl]methyl] acetate;
CAS Number	24558-01-8 ;
PubChem CID	15706387;
ChemSpider	32702188;
UNII	3SZ9ZII529;
CompTox Dashboard (EPA)	DTXSID50179295 ;
Chemical and physical data
Formula	C14H19NO2
Molar mass	233.311 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)O[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2;
	InChI 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)

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]

References

^ 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.
^ US 2928835, Marie JN, Michel JR, "New esters", published 15 March 1960, assigned to Rhône-Poulenc
^ 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.
^ 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
^ 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.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

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
IUPAC name [(R)-phenyl-[(2R)-piperidin-2-yl]methyl] acetate
CAS Number	24558-01-8^Y
PubChem CID	15706387
ChemSpider	32702188
UNII	3SZ9ZII529
CompTox Dashboard (EPA)	DTXSID50179295
Chemical and physical data
Formula	C₁₄H₁₉NO₂
Molar mass	233.311 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)O[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2
InChI 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)