Levophacetoperane

{{Short description|Stimulant drug}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 450988207

| IUPAC_name = [(R)-phenyl-[(2R)-piperidin-2-yl]methyl] acetate

| image = Phacetoperane chemical structure.png

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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| legal_DE =

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| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 24558-01-8

| ATC_prefix = none

| ATC_suffix =

| PubChem = 15706387

| ChemSpiderID = 32702188

| UNII = 3SZ9ZII529

| C=14 | H=19 | N=1 | O=2

| smiles = CC(=O)O[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2

| StdInChI = 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

| StdInChIKey = BKPLVPRTTWIDNL-ZIAGYGMSSA-N

}}

Levophacetoperane (Lidépran, Phacétoperane) is a psychostimulant developed by Rhône-Poulenc in the 1950s.{{cite patent | url=https://www.google.com/patents/US2928835 | country = US | number = 2928835 | title = New esters | assign1 = Rhône-Poulenc | pubdate=15 March 1960 | inventor = Marie JN, Michel JR }} The drug has been used as an antidepressant and anorectic.{{cite journal | vauthors = Delbeke FT, Debackere M | title = 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 = Journal of Chromatography | volume = 106 | issue = 2 | pages = 412–7 | date = March 1975 | pmid = 239015 | doi = 10.1016/S0021-9673(00)93853-6 }}{{cite patent | url=https://www.google.com/patents/US20150038533 | country = US | number = 20150038533 | title = Phacetoperane for the treatment of attention-deficit hyperactivity disorder | assign1 = Assistance Publique – Hôpitaux de Paris | pubdate=5 February 2015 | inventor = Konofal E, Figadere B}} It is the reverse ester of methylphenidate. Phacetoperane and levophacetoperane have been used as wakefulness-promoting agents in the treatment of narcolepsy.{{cite journal | vauthors = Konofal E | title = From past to future: 50 years of pharmacological interventions to treat narcolepsy | journal = Pharmacol Biochem Behav | volume = 241 | issue = | pages = 173804 | date = August 2024 | pmid = 38852786 | doi = 10.1016/j.pbb.2024.173804 | url = | doi-access = free }}