Levophacetoperane - Misplaced Pages

(Redirected from Phacetoperane) Stimulant drug Pharmaceutical compound

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 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
3D model (JSmol)	Interactive image
SMILES CC(=O)O(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. The drug has been used as an antidepressant and anorectic. It is the reverse ester of methylphenidate. Phacetoperane and levophacetoperane have been used as wakefulness-promoting agents in the treatment of narcolepsy.

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.

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine Fluvoxamine Indalpine Paroxetine Sertraline Zimelidine
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine Bupropion Nomifensine
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine Gepirone Indeloxazine Flupentixol Ketamine Medifoxamine Metryptamine Oxaflozane Pivagabine Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine Amitriptyline Amitriptylinoxide Amoxapine Butriptyline Clomipramine Demexiptiline Desipramine Dibenzepin Dimetacrine Dosulepin Doxepin Imipramine Imipraminoxide Iprindole Lofepramine Melitracen Metapramine Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine Protriptyline Quinupramine Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective

Reversible: Caroxazone

Mixed: Bifemelane

MAO_ATooltip Monoamine oxidase A-selective

MAO_BTooltip Monoamine oxidase B-selective

Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Antiobesity agents/Anorectics (A08)

Stimulants

Amphetamines and phenethylamines	4-Methylamphetamine Amfecloral Amfepentorex Amfepramone Amphetamine Amphetaminil Benzphetamine Cathine Cathinone Chlorphentermine Clobenzorex Cloforex Clortermine Dextroamphetamine Dimethylcathinone Ephedrine Ephedra Etilamfetamine Etolorex Fenethylline Fenproporex Fludorex Furfenorex Khat Lisdexamfetamine Mefenorex Methamphetamine Norfenfluramine Pentorex Phentermine (+topiramate) Xylopropamine Zylofuramine
Adrenergic agonists	Albuterol Clenbuterol Ephedrine Ephedra Levopropylhexedrine Synephrine Terbutaline Yohimbine (Yohimbe)
Other	Aminorex Atomoxetine Benfluorex Bupropion (+naltrexone) Dexfenfluramine Dexmethylphenidate Difemetorex Fenbutrazate Fenfluramine (+phentermine) Manifaxine Mazindol Methylphenidate Phendimetrazine Phenethylamine Phenmetrazine Phenylpropanolamine Pipradrol Propylhexedrine Pyrovalerone Sibutramine Tesofensine

Cannabinoid
antagonists

GLP-1, GIP, and / or
glucagon agonists

DACRAs

Cagrilintide (+semaglutide)

5-HT2C
receptor agonists

Absorption inhibitors

Uncouplers

2,4-Dinitrophenol

Others

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Monoamine reuptake inhibitors

DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)

Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 Nefazodone Vanoxerine
Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol Serdexmethylphenidate Tenocyclidine
Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone
Tropanes: Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33
Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine

NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)

Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine
Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine
Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline
Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)

SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)

Selective serotonin reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole

VMATsTooltip Vesicular monoamine transporters

Amiodarone
Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
APP
AZIK
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
GZ-793A
Ibogaine
Ketanserin
Lobeline
Methoxytetrabenazine
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)

Others

DAT enhancers: Luteolin

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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

Categories: