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20-September-2008 09:55:56 - Ethylphenidate Ethylphenidate Systematic IUPAC name ethyl 2-phenyl-2-piperidin-2-ylacetate Identifiers CAS number 57413-43-1 ATC code ? PubChem 3080846 Chemical data Formula C15H21NO2 Mol. mass 247.33274 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability Variable Protein binding Unknown Metabolism Hepatic transesterification of prodrugs methylphenidate and ethanol Half life Dependent on methylphenidate administration1 Excretion Urine Therapeutic considerations Pregnancy cat. ? Legal status Presumably Controlled in the US Routes N/A Enantiomeric dl-threo-Ethylphenidate is a potent psychostimulant that acts as both a dopamine reuptake inhibitor and norepinephrine reuptake inhibitor, meaning it effectively boosts the levels of the norepinephrine and dopamine neaurotransmitters in the brain, by binding to, and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. It is formed when ethanol and methylphenidate are coingested, via hepatic transesterification.1 Ethylphenidate formation appears to be more common when large quantities of methylphenidate and alcohol are consumed at the same time, such as in abuse or overdose scenarios.2 This carboxylesterase-dependent transesterification process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene.3 Ethylphenidate is more selective to the dopamine transporter DAT than methylphenidate, having approximately the same efficacy as the parent compound,4 but has significantly less activity on the norepinephrine transporter NET.5 It has nearly a identical dopaminergic pharmacodynamic profile as methylphenidate, possessing appreciable affinity for the inhibitory G protein-coupled dopamine subtype-2 receptors in the striatum and mesolimbic regions of the brain,6 including the nucleus accumbens,7 which is primarily responsible for its pro-euphorant and reinforcing effects.8 Tablets This pharmacology-related article is a stub. References ^ a b Markowitz JS, DeVane CL, Boulton DW, Nahas Z, Risch SC, Diamond F, Patrick KS. Ethylphenidate formation in human subjects after the administration of a single dose of methylphenidate and ethanol. Drug Metabolism and Disposition. 2000 Jun;286:620-4. ^ Markowitz JS, Logan BK, Diamond F, Patrick KS. Detection of the novel metabolite ethylphenidate after methylphenidate overdose with alcohol coingestion. Journal of Clinical Psychopharmacology. 1999 Aug;194:362-6. ^ Bourland JA, Martin DK and Mayersohn M 1997 Carboxylesterase transesterification of meperidine Demerol and methylphenidate Ritalin in the presence of 2H6ethanol: Preliminary in vitro findings using a rat liver preparation. J Pharm Sci 86: 1494-1496 ^ Patrick KS, Williard RL, VanWert AL, Dowd JJ, Oatis JE Jr, Middaugh LD. Synthesis and pharmacology of ethylphenidate enantiomers: the human transesterification metabolite of methylphenidate and ethanol. Journal of Medicinal Chemistry. 2005 Apr 21;488:2876-81. ^ Williard RL, Middaugh LD, Zhu HJ, Patrick KS. Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity. Behavioural Pharmacology. 2007 Feb;181:39-51. ^ Schweri MM, Skolnick P, Rafferty MF, Rice KC, Janowsky AJ and Paul SM 1985 3HThreo-±-methylphenidate binding to 3,4-dihydroxyphenylethylamine uptake sites in corpus striatum: Correlation with the stimulant properties of ritalinic acid esters. J Neurochem 45: 1062-1070 ^ Volkow ND, Ding Y-S, Wang G-L, Logan J, Gatley JS, Dewey S, Ashby C, Lieberman J, Hitzemann R and Wolf AP 1995 Is methylphenidate like cocaine? Studies on their pharmacokinetics and distribution in the human brain. Arch Gen Psychiatry 52: 456-463 ^ Jatlow P, Elsworth JD, Bradberry CW, Winger G, Taylor JR, Russell R and Roth RH 1991 Cocaethylene: A neuropharmacologically active metabolite associated with concurrent cocaine-ethanol ingestion. Life Sci 48: 1787-1794 See Also Cocaethylene compound formed when cocaine and ethanol are taken together Methylphenidate Ethanol drinking alcohol v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines v d e Alcoholic beverages Alcohol Alcohol abuse · Alcoholism · Alcohol advertising · Short-term effects of alcohol · Long-term effects of alcohol · Alcohol and cancer · Fetal Alcohol Spectrum Disorder · Recommended maximum intake · Drinking culture · Ethanol · History of alcohol Production Brewing · Distilling · Winemaking Fermented beverages Beer types · Wine types · Cider types · Rice wine types · Other fermented beverages · Basi · Chicha · Huangjiu · Kumis · Kvass · Mead · Pulque · Sahti · Gouqi jiu Distilled beverages Agave: Mezcal · Tequila · Apple: Applejack · Calvados · Barley: Irish whiskey · Japanese whisky · Scotch whisky · Cashew: Fenny† · Coconut: Arrack† · Grape: Armagnac · Brandy · Cognac · Pisco · Maize: Bourbon whiskey · Corn whiskey · Tennessee whiskey · Plum: Slivovitz · Tuica · Pomace: Grappa · Marc · Orujo · Tsikoudia · Tsipouro · Zivania · Rice: Awamori · Rice baijiu · Soju · Rye: Rye whiskey · Sorghum: Baijiu Kaoliang · Sugarcane/molasses: Aguardiente · Cachaça · Clairin · Guaro · Rum · Seco Herrerano · Tharra · Various cereals and potato: Canadian whisky · Shochu · Snaps · Vodka · Whisky · Various/other fruit: Kirschwasser · Palinka · Rakia · Schnaps Liqueurs and infused distilled beverages Almond: Amaretto · Anise: Absinthe · Arak · Ouzo · Raki · Pastis · Sambuca · Cinnamon: Tentura · Coconut: Malibu · Herbs: Brennivín · Aquavit · Honey: Bärenjäger · Krupnik · Juniper: Gin · Jenever · Star anise: Sassolino · Sugarcane/molasses: Charanda · Various/other fruit: Limoncello · Schnapps Mixed drinks Beer cocktails · Cocktails true · Flaming beverages · Shooters · Wine cocktails · Mulled wine †Also made from other sources. Retrieved from http://en..org/wiki/Ethylphenidate Categories: Pharmacology stubs | Stimulants | Alcohol | Phenethylamines | Sympathomimetic amines | Piperidines | Dopamine reuptake inhibitors | Norepinephrine reuptake inhibitors | Drug culture | Drug addiction Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 9 August 2008, at 13:09
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