Methylphenidate
General
Type : Piperidine || Not A\/B H target || Drug
Chemical_Nomenclature : methyl 2-phenyl-2-piperidin-2-ylacetate
Canonical SMILES : COC(=O)C(C1CCCCN1)C2=CC=CC=C2
InChI : InChI=1S\/C14H19NO2\/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12\/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
InChIKey : DUGOZIWVEXMGBE-UHFFFAOYSA-N
Other name(s) : Methylphenidan, Concerta, Daytrana, Phenidylate, Calocain, Ritalin, Ritaline, Centedrin, Equasym, Metadate, Methylin
Target
Families : Carb_B_Chordata
References (21)
| Title : Heterogeneity of Response to Methylphenidate in Apathetic Patients in the ADMET 2 Trial - Lanctot_2023_Am.J.Geriatr.Psychiatry__ |
| Author(s) : Lanctot KL , Rivet L , Tumati S , Perin J , Sankhe K , Vieira D , Mintzer J , Rosenberg PB , Shade D , Lerner AJ , Padala PR , Brawman-Mintzer O , van Dyck CH , Porsteinsson AP , Craft S , Levey AI , Padala KP , Herrmann N |
| Ref : American Journal of Geriatry & Psychiatry , : , 2023 |
| Abstract : Lanctot_2023_Am.J.Geriatr.Psychiatry__ |
| ESTHER : Lanctot_2023_Am.J.Geriatr.Psychiatry__ |
| PubMedSearch : Lanctot_2023_Am.J.Geriatr.Psychiatry__ |
| PubMedID: 37385898 |
| Title : Prediction of Carboxylesterase 1 (CES1)-mediated In Vivo Drug Interaction between Methylphenidate and Cannabinoids using Static and Physiologically Based Pharmacokinetic Models - Qian_2022_Drug.Metab.Dispos__ |
| Author(s) : Qian Y , Markowitz JS |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2022 |
| Abstract : Qian_2022_Drug.Metab.Dispos__ |
| ESTHER : Qian_2022_Drug.Metab.Dispos__ |
| PubMedSearch : Qian_2022_Drug.Metab.Dispos__ |
| PubMedID: 35512806 |
| Title : Physiologically-based pharmacokinetic modeling to predict methylphenidate exposure affected by interplay among carboxylesterase 1 pharmacogenetics, drug-drug interactions, and sex - Xiao_2022_J.Pharm.Sci__ |
| Author(s) : Xiao J , Shi J , Thompson BR , Smith DE , Zhang T , Zhu HJ |
| Ref : J Pharm Sci , : , 2022 |
| Abstract : Xiao_2022_J.Pharm.Sci__ |
| ESTHER : Xiao_2022_J.Pharm.Sci__ |
| PubMedSearch : Xiao_2022_J.Pharm.Sci__ |
| PubMedID: 35526575 |
| Title : Plasma Concentrations of Methylphenidate Enantiomers in Adults with ADHD and Substance Use Disorder, with focus on high doses and relationship to Carboxylesterase activity - Arvidsson_2022_Basic.Clin.Pharmacol.Toxicol__ |
| Author(s) : Arvidsson M , Franck J , Ackehed G , Pettersson Bergstrand M , Ekstrom L , Rosenborg S , Dahl ML |
| Ref : Basic Clin Pharmacol Toxicol , : , 2022 |
| Abstract : Arvidsson_2022_Basic.Clin.Pharmacol.Toxicol__ |
| ESTHER : Arvidsson_2022_Basic.Clin.Pharmacol.Toxicol__ |
| PubMedSearch : Arvidsson_2022_Basic.Clin.Pharmacol.Toxicol__ |
| PubMedID: 35040257 |
| Title : Ethanol Interactions With Dexmethylphenidate and dl-Methylphenidate Spheroidal Oral Drug Absorption Systems in Healthy Volunteers - Zhu_2017_J.Clin.Psychopharmacol_37_419 |
| Author(s) : Zhu HJ , Patrick KS , Straughn AB , Reeves OT, 3rd , Bernstein H , Shi J , Johnson HJ , Knight JM , Smith AT , Malcolm RJ , Markowitz JS |
| Ref : J Clin Psychopharmacol , 37 :419 , 2017 |
| Abstract : Zhu_2017_J.Clin.Psychopharmacol_37_419 |
| ESTHER : Zhu_2017_J.Clin.Psychopharmacol_37_419 |
| PubMedSearch : Zhu_2017_J.Clin.Psychopharmacol_37_419 |
| PubMedID: 28590363 |
| Title : Population Pharmacokinetics of Methylphenidate in Healthy Adults Emphasizing Novel and Known Effects of Several Carboxylesterase 1 (CES1) Variants - Lyauk_2016_Clin.Transl.Sci_9_337 |
| Author(s) : Lyauk YK , Stage C , Bergmann TK , Ferrero-Milliani L , Bjerre D , Thomsen R , Dalhoff KP , Rasmussen HB , Jurgens G |
| Ref : Clin Transl Sci , 9 :337 , 2016 |
| Abstract : Lyauk_2016_Clin.Transl.Sci_9_337 |
| ESTHER : Lyauk_2016_Clin.Transl.Sci_9_337 |
| PubMedSearch : Lyauk_2016_Clin.Transl.Sci_9_337 |
| PubMedID: 27754602 |
| Gene_locus related to this paper: human-CES1 |
| Title : The Effects of Methylphenidate on Resting-State Functional Connectivity of the Basal Nucleus of Meynert, Locus Coeruleus, and Ventral Tegmental Area in Healthy Adults - Kline_2016_Front.Hum.Neurosci_10_149 |
| Author(s) : Kline RL , Zhang S , Farr OM , Hu S , Zaborszky L , Samanez-Larkin GR , Li CS |
| Ref : Front Hum Neurosci , 10 :149 , 2016 |
| Abstract : Kline_2016_Front.Hum.Neurosci_10_149 |
| ESTHER : Kline_2016_Front.Hum.Neurosci_10_149 |
| PubMedSearch : Kline_2016_Front.Hum.Neurosci_10_149 |
| PubMedID: 27148006 |
| Title : Dopamine and norepinephrine receptors participate in methylphenidate enhancement of in vivo hippocampal synaptic plasticity - Jenson_2015_Neuropharmacol_90_23 |
| Author(s) : Jenson D , Yang K , Acevedo-Rodriguez A , Levine A , Broussard JI , Tang J , Dani JA |
| Ref : Neuropharmacology , 90 :23 , 2015 |
| Abstract : Jenson_2015_Neuropharmacol_90_23 |
| ESTHER : Jenson_2015_Neuropharmacol_90_23 |
| PubMedSearch : Jenson_2015_Neuropharmacol_90_23 |
| PubMedID: 25445492 |
| Title : Chromatographic and electrophoretic strategies for the chiral separation and quantification of d- and l-threo methylphenidate in biological matrices - Allen_2014_Biomed.Chromatogr_28_1554 |
| Author(s) : Allen SA , Pond BB |
| Ref : Biomedical Chromatography , 28 :1554 , 2014 |
| Abstract : Allen_2014_Biomed.Chromatogr_28_1554 |
| ESTHER : Allen_2014_Biomed.Chromatogr_28_1554 |
| PubMedSearch : Allen_2014_Biomed.Chromatogr_28_1554 |
| PubMedID: 25196779 |
| Title : Ethylphenidate as a Selective Dopaminergic Agonist and Methylphenidate-Ethanol Transesterification Biomarker - Patrick_2014_J.Pharm.Sci_103_3834 |
| Author(s) : Patrick KS , Corbin TR , Murphy CE |
| Ref : J Pharm Sci , 103 :3834 , 2014 |
| Abstract : Patrick_2014_J.Pharm.Sci_103_3834 |
| ESTHER : Patrick_2014_J.Pharm.Sci_103_3834 |
| PubMedSearch : Patrick_2014_J.Pharm.Sci_103_3834 |
| PubMedID: 25303048 |
| Title : Methylphenidate Side Effect Profile Is Influenced by Genetic Variation in the Attention-Deficit\/Hyperactivity Disorder-Associated CES1 Gene - Johnson_2013_J.Child.Adolesc.Psychopharmacol_23_655 |
| Author(s) : Johnson KA , Barry E , Lambert D , FitzGerald M , McNicholas F , Kirley A , Gill M , Bellgrove MA , Hawi Z |
| Ref : J Child Adolesc Psychopharmacol , 23 :655 , 2013 |
| Abstract : Johnson_2013_J.Child.Adolesc.Psychopharmacol_23_655 |
| ESTHER : Johnson_2013_J.Child.Adolesc.Psychopharmacol_23_655 |
| PubMedSearch : Johnson_2013_J.Child.Adolesc.Psychopharmacol_23_655 |
| PubMedID: 24350812 |
| Gene_locus related to this paper: human-CES1 |
| Title : Association of a carboxylesterase 1 polymorphism with appetite reduction in children and adolescents with attention-deficit\/hyperactivity disorder treated with methylphenidate - Bruxel_2013_Pharmacogenomics.J_13_476 |
| Author(s) : Bruxel EM , Salatino-Oliveira A , Genro JP , Zeni CP , Polanczyk GV , Chazan R , Rohde LA , Hutz MH |
| Ref : Pharmacogenomics J , 13 :476 , 2013 |
| Abstract : Bruxel_2013_Pharmacogenomics.J_13_476 |
| ESTHER : Bruxel_2013_Pharmacogenomics.J_13_476 |
| PubMedSearch : Bruxel_2013_Pharmacogenomics.J_13_476 |
| PubMedID: 22688218 |
| Gene_locus related to this paper: human-CES1 |
| Title : Isopropylphenidate: an ester homolog of methylphenidate with sustained and selective dopaminergic activity and reduced drug interaction liability - Markowitz_2013_J.Child.Adolesc.Psychopharmacol_23_648 |
| Author(s) : Markowitz JS , Zhu HJ , Patrick KS |
| Ref : J Child Adolesc Psychopharmacol , 23 :648 , 2013 |
| Abstract : Markowitz_2013_J.Child.Adolesc.Psychopharmacol_23_648 |
| ESTHER : Markowitz_2013_J.Child.Adolesc.Psychopharmacol_23_648 |
| PubMedSearch : Markowitz_2013_J.Child.Adolesc.Psychopharmacol_23_648 |
| PubMedID: 24261661 |
| Title : Differential influences of ethanol on early exposure to racemic methylphenidate compared with dexmethylphenidate in humans - Patrick_2013_Drug.Metab.Dispos_41_197 |
| Author(s) : Patrick KS , Straughn AB , Reeves OT, 3rd , Bernstein H , Bell GH , Anderson ER , Malcolm RJ |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 41 :197 , 2013 |
| Abstract : Patrick_2013_Drug.Metab.Dispos_41_197 |
| ESTHER : Patrick_2013_Drug.Metab.Dispos_41_197 |
| PubMedSearch : Patrick_2013_Drug.Metab.Dispos_41_197 |
| PubMedID: 23104969 |
| Title : Chronic methylphenidate administration alters antioxidant defenses and butyrylcholinesterase activity in blood of juvenile rats - Schmitz_2012_Mol.Cell.Biochem_361_281 |
| Author(s) : Schmitz F , Scherer EB , da Cunha MJ , da Cunha AA , Lima DD , Delwing D , Netto CA , Wyse AT |
| Ref : Molecular & Cellular Biochemistry , 361 :281 , 2012 |
| Abstract : Schmitz_2012_Mol.Cell.Biochem_361_281 |
| ESTHER : Schmitz_2012_Mol.Cell.Biochem_361_281 |
| PubMedSearch : Schmitz_2012_Mol.Cell.Biochem_361_281 |
| PubMedID: 22012612 |
| Title : Enantiospecific determination of dl-methylphenidate and dl-ethylphenidate in plasma by liquid chromatography-tandem mass spectrometry: Application to human ethanol interactions - Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_783 |
| Author(s) : Zhu HJ , Patrick KS , Markowitz JS |
| Ref : Journal of Chromatography B Analyt Technol Biomed Life Sciences , 879 :783 , 2011 |
| Abstract : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_783 |
| ESTHER : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_783 |
| PubMedSearch : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_783 |
| PubMedID: 21402502 |
| Title : Combining Carbamazepine, neuroleptics and acetylcholinesterase inhibitors with Methylphenidate only reduces adverse side effects, but is less effective than a combination with Atomoxetine - |
| Author(s) : Niederhofer H |
| Ref : Med Hypotheses , 76 :764 , 2011 |
| PubMedID: 21397406 |
| Title : Methylphenidate affects memory, brain-derived neurotrophic factor immunocontent and brain acetylcholinesterase activity in the rat - Scherer_2010_Neurobiol.Learn.Mem_94_247 |
| Author(s) : Scherer EB , da Cunha MJ , Matte C , Schmitz F , Netto CA , Wyse AT |
| Ref : Neurobiol Learn Mem , 94 :247 , 2010 |
| Abstract : Scherer_2010_Neurobiol.Learn.Mem_94_247 |
| ESTHER : Scherer_2010_Neurobiol.Learn.Mem_94_247 |
| PubMedSearch : Scherer_2010_Neurobiol.Learn.Mem_94_247 |
| PubMedID: 20561592 |
| Title : Carboxylesterase 1 gene polymorphism and methylphenidate response in ADHD - Nemoda_2009_Neuropharmacol_57_731 |
| Author(s) : Nemoda Z , Angyal N , Tarnok Z , Gadoros J , Sasvari-Szekely M |
| Ref : Neuropharmacology , 57 :731 , 2009 |
| Abstract : Nemoda_2009_Neuropharmacol_57_731 |
| ESTHER : Nemoda_2009_Neuropharmacol_57_731 |
| PubMedSearch : Nemoda_2009_Neuropharmacol_57_731 |
| PubMedID: 19733552 |
| Gene_locus related to this paper: human-CES1 |
| Title : Enantiospecific gas chromatographic-mass spectrometric analysis of urinary methylphenidate: implications for phenotyping - LeVasseur_2008_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_862_140 |
| Author(s) : LeVasseur NL , Zhu HJ , Markowitz JS , DeVane CL , Patrick KS |
| Ref : Journal of Chromatography B Analyt Technol Biomed Life Sciences , 862 :140 , 2008 |
| Abstract : LeVasseur_2008_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_862_140 |
| ESTHER : LeVasseur_2008_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_862_140 |
| PubMedSearch : LeVasseur_2008_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_862_140 |
| PubMedID: 18155648 |
| Title : Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1 - Sun_2004_J.Pharmacol.Exp.Ther_310_469 |
| Author(s) : Sun Z , Murry DJ , Sanghani SP , Davis WI , Kedishvili NY , Zou Q , Hurley TD , Bosron WF |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 310 :469 , 2004 |
| Abstract : Sun_2004_J.Pharmacol.Exp.Ther_310_469 |
| ESTHER : Sun_2004_J.Pharmacol.Exp.Ther_310_469 |
| PubMedSearch : Sun_2004_J.Pharmacol.Exp.Ther_310_469 |
| PubMedID: 15082749 |