Methylphenidate
Used alongside educational and psychosocial intervention to treat attention deficit hyperactivity disorder (ADHD) and to treat narcolepsy. This drug blocks the reuptake of norepinephrine and dopamine into presynaptic neurons, resulting in increased levels of monoamines active in the extraneuronal space. It is metabolised by Carboxylesterases. The d-MPH enantiomer is the most active
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
MW : 233.30
Formula : C14H19NO2
CAS_number : 113-45-1
PubChem : 4158
UniChem : DUGOZIWVEXMGBE-UHFFFAOYSA-N
Wikipedia : Methylphenidate
Target
Structures : No structure
Families : Carb_B_Chordata
References (22)
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| PubMedSearch : Jenson_2015_Neuropharmacol_90_23 |
| PubMedID: 25445492 |
| Title : Contribution of human esterases to the metabolism of selected drugs of abuse - Meyer_2014_Toxicol.Lett_232_159 |
| Author(s) : Meyer MR , Schutz A , Maurer HH |
| Ref : Toxicol Lett , 232 :159 , 2014 |
| Abstract : |
| PubMedSearch : Meyer_2014_Toxicol.Lett_232_159 |
| PubMedID: 25445008 |
| 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 : |
| 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 : |
| PubMedSearch : Patrick_2014_J.Pharm.Sci_103_3834 |
| PubMedID: 25303048 |
| 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 : |
| 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 : |
| 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 : |
| PubMedSearch : Patrick_2013_Drug.Metab.Dispos_41_197 |
| PubMedID: 23104969 |
| 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 : |
| PubMedSearch : Johnson_2013_J.Child.Adolesc.Psychopharmacol_23_655 |
| PubMedID: 24350812 |
| Gene_locus related to this paper: human-CES1 |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| 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 : |
| PubMedSearch : Sun_2004_J.Pharmacol.Exp.Ther_310_469 |
| PubMedID: 15082749 |