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


MW : 233.30

Formula : C14H19NO2

CAS_number : 113-45-1

PubChem :

UniChem :

Iuphar :

Target

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
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
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
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
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
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
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
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
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
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
PubMedID: 25303048

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
PubMedID: 25445008

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
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
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
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
PubMedID: 22688218
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
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
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
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
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
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
PubMedID: 15082749