Editing Dexmethylphenidate (section)

{{Short description|Central nervous system stimulant}}
{{Use dmy dates|date=October 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460779887
| image = Dexmethylphenidate structure.svg
| image_class = skin-invert-image
| width = 200
| alt = 
| image2 = Dextromethylphenidate-based-on-hydrochloride-xtal-1995-3D-balls.png
| alt2 = 

<!--Clinical data-->
| tradename =  Focalin, Focalin XR, others
| Drugs.com = {{drugs.com|monograph|dexmethylphenidate-hydrochloride}}
| MedlinePlus = a603014
| DailyMedID = Dexmethylphenidate
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment = 
| pregnancy_category = 
| dependency_liability = [[Physical dependence|Physical]]: None<br />[[Psychological dependence|Psychological]]: Moderate<ref name="Stahl's Essential Psychopharmacology">{{cite book | vauthors=Stahl SM | title=Prescriber's Guide: Stahl's Essential Psychopharmacology | date=April 2024 | publisher=Cambridge University Press | location=Cambridge, United Kingdom | isbn=9781108228749 | pages=503–510 | edition=8th | chapter=Methylphenidate (D,L) }}</ref>
| addiction_liability = Moderate <!-- PLEASE NOTE: countless sources state that methylphenidate has a "High" abuse liability. This term is not synonymous with "addiction liability", which is the relative risk (compared to other addictive drugs) of developing an addiction (aka "substance use disorder") when it's used as prescribed or recreationally. -->
| routes_of_administration = [[Oral administration|By mouth]]
| ATC_prefix = N06
| ATC_suffix = BA11
| ATC_supplemental =

| legal_AU = Schedule 8
| legal_CA = Schedule III
| legal_DE = Anlage III
| legal_UK = Class B
| legal_US = Schedule II
| legal_US_comment = <ref name="Focalin FDA label" /><ref name="Focalin XR FDA label" />
| legal_UN = P II
| legal_status = Rx-only

<!--Pharmacokinetic data-->
| bioavailability = 11–52%
| protein_bound = 30%
| metabolism = [[Liver]]
| elimination_half-life = 4 hours
| excretion = [[Kidney]]

<!--Identifiers-->
| index2_label = hydrochloride
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 40431-64-9
| CAS_number2 = 19262-68-1
| PubChem = 154101
| PubChem2 = 154100
| IUPHAR_ligand = 7554
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06701
| DrugBank2 = DBSALT001458
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 135807
| ChemSpiderID2 = 135806
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M32RH9MFGP
| UNII2 = 1678OK0E08
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07806
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D03721
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51860
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 827
| ChEMBL2 = 904
| synonyms = d-threo-methylphenidate (D-TMP)

<!--Chemical data-->
| IUPAC_name = (''R'',''R'')-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate
| C=14 | H=19 | N=1 | O=2 
| SMILES = O=C([C@@H]([C@@H]1NCCCC1)C2=CC=CC=C2)OC
| SMILES2 = Cl.[H][C@@](C(=O)OC)(C1=CC=CC=C1)[C@@]1([H])CCCCN1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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/t12-,13-/m1/s1
| StdInChI2 = 1S/C14H19NO2.ClH/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;1H/t12-,13-;/m1./s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DUGOZIWVEXMGBE-CHWSQXEVSA-N
| StdInChIKey2 = JUMYIBMBTDDLNG-OJERSXHUSA-N
}}

<!-- Definition and medical uses -->
'''Dexmethylphenidate''', sold under the brand name '''Focalin''' among others, is a [[central nervous system]] (CNS) [[stimulant]] used in the treatment of [[attention deficit hyperactivity disorder]] (ADHD) in those over the age of five years.<ref name=AHFS2019>{{cite web |title=Dexmethylphenidate Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/dexmethylphenidate-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=15 April 2019}}</ref> It is taken [[Oral administration|by mouth]].<ref name=AHFS2019/> The immediate-release formulation lasts up to five hours while the [[extended-release]] formulation lasts up to twelve hours.<ref>{{cite book |title=Mosby's Drug Reference for Health Professions - E-Book |date=2013 |publisher=Elsevier Health Sciences |isbn=9780323187602 |page=455 |url=https://books.google.com/books?id=41z07XtCfa0C&pg=PA455}}</ref> It is the more active [[enantiomer]] of [[methylphenidate]].<ref name="AHFS2019" />  

<!-- Side effects and mechanism -->
Common side effects include [[abdominal pain]], [[loss of appetite]], and [[fever]].<ref name=AHFS2019/> Serious side effects may include [[psychosis]], [[sudden cardiac death]], [[mania]], [[anaphylaxis]], [[seizures]], and [[priapism]].<ref name=AHFS2019/> Safety during [[pregnancy]] and [[breastfeeding]] is unclear.<ref name=Preg2019>{{cite web |title=Dexmethylphenidate Use During Pregnancy |url=https://www.drugs.com/pregnancy/dexmethylphenidate.html |website=Drugs.com |access-date=15 April 2019}}</ref>

<!-- History and culture -->
Dexmethylphenidate was approved for medical use in the United States in 2001.<ref name="Focalin FDA label">{{cite web | title=Focalin- dexmethylphenidate hydrochloride tablet | website=DailyMed | date=24 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7c552f11-e24a-4d9b-bb8d-be10c928eca8 | access-date=15 November 2020}}</ref> It is available as a [[generic medication]].<ref name=AHFS2019/> In 2022, it was the 109th most commonly prescribed medication in the United States, with more than 5{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live}}</ref><ref>{{cite web | title = Dexmethylphenidate Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Dexmethylphenidate | access-date = 30 August 2024}}</ref>
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