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Revision as of 14:23, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'CAS_number').← Previous edit Latest revision as of 20:40, 1 December 2024 edit undoQuebec99 (talk | contribs)Extended confirmed users63,033 edits removed extra reference "Concerta FDA label" 
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{{Short description|CNS Stimulant}}
{{Use dmy dates|date=October 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443632978
| Watchedfields = changed
| IUPAC_name = (''R'',''R'')-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate
| verifiedrevid = 460779887
| image = Focalin.png
| image = Dexmethylphenidate structure.svg
| width = 140
| width = 200
| alt =
| image2 = Dextromethylphenidate-based-on-hydrochloride-xtal-1995-3D-balls.png | image2 = Dextromethylphenidate-based-on-hydrochloride-xtal-1995-3D-balls.png
| alt2 =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Focalin, Focalin XR, others
| Drugs.com = {{drugs.com|monograph|dexmethylphenidate-hydrochloride}} | Drugs.com = {{drugs.com|monograph|dexmethylphenidate-hydrochloride}}
| MedlinePlus = a603014 | MedlinePlus = a603014
| DailyMedID = Dexmethylphenidate
| pregnancy_category = C
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_category =
| dependency_liability = Physical: None{{medcn|date=December 2023}}; Psychological: High
| routes_of_administration = ]
| ATC_prefix = N06
| ATC_suffix = BA11
| ATC_supplemental =

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


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 11 – 52% | bioavailability = 11–52%
| protein_bound = 30% | protein_bound = 30%
| metabolism = ] | metabolism = ]
| elimination_half-life = 2 – 4 hours | elimination_half-life = 4 hours
| excretion = ] | excretion = ]


<!--Identifiers--> <!--Identifiers-->
| index2_label = hydrochloride
| CAS_number = <!-- blanked - oldvalue: 40431-64-9 -->
| CAS_number_Ref = {{cascite|changed|??}}
| ATC_prefix = N06
| CAS_number = 40431-64-9
| ATC_suffix = BA11
| CAS_number2 = 19262-68-1
| ATC_supplemental =
| PubChem = 154101 | PubChem = 154101
| PubChem2 = 154100
| IUPHAR_ligand = 7554
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06701 | DrugBank = DB06701
| DrugBank2 = DBSALT001458
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 135807 | ChemSpiderID = 135807
| ChemSpiderID2 = 135806
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M32RH9MFGP | UNII = M32RH9MFGP
| UNII2 = 1678OK0E08
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07806 | KEGG = D07806
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D03721
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51860 | ChEBI = 51860
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 827 | ChEMBL = 827
| ChEMBL2 = 904
| synonyms = d-threo-methylphenidate (D-TMP)


<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = (''R'',''R'')-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate
| C=14 | H=19 | N=1 | O=2 | C=14 | H=19 | N=1 | O=2
| SMILES = O=C((1NCCCC1)C2=CC=CC=C2)OC
| molecular_weight = 233.31 g/mol
| smiles = O=C(OC)(c1ccccc1)2NCCCC2 | SMILES2 = Cl.(C(=O)OC)(C1=CC=CC=C1)1()CCCCN1
| InChI = 1/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
| InChIKey = DUGOZIWVEXMGBE-CHWSQXEVBG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DUGOZIWVEXMGBE-CHWSQXEVSA-N | StdInChIKey = DUGOZIWVEXMGBE-CHWSQXEVSA-N
| StdInChIKey2 = JUMYIBMBTDDLNG-OJERSXHUSA-N
}} }}


<!-- Definition and medical uses -->
'''Dexmethylphenidate''', otherwise known as '''d-threo-methylphenidate''' (D-TMP), is the ] enantiomer of ]. It is a ] (NDRI) and ] and thus a ], which affects the ]. Dexmethylphenidate is sold as '''Focalin''' by ], as '''Attenade''' by ] and as a ] by ].
'''Dexmethylphenidate''', sold under the brand name '''Focalin''' among others, is a potent ] (CNS) stimulant used to treat ] (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 ].<ref name=AHFS2019/> The immediate release formulation lasts up to five hours while the ] 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 ] of ].<ref name="AHFS2019" />


<!-- Side effects and mechanism -->
== Mode of activity ==
Common side effects include abdominal pain, loss of appetite, and fever.<ref name=AHFS2019/> Serious side effects may include ], ], ], ], ], and ].<ref name=AHFS2019/> Safety during ] and ] 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> Dexmethylphenidate is a ] (CNS) ].<ref name=Moen2009/><ref name=AHFS2019/> How it works in ADHD is unclear.<ref name=AHFS2019 />


<!-- History and culture -->
Methylphenidate is a ] reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the ] (DAT) and ] (NET),<ref name='Markowitz'/> which are responsible for clearing catecholamines from the ], particularly in the ] and ].<ref>{{Cite pmid|4031878}}</ref>
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 ].<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>
Moreover, it is thought to act as a ] by increasing the release of dopamine and norepinephrine.<ref>Novartis: PDF: </ref>
{{TOC limit}}


==Medical uses==
Although four stereoisomers of methylphenidate (MPH) are possible, only the ] diastereoisomers are used in modern practice. There is a high ] between the SS and RR enantiomers of MPH. "Dexmethylphenidate" is a preparation of the RR ] of MPH.<ref>{{Cite pmid|9181638}}</ref><ref>{{Cite pmid|15236349}}</ref> In theory, ''d''-TMP can be anticipated to be twice the strength of the racemic product.<ref>{{Cite pmid|11862378}}</ref> However, certain authors recommend that the ratio is ~70% increase in potency upon enantiopurification of the racemate.<ref name='Markowitz'>{{Cite pmid|18480678}}</ref>
Dexmethylphenidate is used as a treatment for ], usually along with psychological, educational, behavioral or other forms of treatment. It is proposed that stimulants help ameliorate the symptoms of ADHD by making it easier for the user to concentrate, avoid distraction, and control behavior. Placebo-controlled trials have shown that once-daily dexmethylphenidate XR was effective and generally well tolerated.<ref name=Moen2009>{{cite journal | vauthors = Moen MD, Keam SJ | title = Dexmethylphenidate extended release: a review of its use in the treatment of attention-deficit hyperactivity disorder | journal = CNS Drugs | volume = 23 | issue = 12 | pages = 1057–83 | date = December 2009 | pmid = 19958043 | doi = 10.2165/11201140-000000000-00000 | s2cid = 24975170}}</ref>


Improvements in ADHD symptoms in children were significantly greater for dexmethylphenidate XR versus placebo.<ref name=Moen2009/> It also showed greater efficacy than ] (]) methylphenidate over the first half of the laboratory classroom day but assessments late in the day favoured OROS methylphenidate.<ref name=Moen2009 />
{| class="wikitable" border="1"

==Contraindications==
{{transcluded section|source=Methylphenidate}}
{{trim|{{#section-h:Methylphenidate|Contraindications}}}}

==Adverse effects==
{{transcluded section|source=Methylphenidate|part=yes}}
Products containing dexmethylphenidate have a side effect profile comparable to those containing methylphenidate.<ref name="Dexmethylphenidate">{{cite journal | vauthors = Keating GM, Figgitt DP | title = Dexmethylphenidate | journal = Drugs | volume = 62 | issue = 13 | pages = 1899–904; discussion 1905–8 | year = 2002 | pmid = 12215063 | doi = 10.2165/00003495-200262130-00009 | s2cid = 249894173}}</ref>
{{trim|{{#section-h:Methylphenidate|Adverse effects}}}}

== Interactions ==

{{transcluded section|source=Methylphenidate}}
{{trim|{{#section-h:Methylphenidate|Interactions}}}}

==Mode of activity==
Methylphenidate is a ] reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the ] (DAT) and ] (NET),<ref name="MarkowitzPatrick2008" /> which are responsible for clearing catecholamines from the ], particularly in the ] and ].<ref>{{cite journal | vauthors = Schweri MM, Skolnick P, Rafferty MF, Rice KC, Janowsky AJ, Paul SM | title = Threo-(+/-)-methylphenidate binding to 3,4-dihydroxyphenylethylamine uptake sites in corpus striatum: correlation with the stimulant properties of ritalinic acid esters | journal = Journal of Neurochemistry | volume = 45 | issue = 4 | pages = 1062–70 | date = October 1985 | pmid = 4031878 | doi = 10.1111/j.1471-4159.1985.tb05524.x | s2cid = 28720285}}</ref> Moreover, it is thought to "increase the ] of these monoamines into the extraneuronal space."<ref name="Focalin XR FDA label">{{cite web | title=Focalin XR- dexmethylphenidate hydrochloride capsule, extended release | website=DailyMed | date=27 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1a1da905-42a0-4748-9c39-67eca45deccc | access-date=15 November 2020}}</ref>

Although four ] of ] (MPH) are possible, only the ] ] are used in modern practice. There is a high ] between the SS and RR ] of MPH. Dexmethylphenidate (d-threo-methylphenidate) is a preparation of the RR enantiomer of methylphenidate.<ref>{{cite journal | vauthors = Ding YS, Fowler JS, Volkow ND, Dewey SL, Wang GJ, Logan J, Gatley SJ, Pappas N | title = Chiral drugs: comparison of the pharmacokinetics of d-threo and L-threo-methylphenidate in the human and baboon brain | journal = Psychopharmacology | volume = 131 | issue = 1 | pages = 71–8 | date = May 1997 | pmid = 9181638 | doi = 10.1007/s002130050267 | s2cid = 26046917 | url = https://zenodo.org/record/1232627}}</ref><ref>{{cite journal | vauthors = Ding YS, Gatley SJ, Thanos PK, Shea C, Garza V, Xu Y, Carter P, King P, Warner D, Taintor NB, Park DJ, Pyatt B, Fowler JS, Volkow ND | title = Brain kinetics of methylphenidate (Ritalin) enantiomers after oral administration | journal = Synapse | volume = 53 | issue = 3 | pages = 168–75 | date = September 2004 | pmid = 15236349 | doi = 10.1002/syn.20046 | citeseerx = 10.1.1.514.7833 | s2cid = 11664668}}</ref> In theory, ''D''-TMP (d-threo-methylphenidate) can be anticipated to be twice the strength of the ] product.<ref name="MarkowitzPatrick2008">{{cite journal | vauthors = Markowitz JS, Patrick KS | title = Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter? | journal = Journal of Clinical Psychopharmacology | volume = 28 | issue = 3 Suppl 2 | pages = S54-61 | date = June 2008 | pmid = 18480678 | doi = 10.1097/JCP.0b013e3181733560}}</ref><ref>{{cite journal | vauthors = Davids E, Zhang K, Tarazi FI, Baldessarini RJ | title = Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning | journal = Psychopharmacology | volume = 160 | issue = 1 | pages = 92–8 | date = February 2002 | pmid = 11862378 | doi = 10.1007/s00213-001-0962-5 | s2cid = 8037050}}</ref>

{| class="wikitable"
|- |-
! Compd<ref name=Williard>{{cite journal | vauthors = Williard RL, Middaugh LD, Zhu HJ, Patrick KS | title = Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity | journal = Behavioural Pharmacology | volume = 18 | issue = 1 | pages = 39–51 | date = February 2007 | pmid = 17218796 | doi = 10.1097/FBP.0b013e3280143226 | s2cid = 20232871}}</ref>
! Compd<ref name=Williard>{{Cite pmid|17218796}}</ref>
! DAT (K<sub>i</sub>) ! DAT (K<sub>i</sub>)
! DA (IC<sub>50</sub>) ! DA (IC<sub>50</sub>)
Line 77: Line 129:
|<small>L</small>-TMP||2250||1600||>10K||980 |<small>L</small>-TMP||2250||1600||>10K||980
|- |-
|<small>DL</small>-TMP||121||20||51||788 |<small>DL</small>-TMP||121||20||788||51
|- |-
|} |}


== Therapeutic use == == Pharmacology==
{{main|Methylphenidate#Pharmacology}}
Dexmethylphenidate has a 4–6 hour duration of effect. A long-acting formulation, Focalin XR, which spans 12 hours is also available and has been shown to be as effective as <small>DL (dextro-, levo-)</small>-TMP (threo-methylphenidate) XR (extended release) (Concerta, Ritalin LA), with flexible dosing and good tolerability.<ref>{{cite journal | vauthors = McGough JJ, Pataki CS, Suddath R | title = Dexmethylphenidate extended-release capsules for attention deficit hyperactivity disorder | journal = Expert Review of Neurotherapeutics | volume = 5 | issue = 4 | pages = 437–41 | date = July 2005 | pmid = 16026226 | doi = 10.1586/14737175.5.4.437 | s2cid = 6561452}}</ref><ref>{{cite journal | vauthors = Silva R, Tilker HA, Cecil JT, Kowalik S, Khetani V, Faleck H, Patin J | title = Open-label study of dexmethylphenidate hydrochloride in children and adolescents with attention deficit hyperactivity disorder | journal = Journal of Child and Adolescent Psychopharmacology | volume = 14 | issue = 4 | pages = 555–63 | year = 2004 | pmid = 15662147 | doi = 10.1089/cap.2004.14.555}}</ref> It has also been demonstrated to reduce ADHD symptoms in both children<ref>{{cite journal | vauthors = Arnold LE, Lindsay RL, Conners CK, Wigal SB, Levine AJ, Johnson DE, West SA, Sangal RB, Bohan TP, Zeldis JB | title = A double-blind, placebo-controlled withdrawal trial of dexmethylphenidate hydrochloride in children with attention deficit hyperactivity disorder | journal = Journal of Child and Adolescent Psychopharmacology | volume = 14 | issue = 4 | pages = 542–54 | date =Winter 2004 | pmid = 15662146 | doi = 10.1089/cap.2004.14.542}}</ref> and adults.<ref>{{cite journal | vauthors = Spencer TJ, Adler LA, McGough JJ, Muniz R, Jiang H, Pestreich L | title = Efficacy and safety of dexmethylphenidate extended-release capsules in adults with attention-deficit/hyperactivity disorder | journal = Biological Psychiatry | volume = 61 | issue = 12 | pages = 1380–7 | date = June 2007 | pmid = 17137560 | doi = 10.1016/j.biopsych.2006.07.032 | s2cid = 45976373 | doi-access = free}}</ref> d-MPH has a similar side-effect profile to MPH<ref name="Dexmethylphenidate" /> and can be administered without regard to food intake.<ref>{{cite journal | vauthors = Teo SK, Scheffler MR, Wu A, Stirling DI, Thomas SD, Stypinski D, Khetani VD | title = A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects | journal = Journal of Clinical Pharmacology | volume = 44 | issue = 2 | pages = 173–8 | date = February 2004 | pmid = 14747426 | doi = 10.1177/0091270003261899 | s2cid = 20694072}}</ref>


'''CTx-1301''' is an experimental medication that is an extended-release formulation of dexmethylphenidate that has a half life more than an hour longer than extended-release dexmethylphenidate (d-MPH-ER). It is under development for ].<ref>{{cite journal | vauthors = Brady LS, Lisanby SH, Gordon JA | title = New directions in psychiatric drug development: promising therapeutics in the pipeline | journal = Expert Opinion on Drug Discovery | volume = 18 | issue = 8 | pages = 835–850 | date = 3 August 2023 | pmid = 37352473 | doi = 10.1080/17460441.2023.2224555 | s2cid = 259240509}}</ref><ref>{{cite journal | vauthors = Childress AC, Beltran N, Supnet C, Weiss MD | title = Reviewing the role of emerging therapies in the ADHD armamentarium | journal = Expert Opinion on Emerging Drugs | volume = 26 | issue = 1 | pages = 1–16 | date = March 2021 | pmid = 33143485 | doi = 10.1080/14728214.2020.1846718 | s2cid = 226251694}}</ref><ref>{{cite journal | vauthors = Ryst E, Childress A | title = An updated safety review of the current drugs for managing ADHD in children | journal = Expert Opinion on Drug Safety | volume = 22 | issue = 11 | pages = 1025–1040 | date = 2023 | pmid = 37843488 | doi = 10.1080/14740338.2023.2271392 | s2cid = 264144450}}</ref><ref>{{cite journal | vauthors = Harris E |title=Industry update: what is new in the field of therapeutic delivery? |journal=Therapeutic Delivery |date=1 February 2018 |volume=9 |issue=3 |pages=155–161 |doi=10.4155/tde-2017-0117|doi-access=free}}</ref><ref>{{cite journal | vauthors = Childress AC, Komolova M, Sallee FR | title = An update on the pharmacokinetic considerations in the treatment of ADHD with long-acting methylphenidate and amphetamine formulations | journal = Expert Opinion on Drug Metabolism & Toxicology | volume = 15 | issue = 11 | pages = 937–974 | date = November 2019 | pmid = 31581854 | doi = 10.1080/17425255.2019.1675636 | s2cid = 203660100 | doi-access = free}}</ref>
Dexmethylphenidate is used as a treatment for ], ideally in conjunction with psychological, educational, behavioral or other forms of treatment. It is proposed that stimulants help ameliorate the symptoms of ADHD by making it easier for the user to concentrate, avoid distraction, and control behavior. Dexmethylphenidate may also improve listening skills and organization of tasks, and may help prevent tic disorders. Because it is a psychostimulant, dexmethylphenidate may also help with ] and in certain cases of ].


== Notes ==
Importantly, the propensity for "abuse" with d-TMP is much less than for the corresponding racemic product.<ref>{{US patent|5908850}}</ref>
{{notelist}}


== Pharmacology == == References ==
{{Reflist|refs=


<ref name="Daytrana FDA label">{{cite web | title=Daytrana- methylphenidate patch | website=DailyMed | date=15 June 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2c312c31-3198-4775-91ab-294e0b4b9e7f | access-date=26 March 2022}}</ref>
Dexmethylphenidate has a 4-6 hour duration of effect (a long-acting formulation, ], which spans 12 hours is also available and has been shown to be as effective as <small>'''DL'''</small>-TMP XR (Concerta, Ritalin LA), with flexible dosing and good tolerability.<ref>{{Cite pmid|16026226}}</ref><ref>{{Cite pmid|15662147}}</ref>) It has also been demonstrated to reduce the symptoms of childhood ADHD,<ref>Arnold, L.E., et al. (2004). "". ''J Child Adolesc Psychopharmacol''. 2004 Winter;14(4):542-54.</ref> as well as ADHD in adults.<ref>{{Cite pmid|17137560}}</ref> d-MPH has a similar side-effect profile to MPH<ref>{{Cite pmid|12215063}}</ref> and can be administered without regard to food intake.<ref>{{Cite pmid|14747426}}</ref>


<!--ref name="Concerta FDA label">{{cite web |title=Concerta- methylphenidate hydrochloride tablet, extended release |website=DailyMed |date=1 July 2021 |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1a88218c-5b18-4220-8f56-526de1a276cd |access-date=26 March 2022 |archive-date=26 March 2017 |archive-url=https://web.archive.org/web/20170326230808/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1a88218c-5b18-4220-8f56-526de1a276cd |url-status=live}}</ref-->
Dexmethylphenidate has a chemical structure similar to a family of key brain neurotransmitters called monoamines, which include norepinephrine and dopamine. The increase in dopamine which occurs with the use of this medication can create a sense of euphoria, and therefore may make the user subject to abuse of the drug.<ref>"".</ref>


}}
Typical daily doses of dexmethylphenidate are around 10–20&nbsp;mg for children and 20–40&nbsp;mg for adults. As with all psychostimulant compounds, certain individuals may respond to a small dose and certain individuals may require a larger than average dose, hence, dosing is usually initiated at a typical range and then titrated to suit the patient.<ref>{{Cite pmid|18480679}}</ref>

There is a possibility of withdrawal symptoms if dexmethylphenidate use is discontinued suddenly. As with other stimulants, withdrawal symptoms may include emotional or behavioral depression. Tapering off is recommended, under the supervision of a doctor. ], which involves compulsive or harmful drug-seeking behavior, is rare but not impossible.<ref>"".</ref>

==Efficacy==
Placebo-controlled trials have shown that once-daily dexmethylphenidate XR was effective and generally well tolerated.<ref name="dexmethyl">Moen M, Keam S.. CNSDrugs 2009; 23(12):1057-1083.doi:10.2165/11201140-000000000-00000.</ref> Improvements in ADHD symptoms in children were significantly greater for dexmethylphenidate XR versus placebo.<ref name="dexmethyl"/> It also showed greater efficacy than osmotic release oral system (OROS) methylphenidate over the first half of the laboratory classroom day but assessments late in the day favoured OROS methylphenidate.<ref name="dexmethyl"/>

== Concerns ==
The same concerns that apply to other ]s should be considered: Reports of sudden ] death in children caused Canada to stop marketing ] XR (another stimulant used to treat ]) for a period in 2005, however it was returned to the market in that same year after it was demonstrated that cardiac risk is low in patients free of ]s. Heart problems have been reported, predominantly in young people taking ] stimulants, though the ] has not concluded that psychostimulants increase risk of cardiac problems for a person without a heart condition. ] has been reported in young people who are taking ]s at the same time they are taking an ADHD stimulant and many antidepressants carry a "]" label concerning a possible increase in suicidal ideation in patients under 18 years of age.<ref>{{Cite pmid|19405409}}</ref>

=== Side effects ===
], dizziness, ], stomach pain, ], ], ], ], and weight loss are common side effects.

Rare but much more serious side effects include uncontrolled muscle movements (e.g., stiffness, twitching, shaking), ], ], ] of the feet/hands, blurred vision, mental/mood/behavior changes (e.g., ], ], mood swings, ], ], abnormal thoughts/behavior), extreme tiredness, and severe ], easy bleeding/bruising, shortness of breath, ], chest/jaw/left arm pain, sudden vision changes, signs of infection (fever, persistent sore throat), ], ], ], ], slurred speech, and severe headaches and in some very rare cases death.{{Citation needed|date=April 2009}}

Also, there is a potential for a severe allergic reaction, but it is extremely rare. Trouble breathing, itching, a rash, swelling, or severe dizziness are all signs/symptoms of this allergic reaction. {{Citation needed|date=April 2009}}

=== Interactions ===
Dexmethylphenidate should not be used in combination with a ] such as ] (Marplan), ] (Nardil), ] (Azilect), ] (Eldepryl, Emsam), or ] (Parnate) that has been used in the past 14 days. Serious, life-threatening side effects can occur if dexmethylphenidate is taken with an MAOI. {{Citation needed|date= February 2011}}

==Usage==
The Focalin XR capsules are sometimes prescribed over other extended release stimulants because the capsules can be opened and their contents mixed with applesauce or pudding to help children who cannot, or will not, swallow large capsules. This is possible due to the SODAS (Spheroidal Oral Drug Absorption System) delivery system, also used in Ritalin LA. Focalin XR comes in five, ten, fifteen, twenty, thirty, and forty milligram capsules. To determine appropriate dosage doctors first prescribe one to four 5&nbsp;mg capsules. An appropriate treatment plan is then based on the patient's reaction to the initial dose.<ref>"".</ref> From there, doctors usually increase dose by 5&nbsp;mg to 10&nbsp;mg until finding the right dosage.

==Legal status==
Dexmethylphenidate, due to its abuse potential is classed as a ] ] in the ].<ref>{{Cite pmid|12455205}}</ref>

== External links ==
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== References ==
{{Reflist|2}}


{{ADHD pharmacotherapies|state=expanded}}
{{Drug use}}
{{Stimulants}} {{Stimulants}}
{{Monoamine reuptake inhibitors}}
{{Antihyperkinetics}}
{{Sigma receptor modulators}}
{{Adrenergics}}
{{Dopaminergics}} {{Phenethylamines}}
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