Dexmethylphenidate information

Dexmethylphenidate
Clinical data
Trade names	Focalin, Focalin XR, others
Other names	d-threo-methylphenidate (D-TMP)
AHFS/Drugs.com	Monograph
MedlinePlus	a603014
License data	US DailyMed: Dexmethylphenidate;
Dependence; liability	Physical: None[medical citation needed]; Psychological: High
Routes of; administration	By mouth
ATC code	N06BA11 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); CA: Schedule III; DE: Anlage III (Special prescription form required); UK: Class B; US: Schedule II; UN: Psychotropic Schedule II; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	11–52%
Protein binding	30%
Metabolism	Liver
Elimination half-life	4 hours
Excretion	Kidney
Identifiers
	IUPAC name (R,R)-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate;
CAS Number	40431-64-9 ; hydrochloride: 19262-68-1;
PubChem CID	154101; hydrochloride: 154100;
IUPHAR/BPS	7554;
DrugBank	DB06701 ; hydrochloride: DBSALT001458;
ChemSpider	135807 ; hydrochloride: 135806;
UNII	M32RH9MFGP; hydrochloride: 1678OK0E08;
KEGG	D07806 ; hydrochloride: D03721 ;
ChEBI	CHEBI:51860 ;
ChEMBL	ChEMBL827 ; hydrochloride: ChEMBL904;
CompTox Dashboard (EPA)	DTXSID70893769 ;
Chemical and physical data
Formula	C14H19NO2
Molar mass	233.311 g·mol−1
3D model (JSmol)	Interactive image; hydrochloride: Interactive image;
	SMILES O=C([C@@H]([C@@H]1NCCCC1)C2=CC=CC=C2)OC; ; hydrochloride: Cl.[H][C@@](C(=O)OC)(C1=CC=CC=C1)[C@@]1([H])CCCCN1;
	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/t12-,13-/m1/s1 ; Key:DUGOZIWVEXMGBE-CHWSQXEVSA-N ; ; hydrochloride: InChI=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; Key:JUMYIBMBTDDLNG-OJERSXHUSA-N;
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Dexmethylphenidate, sold under the brand name Focalin among others, is a potent central nervous system (CNS) stimulant used to treat attention deficit hyperactivity disorder (ADHD) in those over the age of five years.^[3] It is taken by mouth.^[3] The immediate release formulation lasts up to five hours while the extended release formulation lasts up to twelve hours.^[4] It is the more active enantiomer of methylphenidate.^[3]

Common side effects include abdominal pain, loss of appetite, and fever.^[3] Serious side effects may include abuse, psychosis, sudden cardiac death, mania, anaphylaxis, seizures, and dangerously prolonged erection.^[3] Safety during pregnancy and breastfeeding is unclear.^[5] Dexmethylphenidate is a central nervous system (CNS) stimulant.^[6]^[3] How it works in ADHD is unclear.^[3]

Dexmethylphenidate was approved for medical use in the United States in 2001.^[1] It is available as a generic medication.^[3] In 2021, it was the 121st most commonly prescribed medication in the United States, with more than 4 million prescriptions.^[7]^[8]

^ ^a ^b "Focalin- dexmethylphenidate hydrochloride tablet". DailyMed. 24 June 2020. Retrieved 15 November 2020.
^ Cite error: The named reference Focalin XR FDA label was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h "Dexmethylphenidate Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 15 April 2019.
^ Mosby's Drug Reference for Health Professions - E-Book. Elsevier Health Sciences. 2013. p. 455. ISBN 9780323187602.
^ "Dexmethylphenidate Use During Pregnancy". Drugs.com. Retrieved 15 April 2019.
^ Cite error: The named reference Moen2009 was invoked but never defined (see the help page).
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Dexmethylphenidate - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[Focalin_FDA_label-1] "Focalin- dexmethylphenidate hydrochloride tablet". DailyMed. 24 June 2020. Retrieved 15 November 2020.

[Focalin_XR_FDA_label-2] Cite error: The named reference Focalin XR FDA label was invoked but never defined (see the help page).

[AHFS2019-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Dexmethylphenidate Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 15 April 2019.

[4] Mosby's Drug Reference for Health Professions - E-Book. Elsevier Health Sciences. 2013. p. 455. ISBN 9780323187602.

[Preg2019-5] "Dexmethylphenidate Use During Pregnancy". Drugs.com. Retrieved 15 April 2019.

[Moen2009-6] Cite error: The named reference Moen2009 was invoked but never defined (see the help page).

[7] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[8] "Dexmethylphenidate - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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