Dexmethylphenidate

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; Psychological: Moderate
Addiction; liability	Moderate
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 central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) in those over the age of five years. It is taken by mouth. The immediate-release formulation lasts up to five hours while the extended-release formulation lasts up to twelve hours. It is the more active enantiomer of methylphenidate.

Common side effects include abdominal pain, loss of appetite, and fever. Serious side effects may include psychosis, sudden cardiac death, mania, anaphylaxis, seizures, and priapism. Safety during pregnancy and breastfeeding is unclear.

Dexmethylphenidate was approved for medical use in the United States in 2001. It is available as a generic medication. In 2022, it was the 109th most commonly prescribed medication in the United States, with more than 5 million prescriptions.