Methylphenidate

Methylphenidate
Clinical data
Pronunciation	/ˌmɛθəlˈfɛnɪdeɪt, -ˈfiː-/
Trade names	Ritalin, Concerta, others
Other names	MPH
AHFS/Drugs.com	Monograph
MedlinePlus	a682188
License data	US DailyMed: Methylphenidate;
Pregnancy; category	AU: D; ;
Dependence; liability	Physical: None; Psychological: Moderate
Addiction; liability	Moderate
Routes of; administration	Medical: Oral, transdermal; Recreational: Oral, insufflation, sublingual, rectal, intravenous
Drug class	Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI)
ATC code	N06BA04 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A3 (Psychoactive drugs); CA: Schedule III; DE: Anlage III (Special prescription form required); NZ: Class B2 -authority required; UK: Class B; US: Schedule II; UN: Psychotropic Schedule II; EU: Rx-only; SE: Förteckning II;
Pharmacokinetic data
Bioavailability	Oral: ~30% (range: 11–52%)
Protein binding	~15% (±5%) binds to plasma proteins
Metabolism	Liver (80%) mostly CES1-mediated
Metabolites	α-phenyl-2-piperidine acetic acid (ritalinic acid)
Onset of action	~20–60 minutes, depending on formulation
Elimination half-life	2–3 hours
Duration of action	IR dosing: 3–4 hours; ER dosing: 8–12 hours;
Excretion	Urine (90%)
Identifiers
	IUPAC name Methyl phenyl(piperidin-2-yl)acetate;
CAS Number	20748-11-2 ;
PubChem CID	4158;
IUPHAR/BPS	7236;
DrugBank	DB00422 ;
ChemSpider	4015 ;
UNII	207ZZ9QZ49;
KEGG	D04999 ;
ChEBI	CHEBI:6887 ;
ChEMBL	ChEMBL796 ;
CompTox Dashboard (EPA)	DTXSID5023299 ;
ECHA InfoCard	100.003.662
Chemical and physical data
Formula	C14H19NO2
Molar mass	233.311 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	74 °C (165 °F)
Boiling point	136 °C (277 °F)
	SMILES COC(=O)C(c1ccccc1)C1CCCCN1;
	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 ; Key:DUGOZIWVEXMGBE-UHFFFAOYSA-N ;
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Methylphenidate, sold under the brand name Ritalin and Concerta, among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It may be taken by mouth or applied to the skin, and different formulations have varying durations of effect. For ADHD, the effectiveness of methylphenidate is comparable to atomoxetine but modestly lower than amphetamine. However, methylphenidate is preferred as a first-line treatment in children, while amphetamine is preferred in adults. Methylphenidate reduces core ADHD symptoms and may do so in part by enhancing executive functions, such as working memory, sustained attention, and inhibitory control.

At therapeutic doses, methylphenidate increases alertness and concentration and reduces hyperactivity and impulsive behavior in individuals with ADHD. Common side effects include loss of appetite, weight loss, trouble sleeping, and small increases in heart rate and blood pressure. Long-term treatment in children has been associated with slightly slower growth. Methylphenidate can be misused; dependence and withdrawal are mainly reported with high-dose or non-medical use and are uncommon at therapeutic doses.

Methylphenidate is believed to work by blocking the reuptake of dopamine and norepinephrine by neurons. It is a central nervous system (CNS) stimulant of the phenethylamine and piperidine classes. It is available as a generic medication. In 2023, it was the 50th most commonly prescribed medication in the United States, with more than 13 million prescriptions.