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	High
Addiction; liability	High
Routes of; administration	Insufflation, intravenous, oral, rectal, sublingual, transdermal
Drug class	Central nervous system stimulant & norepinephrine–dopamine reuptake inhibitor
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 B; UK: Class B; US: WARNINGSchedule II; UN: Psychotropic Schedule II;
Pharmacokinetic data
Bioavailability	Insufflation: approx. 70% Oral: approx. 30% (range: 11–52%)
Protein binding	10–33%
Metabolism	Liver (80%) mostly CES1A1-mediated
Elimination half-life	2–3 hours
Duration of action	Instant-release: 3-4 hours; Extended-release: 6-12 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 ;
	(verify)

Methylphenidate, sold under the brand names Ritalin (/ˈrɪtəlɪn/ RIT-ə-lin) and Concerta (/kənˈsɜːrtə/ kən-SUR-tə) among others, is a central nervous system (CNS) stimulant used medically to treat attention deficit hyperactivity disorder (ADHD) and, to a lesser extent, narcolepsy. It is a primary medication for ADHD (e.g. in the UK); it may be taken by mouth or applied to the skin, and different formulations have varying durations of effect, commonly ranging from 2–4 hours. For ADHD, the effectiveness of methylphenidate is comparable to atomoxetine but modestly lower than amphetamines.

Common adverse reactions of methylphenidate include: euphoria, dilated pupils, tachycardia, palpitations, headache, insomnia, anxiety, hyperhidrosis, weight loss, decreased appetite, dry mouth, nausea, and abdominal pain. Withdrawal symptoms may include: chills, depression, drowsiness, dysphoria, exhaustion, headache, irritability, lethargy, nightmares, restlessness, suicidal thoughts, and weakness.

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.

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