Ritalin

Methylphenidate
Clinical data


Trade names	Ritalin, Concerta, Aptensio, Biphentin, Daytrana, Equasym, Medikinet, Metadate, Methylin, QuilliChew, Quillivant
AHFS/Drugs.com	Monograph
MedlinePlus	a682188
License data	US FDA: Methylphenidate
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Dependence liability	Physical: None Psychological: Moderate
Addiction liability	Moderate
Routes of administration	Oral, insufflation, intravenous, transdermal
ATC code	N06BA04 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule III DE: Anlage III (Prescription only) UK: Class B US: Schedule II
Pharmacokinetic data
Bioavailability	~30% (range: 11–52%)
Protein binding	10–33%
Metabolism	Liver (80%) mostly CES1A1-mediated
Biological half-life	2–3 hours
Excretion	Urine (90%)
Identifiers
IUPAC name Methyl phenyl(piperidin-2-yl)acetate
CAS Number	113-45-1^Y
PubChem CID	4158
IUPHAR/BPS	7236
DrugBank	DB00422^Y
ChemSpider	4015^Y
UNII	207ZZ9QZ49
KEGG	D04999^Y
ChEBI	CHEBI:6887^Y
ChEMBL	CHEMBL796^Y
ECHA InfoCard	100.003.662
Chemical and physical data
Formula	C₁₄H₁₉NO₂
Molar mass	233.31 g/mol
3D model (Jmol)	Interactive image
Melting point	74 °C (165 °F)
Boiling point	136 °C (277 °F)
SMILES O=C(OC)C(C1CCCCN1)C2=CC=CC=C2
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^Y Key:DUGOZIWVEXMGBE-UHFFFAOYSA-N^Y

Methylphenidate, sold under various trade names, Ritalin being one of the most commonly known, is a central nervous system (CNS) stimulant of the phenethylamine and piperidine classes that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. The original patent was owned by CIBA, now Novartis Corporation. It was first licensed by the US Food and Drug Administration (FDA) in 1955 for treating what was then known as hyperactivity.

Medical use began in 1960; the drug has become increasingly prescribed since the 1990s, when the diagnosis of ADHD became more widely accepted. Between 2007 and 2012 methylphenidate prescriptions increased by 50% in the United Kingdom and in 2013 global methylphenidate consumption increased to 2.4 billion doses, a 66% increase from the year before. The United States continues to account for more than 80% of global consumption.

ADHD and other similar conditions are believed to be linked to sub-performance of the dopamine and norepinephrine functions in the brain, primarily in the prefrontal cortex, responsible for executive function (e.g., reasoning, inhibiting behaviors, organizing, problem solving, planning, etc.). Methylphenidate's mechanism of action involves the inhibition of catecholamine reuptake, primarily as a dopamine reuptake inhibitor. Methylphenidate acts by blocking the dopamine transporter and norepinephrine transporter, leading to increased concentrations of dopamine and norepinephrine within the synaptic cleft. This effect in turn leads to increased neurotransmission of dopamine and norepinephrine. Methylphenidate is also a weak 5HT_1A receptor agonist.

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