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Methylphenidate

Chemical Properties and Synthesis: – Methylphenidate is a portmanteau of the chemical name derived from ‘Methyl-phenyl-2-(peri-in-2-yl) acetate’. – It is not a cocaine derivative and […]

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Chemical Properties and Synthesis:
– Methylphenidate is a portmanteau of the chemical name derived from ‘Methyl-phenyl-2-(peri-in-2-yl) acetate’.
– It is not a cocaine derivative and has four possible isomers due to two chiral centers.
– Synthesis methods include the Axten et al. elucidated preparation and classic synthesis.
– Erythro diastereomers are pressor amines, while threo diastereomers exhibit desired effects.
– Threo isomers are energetically favored.

Medical Uses:
– Methylphenidate is commonly used for ADHD and narcolepsy.
– It is prescribed off-label for bipolar and major depressive disorders.
– Positive results reported in geriatric depression studies and treating apathy in Alzheimer’s disease.
– WHO does not include it in the Essential Medicines List for ADHD.
– Used primarily as a stimulant for narcolepsy treatment.

Adverse Effects and Overdose:
– Common side effects include anorexia, dyskinesia, lethargy, dizziness, and cardiac issues.
– Symptoms of overdose include vomiting, agitation, tremors, hallucinations, and hyperthermia.
– Severe overdose symptoms may include convulsions, coma, and circulatory collapse.
– Methylphenidate has addiction and dependence liabilities similar to amphetamine.
– High doses can lead to addiction and psychological dependence.

Pharmacokinetics and Mechanisms of Action:
– Methylphenidate inhibits dopamine and norepinephrine transporters, increasing their levels in the brain.
– It modulates dopamine and norepinephrine levels, improving attention and alertness.
– Bioavailability when taken orally ranges from 11-52% with a half-life of 2-3 hours.
– Duration of action varies based on formulation, from 2-12 hours.
– Acts as a norepinephrine-dopamine reuptake inhibitor.

Society, Culture, and Legal Aspects:
– Methylphenidate is sold globally under various brand names like Ritalin, Concerta, and Focalin.
– Different countries have their own brand names for methylphenidate.
– Dexmethylphenidate (Focalin) has better bioavailability than methylphenidate.
– Legal status: Classified as a Schedule II drug under the Convention on Psychotropic Substances.
– Ritalin packaging includes legal warnings about the drug’s status and potential for abuse or misuse.

Methylphenidate (Wikipedia)

Methylphenidate, sold under the brand names Ritalin (/ˈrɪtəlɪn/ RIT-ə-lin) and Concerta (/kənˈsɜːrtə/ kən-SUR-tə) among others, is a potent 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.

Methylphenidate
Clinical data
Pronunciation/ˌmɛθəlˈfɛnɪdt, -ˈf-/
Trade namesRitalin, Concerta, others
Other namesMPH
AHFS/Drugs.comMonograph
MedlinePlusa682188
License data
Pregnancy
category
  • AU: D
Dependence
liability
High
Addiction
liability
High
Routes of
administration
Insufflation, intravenous, oral, rectal, sublingual, transdermal
Drug classCentral nervous system stimulant & norepinephrine–dopamine reuptake inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityInsufflation: approx. 70% Oral: approx. 30% (range: 11–52%)
Protein binding10–33%
MetabolismLiver (80%) mostly CES1A1-mediated
Elimination half-life2–3 hours
Duration of action
  • Instant-release: 3-4 hours
  • Extended-release: 6-12 hours
ExcretionUrine (90%)
Identifiers
  • Methyl phenyl(piperidin-2-yl)acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.662 Edit this at Wikidata
Chemical and physical data
FormulaC14H19NO2
Molar mass233.311 g·mol−1
3D model (JSmol)
Melting point74 °C (165 °F)
Boiling point136 °C (277 °F)
  • COC(=O)C(c1ccccc1)C1CCCCN1
  • 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 checkY
  • Key:DUGOZIWVEXMGBE-UHFFFAOYSA-N checkY
  (verify)

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. It is available as a generic medication. In 2021, it was the 43rd most commonly prescribed medication in the United States, with more than 15.2 million prescriptions.

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