Dexmethylphenidate

Dexmethylphenidate
Clinical data
Trade namesFocalin, Focalin XR, others
Other namesd-threo-methylphenidate (D-TMP)
AHFS/Drugs.comMonograph
MedlinePlusa603014
License data
Dependence
liability		Physical: None
Psychological: Moderate[1]
Addiction
liability		Moderate
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • CA: Schedule III
  • DE: Anlage III (Special prescription form required)
  • UK: Class B
  • US: Schedule II[2][3]
  • UN: Psychotropic Schedule II
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability11–52%
Protein binding30%
MetabolismLiver
Elimination half-life4 hours
ExcretionKidney
Identifiers
IUPAC name
  • (R,R)-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H19NO2
Molar mass233.311 g·mol−1
3D model (JSmol)
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 Y
  • Key:DUGOZIWVEXMGBE-CHWSQXEVSA-N Y

  • 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
 NY (what is this?)  (verify)

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.[4] It is taken by mouth.[4] The immediate-release formulation lasts up to five hours while the extended-release formulation lasts up to twelve hours.[5] It is the more active enantiomer of methylphenidate.[4]

Common side effects include abdominal pain, loss of appetite, and fever.[4] Serious side effects may include psychosis, sudden cardiac death, mania, anaphylaxis, seizures, and priapism.[4] Safety during pregnancy and breastfeeding is unclear.[6]

Dexmethylphenidate was approved for medical use in the United States in 2001.[2] It is available as a generic medication.[4] In 2022, it was the 109th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[7][8]

  1. ^ Stahl SM (April 2024). "Methylphenidate (D,L)". Prescriber's Guide: Stahl's Essential Psychopharmacology (8th ed.). Cambridge, United Kingdom: Cambridge University Press. pp. 503–510. ISBN 9781108228749.
  2. ^ a b "Focalin- dexmethylphenidate hydrochloride tablet". DailyMed. 24 June 2020. Retrieved 15 November 2020.
  3. ^ Cite error: The named reference Focalin XR FDA label was invoked but never defined (see the help page).
  4. ^ a b c d e f "Dexmethylphenidate Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 15 April 2019.
  5. ^ Mosby's Drug Reference for Health Professions - E-Book. Elsevier Health Sciences. 2013. p. 455. ISBN 9780323187602.
  6. ^ "Dexmethylphenidate Use During Pregnancy". Drugs.com. Retrieved 15 April 2019.
  7. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ^ "Dexmethylphenidate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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