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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H19NO2
Molecular Weight 233.3062
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXMETHYLPHENIDATE

SMILES

COC(=O)[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2

InChI

InChIKey=DUGOZIWVEXMGBE-CHWSQXEVSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H19NO2
Molecular Weight 233.3062
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dexmethylphenidate is the dextrorotary form of methylphenidate. Dexmethylphenidate is marketed under the trade name Focalin. Focalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threoenantiomers. Focalin is a central nervous system (CNS) stimulant, available in three tablet strengths. Each tablet contains dexmethylphenidate hydrochloride 2.5, 5, or 10 mg for oral administration. Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment. Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.

CNS Activity

Curator's Comment: Dexmethylphenidate is a central nervous system (CNS) stimulant

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FOCALIN

Approved Use

Focalin XR is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) in patients aged 6 years and older. The effectiveness of Focalin XR in the treatment of ADHD in patients aged 6 years and older was established in two placebo-controlled studies in patients meeting DSM-IV criteria for ADHD.

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22.13 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
23.72 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
10.7 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
131.9 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
120.9 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
79.8 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.81 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2.68 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.3 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEXMETHYLPHENIDATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Other AEs: Vomiting, Agitation...
Other AEs:
Vomiting
Agitation
Tremor
Hyperreflexia
Muscle twitching
Convulsions
Euphoria
Confusion
Hallucinations
Delirium
Sweating
Flushing
Headache
Hyperpyrexia
Tachycardia
Palpitations
Cardiac arrhythmias
Hypertension
Mydriasis
Mucosal dryness
Rhabdomyolysis
Sources:
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Twitching, Anorexia...
AEs leading to
discontinuation/dose reduction:
Twitching (1%)
Anorexia (1%)
Insomnia (1%)
Tachycardia (1%)
Insomnia (1.8%)
Sources:
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Cardiac disorders, Stroke...
Other AEs: Increased blood pressure, Heart rate increased...
AEs leading to
discontinuation/dose reduction:
Cardiac disorders (grade 3-5)
Stroke (grade 3-5)
Myocardial infarction (grade 3-5)
Seizures
Raynaud's phenomenon
Other AEs:
Increased blood pressure
Heart rate increased
Psychotic symptom (grade 3-5)
Psychotic symptom
Manic symptom
Aggression
Growth suppression
Priapism
Erection prolonged
Vascular disorders
Visual disturbance
Sources:
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Feeling jittery, Anorexia...
AEs leading to
discontinuation/dose reduction:
Feeling jittery (1.8%)
Anorexia (1.2%)
Anxiety (1.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Agitation
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Cardiac arrhythmias
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Confusion
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Convulsions
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Delirium
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Euphoria
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Flushing
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Hallucinations
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Headache
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Hyperpyrexia
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Hyperreflexia
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Hypertension
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Mucosal dryness
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Muscle twitching
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Mydriasis
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Palpitations
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Rhabdomyolysis
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Sweating
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Tachycardia
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Tremor
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Vomiting
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy
Anorexia 1%
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Insomnia 1%
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Tachycardia 1%
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Twitching 1%
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Insomnia 1.8%
Disc. AE
30 mg 1 times / day multiple, oral
Recommended
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Aggression
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Erection prolonged
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Growth suppression
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Heart rate increased
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Increased blood pressure
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Manic symptom
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Priapism
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Psychotic symptom
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Vascular disorders
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Visual disturbance
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Raynaud's phenomenon Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Seizures Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Psychotic symptom grade 3-5
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Cardiac disorders grade 3-5
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Myocardial infarction grade 3-5
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Stroke grade 3-5
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Anorexia 1.2%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Anxiety 1.2%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Feeling jittery 1.8%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
weak
yes
PubMed

PubMed

TitleDatePubMed
[Prescribing ritalin in combined modality management of hyperactivity with attention deficit].
2001 Sep-Oct
A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects.
2004 Feb
Efficacy of two once-daily methylphenidate formulations compared across dose levels at different times of the day: preliminary indications from a secondary analysis of the COMACS study data.
2004 Sep 30
Evolution of the treatment of attention-deficit/hyperactivity disorder in children: a review.
2008 May
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
Once-daily medications for the pharmacological management of ADHD in adults.
2009 Apr
Long-term effectiveness and safety of dexmethylphenidate extended-release capsules in adult ADHD.
2009 Mar
Efficacy of dexmethylphenidate for the treatment of fatigue after cancer chemotherapy: a randomized clinical trial.
2009 Nov
Patents

Sample Use Guides

Focalin (Dexmethylphenidate) is administered twice daily, at least 4 hours apart. Focalin may be administered with or without food. The recommended starting dose of Focalin for patients who are not currently taking racemic methylphenidate, or for patients who are on stimulants other than methylphenidate, is 5 mg/day (2.5 mg twice daily). Dosage may be adjusted in 2.5 to 5 mg increments to a maximum of 20 mg/day (10 mg twice daily). In general, dosage adjustments may proceed at approximately weekly intervals.
Route of Administration: Oral
Dexmethylphenidate inhibition [3H]dopamine uptake at human DAT expressed in mouse N2A cells with IC50 156 nM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:07:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:24 GMT 2025
Record UNII
M32RH9MFGP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXMETHYLPHENIDATE
INN   VANDF   WHO-DD  
INN  
Official Name English
METHYLPHENIDATE D-THREO-FORM
MI  
Preferred Name English
Dexmethylphenidate [WHO-DD]
Common Name English
2-PIPERIDINEACETIC ACID, .ALPHA.-PHENYL-, METHYL ESTER, (.ALPHA.R,2R)-
Common Name English
METHYLPHENIDATE D-THREO-FORM [MI]
Common Name English
dexmethylphenidate [INN]
Common Name English
DEXMETHYLPHENIDATE [VANDF]
Common Name English
METHYL (2R)-PHENYL((2R)-PIPERIDIN-2-YL)ACETATE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QN06BA11
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
NDF-RT N0000175729
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
NCI_THESAURUS C47795
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
WHO-ATC N06BA11
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
LIVERTOX 291
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
NDF-RT N0000175739
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
Code System Code Type Description
EVMPD
SUB30294
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL827
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
WIKIPEDIA
DEXMETHYLPHENIDATE
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
MERCK INDEX
m7453
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY Merck Index
CAS
40431-64-9
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
IUPHAR
7554
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
RXCUI
352372
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY RxNorm
PUBCHEM
154101
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
LACTMED
Dexmethylphenidate
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
SMS_ID
100000092743
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
CHEBI
51860
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
DRUG BANK
DB06701
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID70893769
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
DRUG CENTRAL
836
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
NCI_THESAURUS
C26642
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
INN
8289
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
DAILYMED
M32RH9MFGP
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
FDA UNII
M32RH9MFGP
Created by admin on Mon Mar 31 18:07:24 GMT 2025 , Edited by admin on Mon Mar 31 18:07:24 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC following oral administration of serdexmethylphenidate single moiety alone
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC INTRAVENOUS ADMINISTRATION
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC IN HEALTHY ADULT SUBJECTS
PHARMACOKINETIC