U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H19NO2.ClH
Molecular Weight 269.767
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLPHENIDATE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=JUMYIBMBTDDLNG-OJERSXHUSA-N
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

HIDE SMILES / InChI
Molecular Formula C14H19NO2
Molecular Weight 233.3062
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Methylphenidate is a CNS stimulant approved for the treatment of narcolepsy and attention deficit hyperactivity disorder. The drug is believed to bind the dopamine transporter in the presynaptic cell membrane, thereby blocking the reuptake of dopamine and causing an increase in extracellular dopamine levels.

CNS Activity

Originator

Approval Year

1955
124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sodium-dependent dopamine transporter
43
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
RITALIN

Approved Use

Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy.

Launch Date

1955
Primary
Approved
8583
RITALIN

Approved Use

Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy.

Launch Date

1955
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021121s038lbl.pdf
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
41.8 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021121s038lbl.pdf
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021121s038lbl.pdf
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010187s091,018029s059lbl.pdf
unknown, unknown
 METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2C8
1057

CYP2C19
2057

CYP2E1
1060

CYP3A
227
CYP450
59
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
CYP2C19
2141
 no
CYP2C8
1117
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP2E1
1146
 no
CYP3A
317
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
59
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY439381
ACT Chemical
ACT11949
Cayman Chemical
11639
Compound Cloud
4158
Compound Cloud
9280
Frontier Scientific Services
500043407
Hairui
HR149584
Hairui
HR149758
Hangzhou Yuhao Chemical Technology
YH52696
HongKong Chemhere
SCD01790
HongKong Chemhere
SCD01793
Innovapharm
BBV-00092182
Lab Seeker
SC-83308
mcule
MCULE-3118022991
mcule
MCULE-3797509037
mcule
MCULE-5458926987
Molcore
MC439381
MuseChem
M071965
MuseChem
M125947
Princeton BioMolecular Research
PBMR221641
ShangHai Biochempartner
BCP18286
Sigma Aldrich
M-083
Sigma Aldrich
M-083|CERILLIAN
Sigma Aldrich
M2892
Sigma Aldrich
M6935|SIGMA
Sigma Aldrich
Y0001017|SIAL
Tetrahedron
TS00164
Tocris
1812
Toronto Research Chemicals
KIT2500
Toronto Research Chemicals
M325671
Toronto Research Chemicals
M325680
ZINC
ZINC000002522648
http://zinc15.docking.org/substances/ZINC000002522648
PubMed

PubMed

TitleDatePubMed
Methylphenidate increases the motor effects of L-Dopa in Parkinson's disease: a pilot study.
2001-08-02
Understanding Rx options for the youngest patients.
2001-08
Concerns about Ritalin.
2001-08
Rewarding properties of methylphenidate: sensitization by prior exposure to the drug and effects of dopamine D1- and D2-receptor antagonists.
2001-08
Rehabilitative management of post-stroke visuospatial inattention.
2001-07-10
[Methylphenidate therapy in 141 patients with hyperkinetic disorder or with pervasive developmental disorder and hyperkinesia].
2001-07
A comparison of the visual symptoms between ADD/ADHD and normal children.
2001-07
Stimulant drugs for severe hyperactivity in childhood.
2001-07
Methylphenidate for fatigue in advanced cancer: a prospective open-label pilot study.
2001-06-16
Practice parameters for the treatment of narcolepsy: an update for 2000.
2001-06-15
Gilles de la Tourette Syndrome.
2001-06-08
Correlations between motor persistence and plasma levels in methylphenidate-treated boys with ADHD.
2001-06
Advances in paediatric neuropsychopharmacology: an overview.
2001-06
Adult ADHD. Controlled medication assessment.
2001-06
Effect of repeated methylphenidate administration on presynaptic dopamine and behaviour in young adult rats.
2001-06
Comparison in symptoms between aged and younger patients with narcolepsy.
2001-06
The development of selective attention in children with attention deficit hyperactivity disorder.
2001-06
Attention deficit hyperactivity disorder and substance use disorders: Is there a causal link?
2001-06
Effects of TENS and methylphenidate in tuberculous meningo-encephalitis.
2001-06
Explosive outbursts associated with methylphenidate.
2001-06
Managing stimulant medication for attention-deficit/hyperactivity disorder.
2001-06
Once-a-day Concerta methylphenidate versus three-times-daily methylphenidate in laboratory and natural settings.
2001-06
Reinforcing and subject-rated effects of methylphenidate and d-amphetamine in non-drug-abusing humans.
2001-06
[Is Ritalin prescribed insufficiently to hyperactive children in Nordland?].
2001-05-30
Methylphenidate sensitization is modulated by valproate.
2001-05-25
Emergence of tics in children with attention deficit hyperactivity disorder treated with stimulant medications.
2001-05-12
[Neuropsychological follow-up of attention deficit/hyperactive disorder in adulthood before and after treatment with methylphenidate].
2001-05
Short-term cardiovascular effects of methylphenidate and adderall.
2001-05
Psychostimulants in preschool children with attention-deficit/hyperactivity disorder: clinical evidence from a developmental disorders institution.
2001-05
An auditable protocol for treating attention deficit/hyperactivity disorder.
2001-05
Synthesis and pharmacology of site specific cocaine abuse treatment agents: a new synthetic methodology for methylphenidate analogs based on the Blaise reaction.
2001-04
Toward individualized evidence-based medicine: five "N of 1" trials of methylphenidate in geriatric patients.
2001-04
Pharmacotherapeutic management of autism.
2001-04
Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder.
2001-04
An adolescent who abruptly stops his medication for attention-deficit hyperactivity disorder.
2001-04
The influence of a token economy and methylphenidate on attentive and disruptive behavior during sports with ADHD-diagnosed children.
2001-04
[Prescription of central nervous system stimulants].
2001-03-20
alpha(2C)-Adrenoceptors modulate the effect of methylphenidate on response rate and discrimination accuracy in an operant test.
2001-03-15
Commentary on Greene and Ablon: What does the MTA study tell us about effective psychosocial treatment for ADHD?
2001-03
Assessing the abuse potential of methylphenidate in nonhuman and human subjects: a review.
2001-03
Methylphenidate augmentation of citalopram in elderly depressed patients.
2001
Methylphenidate improves HIV-1-associated cognitive slowing.
2001
Methylphenidate in stimulants abuse: three case reports.
2001
Myoclonus during prolonged treatment with sertraline in an adolescent patient.
2001
Pharmacokinetic interactions between cyclosporine and bupropion or methylphenidate.
2001
Efficacy of Adderall and methylphenidate in attention deficit hyperactivity disorder: a reanalysis using drug-placebo and drug-drug response curve methodology.
2001
Retrospective comparison of Adderall and methylphenidate in the treatment of attention deficit hyperactivity disorder.
2001
Early methylphenidate administration to young rats causes a persistent reduction in the density of striatal dopamine transporters.
2001
Can methylphenidate facilitate sleep in children with attention deficit hyperactivity disorder?
2001
Letter: Methylphenidate reaction.
1975-06
Patents

Patents

JP2007119479A
3
JP2009526755A
475
JP2010265299A
3
JPH1143486A
3

Sample Use Guides

In Vivo Use Guide
Administer in divided doses 2 or 3 times daily, preferably 30 to 45 minutes before meals. Average dosage is 20 to 30 mg daily. Some patients may require 40 to 60 mg daily. In children the starting dose is 5 mg twice daily (before breakfast and lunch) with gradual increments of 5 to 10 mg weekly.
Route of Administration: Oral
In Vitro Use Guide
Murine neural stem cells were treated directly after seeding to the cover-slip using different concentration (0 nM, 1 nM, 10 nM, 100 nM) of methylphenidate. The drug was found to enhance neuronal differentiation and inhibit neural proliferation.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:04:16 GMT 2025
Edited
by admin
on Mon Mar 31 18:04:16 GMT 2025
Record UNII
4B3SC438HI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLPHENIDATE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
ADHANSIA XR
Preferred Name English
METHYLIN
Brand Name English
QUILLIVANT
Brand Name English
APTENSIO
Brand Name English
QUILLICHEW
Brand Name English
Methyl ?-phenyl-2-piperidineacetate hydrochloride
Systematic Name English
Methylphenidate hydrochloride [WHO-DD]
Common Name English
CONCERTA
Brand Name English
JORNAY PM
Brand Name English
METHYLPHENIDATE HCL
Common Name English
METHYLPHENIDATE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
METADATE
Brand Name English
METHYLPHENIDATE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
METHYLPHENIDATE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
SPD-544
Code English
EQUASYM
Brand Name English
METHYLPHENIDATE HYDROCHLORIDE [MART.]
Common Name English
FOQUEST
Brand Name English
APTENSIO XR
Brand Name English
METADATE CD
Brand Name English
SPD544
Code English
METHYLPHENIDATE HYDROCHLORIDE [VANDF]
Common Name English
METHYLPHENIDATE HYDROCHLORIDE CII [USP-RS]
Common Name English
NSC-169868
Code English
OROS MPH
Common Name English
EQUASYM XL
Brand Name English
METHYLPHENIDATE HYDROCHLORIDE [MI]
Common Name English
METHYLPHENIDATE HYDROCHLORIDE [JAN]
Common Name English
2-PIPERIDINEACETIC ACID, .ALPHA.-PHENYL-, METHYL ESTER, HYDROCHLORIDE, (R*,R*)-(±)-
Common Name English
RITALIN
Brand Name English
METADATE ER
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
Code System Code Type Description
EVMPD
SUB03254MIG
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
DAILYMED
4B3SC438HI
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-065-3
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
DRUG BANK
DBSALT000117
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
CAS
298-59-9
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
203188
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C646
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
NSC
169868
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
ChEMBL
CHEMBL796
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
CHEBI
31836
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
EPA CompTox
DTXSID8020886
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
SMS_ID
100000090133
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
CAS
23655-65-4
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
RS_ITEM_NUM
1433008
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
FDA UNII
4B3SC438HI
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY
MERCK INDEX
m7453
Created by admin on Mon Mar 31 18:04:16 GMT 2025 , Edited by admin on Mon Mar 31 18:04:16 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of METHYLPHENIDATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of RITALINIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHYLPHENIDATE, (±)-ERYTHRO-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of .ALPHA.-PHENYL-2-PIPERIDINEACETAMIDE, THREO-(±)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of .ALPHA.-PHENYL-2-PYRIDINEACETAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BIS-METHYLPHENIDATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ETHYLPHENIDATE, THREO-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PHENYLACETIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of .ALPHA.-PHENYL-2-PIPERIDINEACETAMIDE, ERYTHRO-(±)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of METHYLPHENIDATE
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