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

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
Atrioventricular nodal re-entrant tachycardia associated with stimulant treatment.
1999
Cocaine-associated stroke: three cases and rehabilitation considerations.
2000 Apr
Cerebral arteritis following methylphenidate use.
2000 Apr
Synthesis and pharmacology of site specific cocaine abuse treatment agents: a new synthetic methodology for methylphenidate analogs based on the Blaise reaction.
2001 Apr
Pharmacotherapeutic management of autism.
2001 Apr
Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder.
2001 Apr
An adolescent who abruptly stops his medication for attention-deficit hyperactivity disorder.
2001 Apr
Understanding Rx options for the youngest patients.
2001 Aug
Concerns about Ritalin.
2001 Aug
Stimulant therapy and seizure risk in children with ADHD.
2001 Feb
Findings from the NIMH Multimodal Treatment Study of ADHD (MTA): implications and applications for primary care providers.
2001 Feb
Methylphenidate dosage for children with ADHD over time under controlled conditions: lessons from the MTA.
2001 Feb
Drugs used in the treatment of attention-deficit/hyperactivity disorder affect postsynaptic firing rate and oscillation without preferential dopamine autoreceptor action.
2001 Feb 15
Haplotype study of three polymorphisms at the dopamine transporter locus confirm linkage to attention-deficit/hyperactivity disorder.
2001 Feb 15
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
Treatment of attention-deficit hyperactivity disorder.
2001 Jan
Benefit of long-term stimulants on driving in adults with ADHD.
2001 Jan
Frontal lobe disinhibition, Rett syndrome and attention deficit hyperactivity disorder.
2001 Jan
[Methylphenidate therapy in 141 patients with hyperkinetic disorder or with pervasive developmental disorder and hyperkinesia].
2001 Jul
Stimulant drugs for severe hyperactivity in childhood.
2001 Jul
Rehabilitative management of post-stroke visuospatial inattention.
2001 Jul 10
Methylphenidate increases the motor effects of L-Dopa in Parkinson's disease: a pilot study.
2001 Jul-Aug
Correlations between motor persistence and plasma levels in methylphenidate-treated boys with ADHD.
2001 Jun
The development of selective attention in children with attention deficit hyperactivity disorder.
2001 Jun
Attention deficit hyperactivity disorder and substance use disorders: Is there a causal link?
2001 Jun
Effects of TENS and methylphenidate in tuberculous meningo-encephalitis.
2001 Jun
Explosive outbursts associated with methylphenidate.
2001 Jun
Practice parameters for the treatment of narcolepsy: an update for 2000.
2001 Jun 15
Stimulant effects in attention deficit hyperactivity disorder: theoretical and empirical issues.
2001 Mar
ADHD treatment in the 21st century: pushing the envelope.
2001 Mar
Tailored psychosocial treatments for ADHD: the search for a good fit.
2001 Mar
[Problem in methylphenidate use for the treatment of attention deficit hyperactivity disorder in Japan].
2001 Mar
[Prescription of central nervous system stimulants].
2001 Mar 20
Evidence and belief in attention deficit hyperactivity disorder. Reintroduction of methylphenidate in Italy needs careful monitoring.
2001 Mar 3
Methylphenidate improves HIV-1-associated cognitive slowing.
2001 Spring
Retrospective comparison of Adderall and methylphenidate in the treatment of attention deficit hyperactivity disorder.
2001 Spring
Depression with psychomotor retardation: diagnostic challenges and the use of psychostimulants.
2001 Spring
Methylphenidate augmentation of citalopram in elderly depressed patients.
2001 Summer
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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