METHYLPHENIDATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H19NO2
Molecular Weight	233.3062
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DUGOZIWVEXMGBE-STQMWFEESA-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-/m0/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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/010187s087lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25120227

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

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent dopamine transporter 42 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25120227	Blocker 534

Conditions

Condition	Modality	Targets	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/010187s087lbl.pdf	Primary		Approved 8360	RITALIN Approved Use Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy. Launch Date -4.62153613E11
Narcolepsy 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/010187s087lbl.pdf	Primary		Approved 8360	RITALIN Approved Use Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy. Launch Date -4.62153613E11

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Doses

Dose	Population	Adverse events
700 mg multiple, oral Studied dose Dose: 700 mg Route: oral Route: multiple Dose: 700 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12444349/ https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010187s091,018029s059lbl.pdf	unhealthy, 45 years n = 1 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorders Age Group: 45 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12444349/ https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010187s091,018029s059lbl.pdf	Other AEs: Abuse... Other AEs: Abuse Sources: https://pubmed.ncbi.nlm.nih.gov/12444349/ https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/010187s091,018029s059lbl.pdf
210 mg 1 times / day single, oral Studied dose Dose: 210 mg, 1 times / day Route: oral Route: single Dose: 210 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20158630/	unhealthy, 8 years n = 1 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorders Age Group: 8 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20158630/	Other AEs: Hypertension, Tachycardia... Other AEs: Hypertension (grade 1) Tachycardia (grade 1) Confusion Irritability Agitation Hallucinations Sources: https://pubmed.ncbi.nlm.nih.gov/20158630/
15 mg 2 times / day single, oral (mean) Recommended Dose: 15 mg, 2 times / day Route: oral Route: single Dose: 15 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15	healthy, mean age 30 years n = 61 Health Status: healthy Age Group: mean age 30 years Sex: M+F Population Size: 61 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15	Disc. AE: Headache, Nausea... AEs leading to discontinuation/dose reduction: Headache (1.6%) Nausea (1.6%) Hot flushes (1.6%) Panic attack (1.6%) Nausea (1.6%) Vomiting (1.6%) Dizziness (1.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15
12.5 mg 2 times / day multiple, oral (mean) Recommended Dose: 12.5 mg, 2 times / day Route: oral Route: multiple Dose: 12.5 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15	unhealthy, median age 9 years n = 65 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorders Age Group: median age 9 years Sex: M+F Population Size: 65 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15	Disc. AE: Fatigue, Lethargy... AEs leading to discontinuation/dose reduction: Fatigue (1.5%) Lethargy (1.5%) Hypomania (1.5%) Anger (1.5%) Anxiety (1.5%) Migraine (1.5%) Depression (1.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-284_Ritalin%20LA_medr.pdf Page: nda/2002/21-284_Ritalin%20LA_medr.pdf - p.15

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1752	inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2C8 901 CYP2C19 1463 CYP2E1 876 CYP3A 211	CYP450 65

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP3A 295	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 65	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 Sources: https://pubmed.ncbi.nlm.nih.gov/19281853/

Sourcing

Vendor/Aggregator	ID	URL
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
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
mcule	MCULE-3118022991
mcule	MCULE-3797509037
mcule	MCULE-5458926987

PubMed

Title	Date	PubMed


Evidence for a direct cholinergic involvement in the scopolamine-induced amnesia in monkeys: effects of concurrent administration of physostigmine and methylphenidate with scopolamine.	1978 Dec	106402
[Methylphenidate, tics and compulsions].	2000 Mar-Apr	10858915
Pharmacotherapeutic management of autism.	2001 Apr	11336609
Understanding Rx options for the youngest patients.	2001 Aug	11496582
Concerns about Ritalin.	2001 Aug	11487772
A randomized, double-blind, placebo-controlled trial of psychostimulants for the treatment of fatigue in ambulatory patients with human immunodeficiency virus disease.	2001 Feb 12	11176767
Drugs used in the treatment of attention-deficit/hyperactivity disorder affect postsynaptic firing rate and oscillation without preferential dopamine autoreceptor action.	2001 Feb 15	11239905
Benefit of long-term stimulants on driving in adults with ADHD.	2001 Jan	11206669
[Methylphenidate therapy in 141 patients with hyperkinetic disorder or with pervasive developmental disorder and hyperkinesia].	2001 Jul	11494575
Stimulant drugs for severe hyperactivity in childhood.	2001 Jul	11471516
Correlations between motor persistence and plasma levels in methylphenidate-treated boys with ADHD.	2001 Jun	11466170
Effect of repeated methylphenidate administration on presynaptic dopamine and behaviour in young adult rats.	2001 Jun	11448090
Comparison in symptoms between aged and younger patients with narcolepsy.	2001 Jun	11422857
Practice parameters for the treatment of narcolepsy: an update for 2000.	2001 Jun 15	11403530
Commentary on Greene and Ablon: What does the MTA study tell us about effective psychosocial treatment for ADHD?	2001 Mar	11482297
Comprehensive versus matched psychosocial treatment in the MTA study: conceptual and empirical issues.	2001 Mar	11294072
Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers.	2001 Mar	11229977
Locomotor effects of acute and repeated threshold doses of amphetamine and methylphenidate: relative roles of dopamine and norepinephrine.	2001 Mar	11181919
[Neuropsychological follow-up of attention deficit/hyperactive disorder in adulthood before and after treatment with methylphenidate].	2001 May	11428307
[Is Ritalin prescribed insufficiently to hyperactive children in Nordland?].	2001 May 30	11446022
Emergence of tics in children with attention deficit hyperactivity disorder treated with stimulant medications.	2001 May-Jun	11349243
Retrospective comparison of Adderall and methylphenidate in the treatment of attention deficit hyperactivity disorder.	2001 Spring	11322743
Methylphenidate augmentation of citalopram in elderly depressed patients.	2001 Summer	11481139
Pharmacokinetic interactions between cyclosporine and bupropion or methylphenidate.	2001 Summer	11436960
Efficacy of Adderall and methylphenidate in attention deficit hyperactivity disorder: a reanalysis using drug-placebo and drug-drug response curve methodology.	2001 Summer	11436957

Patents

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 `Wed Jul 05 23:43:33 UTC 2023` Edited by `admin` on `Wed Jul 05 23:43:33 UTC 2023`
Record UNII	207ZZ9QZ49
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYLPHENIDATE

Official Name

English

METHYLPHENIDATE [VANDF]

Common Name

English

α-Phenyl-2-piperidineacetic acid methyl ester

Systematic Name

English

METHYLPHENIDATE [ORANGE BOOK]

Common Name

English

methylphenidate [INN]

Common Name

English

METHYLPHENIDATE EXTENDED RELEASE

Common Name

English

2-PIPERIDINEACETIC ACID, .ALPHA.-PHENYL-, METHYL ESTER

Common Name

English

METHYLPHENIDATE [HSDB]

Common Name

English

PRC-063

Common Name

English

THREO-DL-METHYLPHENIDATE

Common Name

English

COTEMPLA XR-ODT

Brand Name

English

Methylphenidate [WHO-DD]

Common Name

English

DAYTRANA

Brand Name

English

METHYLPHENIDATE [MI]

Common Name

English

METHYLPHENIDATE [MART.]

Common Name

English

METHYLPHENIDATE [II]

Common Name

English

METHYLPHENIDATE [USAN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK547941