METHYLPHENIDATE HYDROCHLORIDE

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

Structure Search

SMILES

Cl.[H][C@@]1(CCCCN1)[C@H](C(=O)OC)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

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 537

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 8429	RITALIN Approved Use Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy. Launch Date 1955
Narcolepsy 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/010187s087lbl.pdf	Primary		Approved 8429	RITALIN Approved Use Ritalin is indicated for the treatment of Attention Deficit Disorders and Narcolepsy. Launch Date 1955

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 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C8 911 CYP2C19 1478 CYP2E1 882 CYP3A 214	CYP450 65

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021284s020lbl.pdf#page=10 Page: 10.0	no
CYP3A 298	inhibitor 3277 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 3367 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 1647	inhibitor 1626 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
Atrioventricular nodal re-entrant tachycardia associated with stimulant treatment.	1999	10461823
Cocaine-seeking produced by experimenter-administered drug injections: dose-effect relationships in rats.	1999 Dec	10639687
Haplotype relative risk study of catechol-O-methyltransferase (COMT) and attention deficit hyperactivity disorder (ADHD): association of the high-enzyme activity Val allele with ADHD impulsive-hyperactive phenotype.	1999 Oct 15	10490706
Cocaine-associated stroke: three cases and rehabilitation considerations.	2000 Apr	10815846
A pilot study of methylphenidate, clonidine, or the combination in ADHD comorbid with aggressive oppositional defiant or conduct disorder.	2000 Jan	10660814
Blockade of sensitization to methylphenidate by MK-801: partial dissociation from motor effects.	2001	11114409
Toward individualized evidence-based medicine: five "N of 1" trials of methylphenidate in geriatric patients.	2001 Apr	11347795
Understanding Rx options for the youngest patients.	2001 Aug	11496582
Concerns about Ritalin.	2001 Aug	11487772
Methylphenidate increased regional cerebral blood flow in subjects with attention deficit/hyperactivity disorder.	2001 Feb	11293498
Impairment and deportment responses to different methylphenidate doses in children with ADHD: the MTA titration trial.	2001 Feb	11211366
Treatment of attention-deficit hyperactivity disorder.	2001 Jan	11237228
Benefit of long-term stimulants on driving in adults with ADHD.	2001 Jan	11206669
Decreased level of EEG-vigilance in acute mania as a possible predictor for a rapid effect of methylphenidate: a case study.	2001 Jan	11202141
Therapeutic doses of oral methylphenidate significantly increase extracellular dopamine in the human brain.	2001 Jan 15	11160455
Questioning the treatment for ADHD.	2001 Jan 26	11229399
[Methylphenidate therapy in 141 patients with hyperkinetic disorder or with pervasive developmental disorder and hyperkinesia].	2001 Jul	11494575
Advances in paediatric neuropsychopharmacology: an overview.	2001 Jun	11466164
Comparison in symptoms between aged and younger patients with narcolepsy.	2001 Jun	11422857
Psychosocial treatment issues in the MTA: a reply to Greene and Ablon.	2001 Mar	11294071
What does the MTA study tell us about effective psychosocial treatment for ADHD?	2001 Mar	11294069
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes.	2001 Mar	11248372
Near-fatal methylphenidate misuse.	2001 Mar	11230045
Association of dopamine transporter reduction with psychomotor impairment in methamphetamine abusers.	2001 Mar	11229977
alpha(2C)-Adrenoceptors modulate the effect of methylphenidate on response rate and discrimination accuracy in an operant test.	2001 Mar 15	11397547
Evidence and belief in attention deficit hyperactivity disorder. Reintroduction of methylphenidate in Italy needs careful monitoring.	2001 Mar 3	11263458
[Neuropsychological follow-up of attention deficit/hyperactive disorder in adulthood before and after treatment with methylphenidate].	2001 May	11428307
An auditable protocol for treating attention deficit/hyperactivity disorder.	2001 May	11316683
Methylphenidate for fatigue in advanced cancer: a prospective open-label pilot study.	2001 May-Jun	11406895
Methylphenidate in stimulants abuse: three case reports.	2001 Spring	11444161
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

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.

Name

Type

Language

METHYLPHENIDATE HYDROCHLORIDE

Common Name

English

METHYLIN

Brand Name

English

QUILLIVANT

Brand Name

English

APTENSIO

Brand Name

English

QUILLICHEW

Brand Name

English

Methyl α-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

ADHANSIA XR

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