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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 of METHYLPHENIDATE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RITALIN
Primary
RITALIN

Cmax

ValueDoseCo-administeredAnalytePopulation
3.7 ng/mL
18 mg single, oral
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
41.8 ng × h/mL
18 mg single, oral
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
18 mg single, oral
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
unknown, unknown
METHYLPHENIDATE HYDROCHLORIDE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

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
Record UNII
207ZZ9QZ49
Record Status Validated (UNII)
Record Version