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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H19NO2
Molecular Weight 233.3062
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXMETHYLPHENIDATE

SMILES

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

InChI

InChIKey=DUGOZIWVEXMGBE-CHWSQXEVSA-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-/m1/s1

HIDE SMILES / InChI

Description

Dexmethylphenidate is the dextrorotary form of methylphenidate. Dexmethylphenidate is marketed under the trade name Focalin. Focalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threoenantiomers. Focalin is a central nervous system (CNS) stimulant, available in three tablet strengths. Each tablet contains dexmethylphenidate hydrochloride 2.5, 5, or 10 mg for oral administration. Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment. Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
161.0 nM [Ki]
206.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FOCALIN

Cmax

ValueDoseCo-administeredAnalytePopulation
23.72 ng/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
22.13 ng/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
10.7 ng/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
120.9 ng × h/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
131.9 ng × h/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
79.8 ng × h/mL
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.68 h
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
2.81 h
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens
3.3 h
20 mg single, oral
DEXMETHYLPHENIDATE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Focalin (Dexmethylphenidate) is administered twice daily, at least 4 hours apart. Focalin may be administered with or without food. The recommended starting dose of Focalin for patients who are not currently taking racemic methylphenidate, or for patients who are on stimulants other than methylphenidate, is 5 mg/day (2.5 mg twice daily). Dosage may be adjusted in 2.5 to 5 mg increments to a maximum of 20 mg/day (10 mg twice daily). In general, dosage adjustments may proceed at approximately weekly intervals.
Route of Administration: Oral
In Vitro Use Guide
Dexmethylphenidate inhibition [3H]dopamine uptake at human DAT expressed in mouse N2A cells with IC50 156 nM.