methylphenidate   

GtoPdb Ligand ID: 7236

Synonyms: Concerta® | Jornay PM® (a.k.a. HLD200) | Ritalin®
methylphenidate is an approved drug (FDA (1955))
Compound class: Synthetic organic
Comment: Methylphenidate is a racemic mixture of optical isomers (enantiomers). We show the chemical structure without specified stereochemistry to represent the mixture. The most active (R,R) enantiomer is the approved drug dexmethylphenidate. Methylphenidate is administered as the hydrochloride salt (PubChem CID 9280).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 38.33
Molecular weight 233.14
XLogP 2.5
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C(c1ccccc1)C1CCCCN1
Isomeric SMILES COC(=O)C(c1ccccc1)C1CCCCN1
InChI 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
InChI Key DUGOZIWVEXMGBE-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used alongside educational and psychosocial intervention to treat attention deficit hyperactivity disorder (ADHD) and to treat narcolepsy.
An extended release, chewable formulation of methylphenidate hydrochloride (QuilliChew ER) was approved by the US FDA in December 2015. Cotempla XR-ODT, an extended-release orally disintegrating methylphenidate-containing tablet was FDA approved for ADHD in June 2017.
Mechanism Of Action and Pharmacodynamic Effects
This drug blocks the reuptake of norepinephrine and dopamine into presynaptic neurons, resulting in increased levels of monoamines active in the extraneuronal space. Neurotransmitter reuptake is performed by the transporter proteins SLC6A3 (dopamine) and SLC6A2 (norepinephrine). As these neurotransmitters are involved in maintaining alertness and sustaining thought and motivation this action may underlie the clinical benefits in ADHD. However the full molecular mechanism of action remains to be fully resolved. See the DrugBank link for further details.
External links