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
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
NET Hs Inhibitor Inhibition 7.2 pIC50 -
pIC50 7.2 (IC50 6.1x10-8 M)
DAT Hs Inhibitor Inhibition 7.1 pIC50 - 1
pIC50 7.1 (IC50 7.9x10-8 M) [1]