dexmethylphenidate   Click here for help

GtoPdb Ligand ID: 7554

Synonyms: Attenade® | D-TMP | Focalin®
Approved drug
dexmethylphenidate is an approved drug (FDA (2001))
Compound class: Synthetic organic
Comment: Dexmethylphenidate is a phenethylamine and piperidine class central nervous system stimulant. Chemically, it is the active dextrorotatory (R,R) enantiomer of racemic methylphenidate.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
Canonical SMILES COC(=O)C(c1ccccc1)C1CCCCN1
Isomeric SMILES COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1
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/t12-,13-/m1/s1
1. Kim DI, Deutsch HM, Ye X, Schweri MM. (2007)
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate.
J Med Chem, 50 (11): 2718-31. [PMID:17489581]
2. Lapinsky DJ, Velagaleti R, Yarravarapu N, Liu Y, Huang Y, Surratt CK, Lever JR, Foster JD, Acharya R, Vaughan RA et al.. (2011)
Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.
Bioorg Med Chem, 19 (1): 504-12. [PMID:21129986]