Compound: Dexmethylphenidate
SMILES: O=C(OC)[C@H](c1ccccc1)[C@@H]2NCCCC2
InChIKey: DUGOZIWVEXMGBE-CHWSQXEVSA-N
Synonyms: Dexmethylphenidate, d-threo-Methylphenidate, (+)-threo-Methylphenidate, dexmetilfenidato, 40431-64-9, Attenade, D-TMP, M32RH9MFGP, dexmethylphenidatum, methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate, CHEBI:51860, methyl (R)-phenyl[(R)-piperidin-2-yl]acetate, DTXSID70893769, methyl (2R)-phenyl[(2R)-piperidin-2-yl]acetate, 2-Piperidineacetic acid, alpha-phenyl-, methyl ester, (alphaR,2R)-, METHYL (2R)-PHENYL((2R)-PIPERIDIN-2-YL)ACETATE, methyl (R)-phenyl((R)-piperidin-2-yl)acetate, methyl (2R)-2-phenyl-2-((2R)-piperidin-2-yl)acetate, RefChem:56469, Methylphenidate d-threo-, N06BA11, DTXCID301323804, Dexmethylphenidate [INN], CHEMBL827, Methylphenidate d-threo-form, 40572-71-2, Focalin XR, Dexmethylphenidate (INN), Methyl D-phenidate, d-Methylphenidate, Dex methylphenidate, D-MPH, UNII-M32RH9MFGP, threo-(+)-Methylphenidate, dex-methylphenidate, d-threo methylphenidate, A1D5U, SCHEMBL34326, GTPL7554, DEXMETHYLPHENIDATE [VANDF], DEXMETHYLPHENIDATE [WHO-DD], BDBM50062915, PDSP1_000871, PDSP1_000903, PDSP2_000857, PDSP2_000889, DB06701, FT28256, METHYLPHENIDATE D-THREO-FORM [MI], NS00121152, D07806, Q1207210, (2S,2'S)-(-)-threo-methyl a-phenyl-a-(2-piperidyl)acetate hydrochloride, 2-Piperidineacetic acid, .alpha.-phenyl-, methyl ester, (.alpha.S,2S)-, 2-PIPERIDINEACETIC ACID, .ALPHA.-PHENYL-, METHYL ESTER, (.ALPHA.R,2R)-
Theoretical properties:
molecular_formula: C14H19NO2
molecular_weight: 233.31 g/mol
exact_mass: 233.141578849 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 17
topological_polar_surface_area: 38.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: >203
Descriptions:
pubchem: Dexmethylphenidate is a methyl phenyl(piperidin-2-yl)acetate in which both stereocentres have R configuration. It is the active enantiomer in the racemic drug methylphenidate. It has a role as an adrenergic agent. It is an enantiomer of a methyl (S)-phenyl[(S)-piperidin-2-yl]acetate.
chebi: A methyl phenyl(piperidin-2-yl)acetate in which both stereocentres have <i>R</i> configuration.  It is the active enantiomer in the racemic drug methylphenidate.
chembl: DEXMETHYLPHENIDATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dexmethylphenidate, sold under the brand name Focalin among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) in those over the age of five years. It is taken by mouth. The immediate-release formulation lasts up to five hours while the extended-release formulation lasts up to twelve hours. It is the more active enantiomer of methylphenidate. Methylphenidate has been shown to be more effective than atomoxetine and superior in treating ADHD symptoms when compared.  
Common side effects include abdominal pain, loss of appetite, and fever. Serious side effects may include psychosis, sudden cardiac death, mania, anaphylaxis, seizures, and priapism. Safety during pregnancy and breastfeeding is unclear.
Dexmethylphenidate was approved for medical use in the United States in 2001. It is available as a generic medication. In 2023, it was the 127th most commonly prescribed medication in the United States, with more than 4 million prescriptions.