methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate hydrochloride

• ChemBase ID: 174113
• Molecular Formular: C14H20ClNO2
• Molecular Mass: 269.7671
• Monoisotopic Mass: 269.11825657
• SMILES: C1CN[C@H](CC1)[C@@H](c1ccccc1)C(=O)OC.Cl
• Canonical SMILES: COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1.Cl
• InChI: InChI=1S/C14H19NO2.ClH/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;1H/t12-,13-;/m1./s1
• InChIKey: JUMYIBMBTDDLNG-OJERSXHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate hydrochloride
• IUPAC Traditional name: dexmethylphenidate hydrochloride
• Synonyms: (2R,2’R)-(+)-threo-Methyl α-Phenyl-α-(2-piperidyl)acetate Hydrochloride; (αR,2R)-α-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride; Dexmethylphenidate Hydrochloride; Focalin; d-Ritalin Hydrochloride; D-threo-Methylphenidate Hydrochloride

Database IDs

• CAS Number: 19262-68-1
• PubChem SID: 164230023
• PubChem CID: 154100

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.8258359
• LogD (pH = 7.4): 0.5692904
• Log P: 2.254935
• Molar Refractivity: 66.7282 cm^3
• Polarizability: 26.621723 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - M325675

Controlled substance. CNS stimulant. The more potent isomers of Methylphenidate. The threo enantomers have shown that the pharmacological activity residues predominantly in the d-threo enantiomer.

REFERENCES

• Greenblatt, E.N., et al.: J. Pharmacol. Exp. Ther., 131, 115 (1961)
• Padmanabhan, G.R., et al.: Anal. Profiles Drug Subs., 10, 473 (1961)
• Kuczenski, R., et al.: J. Pharmacol. Exp. Ther., 296, 876 (1961)
• Pelham, W.E., et al.: J. Consult. Clin. Psychol.,