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

• ChemBase ID: 174114
• 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+;/m0./s1
• InChIKey: JUMYIBMBTDDLNG-JHEYCYPBSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 29419-97-4
• PubChem SID: 164230024
• PubChem CID: 10199290

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

DETAILS

Toronto Research Chemicals - M325676

Controlled substance. The erythro isomers have been shown to exhibit very little therapeutic effect and contribute mainly to the toxic hypertensive effects of this drug.

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.,