methyl (2S)-2-phenyl-2-[(2S)-(2,3,3,4,4,5,5,6,6-2H9)piperidin-2-yl](2H)acetate hydrochloride

• ChemBase ID: 174112
• Molecular Formular: C14H20ClNO2
• Molecular Mass: 269.7671
• Monoisotopic Mass: 269.11825657
• SMILES: C1CC[C@H](NC1)[C@@H](C(=O)OC)c1ccccc1.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-QNTKWALQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-phenyl-2-[(2S)-(2,3,3,4,4,5,5,6,6-^2H₉)piperidin-2-yl](^2H)acetate hydrochloride
• IUPAC Traditional name: methyl (2S)-2-phenyl-2-[(2S)-(2,3,3,4,4,5,5,6,6-^2H₉)piperidin-2-yl](^2H)acetate hydrochloride
• Synonyms: (αR,2R)-rel-α-Phenyl-2-piperidineacetic Acid-d10 Methyl Ester Hydrochloride; (R*,R*)-(+/-)-α-Phenyl-2-piperidineacetic Acid-d10 Methyl Ester Hydrochloride; Methyl threo-α-Phenyl-α-(2-piperidyl-d10)acetate Hydrochloride; dl-threo-Methylphenidate-d10 Hydrochloride; rac-threo-Methylphenidate-d10 Hydrochloride

Database IDs

• PubChem SID: 164230022
• PubChem CID: 71750521

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: 26.622828 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: Off-White Solid
• Melting Point: 219-220°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M325673

Controlled substance. Labelled DL-threo-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.,