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

• ChemBase ID: 168746
• Molecular Formular: C15H22ClNO2
• Molecular Mass: 283.79368
• Monoisotopic Mass: 283.13390663
• SMILES: C1CC[C@H](NC1)[C@@H](C(=O)OCC)c1ccccc1.Cl
• Canonical SMILES: CCOC(=O)[C@@H](c1ccccc1)[C@@H]1CCCCN1.Cl
• InChI: InChI=1S/C15H21NO2.ClH/c1-2-18-15(17)14(12-8-4-3-5-9-12)13-10-6-7-11-16-13;/h3-5,8-9,13-14,16H,2,6-7,10-11H2,1H3;1H/t13-,14-;/m0./s1
• InChIKey: ZNSNAOXTBUHNKX-IODNYQNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-phenyl-2-[(2S)-piperidin-2-yl]acetate hydrochloride
• IUPAC Traditional name: ethyl (2S)-2-phenyl-2-[(2S)-piperidin-2-yl]acetate hydrochloride
• Synonyms: (αS,2S)-α-Phenyl-2-piperidineacetic Acid Ethyl Ester Hydrochloride; L-threo-Ethylphenidate Hydrochloride; (αR,2R)-rel-α-Phenyl-2-piperidineacetic Acid Ethyl Ester Hydrochloride; rac-threo-Ethylphenidate Hydrochloride

Database IDs

• CAS Number: 851764-85-7; 214149-46-9
• PubChem SID: 162262878
• PubChem CID: 11358065

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.4690254
• LogD (pH = 7.4): 0.9261061
• Log P: 2.611743
• Molar Refractivity: 71.4768 cm^3
• Polarizability: 28.465498 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E925630

The threo isomer of Ethylphenidate, a metabolite of Methylphenidate (M325680). threo-Ethylphenidate is formed by metabolic transesterification of Methylphenidate and ethanol.

Toronto Research Chemicals - E925636

The L-threo isomer of Ethylphenidate, a metabolite of Methylphenidate (M325680). L-threo-Ethylphenidate is formed by metabolic transesterification of Methylphenidate and ethanol.

REFERENCES

• Froimowitz, M. et al.: Struct. Chem., 9, 295 (1998)
• Froimowitz, M. et al.: Struct. Chem., 9, 295 (1998)
• Patrick, K. et al.: J. Med. Chem., 48, 2876 (1998)