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

• ChemBase ID: 153533
• Molecular Formular: C14H20ClNO2
• Molecular Mass: 269.7671
• Monoisotopic Mass: 269.11825657
• SMILES: COC(=O)[C@@H](c1ccccc1)[C@@H]1CCCCN1.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)-piperidin-2-yl]acetate hydrochloride
• IUPAC Traditional name: methyl (2S)-2-phenyl-2-[(2S)-piperidin-2-yl]acetate hydrochloride
• Synonyms: (αR,2R)-rel-α-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride; (R*,R*)-(+/-)-α-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride; Methyl threo-α-Phenyl-α-(2-piperidyl)acetate Hydrochloride; dl-threo-Methylphenidate Hydrochloride; rac-threo-Methylphenidate Hydrochloride; (2S,2’S)-(-)-threo-Methyl α-Phenyl-α-(2-piperidyl)acetate Hydrochloride; (αS,2S)-α-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride; (-)-threo-Methylphenidate Hydrochloride; L-threo-Methylphenidate Hydrochloride; (2S,2′S)-(-)-threo-Methyl α-phenyl-α-(2-piperidyl)acetate hydrochloride; L-Ritalin hydrochloride; L-threo-Methylphenidate hydrochloride

Database IDs

• CAS Number: 29419-95-2; 40572-71-2; 23655-65-4
• MDL Number: MFCD08690557
• PubChem SID: 162247672
• PubChem CID: 45259401

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: H2O: soluble32 mg/mL; Methanol; Water
• Apperance: white solid; White Solid
• Melting Point: 224-226°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C14H19NO2 · HCl

DETAILS

Sigma Aldrich - M6935

Biochem/physiol Actions
Central nervous system stimulant. Less potent enantiomer.

Toronto Research Chemicals - M325671

Controlled substance. The threo enantomers have shown that the pharmacological activity residues predominantly in the d-threo enantiomer.

Toronto Research Chemicals - M325680

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

REFERENCES

• Pelham, W.E., et al.: J. Consult. Clin. Psychol.,
• 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)
• 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.,