methyl 2-phenyl-2-(piperidin-2-yl)acetate hydrochloride

• ChemBase ID: 131110
• Molecular Formular: C14H20ClNO2
• Molecular Mass: 269.7671
• Monoisotopic Mass: 269.11825657
• SMILES: COC(=O)C(c1ccccc1)C1CCCCN1.Cl
• Canonical SMILES: COC(=O)C(c1ccccc1)C1CCCCN1.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
• InChIKey: JUMYIBMBTDDLNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-phenyl-2-(piperidin-2-yl)acetate hydrochloride
• IUPAC Traditional name: methylphenidate hydrochloride
• Synonyms: threo-Methyl α-phenyl-α-(2-piperidyl)acetate hydrochloride; Ritalin hydrochloride; Methylphenidate hydrochloride; α-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride; Methyl Phenidylacetate Hydrochloride; Methylphenidan Hydrochloride; Ciba 4311b; Centedrin; Centedrine; Concerta; Medikinet; Meridil; Metadate CD; NSC 169868; Ritalin SR; Methylphenidate Hydrochloride

Database IDs

• CAS Number: 298-59-9
• EC Number: 206-065-3
• MDL Number: MFCD00058191
• PubChem SID: 24896775; 162225388
• PubChem CID: 9280

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: 196-198°C

Safety Information

• Storage Condition: Controlled Substance, -20°C FreezerUnder Argon
• RTECS: TM3850000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H334
• GHS Precautionary statements: P261-P342 + P311
• 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

DETAILS

Sigma Aldrich - M2892

Biochem/physiol Actions
CNS stimulant; releases catecholamines; potent inhibitor of dopamine reuptake

Toronto Research Chemicals - M325880

Controlled substance (stimulant). CNS stimulant. Four isomers of Methylphenidate are known to exist. One pair of threo isomers and one pair of erythro are distinguished, from which only d-threo-Methylphenidate exhibits the pharmacologically usually desire

REFERENCES

• Greenblatt, E.N., et al.: J. Pharmacol. Exp. Ther., 131, 115 (1961)
• Padmanabhan, G.R., Anal. Profiles Drug Subs., 10, 473 (1961)
• Srinivas, N.R., et al.: Pharm. Res., 10, 14 (1961)