CAS 298-59-9|methyl 2-phenyl-2-(piperidin-2-yl)acetate hydrochloride|Ritalin hydrochloride|Methylphenidate hydrochloride|threo-Methyl α-phenyl-α-(2-piperidyl)acetate hydrochloride|methylphenidate ...

Molecular Formula

C₁₄H₂₀ClNO₂

Molecular Mass

269.7671

Exact Mass

269.11825657

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

Canonic Smiles

COC(=O)C(c1ccccc1)C1CCCCN1.Cl

Isomeric Smiles

COC(=O)C(c1ccccc1)C1CCCCN1.Cl

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.8258359

LogD (pH = 7.4)

0.5692904

Log P

2.254935

Molar Refractivity

66.7282

Polarizability

26.621723

Polar Surface Area

38.33

Rotatable Bonds

Lipinski's Rule of Five

true

Commercial Catalog

Academic Data

IUPAC name

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

Synonyms

Methylphenidate hydrochlorideRitalin hydrochloridethreo-Methyl α-phenyl-α-(2-piperidyl)acetate hydrochlorideNSC 169868Methylphenidate HydrochlorideCiba 4311bMethyl Phenidylacetate HydrochlorideConcertaCentedrinCentedrineMetadate CDMedikinetMeridilRitalin SRα-Phenyl-2-piperidineacetic Acid Methyl Ester HydrochlorideMethylphenidan Hydrochloride

IUPAC Traditional name

methylphenidate hydrochloride

MDL Number

MFCD00058191

PubChem SID

24896775162225388

Drug Control

USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

RTECS

TM3850000

Safety Statements

22-26-36

European Hazard Symbols

Harmful (Xn)

GHS Signal Word

Danger

GHS Precautionary statements

P261-P342+P311

GHS Pictograms

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

German water hazard class

GHS Hazard statements

H302-H334

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Risk Statements

22-42

Storage Condition

Controlled Substance, -20°C FreezerUnder Argon

MSDS Link

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Physical Property

Solubility

Methanol

Water

Apperance

White Solid

Melting Point

196-198°C

Product Information

Certificate of Analysis

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Sigma Aldrich

M2892

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

TRC

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

From Data Sources

• Padmanabhan, G.R., Anal. Profiles Drug Subs., 10, 473 (1961)

• Greenblatt, E.N., et al.: J. Pharmacol. Exp. Ther., 131, 115 (1961)

• Srinivas, N.R., et al.: Pharm. Res., 10, 14 (1961)