| Identification | More | [Name]
Methylphenidate hydrochloride | [CAS]
298-59-9 | [Synonyms]
METHYLPHENIDATE HCL
METHYLPHENIDATE HYDROCHLORIDE
RITALIN HYDROCHLORIDE
2-piperidineaceticacid,alpha-phenyl-,methylester,hydrochloride
meridilhydrochloride
methylalpha-phenyl-2-piperidineacetatehydrochloride
methylphenidate hydrochloride methanol*solution
METHYLPHENIDATE HYDROCHLORIDE--DEA*SCHED
METHYLPHENIDATE HYDROCHLORIDE(RITALIN HYDROCHLORIDE)
Concerta
threo-methyl α-phenyl-α-(2-piperidyl)acetate hydrochloride
METHYLPHENIDATEHYDROCHLORIDE,USP
2-Piperidineacetic acid, a-phenyl-, methyl ester, hydrochloride (6CI, 8CI, 9CI)
Centedrin
Centedrine
Metadate CD
Methyl a-phenyl-2-piperidineacetate hydrochloride
NSC 169868
a-Phenyl-2-piperidineacetic Acid Methyl Ester Hydrochloride
Ciba 4311b | [EINECS(EC#)]
206-065-3 | [Molecular Formula]
C14H20ClNO2 | [MDL Number]
MFCD00058191 | [Molecular Weight]
269.77 | [MOL File]
298-59-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
196-198?C | [Fp ]
9℃ | [storage temp. ]
Store at RT | [solubility ]
Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride. | [form ]
Powder | [pka]
8.9(at 25℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, alkalies, barbiturates. | [Water Solubility ]
Soluble to 50 mM in water and to 100 mM in ethanol | [Usage]
Controlled substance (stimulant). CNS stimulant | [BCS Class]
2 | [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 | [SMILES]
C(C(=O)OC)(C1NCCCC1)C1C=CC=CC=1.Cl | [CAS DataBase Reference]
298-59-9(CAS DataBase Reference) | [EPA Substance Registry System]
298-59-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R42:May cause sensitization by inhalation. | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
TM3850000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Toxicity]
LD50 orally in mice: 190 mg/kg (Greenblatt, Osterberg) |
| Hazard Information | Back Directory | [General Description]
Odorless white crystalline powder. Metallic taste. Solutions are acid to litmus. Absence of general acid/base catalysis. | [Reactivity Profile]
METHYLPHENIDATE HYDROCHLORIDE(298-59-9) is incompatible with alkalis and solutions of barbiturates . Undergoes typical ester hydrolysis in aqueous solutions at 176°F. | [Air & Water Reactions]
Water soluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, METHYLPHENIDATE HYDROCHLORIDE is probably combustible. | [Chemical Properties]
white crystalline powder | [Originator]
Ritalin,Ciba,US,1958 | [Uses]
antiinflammatory | [Uses]
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-Methyl
phenidate exhibits the pharmacologically usually desired effects. | [Uses]
Methylphenidate (a.k.a., Ritalin) is a schedule II drug in the United States commonly used as a psychostimulant for the treatment of attention-deficit hyperactivity disorder. It blocks dopamine and norepinephrine transporters as well as facilitates NMDA-receptor mediated synaptic transmission through σ1 receptors via PLC/PKC signaling. This interaction with the σ1 receptor has been suggested to underlie methylphenidate’s considerable abuse potential and potential psychiatric side effects. This product is intended for forensic and biological research applications.[Cayman Chemical] | [Manufacturing Process]
As described in US Patent 2,507,631, 80 g of pulverized sodium amide are gradually added, while stirring and cooling, to a solution of 117 g of phenylacetonitrile and 113 g of 2-chloropyridine in 400 cc of absolute toluene. The mixture is then slowly heated to 110° to 120°C and maintained at this temperature for 1 hour. Water is added thereto after cooling, the toluene solution is shaken with dilute hydrochloric acid and the hydrochloric acid extracts are made alkaline with concentrated caustic soda solution. A solid mass is separated thereby which is taken up in acetic ester and distilled, αphenyl-α-pyridyl-(2)-acetonitrile passing over at 150° to 155°C under 0.5 mm pressure. When recrystallized from ethyl acetate it melts at 88° to 89°C, the
yield amounting to 135 g.
100 g of α-phenyl-α-pyridyl-(2)-acetonitrile are introduced into 400 cc of
concentrated sulfuric acid, allowed to stand overnight at room temperature,
poured into ice and rendered alkaline with sodium carbonate. α-Phenyl-αpyridyl-(2)-acetamide is precipitated thereby which melts at 134°C after
recrystallization from ethyl acetate.
100g of the resulting α-phenyl-α-pyridyl-(2)-acetamide, when dissolved in one
liter of methyl alcohol and treated for 6 hours at water-bath temperature with
hydrogen chloride, and after concentrating, diluting with water and rendering
alkaline with sodium carbonate, yield 90 g of the α-phenyl-α-pyridyl-(2)-acetic
acid methylester of MP 74° to 75°C (from alcohol of 50% strength).
The α-phenyl-α-piperidyl-(2)-acetic acid methylester of BP 135° to 137°C
under 0.6 mm pressure is obtained in theoretical yield by hydrogenation of 50
g of α-phenyl-α-pyridyl(2)-acetic acid methylester in glacial acetic acid in the
presence of 1 g of platinum catalyst at room temperature, while taking up 6
hydrogen atoms. Reaction with HCl gives the hydrochloride. Resolution of
stereoisomers is described in US Patent 2,957,880. | [Therapeutic Function]
Psychostimulant | [Biological Activity]
Psychomotor stimulant. Inhibitor of dopamine and noradrenalin transporters that increases the extracellular concentration of dopamine and noradrenalin. Increases locomotor activity in vivo . | [Veterinary Drugs and Treatments]
Methylphenidate may be useful for treating cataplexy/narcolepsy or
hyperactivity in dogs. | [storage]
Store at RT |
|