2-Piperidinessigsäure-alpha-phenyl-methylester-hydrochlorid

Bezeichnung:2-Piperidinessigsäure-alpha-phenyl-methylester-hydrochlorid

CAS-Nr298-59-9

Englisch Name:Methylphenidate hydrochloride

CBNumberCB0188559

SummenformelC14H20ClNO2

Molgewicht269.77

MOL-Datei298-59-9.mol

Synonyma

Methylphenidathydrochlorid

2-Piperidinessigsäure-alpha-phenyl-methylester-hydrochlorid

2-Piperidinessigsäure-alpha-phenyl-methylester-hydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	196-198?C
Flammpunkt	9℃
storage temp.	Store at RT
Löslichkeit	Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
Aggregatzustand	Powder
pka	8.9(at 25℃)
Wasserlöslichkeit	Soluble to 50 mM in water and to 100 mM in ethanol
BCS Class	2
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents, alkalies, barbiturates.
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 Datenbank	298-59-9(CAS DataBase Reference)
EPA chemische Informationen	Methylphenidate hydrochloride (298-59-9)

Sicherheit

Kennzeichnung gefährlicher	Xn,T,F
R-Sätze:	22-42-39/23/24/25-23/24/25-11
S-Sätze:	22-26-36-45-36/37-16
RIDADR	3249
WGK Germany	3
RTECS-Nr.	TM3850000
HazardClass	6.1(b)
PackingGroup	III
Toxizität	LD50 orally in mice: 190 mg/kg (Greenblatt, Osterberg)

Gefahreninformationscode (GHS)

Methylphenidate hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R42:Sensibilisierung durch Einatmen möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white crystalline powder
Originator
Ritalin,Ciba,US,1958
Verwenden
antiinflammatory
Verwenden
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]
Verwenden
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.
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
Allgemeine Beschreibung
Because methylphenidate (Ritalin) has two asymmetriccenters, there are four possible isomers. The threo racemateis the marketed compound and is about 400 times aspotent as the erythro racemate.The absolute configurationof each of the threo-methylphenidate isomers has beendetermined.Considering that the structure is fairly complex(relative to amphetamine), it is likely that one of thetwo components of the threo racemate contains most of theactivity. Evidence indicates that the (+) -(2R,2'R)threoisomer is involved principally in the behavioral andpressor effects of the racemate.As is likely with many central psychomotor stimulants, there are multiple modesof action.
Methylphenidate, probably largely via its p-hydroxymetabolite, blocks NE reuptake, acts as a postsynapticagonist, depletes the same NE pools as reserpine, and haseffects on dopaminergic systems, such as blocking DAreuptake.
Methylphenidate is a potent CNS stimulant. Indicationsinclude narcolepsy and attention-deficit disorder.
Allgemeine Beschreibung
Odorless white crystalline powder. Metallic taste. Solutions are acid to litmus. Absence of general acid/base catalysis.
Air & Water Reaktionen
Water soluble.
Reaktivität anzeigen
Methylphenidate hydrochloride is incompatible with alkalis and solutions of barbiturates . Undergoes typical ester hydrolysis in aqueous solutions at 176°F.
Brandgefahr
Flash point data for Methylphenidate hydrochloride are not available; however, Methylphenidate hydrochloride is probably combustible.
Biologische Aktivität
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.
Lager
Store at RT

Methylphenidate hydrochloride Upstream-Materialien And Downstream Produkte

2-Piperidinessigsäure-alpha-phenyl-methylester-hydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

298-59-9, Methylphenidate hydrochloride Verwandte Suche:

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