| Identification | Back Directory | [Name]
Ritalin | [CAS]
113-45-1 | [Synonyms]
C07196
Rubifen
meridil
Calocain
4311/b Ciba
Phenidylate
Methylphenidan
Ritalin USP/EP/BP
DEXMETHYLPHENIDATE
OROS methylphenidate
Methyl phenidyl acetate
DUGOZIWVEXMGBE-UHFFFAOYSA-N
Methyl phenyl(2-piperidinyl)acetate
Methyl-α-phenyl-2-piperidineacetate
Methyl a-phenyl-a-2-piperidylacetate
Methyl a-phenyl-a-2-piperidinylacetate
methyl alpha-phenyl-2-piperidylacetate
Methyl alpha-phenyl-2-piperdine acetate
methyl 2-phenyl-2-(piperidin-2-yl)acetate
2-Piperidineacetic acid, α-phenylmethyl ester
a-Phenyl-2-piperidineacetic acid methyl ester
Methylphenidate (base and/or unspecified salts)
alpha-Phenyl-2-piperidineacetic acid methyl ester
2-phenyl-2-(2'-piperidyl)acetic acid Methyl ester
2-Piperidineacetic acid, .alpha.-phenyl-, methyl ester
methyl 2-phenyl-2-(piperidin-2-yl)acetate hydrochloride
2-Piperidineacetic acid, a-phenyl-, methyl ester (6CI, 8CI, 9CI) | [EINECS(EC#)]
204-028-6 | [Molecular Formula]
C14H19NO2 | [MOL File]
113-45-1.mol | [Molecular Weight]
233.306 |
| Hazard Information | Back Directory | [Uses]
Stimulant. | [Brand name]
Daytrana(Shire). | [Originator]
Ritalin,Ciba,US,1958 | [History]
Methylphenidate is a piperidine derivative that is a central nervous system stimulant. Methylphenidate, in its hydrochloride form, is the active ingredient in the common medication Ritalin. Methylphenidate was first synthesized from benzyl cyanide and 2-chloropyridine in Basel, Switzerland in 1944 by Ciba chemist Leandro Panizzon (1907 ?).
Panizzon named the substance Ritaline after his wife, whose nickname was Rita. Panizzon and Max Hartmann proposed an improved synthesis for methylphenidate and obtained a U.S. patent for its preparation in 1950 (U.S. Patent Number 2507631). In 1954, methylphenidate was patented for use as an agent for treating psychological disorders under the name Ritalin by the Ciba pharmaceutical company.(Ciba subsequently merged with the Geigy company to become Ciba-Geigy, and then Ciba-Geigy merged with Sandoz to form Novartis.) Methylphenidate was first used to reverse drug-induced coma. Ritalin was approved by the Food and Drug Administration (FDA) in 1955 and introduced in the United States in 1956 for several conditions including depression, senile behavior, lethargy, and narcolepsy.
Hyperactive children were first treated with stimulants in 1937. Since methylphenidate first appeared on the market, its use for treating ADHD has steadily increased. It is the most commonly used medication for treating children diagnosed with ADHD. | [Definition]
ChEBI: Methyl phenyl(piperidin-2-yl)acetate is a amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group. It is a member of piperidines, a methyl ester and a beta-amino acid ester. | [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 | [World Health Organization (WHO)]
Methylphenidate, a piperidine derivative with mild central
stimulant activity, was introduced in 1956. Its pharmacological properties resemble
those of amfetamines and it shares their abuse potential. Methylphenidate retains a
place as an adjunct in the treatment of hyperkinetic syndromes in both children
and adults. It is controlled under Schedule II of the 1971 Convention on
Psychotropic Substances.
(Reference: (UNCPS2) United Nations Convention on Psychotropic Substances (II),
, , 1971) |
| Safety Data | Back Directory | [Safety Profile]
Poison experimentally
by ingestion, intraperitoneal, intravenous,
and subcutaneous routes. Moderately toxic
to humans by intravenous route. Human
systemic effects by intravenous route:
dyspnea. An experimental teratogen. When
heated to decomposition it emits toxic
fumes of NOx. | [Hazardous Substances Data]
113-45-1(Hazardous Substances Data) | [Toxicity]
LD50 oral in rat: 367mg/kg |
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