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Ritalin

Product Name
Ritalin
CAS No.
113-45-1
Chemical Name
Ritalin
Synonyms
DEXMETHYLPHENIDATE;Rubifen;Phenidylate;Methylphenidan;methyl 2-phenyl-2-(piperidin-2-yl)acetate;alpha-Phenyl-2-piperidineacetic acid methyl ester;C07196;meridil;Calocain;4311/b Ciba
CBNumber
CB1874770
Molecular Formula
C14H19NO2
Formula Weight
233.31
MOL File
113-45-1.mol
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Ritalin Property

Melting point:
74.5°C
Boiling point:
327℃
Density 
1.070
refractive index 
1.5110 (estimate)
Flash point:
152℃
pka
9.51±0.10(Predicted)
CAS DataBase Reference
113-45-1
EPA Substance Registry System
2-Piperidineacetic acid, ?-phenyl-, methyl ester (113-45-1)
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Safety

Hazardous Substances Data
113-45-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 367mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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Ritalin Chemical Properties,Usage,Production

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.

Uses

Methylphenidate's mode of action is not completely known, but it is believed that ADHD symptoms are related to the dopaminergic areas of the brain. Animal studies indicate that methylphenidate affects several neurotransmitters to counteract ADHD behavior. Methylphenidate binds to dopamine transporters in the presynaptic neuron, blocking the reuptake of dopamine and increasing extracellular dopamine. Methylphenidate also infl uences norepinephrine reuptake and infl uences serotonin to a minor degree.
In addition to ADHD, methylphenidate is used for several other medical conditions.It continues to be used for narcolepsy. It has also been used in treating depression, especially in elderly populations. Methylphenidate has been suggested for use in the treatment of brain injury from stroke or brain trauma; it has also been suggested to improve appetite and the mood of cancer and HIV patients. Another use is for pain control and/or sedation for patients using opiates.
Health concerns are associated with the use of methylphenidate.Some of the commonly reported adverse effects associated with its use are insomnia, nervousness, hypertension, headache, anorexia, and tachycardia;less common effects include weight loss, nausea, and angina. Studies have indicated that methylphenidate lead to liver tumors in mice, but limited studies on its carcinogenicity in animals have not led the FDA to change recommendations on its use. Because methylphenidate is a stimulant and readily available, it has a potential for drug abuse.

Uses

Stimulant.

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.

brand name

Daytrana(Shire);4311 ciba;Centedrin;Cetedrin;Methidate;Ritalin sr;Ritaline.

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 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.

Ritalin Preparation Products And Raw materials

Raw materials

Preparation Products

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Ritalin Suppliers

113-45-1, RitalinRelated Search:


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