298-59-9 Usage
Description
Methylphenidate hydrochloride, commonly known as Ritalin, is a potent central nervous system (CNS) stimulant that is primarily used for the treatment of attention-deficit hyperactivity disorder (ADHD). It is a white, odorless crystalline powder with a metallic taste, and its solutions are acidic. Methylphenidate has two asymmetric centers, resulting in four possible isomers, with the threo racemate being the marketed compound. It is a schedule II controlled substance in the United States due to its potential for abuse and psychiatric side effects.
Uses
1. Used in Pharmaceutical Industry:
Methylphenidate hydrochloride is used as a psychostimulant for the treatment of attention-deficit hyperactivity disorder (ADHD). It works by blocking dopamine and norepinephrine transporters, as well as facilitating 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.
2. Used in Narcolepsy Treatment:
Methylphenidate hydrochloride is also used as a potent CNS stimulant for the treatment of narcolepsy, a sleep disorder characterized by excessive daytime sleepiness and sudden episodes of sleep.
3. Used in Anti-Inflammatory Applications:
Although not explicitly mentioned in the provided materials, Methylphenidate hydrochloride has been studied for its potential anti-inflammatory properties, which could be useful in various medical applications.
4. Used in Forensic and Biological Research:
Methylphenidate hydrochloride is used in forensic and biological research applications, likely due to its complex structure and multiple modes of action, which can provide valuable insights into the mechanisms of CNS stimulants and their effects on the brain.
Therapeutic Function
Psychostimulant
Air & Water Reactions
Water soluble.
Reactivity Profile
Methylphenidate hydrochloride is incompatible with alkalis and solutions of barbiturates . Undergoes typical ester hydrolysis in aqueous solutions at 176°F.
Fire Hazard
Flash point data for Methylphenidate hydrochloride are not available; however, Methylphenidate hydrochloride is probably combustible.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 298-59-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 8 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 298-59:
(5*2)+(4*9)+(3*8)+(2*5)+(1*9)=89
89 % 10 = 9
So 298-59-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H19NO2/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/t12-,13+/m0/s1
298-59-9Relevant articles and documents
Changing stereoselectivity and regioselectivity in copper(i)-catalyzed 5-: Exo cyclization by chelation and rigidity in aminoalkyl radicals: Synthesis towards diverse bioactive N-heterocycles
Sadanandan, Sandhya,Gupta, Dharmendra Kumar
, p. 3350 - 3365 (2020/03/06)
The work reveals that a chelate-Type interaction in the transition state of a β-Aminoalkyl radical in a copper(i)-catalyzed 5-exo-Trig radical cyclization step changes the usual stereochemistry of the NH-pyrrolidine ring predicted by the Beckwith-Houk transition state model. In contrast, the rigidity in the fused β-Aminoalkyl radical changes the Baldwin's predicted 5-exo to 6-endo cyclization mode, preferentially forming a piperidine ring over a pyrrolidine ring via a geometrically constrained transition state. The resultant diverse NH-pyrrolidines, pyrrolines and piperidines are sources of the bioactive natural product roseophilin and the drug Ritalin among others.
IMPROVEMENTS IN OR RELATING TO ORGANIC MATERIAL
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Paragraph 0056; 0057, (2018/04/13)
The invention provides a method for the preparation of an intermediate for use in synthesizing a lower alkyl phenidate compound of formula (I), wherein each R1 independently represents an optionally substituted aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, acyl, carboxyl, hydroxyl, halogen, amino, nitro, sulfo or sulfhydryl group, R2 represents a hydrogen atom or a lower alkyl group, n represents an integer from 1 to 5 and m represents an integer from 1 to 3 or a pharmaceutically acceptable salt thereof; which method comprises the steps of: (a) flowing a tosylhydrazone compound of formula (IV), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I), an organic base and an organic solvent into a fluidic network; and (b) reacting the tosylhydrazone compound of formula (IV) and the base in the fluidic network under thermal and/or photochemical conditions to form a transient diazoamide compound of formula (V), wherein R1, n and m are as defined above in relation to the methylphenidate of formula (I).
LOW-TEMPERATURE SYNTHESIS OF METHYLPHENIDATE HYDROCHLORIDE
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Page/Page column 25, (2012/06/30)
The present invention describes a process for the preparation of methylphenidate hydrochloride. The process involves the esterification of ritalinic acid and methanol in the presence of an acid catalyst at a low temperature. The process may optionally involve the addition of an orthoester.
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