298-59-9 Usage
Chemical Properties
white crystalline powder
Uses
Different sources of media describe the Uses of 298-59-9 differently. You can refer to the following data:
1. antiinflammatory
2. 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.
3. 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]
Therapeutic Function
Psychostimulant
General Description
Different sources of media describe the General Description of 298-59-9 differently. You can refer to the following data:
1. 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.
2. Odorless white crystalline powder. Metallic taste. Solutions are acid to litmus. Absence of general acid/base catalysis.
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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