CHEBI:6887 - methylphenidate

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ChEBI Name methylphenidate
ChEBI ID CHEBI:6887
Definition A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H19NO2
Roles Classification
Biological Role(s): adrenergic agent
Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Application(s): adrenergic agent
Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methylphenidate (CHEBI:6887) has part dexmethylphenidate (CHEBI:51860)
methylphenidate (CHEBI:6887) has part methyl (S)-phenyl[(S)-piperidin-2-yl]acetate (CHEBI:51857)
methylphenidate (CHEBI:6887) has role adrenergic agent (CHEBI:37962)
methylphenidate (CHEBI:6887) has role adrenergic uptake inhibitor (CHEBI:35640)
methylphenidate (CHEBI:6887) has role central nervous system stimulant (CHEBI:35337)
methylphenidate (CHEBI:6887) has role dopamine uptake inhibitor (CHEBI:51039)
methylphenidate (CHEBI:6887) has role psychotropic drug (CHEBI:35471)
methylphenidate (CHEBI:6887) has role sympathomimetic agent (CHEBI:35524)
methylphenidate (CHEBI:6887) is a racemate (CHEBI:60911)
methylphenidate (CHEBI:6887) is conjugate base of methylphenidate(1+) (CHEBI:51856)
Incoming methylphenidate(1+) (CHEBI:51856) is conjugate acid of methylphenidate (CHEBI:6887)
IUPAC Name
rac-methyl (2R)-phenyl[(2R)-piperidin-2-yl]acetate
INNs Sources
méthylphénidate WHO MedNet
methylphenidate KEGG DRUG
methylphenidatum ChemIDplus
metilfenidato ChemIDplus
Synonyms Sources
dl-threo-methylphenidate ChemIDplus
methyl rac-threo-α-phenyl-α-2-piperidinylacetate ChEBI
methyl rac-threo-phenidylacetate ChEBI
methylphenidan ChemIDplus
rac-threo-α-phenyl-2-piperidineacetic acid methyl ester ChEBI
rac-threo-methyl α-phenyl-α-(2-piperidyl)acetate ChEBI
threo-(±)-methylphenidate ChemIDplus
Brand Name Source
Daytrana KEGG DRUG
Database Links Databases
C07196 KEGG COMPOUND
D04999 KEGG DRUG
DB00422 DrugBank
HMDB0014566 HMDB
Methylphenidate Wikipedia
US2507631 Patent
US2957880 Patent
View more database links
Registry Numbers Types Sources
113-45-1 CAS Registry Number KEGG COMPOUND
113-45-1 CAS Registry Number NIST Chemistry WebBook
200061 Beilstein Registry Number Beilstein
200061 Reaxys Registry Number Reaxys
20748-11-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10786896 PubMed citation Europe PMC
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Last Modified
22 February 2017