Ritalin

Ritalin is the brand name for methylphenidate, a synthetic central nervous system stimulant.

• Chemical name (IUPAC):
  Methyl 2-phenyl-2-(piperidin-2-yl)acetate
• Molecular formula:
  C₁₄H₁₉NO₂
• Molar mass:
  233.31 g/mol

Chemical class

• Piperidine derivative
• Phenylacetate ester
• Synthetic stimulant

Key structural features

• A piperidine ring (six-membered nitrogen-containing heterocycle)
• A phenyl (benzene) ring
• A methyl ester group
• A chiral carbon linking the phenyl and piperidine portions of the molecule

Functional groups

• Ester (–COOCH₃)
• Secondary amine (within the piperidine ring)
• Aromatic phenyl ring

Stereochemistry

• Contains two chiral centers
• Therefore exists as multiple stereoisomers
• The clinically used form is primarily associated with specific stereochemical configurations, particularly the threo isomers

Pharmacological chemical class

• Central nervous system stimulant
• Norepinephrine–dopamine reuptake inhibitor (NDRI)

Structural significance

Methylphenidate is structurally distinct from amphetamine and methamphetamine. Rather than being a phenethylamine, it is built around a piperidine ring attached to a phenylacetate ester framework.

Physical characteristics

• Pure methylphenidate is a white crystalline solid
• Commonly formulated as methylphenidate hydrochloride
• Moderately soluble in water in its salt form

Relationship to other stimulants

Although often grouped with stimulant medications, methylphenidate differs structurally from:

• Amphetamine
• Methamphetamine
• MDMA