Chemistry of Caffeine - Quantum - East Stroudsburg University

By: Nevina Keskineva
Chemistry Department, East
Stroudsburg University

History
Structure
Mechanism of action
Metabolism

Average Doses – 85-250mg or 1-3 cups of
coffee 1
High doses – 250-500mg 1
• Restlessness 1
• Insomnia 1
• Seizures 1
• Cardiovascular instability 1
10g of caffeine is fatal. 1

Since Stone Age
Ethiopian Legend
Friedrich Ferdinand Runge
Hermann Emil Fischer

Nitrogen
• The name derives from the word
alkaline, which is used to describe any
nitrogen containing base(an amine) .
• Therefore alkaloids are described as
basic, nitrogen containing compounds
of plant or animal origin.
• “True alkaloids” are compounds that:
• The nitrogen atom is part of a
heterocyclic system
• Compound has a complex
molecular structure
• Manifests pharmacological activity
• Compound is restricted to the
plant kingdom.
Caffeine
Heterocyclic
System

π e - π e -
π e -
π e -
π e -
Caffeine
Caffeine Zwitterion Resonance
• Aromatic molecules are planar, cyclic, species that have 4n +2π
electrons. (Huckel’s rule)
• Molecules with 2,6,10,14,18….π electrons are aromatic.
• Caffeine has 10π electrons, therefore is aromatic.

http://www.youtube.com/watch?v=u0oi3V_
EqhI

Heart
Anxiety and sleep disorders

Caffeine is the most popular drug
Binds to the adenosine receptors
It is almost completely metabolized
It has positive and negative effects on the
body