By: Nevina Keskineva
Chemistry Department, East
Stroudsburg University

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History
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Structure
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Mechanism of action
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Metabolism

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

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Since Stone Age
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Ethiopian Legend
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Friedrich Ferdinand Runge
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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.
Heterocyclic
System
Caffeine

π 𝑒
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π 𝑒
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π 𝑒
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π 𝑒 -
π 𝑒 -
Caffeine Zwitterion Resonance Caffeine
• 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

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Heart
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Anxiety and sleep disorders

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