Chemistry of Caffeine - Quantum - East Stroudsburg University
Chemistry of Caffeine - Quantum - East Stroudsburg University
Chemistry of Caffeine - Quantum - East Stroudsburg University
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By: Nevina Keskineva<br />
<strong>Chemistry</strong> Department, <strong>East</strong><br />
<strong>Stroudsburg</strong> <strong>University</strong>
History<br />
Structure<br />
Mechanism <strong>of</strong> action<br />
Metabolism
Average Doses – 85-250mg or 1-3 cups <strong>of</strong><br />
c<strong>of</strong>fee 1<br />
High doses – 250-500mg 1<br />
• Restlessness 1<br />
• Insomnia 1<br />
• Seizures 1<br />
• Cardiovascular instability 1<br />
10g <strong>of</strong> caffeine is fatal. 1
Since Stone Age<br />
Ethiopian Legend<br />
Friedrich Ferdinand Runge<br />
Hermann Emil Fischer
Nitrogen<br />
• The name derives from the word<br />
alkaline, which is used to describe any<br />
nitrogen containing base(an amine) .<br />
• Therefore alkaloids are described as<br />
basic, nitrogen containing compounds<br />
<strong>of</strong> plant or animal origin.<br />
• “True alkaloids” are compounds that:<br />
• The nitrogen atom is part <strong>of</strong> a<br />
heterocyclic system<br />
• Compound has a complex<br />
molecular structure<br />
• Manifests pharmacological activity<br />
• Compound is restricted to the<br />
plant kingdom.<br />
<strong>Caffeine</strong><br />
Heterocyclic<br />
System
π e - π e -<br />
π e -<br />
π e -<br />
π e -<br />
<strong>Caffeine</strong><br />
<strong>Caffeine</strong> Zwitterion Resonance<br />
• Aromatic molecules are planar, cyclic, species that have 4n +2π<br />
electrons. (Huckel’s rule)<br />
• Molecules with 2,6,10,14,18….π electrons are aromatic.<br />
• <strong>Caffeine</strong> has 10π electrons, therefore is aromatic.
http://www.youtube.com/watch?v=u0oi3V_<br />
EqhI
Heart<br />
Anxiety and sleep disorders
<strong>Caffeine</strong> is the most popular drug<br />
Binds to the adenosine receptors<br />
It is almost completely metabolized<br />
It has positive and negative effects on the<br />
body