CAFFEINE

Brief History and Background of Caffeine

1,3,7-Trimethylpurine-2,6-dione

Most widely consumed psychoactive drug

Consumed since the Stone Age

From the German word kaffee and French word caf

First extracted from coffee in 1821 by Friedrich Ferdinand Runge

Introduced to the Europeans in 1573

First known as Arabian wine

Global consumption estimated at 120 000 MT per annum

Pharmacology of Caffeine

Central nervous system and metabolic stimulant

First stimulates the brain, resulting in:

Increased alertness and wakefulness

Faster and clearer flow of thought

Increased focus

Better general body coordination

At even higher doses, it stimulates the lower central nervous system

Pharmaceutical Caffeine

Health Effects of Caffeine

Synthesis of Pharmaceuticals

Alkylation

Carboxylation

Condensation and Cyclization

Dehydration

Esterification

Halogenation

Oxidation

Sulfonation

Synthesis of Caffeine

Synthesis of Caffeine
1.

N-methylation of uracil

2.

Nitration of 1,3-dimethyluracil

3.

Reduction of 1,3-dimethyl-5-nitrouracil

4.

Formylation and Nitration of 5-amino-1,3-dimethyluracil

5.

Intramolecular cyclization of intermediate

6.

N-methylation of theophylline

N-methylation of uracil

Nitration of 1,3-dimethyluracil

Reduction of 1,3-dimethyl-5-nitrouracil

Formylation and Nitration of 5-amino1,3-dimethyluracil

Intramolecular cyclization of
intermediate

N-methylation of theophylline

Sources

Zajac, M. A., Zakrzewski, A. G., & Kowal, M. G. (2003). A Novel Method of

Caffeine Synthesis from Uracil. Retrieved from
http://nvlpubs.nist.gov/nistpubs/jres/76A/jresv76An5p483_A1b.pdf

Shreve, R. (1967). The Pharmaceutical Industry. In Chemical Process

Industries (3rd ed.). New York, New York: McGraw-Hill Book Company.

National Headache Foundation: Clinical Update : Pharamacology. (n.d.).

Retrieved March 24, 2015, from
https://www.headaches.org/educational_modules/caffeine_module/medical
_uses.htm