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Mysteries Unraveled: Caffeine, Theophylline, Theobromine

Caffeine (C8H10N4O2), Theophylline (C7H8N4O2), Theobromine (C7H8N4O2)

Theobromine: 3,7-Dimethylxanthine

  • The differences: caffeine is found in coffee and Theobromine in chocolate
  • A. Woskresensky discovered Theobromine in cacao beans in 1841, and E. Fischer synthesized it in 1882.

Risks/Benefits

The weaker Caffeine

  • Neither Caffeine (in low doses) nor Theobromine are addictive substances

Risks

Benefits

- Like caffeine, Theobromine is found naturally and predominantly in cocoa beans but is much weaker (10x).

- Found in higher amounts than caffeine in cocoa

- does not affect the CNS like caffeine due to lacking methyl group

-bitter, like caffeine. Gives dark chocolate its flavor: which it's found in it's highest amount

-Half-life of theobromine is higher than caffeine

  • Can be toxic to pets if ingested: causing arrhythmia and seizures.
  • If too much is ingested it can produce much the same effects of caffeine like anxiety, feelings of restlessness, upset stomach, etc.
  • Safe for human consumption
  • May prevent cough/cough intensity by inhibiting the activation of afferent nerve (Undergoing clinical trials)
  • has a relaxing effect and decreases blood pressure
  • weaker effect than caffeine
  • can help asthma and other respiratory tract problems
  • Used to be used for high blood pressure
  • anti-inflammatory

Physical Properties

  • Odorless
  • White crystalline powder. Bitter taste.
  • Molecular Weight 180.167 g/mol
  • Mp: 357 °C
  • Slightly soluble in water and ethanol

Structures of Theobromine and Theophylline

Physical properties

Csp2-H

N-H

Csp3-H

N-H

Csp2-H

C-N

C=C

C-N

C=O

Csp3-H

C=O

Effects on the body

- 194.08 g/mol

- bp 178º C

- mp 236.2º C

- soluble in water

-pKa = 14.0 at 25ºC

Theophylline

Theobromine

Caffeine stimulates the central nervous system by inhibiting adenosine receptors. Caffeine competes against paraxanthine to bind to it.

Dopamine, norepinephrine, acetylcholine, serotonine, glutamate, and GABA are released, albeit indirectly

Theophylline: Dimethylxanthine

  • Occurs naturally in tea and cocoa beans
  • First extracted from tea and synthesized chemically in 1895 and initially used as a diuretic
  • Samuel Hirsch discovered the bronchospasmolytic effect of theophylline in 1992.

Caffeine

Modern uses:

Risks/Benefits

  • Not the most effect bronchodilator, because inhaled β2-agonists are far more effective.
  • The Global Initiative for Chronic Obstructive Lung Disease recommends its use only if inhaled long-acting bronchodilators are unavailable or unaffordable

Caffeine's Structure

Risks/ benefits

  • It has anti-inflammatory effects and is used to treat asthma and chronic obstructive pulmonary disease (COPD).
  • Theophylline has two distinct actions in the airways: smooth muscle relaxation (i.e., bronchodilation) and suppression of the response of the airways to stimuli-thus used as a bronchodilator

Risks

Benefits

Originated in Ethiopia and spread to other countries between the 12th-15th century. It was used for centuries, but wasn't coined "caffeine" until the early 19th century

  • Relatively high frequency of adverse effects in conventional doses.
  • Side effects: Nausea, vomiting, diarrhea, increased acid secretion, and gastroesophageal reflux
  • High concentrations: convulsions and cardiac arrhythmias
  • Low cost, widely available
  • Theophylline can potentially reverse corticosteroid resistance (trials in progress)
  • Anti-inflammatory: Decreases response of airway to irritants

Benefits

Risks

History

Physical Properties: Theophylline

  • Slightly soluble in water
  • Mp: 270-274°C
  • Molecular Weight 180.167 g/mol
  • White Crystalline powder
  • Odorless, bitter taste

-In 1819 Johann Wolfgang von Goethe (German poet) met chemist Johann Wolf Dobereiner through his fascination with science.

-Through his lab, he was able to meet Friedlieb Ferdinand Runge. Chromatography was used to purify a white, odorless crystalline called caffeine

- Safe in low-moderate doses

- increase alertness

- reduce fatigue

- improve performance

- better mental health

- lower risk of diabetes and cancer

-Safe in low-moderate doses, but can be addicting.

-Frequent consumption can disrupt brain function especially if consumed early in life.

-withdrawals can include stress, fatigue, decreased alertness, headaches, depression, and anxiety

Modern uses

Csp2-H

C-N

C=C

C=O

Csp3-H

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

-The most popular drug that is found in naturally seeds, nuts, or leaves of plants, this drug is commonly used to make users feel alert

-Found in processed foods like teas, coffees, chocolates, sodas, and energy drinks (consumed orally).

Sources

  • Barnes PJ, 2013. Theophylline. American Journal of Respiratory and Critical Care Medicine. Vol. 188, No. 8. [Internet]. Available from: http://www.atsjournals.org/doi/full/10.1164/rccm.201302-0388PP#citart1
  • National Center for Biotechnology Information. PubChem Compound Database; CID=2153, https://pubchem.ncbi.nlm.nih.gov/compound/2153
  • National Center for Biotechnology Information. PubChem Compound Database; CID=5429, https://pubchem.ncbi.nlm.nih.gov/compound/5429
  • National Center for Biotechnology Information. PubChem Compound Database; CID=2519, https://pubchem.ncbi.nlm.nih.gov/compound/2519
  • Martínez-Pinilla, E., Oñatibia-Astibia, A., & Franco, R. (2015). The relevance of theobromine for the beneficial effects of cocoa consumption. Frontiers in Pharmacology, 6, 30. http://doi.org/10.3389/fphar.2015.00030
  • Watson RR, Preedy VR, Zibadi S. Chocolate in health and nutrition. New York: Humana Press; 2013.

Presented by: Fay and Khahae

Portland Community College

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