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Theobromine

the main component of chocolate

The Basics

Effects of Toxicity

The Toxicity of Theobromine

(Chem Spider)

7 8 4 2

(Clegg)

(HMDB: The Human Metabolone Database)

(Clegg)

(PubChem)

Theobromine vs. Caffeine

(Clegg)

(PubChem)

  • theobromine is a toxic substance to mammals
  • LD50 - dosage that will kill 50 % of a species
  • humans: about 1000 mg/kg
  • dogs: about 300 mg/kg
  • cats: about 200 mg/kg

molecular formula: C H N O

molecular weight: 180.164 g/mol

form: odorless white crystalline powder, bitter taste

pH: 5.5-7

sublimes: 290-295 °C

melting point: 357 °C

solubility: One gram dissolves in about 200 mL water

(Blum)

  • humans
  • dosages of .8-1.5 g in a day have been known to cause sweating, trembling, or headache
  • it would be almost impossible to eat enough theobromine to kill you , and you would have to eat a lot of theobromine to create the above symptoms
  • dogs
  • toxic to dogs, especially dark chocolate
  • causes nausea and overstimulates the heart
  • actually affects all canines in this way, and has therefore been used as a means of controlling coyote populations
  • cats
  • lower LD50
  • don't have sweet taste receptors, so therefore don't enjoy chocolate the way humans do

(Clegg)

(“Theobromine.” PubChem)

(Blum)

Investigation of Theobromine vs. Caffeine Effects

(HMDB: The Human Metabolone Database)

Comparison of the Structures of Theobromine and Caffeine

2D Structure of Theobromine

(Blum)

(Lowry)

(Clegg)

(Blum)

(PubChem)

(Clegg)

( Xocoatl: Theobroma Cacao)

(Helmenstein)

In General

Alkaloids

  • study performed on group of healthy adults
  • each was given two capsules per session: either theobromine and placebo or caffeine and placebo
  • effects found of caffeine: strong stimulant, anxiety, addictive, no effect on heart rate
  • effects found of theobromine: increased heart rate
  • test measuring reaction times: theobromine had no effect on reaction times, caffeine increased reaction times

Theobromine

Caffeine

(Blum)

  • alkaloid - part of the everyday chemistry of the plant world
  • plant alkaloids:
  • nitrogen based
  • neutral or weakly acidic properties
  • xanthine alkaloid or methylxanthine, like caffeine

(DrugBank.)

(Encyclopædia Britannica)

  • mild effect
  • long lasting
  • mild antidepressant
  • mild effect on central nervous system
  • not addictive
  • mild diuretic
  • strong effect
  • increases emotional stress
  • strong effect on central nervous system
  • addictive
  • strong diuretic

Effects of Theobromine

Where Theobromine is Found

(Baggott)

(Clegg)

(Baggott)

  • cola nut
  • cocoa bean
  • contain about 40 g/kg of theobromine
  • chocolate
  • dark chocolate: about 10 g/kg
  • milk chocolate: 2-5 g/kg

(Clegg)

(Xocoatl: Theobroma Cacao)

(Phytochemicals.)

(Clegg)

(Phytochemicals.)

Image Bibliography

(PubChem)

Works Cited

Helmenstine, Anne Marie, Ph.D. Theobromine Chemical Structure. Digital

image. AboutEducation. N.p., n.d. Web. 2 Feb. 2016. <http://chemistry.about.com/od/factsstructures/ig/Chemical-Structures---T/Theobromine.htm>

Nancy Lowry. Structures of Caffeine and Theobromine. Digital image. N.p.,

n.d. Web. 30 Jan. 2016. <http://helios.hampshire.edu/~nlNS/mompdfs/ChocolateIs.pdf>.

Two Structurally Related Methylxanthines. Digital image. Xocoatl:

Theobroma Cacao. N.p., n.d. Web. 25 Jan. 2016. <http://www.xocoatl.org/caffeine.htm>.

  • reduces sleepiness
  • cough suppressant
  • bronchodilator - can help open up airways to reduce asthma symptoms
  • vasodilator - opens blood vessels (can treat high blood pressure
  • diuretic - stimulates urine production
  • may be useful in management of fatigue and orthostatic hypotension

Name

(PubChem)

Works Consulted

(Blum)

(Clegg)

"All about Chocolate -- No Caffeine." Xocoatl: Theobroma Cacao. N.p., n.d. Web. 25 Jan. 2016. <http://www.xocoatl.org/caffeine.htm>.

Baggott, Matthew J., Emma Childs, Amy B. Hart, Eveline De Bruin, Abraham A. Palmer, Joy E. Wilkinson, and Harriet De Wit.

"Psychopharmacology of Theobromine in Healthy Volunteers." (2013): n. pag. Web. 30 Jan. 2016.

<http://palmerlab.org/wp-content/uploads/2012/09/Baggott-et-al-Psychopharm-2013.pdf>.

Blum, Deborah. "The Poisonous Chemistry of Chocolate." Wired.com. Conde Nast Digital, 14 Feb. 2013. Web. 24 Jan. 2016. <http://

www.wired.com/2013/02/the-poisonous-nature-of-chocolate/>.

Clegg, Brian. "Theobromine." Royal Society of Chemistry. Royal Society of Chemistry, n.d. Web. 24 Jan. 2016. <http://www.rsc.org/

chemistryworld/podcast/CIIEcompounds/transcripts/theobromine.asp>.

"Recrystallization and Acid/Base Extraction - The Basics." Chemistry Archive. N.p., n.d. Web. 25 Jan. 2016.

<https://www.erowid.org/archive/rhodium/chemistry/equipment/rextal.a-b.basics.html>.

"Theobromine." ChemSpider. Royal Society of Chemistry, 2015. Web. 24 Jan. 2016.

<http://www.chemspider.com/Chemical-Structure.5236.html>.

"Theobromine." DrugBank. N.p., 17 July 2007. Web. 25 Jan. 2016. <http://www.drugbank.ca/drugs/DB01412>.

"theobromine". Encyclopædia Britannica. Encyclopædia Britannica Online. Encyclopædia Britannica Inc., 2016. Web. 24 Jan. 2016

<http://www.britannica.com/science/theobromine>.

"Theobromine." HMDB: The Human Metabolone Database. N.p., n.d. Web. 24 Jan. 2016.

<http://www.hmdb.ca/metabolites/hmdb02825>.

"Theobromine." Phytochemicals. N.p., n.d. Web. 25 Jan. 2016. <http://www.phytochemicals.info/phytochemicals/theobromine.php>.

"Theobromine." PubChem. N.p., n.d. Web. 24 Jan. 2016. <https://pubchem.ncbi.nlm.nih.gov/compound/theobromine#section=Top>.

(Clegg)

  • theo "gods" + brosi "food" (Greek) --> theobroma cacao (Latin for cocoa tree) --> theobromine
  • doesn't actually contain theobromine

  • "ine" ending means theobromine has a "free base" structure
  • not reacted with an acid
  • when reacted with an acid, will form a salt

"Caffeine & Theobromine." The Hershey Company. N.p., n.d. Web. 01 Feb.

2016. <https://www.thehersheycompany.com/our-ingredients/what-we-believe/ingredient-information/ingredient-topics/caffeine-theobromine.aspx>.

"Orthostatic Hypotension (postural Hypotension)." Mayo Clinic. N.p., n.d.

Web. 25 Jan. 2016. <http://www.mayoclinic.org/diseases-conditions/orthostatic-hypotension/basics/definition/con-20031255>.

"THEOBROMINE." HouseOfNutrition.com. N.p., n.d. Web. 03 Feb. 2016.

<http://www.houseofnutrition.com/theobromine.html>.

(DrugBank)

(Xocoatl: Theobroma Cacao)

(Chemistry Archive)

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