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Theobromine

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Theobromine
Theobromin - Theobromine.pngTheobromine 3D spacefill.png
General
Systematic name Theobromine
Other names diurobromine, 3,7-Dimethylxanthine
Molecular formula C7H8N4O2
Molar mass 180.164 g/mol
Properties
Density and phase Density::1.522 g/cu cm at 20 °C, 3
Solubility in water 330 mg/L (25°C)
Melting point Melting point::357 °C
Decompose point Decompose point::300 °C
Acidity (pKa ) 9.28
Basicity (pKb) -0.91
Structure
Crystal structure hexagonal similar
Hazards
MSDS Material safety data sheet
Main hazards toxic in high concentrations
Flash point 293°C
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Theobromine is a bitter alkaloid of the cacao plant, with the chemical formula C7H8N4O2.

Properties

Chemical

Theobromine is soluble in water, slightly soluble in ethanol and ammonia, and insoluble in ethyl ether, benzene, carbon tetrachloride, chloroform, and ligroin. Theobromine sublimes at 290-295 C [1] Theobromine is an isomer of theophylline and paraxanthine.

Physical

Theobromine is a white, amorphous powder of monoclinic needles. It is a bitter tasting alkaloid with a bit of a saline taste.

Synthesis

Cacao bean pod

Theobromine was first discovered in 1841 in cacao beans Alexander Voskresensky[2], It was not synthesized until Hermann Emil Fischer achieved it by using xanthine in 1882.[3]. For a more viable means of mass production of the chemical, chemists have modified the genes of camellia sinensis to produce Theobromine, rather than caffeine.[4] This process was further developed and patented. [5]. Aside from being synthesized, it is found naturally in cacao beans. This also means that it is present in chocolate, the darker the chocolate, the more theobromine. It is also found in the tea plant and the kola nut. [3]

Uses

Theobromine in small doses can help with asthma, as it relaxes the muscles in the lungs and throat [6]. Theobromine dilates blood vessels, decreasing blood pressure. [7]Theobromine has similar effects on the nervous system as caffeine, although the effect is weakened and it does not affect the central nervous system. [3] Although consuming both at the same time is ill-advised, as theobromine is toxic if taken in large amounts, especially in the elderly. Having neurologic effects, it is used in cigarettes for more stimulation and flavoring.[1]

Effects

Theobromine has been used in diuretics, myocardial stimulants, vasodilators, and smooth muscle relaxants. It was used to dilate arteries by using doses in 300mg and 600mg a day. Overdoses of theobromine are commonly shown with sweating, trembling, severe headache, and nausea. The average human can intake 1000 mg of theobromine without it becoming deadly, but it is not advised to do so, as the effects of theobromine poisoning will begin showing at this dosage. Like caffeine, it increases heart rate and alertness, but the effects are not as prominent [1]. Ingestion of Theobromine through milk chocolate containing 240mg of theobromine and 16mg of caffeine by mothers showed that their milk contained a concentration mean of 5.3 mg/l at 2-3 hours after ingestion.[8]

Toxicity

For common animals(e.g. cats, dogs, horses), Theobromine is toxic, even in small amounts. This is why you should keep your chocolate hidden from your pets, as they might get Theobromine poisoning from eating it.[9] It accounts for the deaths of hundreds of pets each year. The pets normally ingest Theobromine through chocolate, which is made from the cacao bean. Cacao beans contain Theobromine much like the coffee bean has caffeine, and in fact, theobromine and caffeine have very similar chemical structure. Although Theobromine poisoning is common among pets, among humans it is quite rare. The average intake of Theobromine daily in the US is 39.05 mg, mainly coming from coffee and tea. That amount is enough to make pets become nauseous and have diarrhea.

Humans have a much larger tolerance to theobromine with the toxic level of theobromine being at 1,000 mg/kg. Theobromine has a biological half life of about 8 hours, this means that theobromine is processed and no longer theobromine. Theobromine is most common in humans that deal with processing cacao plants for chocolate or where theobromine is produced or used. Dogs and cats are much more vulnerable. Dogs have a resistance of 300 mg/kg. Cats are even less resistant than dogs at 200 mg/kg, but are less likely to eat it due to not being able to taste sweetness. [1]. Dogs are taken in for theobromine poisoning most often on valentines day [10]. Theobromine was first recorded by Alexander Voskresensky in cacao beans. Despite its name, Theobromine does not contain any Bromine. The name comes from the genus of tree from which the cacao bean comes from Theobroma.

Video

Theobromine effects on human body

References

  1. 1.0 1.1 1.2 1.3 [1] U.S. National library of Medicine. Web. last modified February 28 2017. . Unknown Author.
  2. Voskresensky, Alexander. Annalen der Chemie und Pharmacie Google. Book. Published January 1, 1842.
  3. 3.0 3.1 3.2 . CHEBI:28946 - theobromine EMBL-EBI. Web. last modified February 22, 2017. Author Unknown
  4. Zheng XQ , Koyama Y , Nagai C , Ashihara H. Biosynthesis, accumulation and degradation of theobromine in developing Theobroma cacao fruits. Europe PMC . Web. April 1, 2004. Published
  5. Misako Mizuno, Hiroshi Ashihara, Kouichi Mizuno, and Tatsuhito Fujimura. CAMELLIA SINENSIS GENE ENCODING A CAFFEINE SYNTHESIS ASSOCIATED N-METHYL TRANSFERASE WITH 7-METHYLXANTHINE N3 METHYL TRANSFERASE, THEOBROMINE N1 METHYL TRANSFERASE, AND PARAXANTHINE N3 METHYL TRANSFERASE ACTIVITIES AND USE THEREOF US Patent. Web. August 16, 2005. Published
  6. Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ.. Theobromine inhibits sensory nerve activation and cough Pubmed. Web. Feb 19, 2005. Published
  7. Helmenstine M. Anne.Theobromine Chemistry Thoughtco. Web. March 02, 2017. Last Edited
  8. Cone, M. Virginia. Chemicals Identified in Human Breast Milk U.S. Environmental Protection Agency, Office of Pesticides and Toxic Substances. Paper. Published 1983.
  9. U.S. National Library of Medicine.Theobromine Pubchem. Web. May 5, 2017. accessed
  10. Onyett, Chris. [2] PRweb. Web. Published February 12, 2013. )