|Systematic (IUPAC) name|
|ATC code||C03 R03|
|Mol. mass||180.164 g/mol|
|Metabolism||Hepatic demethylation and oxidation|
|Half life||7.1 +/- 0.7 hours|
|Excretion||Renal (10% unchanged, rest as metabolites)|
|Legal status||Uncontrolled substance|
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Theobromine, also known as xantheose, is a bitter alkaloid of the cacao plant, found in chocolate, as well as in a number of other foods, including the leaves of the tea plant, and the kola or cola nut. It is in the methylxanthine class of chemical compounds, which also includes the similar compounds theophylline and caffeine. (In caffeine, the only difference is that the NH group of theobromine is an N-CH3 group.) Despite its name, the compound contains no bromine — theobromine is derived from Theobroma, the name of the genus of the cacao tree, (which itself is made up of the Greek roots theo ("God") and brosi ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.
Theobromine is a water insoluble, crystalline, bitter powder; the colour has been listed as either white or colourless. It has a similar, but lesser, effect to caffeine, making it a lesser homologue. Theobromine is an isomer of theophylline as well as paraxanthine. Theobromine is categorized as a dimethyl xanthine, which means it is a xanthine with two methyl groups.
Theobromine is the primary alkaloid found in cocoa and chocolate. Cocoa powder can vary in the amount of theobromine, from 2% theobromine to at least 10%. Theobromine can also be found in small amounts in the kola nut (1.0-2.5%), the guarana berry, and the tea plant.
The mean theobromine concentrations in cocoa and carob products are:
|Item||Mean theobromine content (mg/g)|
|Chocolate bakery products||1.47|
|Chocolate ice creams||0.621|
Following its discovery in the late 19th century, theobromine was put to use by 1916, where it was recommended by the publication Principles of Medical Treatment as a treatment for edema (excessive liquid in parts of the body), syphilitic angina attacks, and degenerative angina. The American Journal of Clinical Nutrition notes that theobromine was once used as a treatment for other circulatory problems including arteriosclerosis, certain vascular diseases, angina pectoris, and hypertension.
In modern medicine, theobromine is used as a vasodilator (a blood vessel widener), a diuretic (urination aid), and heart stimulant. In addition, the future use of theobromine in such fields as cancer prevention has been patented.
Theobromine has also been used in birth defect experiments involving mice and rabbits. A decreased fetal weight was noted in rabbits following forced feeding, but not after other administration of theobromine. Birth defects were not seen in rats.
Even without dietary intake, theobromine may occur in the body as it is a product of the human metabolism of caffeine, which is metabolised in the liver into 10% theobromine, 4% theophylline, and 80% paraxanthine.
Like other methylated xanthine derivatives, theobromine is both a
As a phosphodiesterase inhibitor, theobromine helps prevent the phosphodiesterase enzymes from converting the active cAMP to an inactive form. cAMP works as a second messenger in many hormone- and neurotransmitter-controlled metabolic systems, such as the breakdown of glycogen. When the inactivation of cAMP is inhibited by a compound such as theobromine, the effects of the neurotransmitter or hormone that stimulated the production of cAMP are much longer-lived. In general, the net result is a stimulatory effect.
The amount of theobromine found in chocolate is small enough that chocolate can, in general, be safely consumed by humans. However, theobromine poisoning may result from the chronic or acute consumption of large quantities, especially in the elderly. In extreme cases, emergency room treatment may be required.
While theobromine and caffeine are similar in that they are related alkaloids, theobromine is weaker in both its inhibition of cyclic nucleotide phosphodiesterases and its antagonism of adenosine receptors. Therefore, theobromine has a lesser impact on the human central nervous system than caffeine. However, theobromine stimulates the heart to a greater degree. While theobromine is not as addictive, it has been cited as possibly causing addiction to chocolate. Theobromine has also been identified as one of the compounds contributing to chocolate's reputed role as an aphrodisiac.
As it is a myocardial stimulant as well as a vasodilator, it increases heartbeat, yet it also dilates blood vessels, causing a reduced blood pressure. However, a recent paper published suggested that the decrease in blood pressure may be caused by flavanols. Furthermore, its draining effect allows it to be used to treat cardiac failure, which can be caused by an excessive accumulation of fluid.
A 2004 study published by Imperial College London concluded that theobromine has an antitussive (cough-reducing) effect superior to codeine by suppressing vagus nerve activity. In the study, theobromine significantly increased the capsaicin concentration required to induce coughs when compared with a placebo. In addition, theobromine is helpful in treating asthma, since it relaxes the smooth muscles, including the ones found in the bronchi.
A study conducted in Utah between 1983 and 1986, and published in 1993, showed a possible association between theobromine and an increased risk of suffering from prostate cancer in older men. This association was not found to be linear for aggressive tumors. While the association may be spurious, it is plausible. Prenatal and infant exposure to theobromine appeared possibly associated with hypospadias and testicular cancer in one population study PMID 19440400.
Theobromine can cause sleeplessness, tremors, restlessness, anxiety, as well as contribute to increased production of urine. Additional side effects include loss of appetite, nausea, and vomiting.
Animals that metabolize theobromine more slowly, such as dogs, can succumb to theobromine poisoning from as little as 50 grams of chocolate for a smaller dog and 400 grams for an average-sized dog. The same risk is reported for cats as well, although cats are less likely to ingest sweet food, having no sweet taste receptors. Birds, again due to their smaller size and more rapid metabolism, are even more susceptible to its toxic effects. Complications include digestive issues, dehydration, excitability, and a slow heart rate. Later stages of theobromine poisoning include epileptic-like seizures and death. If caught early on, theobromine poisoning is treatable. Although not usual, the effects of theobromine poisoning, as stated, can become fatal.
Theobromine is known to induce gene mutations in lower eukaryotes and bacteria. At the time of a 1991 report, further updated in 1997, by the IARC, genetic mutations had been found in higher eukaryotic cells, specifically cultured mammalian cells, but the compound was still listed as having inadequate evidence for classification of human carcinogencity.
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Theobromine is a chemical substance, also known as xantheose It is an alkaloid. It occurs in the cacao plant. Chemically, it is very similar to caffeine. Because the cacao plant is used to make chocolate it also occurs in chocolate. Despite its name, there is no bromine in it — theobromine comes from Theobroma, the name of the genus of the cacao tree, (which itself is made up of the Greek roots theo ("God") and brosi ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.
Theobromine is a water insoluble, crystalline, bitter powder. It colour is listed as either white or colourless. It has a similar, but lesser, effect to caffeine, making it a lesser homologue. Theobromine is an isomer of theophylline as well as paraxanthine. Theobromine is categorized as a dimethyl xanthine, which means it is a xanthine with two methyl groups.