|Metabolism||Hepatic demethylation and oxidation|
|Elimination half-life||7.1±0.7 hours|
|Excretion||Renal (10% unchanged, rest as metabolites)|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||180.167 g·mol−1|
|3D model (JSmol)|
Theobromine, also known as xantheose, is an alkaloid whose name is derived from the Theobroma family. It is the principal alkaloid of Theobroma cacao (cacao plant), and can be extracted from cacao beans. It tastes bitter and has the chemical formula C7H8N4O2. In industry, theobromine is used to synthesize caffeine, and is an additive in manufacturing foods and cosmetics.
It is found in chocolate, as well as in a number of other foods, including the leaves of the tea plant, and the kola nut.
It is classified as a xanthine alkaloid (more specifically, a methylxanthine), others of which include theophylline and caffeine. Caffeine differs from these compounds in that it has an extra methyl group (see under Pharmacology section).
Theobromine is a slightly water-soluble (330 mg/L), crystalline, bitter powder. Theobromine is white or colourless, but commercial samples can be yellowish. Theobromine is an isomer of theophylline, as well as paraxanthine. Theobromine is categorized as a dimethyl xanthine.
Theobromine was first discovered in 1841 in cacao beans by Russian chemist Aleksandr Voskresensky. Synthesis of theobromine from xanthine was first reported in 1882 by Hermann Emil Fischer.
Theobromine is derived from Theobroma, the name of the genus of the cacao tree, with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds. That name in turn is made up of the Greek roots theo ("god") and broma ("food"), meaning "food of the gods".
Despite its name, the compound contains no bromine.
Theobromine is the primary alkaloid found in cocoa and chocolate. Cocoa butter only contains trace amounts of theobromine. There are usually higher concentrations in dark than in milk chocolate.
There are approximately 60 milligrams (1 grain) of theobromine in 28 grams (1 oz) of milk chocolate, while the same amount of dark chocolate contains about 200 milligrams (3 grains). Cocoa beans naturally contain approximately 1% theobromine.
Plant species and components with substantial amounts of theobromine are:
Theobromine can also be found in trace amounts in the kola nut, the guarana berry, yerba mate (Ilex paraguariensis), Ilex vomitoria, Ilex guayusa, and the tea plant.
The mean theobromine concentrations in cocoa and carob products are:
|Item||Mean theobromine per 100 g|
|Cocoa powder||2060 mg|
|Cocoa beverages||266 mg|
|Chocolate toppings||195 mg|
|Chocolate bakery products||147 mg|
|Cocoa cereals||69.5 mg|
|Chocolate ice creams||62.1 mg|
|Chocolate milks||22.6 mg|
|Carob products||0.00–50.4 mg|
Theobromine is a purine alkaloid derived from xanthosine, a nucleoside. Cleavage of the ribose and N-methylation yields 7-methylxanthosine. 7-Methylxanthosine in turn is the precursor to theobromine, which in turn is the precursor to caffeine.
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 12% theobromine, 4% theophylline, and 84% paraxanthine.
In the liver, theobromine is metabolized into xanthine and subsequently into methyluric acid. Important enzymes include CYP1A2 and CYP2E1.
"The main mechanism of action for methylxanthines has long been established as an inhibition of adenosine receptors". Its effect as a phosphodiesterase inhibitor is thought to be small.
See also: Theobromine poisoning
Theobromine has no effect in the human nervous system. It is a bronchodilator and causes relaxation of vascular smooth muscle. It is not currently used as a prescription drug. The amount of theobromine found in chocolate is small enough that chocolate can, in general, be safely consumed by humans.
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. The potential phosphodiesterase inhibitory effect of theobromine is seen only at amounts much higher than what people normally would consume in a typical diet including chocolate.
At doses of 0.8–1.5 g/day (50–100 g cocoa), sweating, trembling and severe headaches were noted, with limited mood effects found at 250 mg/day.
Also, chocolate may be a factor for heartburn in some people because theobromine may affect the esophageal sphincter muscle in a way that permits stomach acids to enter the esophagus.
Theobromine is the reason chocolate is poisonous to dogs. Dogs and other animals that metabolize theobromine (found in chocolate) more slowly can succumb to theobromine poisoning from as little as 50 grams (1.8 oz) of milk chocolate for a smaller dog and 400 grams (14 oz), or around nine 44-gram (1.55 oz) small milk chocolate bars, for an average-sized dog. The concentration of theobromine in dark chocolates (approximately 10 g/kg (0.16 oz/lb)) is up to 10 times that of milk chocolate (1 to 5 g/kg (0.016 to 0.080 oz/lb)) – meaning dark chocolate is far more toxic to dogs per unit weight or volume than milk chocolate.
The same risk is reported for cats as well, although cats are less likely to ingest sweet food, with most cats having no sweet taste receptors. 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 common, the effects of theobromine poisoning can be fatal.
Mean theobromine and caffeine levels respectively, were 0.695 mg/g and 0.071 mg/g in cocoa cereals; 1.47 mg/g and 0.152 mg/g in chocolate bakery products; 1.95 mg/g and 0.138 mg/g in chocolate toppings; 2.66 mg/g and 0.208 mg/g in cocoa beverages; 0.621 mg/g and 0.032 mg/g in chocolate ice creams; 0.226 mg/g and 0.011 mg/g in chocolate milks; 74.8 mg/serving and 6.5 mg/serving in chocolate puddings.... Theobromine and caffeine levels in carob products ranged from 0–0.504 mg/g and 0-0.067 mg/g, respectively.