Theobromine, formerly known as xantheose, is a bitter alkaloid of the cacao plant, with the chemical formula C7H8N4O2. 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).
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 broma ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.
Theobromine is a slightly water-soluble (330 mg/L), crystalline, bitter powder. Theobromine is white or colourless, but commercial samples can be yellowish. It has an effect similar to, but lesser than, that of caffeine in the human nervous system, making it a lesser homologue. 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 the primary alkaloid found in cocoa and chocolate. Cocoa powder can vary in the amount of theobromine, from 2% theobromine, up to higher levels around 10%. Cocoa butter only contains trace amounts of theobromine. There are usually higher concentrations in dark than in milk chocolate. 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. 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:
Theobroma cacao – seed and seed coat
Theobroma bicolor – seed coat
Ilex paraguariensis – leaf
Camellia sinensis – leaf
The amount of toxic theobromine varies with the type of chocolate. The darker and more bitter the chocolate, the more dangerous it is to dogs. Baking chocolate and gourmet dark chocolate are highly concentrated and contain 130-450 mg of theobromine per ounce. Common milk chocolate only contains about 44-58 mg/ounce. White chocolate rarely poses any threat of chocolate poisoning with only 0.25 mg of theobromine per ounce of chocolate. Even if the amount ingested is not a toxicity concern, dogs can still become ill from the fat and sugar in chocolate.
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