European Pharmacopoeia (EP) Reference Standard
Synonym: 2,6-Dihydroxy-3,7-dimethylpurine,
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 3,7-Dimethylxanthine
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Empirical Formula (Hill Notation) C7H8N4O2
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Molecular Weight 180.16
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Beilstein Registry Number 16464
Properties
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Related Categories
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InChI Key
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YAPQBXQYLJRXSA-UHFFFAOYSA-N
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form
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neat
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mp
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345-350 °C
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solubility
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H2O:
<1 mg/L
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format
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neat
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Theobromine, formerly known as xantheose,[1] is a bitter alkaloid of the cacao plant, with the
chemical formula C7H8N4O2.[1] It is 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.
Detailed description
It is classified as a xanthine alkaloid,[2] which also include
the similar compounds theophylline and caffeine.[1] The compounds differ
in that caffeine has an extra methyl group (see under #Pharmacology).
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"[3] with the suffix -ine given to alkaloids and other basic nitrogen-containing
compounds.[4]
Theobromine is a slightly water-soluble (330 mg/L[5]), crystalline, bitter powder.
Theobromine is white or colourless, but commercial samples can be yellowish.[6] 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.[7]
Theobromine was first discovered in 1841[8] in cacao beans by
Russian chemist Alexander Voskresensky.[9] Synthesis of
theobromine from xanthine was first reported
in 1882 by Hermann Emil Fischer.
Therapeutic uses
Theobromine is a vasodilator (a blood vessel
widener), a diuretic (urination aid), and heart stimulant.[1] It is not currently
used as a medicinal drug.[21]
Theobromine increases urine production. Because of
this diuretic effect, and its
ability to dilate blood vessels, theobromine has been used to treat high blood
pressure.[22] The American Journal
of Clinical Nutrition notes that historic
use of theobromine as a treatment for other circulatory problems including arteriosclerosis, certain vascular diseases, angina pectoris, and hypertension should be considered
in future studies.[23]
Following its discovery in the late 19th century,
theobromine was put to use by 1916, when 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.[24]
In the human body, theobromine levels are halved
between 6–10 hours after consumption.
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. Possible future uses
of theobromine in such fields as cancer prevention have been
patented.
Theobromine has also been shown to improve the
microhardness of tooth enamel which could potentiality increase resistance to
tooth decay.
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