Theobromine
public_id
FDB000455
IUPAC 名称
3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
描述
Constituent of tea leaves (Camellia thea), cocoa Theobroma cacao, cola nut (Cola acuminata) and guarana (Paullinia cupana); flavouring ingredient with a bitter taste 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9) -- Pubchem; As a methylated xanthine, theobromine is a potent Cyclic adenosine monophosphate (cAMP) phosphodiesterase inhibitor; this means that it helps prevent the enzyme phosphodiesterase 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 which stimulated the production of cAMP are much longer lived. The net result is generally a stimulatory effect.; 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.; 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.; In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. -- Wikipedia; It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. -- Wikipedia; Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine.Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". -- Wikipedia; Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus. -- Wikipedia; Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; 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, also known as xantheose, is a bitter alkaloid of the cacao plant, found in chocolate, as well as in a number of chocolate-free foods made from theobromine sources including the leaves of the tea plant, the kola or cola nut, and acai berries[citation needed]. 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.; 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.[citation needed] 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.; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. -- Wikipedia.
CAS号
83-67-0
异构
CN1C=NC2=C1C(=O)NC(=O)N2C
InChI标识符
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
YAPQBXQYLJRXSA-UHFFFAOYSA-N
平均分子量
180.06472552
id
455
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