Теобромин

Описание

Theobromine is a methylxanthine alkaloid and derivative of caffeine that has been found in cocoa beans and has diverse biological activities. It is an adenosine A₁ receptor antagonist (IC₅₀s = 200-280 μM in radioligand binding assays using rat brain membranes). Theobromine (150 μg/ml) increases AMPK phosphorylation and inhibits adipocyte differentiation, ERK and JNK phosphorylation, and IL-6 and TNF-α production in 3T3-L1 preadipocytes cultured in differentiation medium. It inhibits decreases in renal cortex SIRT1 activity and increases in NADPH oxidase-dependent reactive oxygen species (ROS) production, as well as reduces kidney hypertrophy and albuminuria in a spontaneously hypertensive rat model of streptozotocin-induced diabetes when administered at a dose of 5 mg/kg per day. Theobromine is toxic to dogs with an LD₅₀ value of 250 to 500 mg/kg.

Химические свойства

A methyl xanthine similar to caffeine. Theobromine has a bitter taste.

Вхождение

Reported found in cocoa bean, cocoa powder, cola nut and tea.

Определение

ChEBI: A dimethylxanthine having the two methyl groups located at positions 3 and 7. It is a purine alkaloid derived from cocoa tree.

Общее описание

Odorless white crystalline powder. Bitter taste. pH (saturated solution in water): 5.5-7.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

Theobromine may be sensitive to prolonged exposure to light. Theobromine has weakly acidic properties, combining with bases to forms salts. Theobromine also has even weaker basic properties, combining with acids to form salts which are decomposed in aqueous solution. .

Опасность

Toxic by ingestion. Questionable carcinogen.

Пожароопасность

Flash point data for Theobromine are not available; however, Theobromine is probably combustible.

Профиль безопасности

Poison by ingestion. Moderately toxic by subcutaneous route. An experimental teratogen. Human systemic effects by ingestion: central nervous system and gastrointestinal changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as a diuretic, smooth muscle relaxant, cardiac stimulant, and vasoddator.

Методы очистки

It crystallises from H2O. Its solubility in H2O is 0.06% at 15o and 1.25% at 100o, and it is poorly soluble in organic solvents. It forms salts with heavy metals and is a diuretic, vasodilator and a cardiac stimulant. [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp254-225 1971, ISBN 0-471-38205-1, Beilstein 26 H 457, 26 I 135, 26 II 264, 26 III/IV 2336.]

использованная литература

Biltz, Max., Annalen, 423,320 (1921)
Dubosc., Chem. Zentr., IV, 956 (1932)
Gepner, Kreps., Chem. Abstr., 41,96 (1947)
Bohinc, Korber-Smid, J agodic., Farm. Vestn., (Ljubljana), 23, 143 (1972)