Theobromine

Description

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.

Description

Theobromine is the primary alkaloid in chocolate—it gives unsweetened chocolate its bitter taste. It gets its name from the cacao tree genus?Theobroma, but it’s also found in tea leaves and kola nuts. A. Woskresensky discovered theobromine in cacao beans in 1841, and E. Fischer synthesized it in 1882. If you replace the nitrogen-bearing hydrogen group with a methyl group, you have caffeine.

Description

A purine alkaloid which is present in a number of plants, particularly Theobroma coco and kola nuts. The alkaloid sublimes at 290°C and may be purified by this method when it forms colourless, rhombic microcrystals. It is soluble in 1600 parts of H20 at 17°C, insoluble in cold Et20 or ligroin. It is a weak base and the salts are decomposed by H20. The perchlorate forms colourless crystals of the monohydrate which decompose at 271-3°C; the mercurinitrate is also crystalline and has a melting point above 300°C. The mercury salt is obtained as colourless crystals which darken at 29S-300°C and melt at 310°C. One imino group is present yielding alkyl derivative, e.g. the N-methyl compound identical with Caffeine (q.v.); the N~ethyl derivative, m.p. 164-SoC, forming an aurichloride, m.p. 226°C; N-propyl, m.p. 136°C giving an aurichloride, m.p. 9SoC; N-butyl, m.p. 119°C and the N-iso butyl, m.p. 129-130oC also giving an aurichloride,m.p. 97°C. The alkaloid also furnishes a methochloride as colourless rods, m.p. 320-340°C (dec.) which is very soluble in H20 and the methoaurichloride, m.p. 265°C (dec.).
Like Caffeine (q.v.) and Theophylline (q.v.), the alkaloid and its salts are mild stimulants and also possess a diuretic action.

Chemical properties

white to light yellow crystal powder

Chemical properties

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

Occurrence

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

The Uses of Theobromine

A metabolite of Caffeine

The Uses of Theobromine

diuretic, bronchodilator, cardiotonic

The Uses of Theobromine

A metabolite of Caffeine.

What are the applications of Application

Theobromine is a weak phosphodiesterase inhibitor and adenosine receptor blocker

Definition

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

General Description

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

Air & Water Reactions

Insoluble in water.

Reactivity Profile

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. .

Hazard

Toxic by ingestion. Questionable carcinogen.

Fire Hazard

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

Flammability and Explosibility

Non flammable

Safety Profile

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.

Purification Methods

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.]

References

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)