What is theophylline?

Methylxanthines is one of the most recognizable active components of cacao. The three mains vital methylxanthines are theobromine, caffeine, aminophylline and theophylline.

Theophylline (dimethylxanthine) occurs naturally in tea and cocoa beans in trace amounts. It was first extracted from tea and synthesized chemically in 1895 and initially used as a diuretic. Its bronchodilator property was later identified, and it was introduced as a clinical treatment for asthma in 1922.

More recently it has been shown to have anti-inflammatory effects in asthma and COPD at lower concentrations. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator.

Theophylline is a methylxanthine, similar in structure to the common dietary xanthines caffeine and theobromine. It occurs as a white, odorless, crystalline powder with a bitter taste. Anhydrous theophylline has the chemical name 1H-Purine-2,6-dione,3,7-dihydro-1,3-dimethyl- and the molecular formula of anhydrous theophylline is C7H8N4O2 with a molecular weight of 180.17.

Many salts of theophylline have also been marketed, the most common being aminophylline, the ethylene diamine salt used to increase solubility at neutral pH, so that intravenous administration is possible.
What is theophylline?

Methylxanthines

During several centuries man has enjoyed food and beverages containing stimulating ingredients such methylxanthines. Methylxanthines is one of the most recognizable active components of cacao.

The three main vital methylxanthines are theobromine, caffeine, aminophylline and theophylline.

The blood pressure and peripheral vascular resistance are slightly raised by normal consumption of methylxanthine- containing beverages. Methylxanthines also have relaxing and anti-inflammatory effects.

Theobromine

Aminophylline and theophylline are typically use in the treatment COPD and asthma. Caffeine is widely consumed throughout the world.

Methylxanthines (caffeine and theobromine) impart bitterness an during fermentation of cocoa, the levels of methylxanthines fall by around 30% probably by diffusion from the cotyledans.
Methylxanthines

Theobromine in cocoa

The cocoa bean is the major natural source of the methylxanthine theobromine (3,7-dimethylxanthine), but contains only small amounts of caffeine (1,3,7-trimethylxanthine).

As theobromine is present in high amounts in cocoa powder and dark chocolate, it is used as a marker for the absorption of cocoa powder and dark chocolate.

Together, theobromine and caffeine account for up to 99% of the alkaloid content of T. cacao beans. The higher content is due to their present in the non-lipid portion of the cocoa mass.

Theobromine

Extraction of theobromine and caffeine from cocoa seeds and shells can be done using supercritical carbon dioxide.

In 1841 Woskresensky was the first to discover the alkaloid theobromine in cocoa beans. Theobromine is a white crystalline powder, odorless, easily decomposed, with an extremely bitter taste remotely resembling that of cocoa.

Flavanol-rich cocoa products have been reported to lower blood pressure. It has been suggested that theobromine is partially responsible for this effect. This is due to its ability to dilate blood vessels.
Theobromine in cocoa