Theobromin

C8H10N4O2. An alkaloid occurring in tea, coffee and guarana, from which it may be prepared by extraction, It is also manufactured by the methylation of theobromine and by the condensation of cyanoacetic acid with urea. Crystallizes with H2O or anhydrous from organic solvents. M.p. (anhydrous) 235"C, sublimes at 176 C. Odourless, and with a very bitter taste. Caffeine acts as a stimulant and diuretic, and is a constituent of cola drinks, tea and coffee. 

C7H9N402- M.p. 337 C, an alkaloid obtained from cacao seeds or prepared synthetically. Constitutionally it is similar to caffeine, and is also a weak base. It is usually administered as the sodium compound combined with either sodium ethanoate or sodium salicylate, and is employed almost entirely as a diuretic. Physiologically theobromine resembles caffeine, but its effect on the central nervous system is less, while its action on the kidneys, is more pronounced. 

Pyrimidines and purines occur naturally in substances other than nucleic acids Coffee for example is a familiar source of caffeine Tea contains both caffeine and theobromine... 

Classify caffeine and theobromine according to whether each is... 

Caffeine and theobromine are both purines Caffeine lacks H—N—C=0 units so cannot enobze Two consitutionally isomenc enols are possible for theobromine... 

This experiment describes a quantitative analysis for caffeine, theobromine, and theophylline in tea, pain killers, and cocoa. Separations are accomplished by MEKC using a pH 8.25 borate-phosphate buffer with added SDS. A UV detector set to 214 nm is used to record the electropherogram. An internal standard of phenobarbital is included for quantitative work. 

The leaf and leaf buds of Cammelia sinensis (L.) O Kuntze and other related plants and most teas contain, depending upon climate, specific variety, time of harvest, etc, somewhat less than 5% caffeine (16) and smaller amounts of theophylline (133, Rj = Rg = CHg Rg = H) and theobromine (133,... 

Two other commonly found sources of caffeine (16) are kola Cold) from the seeds of, for example. Cola nitida (Vent.) Schott and Engl., which contains 1—4% of the alkaloid, but Httie theophylline or theobromine, and cocoa (from the seeds of Theobroma cacao L.), which generally contains about 3% theobromine and significantiy less caffeine. 

AH three of these materials are apparentiy central nervous system (CNS) stimulants. It is beheved that for most individuals caffeine causes greater stimulation than does theophylline. Theobromine apparentiy causes the least stimulation. There is some evidence that caffeine acts on the cortex and reduces drowsiness and fatigue, although habituation can reduce these effects. 

Ai,A/-bis(hydroxymethyl) formamide [6921-98-8] (21), which in solution is in equiUbrium with the monomethylol derivative [13052-19-2] and formaldehyde. With ben2aldehyde in the presence of pyridine, formamide condenses to yield ben2yhdene bisformamide [14328-12-2]. Similar reactions occur with ketones, which, however, requite more drastic reaction conditions. Formamide is a valuable reagent in the synthesis of heterocycHc compounds. Synthetic routes to various types of compounds like imida2oles, oxa2oles, pyrimidines, tria2ines, xanthines, and even complex purine alkaloids, eg, theophylline [58-55-9] theobromine [83-67-0], and caffeine [58-08-2], have been devised (22). 

For many years oral xanthines, shown in Table 2, were the preferred first-line treatment for asthma in the United States, and if the aerosol and oral formulations of P2" go sts are considered separately, as they are in Table 1, this was still the case in 1989. Within this class of compounds theophylline (8), or one of its various salt forms, such as aminophylline [317-34-0] (theophylline ethylenediamine 2 l), have been the predominant agents. Theophylline, 1,3-dimethylxanthine [58-55-9], is but one member of a class of naturally occurring alkaloids. Two more common alkaloids are theobromine (9), isomeric with theophylline and the principal alkaloid in cacao beans, and caffeine, (10), 1,3,7-Trimethylxanthine [58-08-2], found in coffee and tea. 

Pentoxifylline is stmcturaHy related to other methylxanthine derivatives such as caffeine [58-02-2] (1,3,7-trimethylxanthine), theobromine [83-67-0] (3,7-dimethylxanthine), and theophylline [58-55-9] (3,7-dihydro-1,3-dimethyl-1 H-piirine-2,6-dione or 1,3-dimethylxanthine), which also show radioprotective activity in some instances, suggesting that methylxanthines as a dmg class may radioprotect through a common mechanism (see Alkaloids). In a retrospective analysis of cervical and endometrial cancer patients receiving primary or adjuvant XRT, no association between caffeine consumption and incidence of acute radiation effects has been found. However, there was a decreased incidence of severe late radiation injury in cervical cancer patients who consumed higher levels of caffeine at the time of thek XRT (121). The observed lack of correlation between caffeine consumption and acute radiation effects is consistent with laboratory investigations using pentoxifylline. 

Table 8. Variations in Theobromine and Caffeine Content of Various Chocolate Liquors...

Country of origin Theobromine, % Caffeine, % Total alkaloid, % The oh r omine-1 o - c affei ne ratio... 

The theobromine and caffeine contents of several finished chocolate products as determined by hplc at Hershey s laboratories are presented in... 

Table 9. Theobromine and Caffeine Content of Finished Chocolate Products ...

Theobromine, 6-thio-methylation, 5, 535 Theophylline alkylation, 5, 532 C-alkylation, 5, 537... 

The pur pose of work is to develop the technique of separ ation of purine bases (caffeine, theophylline, theobromine) and the technique of detection of purine bases in biological fluid by TLC using micellar mobile phases containing of different surfactants. 

The effect of concentration of cationic (cetylpyridinium chloride, CPC), anionic (sodium dodecylsulfate, SDS) and nonionic (Twin-80) surfactants as well as effect of pH value on the characteristics of TLC separ ation has been investigated. The best separ ation of three components has been achieved with 210 M CPC and LIO M Twin-80 solutions, at pH 7 (phosphate buffer). Individual solution of SDS didn t provide effective separation of caffeine, theophylline, theobromine, the rate of separ ation was low. The separ ation factor and rate of separ ation was increase by adding of modifiers - alcohol 1- propanol (6 % vol.) or 1-butanol (0.1 % vol.) in SDS solution. The optimal concentration of SDS is 210 M. 

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