Theobromin/theophyllin

Terada, H., Sakabe, Y., High performance liquid chromatographic determination of theobromine, theophylline and caffeine in food products, J. Chromat., 291, 453, 1984. 

Ilex cassine Ilex vormitoria Caffeine Theobromine Theophylline Caffeine Theobromine Theophylline... 

Textile manufacturing industry, exposures in Theobromine Theophylline Thioacetamide 4,4 -Thiodianiline... 

In 1982 a method has been presented to remove xanthines like theobromine, theophylline and caffeine from cacao products [1] working very similar to the procedures applied to the decaf-feination of coffee and tea. The authors intend to reduce the quantity of xanthines, but like to keep the content of valuable cacao butter unchanged. For this purpose they suggest to swell the cacao material (nibs) with water to about 40 % w/w and extract the undesired components with Carbon dioxide. They claim that the concentration of theobromine is reduced, caffeine is removed completely without affecting the cacao butter. 

Tranquillisers hQn Qx do, captodiame, clopenthixol, flupen-thixol, haloperidol, phenothiazines, prothipendyl, trifluperidol Vitamins acetomenaphthone, ascorbic acid, ergocalciferol, nicotinamide, pyridoxine, riboflavine, thiamine Xanthines acepifylline, bamifylline, bufylline, caffeine, dipro-phylline, etamiphylline, theobromine, theophylline Miscellaneous substances aminosalicylic acid, benzoic acid, betanaphthol, carbamazepine, chlorphenesin, dibromoprop-amidine, diethylpropion, halquinol, isoniazid, methaqualone, metronidazole... 

Theobromine and theophylline are metabolites of caffeine in the horse (M. S. Moss, 1977), and theobromine is frequently ingested with caffeine as a result of the contamination of pelleted horse feed with cocoa husk. Theophylline may also occur as a result of administering aminophylline for respiratory problems. Caffeine appears occasionally in greyhound urine as a result of the widespread practice of giving tea prior to racing. Theobromine, theophylline, and 1,7-dimethylxanthine are all metabolites of caffeine in the horse and man but tiieir proportions vary greatly between the species. In human sport, the upper limit on the urinary concentration of caffeine has recently been set at 15 xg/ml. 

The technique of ultrafiltration for serum sample preparation has been studied by several investigators (H7, HIO, K9, S19, V4, V5). In this technique the serum sample is passed through an exclusion membrane which exhibits a 95% retention for compounds with MW > 25,000. Thus, low-molecular-weight constituents pass through the membrane, whereas proteins or protein-bound constituents are retained. Hartwick ct al. (HIO) reported excellent recoveries for xanthosine, inosine, guanosine, theobromine, theophylline, and caffeine. Tryptophan showed poor quantitative recovery in accordance with the findings of previous investigators (K33, 01). 

No doubt the commercial importance of the various methylated xanthines such as theobromine, theophylline and caffeine has contributed to the substantial literature on... 

Fig. 1.16. Scparaiion of theobromine (/). theophylline (2) and caffeine (.t) in aquet>us-organic ((A) methanol-water. % 70) and micellar ((B) 0.02 mol/l CTAB in wa(er) mobile pha.ses. Column Sila,sorb SPH Cs. 7.5 im (300 x 3.6 mm i d.) (low rale I ml/min. detection UV, 254 nm. temperature 25 C. Deteelor response in milliabsorbance units.

The purine group of alkaloids includes the vegetable alkaloids caffeine, theobromine, theophylline and the animal alkaloids xanthine, hypoxanthine, guanine and adenine. The most common substance which is a purine compound is uric acid, but, though directly related to the alkaloids given above, it is not itself usually considered as an alkaloid. The constitution of uric acid has been fully considered (Part I, p. 442). It is the tri-hydroxy derivative of a substance known as purine which is the mother substance of the purine alkaloids also. 

S3mthesis of Xanthine.— The synthesis of xanthine which is the immediate mother substance of theobromine, theophylline and caffeine has been accomplished as follows Starting with urea or carbamide, this is treated with cyano acetic acid in the presence of phosphorus oxychloride whereby the cyan acetyl radical is introduced into urea. The cyan acetyl urea by treatment with sodium hydroxide yields an isomeric imino compound. 

Interest in studying these alkylations of 8-azaxanthine was fueled by the desire to find practicable syntheses for 8-aza-theobromine, theophylline, and caffeine, and less work was done on the monooxo-8-azapurines. 9-Ben-... 

N.m.r. spectra of xanthine, theobromine, theophylline, caffeine, and their conjugate acids have been analysed. The AT-ray crystal structure of (theobromine)2 H2I8 shows it to be a polyiodide salt with alternating cationic (H-bonded protonated theobromines) and anionic (Iti ions) layers. ... 

Some other drugs that appear to owe part of their action to phosphodiesterase inhibition include a number of naturally occurring methylxanthine drugs and their derivatives (e.g. aminophylline. caffeine, theobromine, theophylline), but they also have ADENOSINE RECEPTOR ANTAGONIST properties see BRONCHODILATORS CENTRAL STIMULANTS. 

Caffeine, theobromine, theophylline and xanthine. Ion-exchange Zipax SAX 0.01M sodium borate... 

Brominelammonia. Expose the chromatogram to bromine vapor for 2 minutes, hold it in the steam from a boiling water bath for 1 minute, then heat in the oven at 110°-120° for 5 minutes. With caffeine, theobromine, theophylline and other xanthine derivatives a rose pink spot develops which becomes reddish purple when exposed to ammonia. 

I he Purine drugs 1-4 can be identified by their characteristic contents of caffeine, theobromine, theophylline, various caffeoylquinic acids, flavonoid glycosides and saponine.s,... 

Experiments with liver slices and cultured cell lines have corroborated this pathway of purine degradation. In human liver slices 16 xanthine derivatives were produced from caffeine by action of P-450 system. Demethylation at N-3 was the most prominent process [18, 19]. Comparison of cell lines from humans, hamsters, mice, and rats show some interspecies differences but all of them demethylated and oxidized caffeine [20]. Human liver cells give 1,3,7-trimethylurate as the major metabolite of caffeine, but also made were the intermediate products theobromine, theophylline, and paraxanthine [21]. Human liver microsomes convert theophylline to 1-methylxanthine, 3-methylxanthine, and 1,3-dimethyluric acid [22, 23]. Human kidney microsomes produced each of the three possible demethylated products as well as 1,3,7-... 

Also analyzed caffeine, dipyrone (sulpyrin), bucetin (3-hydroxy-p-butyrophenetidine), phenacetin, mefenamic acid, aspirin, salicylamide, salicylic acid, ethenzamide (o-ethoxyben-zamide), theobromine, theophylline... 

Wong, S.H.Y. Marzouk, N. McHugh, S.L. Cazes, E. Simultaneous determination of theophylline and caffeine by reversed phase liquid chromatography using phenyl column. J.Liq.Chromatogr., 1985,8, 1797-1816 [also caffeine, cimetidine, codeine, dimethylxanthine, meperidine, pentobarbital, pheno-barbital, secobarbital, theobromine, theophylline hydroxyethyltheophylline is IS]... 

Theodoridis, G. Papadoyannis, I. Vasilikiotis, G. Tsoukali-Papadopoulou, H. Reversed-phase high-performance liquid chromatography-photodiode-array analysis of alkaloid drugs of forensic interest. J.Chromatogr.B, 1995, 668, 253-263 [also amphetamine, bamifylline, caffeine, cocaine, codeine, dia-morphine, ethylmorphine, flufenamic acid, methadone, morphine, nalorphine, norcodeine, papaverine, quinine, scopolamine, strychnine, theobromine, theophylline, tolfenamic acid]... 

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