Theobromine

About: Theobromine is a research topic. Over the lifetime, 1137 publications have been published within this topic receiving 29723 citations. The topic is also known as: 3,7-Dimethylxanthine & Theobromin.

Preparation of theobromine derivative

Abstract: PURPOSE:To prepare the title compound in high yield, with one step, by reacting 1,3-dibromopropane with theobromine in an organic solvent which is a poor solvent of alkali metal salts of theobromine, in the presence of an alkali carbonate or an alkali hydroxide. CONSTITUTION:In the preparation of a theobromine derivative of formula [e.g. 1-(3-bromopropyl)theobromine] by reacting 1,3-dibromopropane which is available at a relatively low cost, with theobromine in the presence of an alkali carbonate or an alkali hydroxide, the reaction is carried out in an organic solvent which is a poor solvent of the alkali metal salt of theobromine (pref. ethanol, acetone, etc.). The amount of the solvent is >=4 parts, pref. 8-10 parts, per 1 part of theobromine. When an alkali metal salt of theobromine is used as a reactant in place of theobromine, the alkali carbonate or hydroxide is not necessary. USE:Important raw material for the synthesis of (5-oxohexyl)-theobromine having vasodilating activity.

Theobromine and Caffeine Recovery with Solvent Extraction

Abstract: A chloroform extraction process was developed for recovery of theobromine and caffeine from the effluent of a theobromine synthesis plant. The product distributions in the extraction process were studied experimentally. In a chloroform–water system, the caffeine distribution ratio was about 15 and was not affected by pH in the 2 to 12 range, while the distribution ratio of theobromine was about 0.45 for pH 10. Therefore, theobromine and caffeine can be recovered separately by adjusting the pH in the aqueous phase. The crude products of theobromine and caffeine can been obtained in the recovery process by evaporation. The thermal stability of theobromine in aqueous solution was also studied. A reciprocating plate column (RPC) is suitable for this extraction process. Pilot tests were conducted with two columns having 38-mm I.D. Scale-up of the RPCs for an industrial system of 23 t/d capacit...

Identification and quantification of drugs in human amniotic fluid.

Abstract: Since drugs administered to gravid females are rapidly transferred to the fetus, transplacentally acquired drugs and drug metabolities should be excreted by the fetus into amniotic fluid. Analyses have been carried out on amniotic fluid obtained at the time of delivery using a gas chromatograph-mass spectrometer-computer system. The drugs that have been identified are caffeine, secobarbital and phenobarbital. Theobromine (3,7-dimethylxanthine) and smaller amounts of 1,7- and 1,3-dimethylxanthine, three metabolites of caffeine, were also found in amniotic fluid, but metabolites of secobarbital and phenobarbital were not detected. It is known that human fetal tissues have active enzyme systems for metabolizing drugs, but these results suggest that this may be a selective rather than general occurence.

Aminoalkyl Derivatives of 8-Alkoxypurine-2,6-diones: Multifunctional 5-HT1A /5-HT7 Receptor Ligands and PDE Inhibitors with Antidepressant Activity.

Abstract: In the search for potential psychotropic agents, a new series of 3,7-dimethyl- and 1,3-dimethyl-8-alkoxypurine-2,6-dione derivatives of arylpiperazines, perhydroisoquinolines, or tetrahydroisoquinolines with flexible alkylene spacers (5–16 and 21–32) were synthesized and evaluated for 5-HT1A/5-HT7 receptor affinities as well as PDE4B1 and PDE10A inhibitory properties. The 1-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)butyl)-3,7-dimethyl-8-propoxypurine-2,6-dione (16) and 7-(2-hydroxyphenyl)piperazinylalkyl-1,3-dimethyl-8-ethoxypurine-2,6-diones (31 and 32) as potent dual 5-HT1A/5-HT7 receptor ligands with antagonistic activity produced an antidepressant-like effect in the forced swim test in mice. This effect was similar to that produced by citalopram. All the tested compounds were stronger phosphodiesterase isoenzyme inhibitors than theophylline and theobromine. The most potent compounds, 15 and 16, were characterized by 51 and 52% inhibition, respectively, of PDE4B1 activity at a concentration of 10−5 M. Concerning the above findings, it may be assumed that the inhibition of PDE4B1 may impact on the signal strength and specificity resulting from antagonism toward the 5-HT1 and 5-HT7 receptors, especially in the case of compounds 15 and 16. This dual receptor and enzyme binding mode was analyzed and explained via molecular modeling studies.