Theobromine Revisited

A clever N’Tran caught an error in my “brainy” scribbling. The picture was cropped too closely and some bits were left out.

I shall make amends:

This is Theobromine. It is quite similar to Caffeine. Both are vital to my existence.

(Woooo. Two Hydrogen and a Carbon separate the two! Now you know why a dash of cocoa mix in your coffee seems to blend so well. For the chemically challenged: the caffeine is on the left.)

In addition to coffee beans, caffeine is also found in tea leaves, cocoa beans, cola nuts and guarana seeds. It is composed of a skeleton consisting of a fused five and six-numbered ring comprising carbon and nitrogen atoms to which are attached carbon, hydrogen and oxygen atoms, all arranged as shown in the figure above. Molecules which are based on the same skeleton as caffeine are called purines, and two examples of such molecules, adenine and guanine, are constituents of our DNA. Another closely related purine is theobromine (Figure above, right side), which is a constituent of the cocoa bean, and hence is found in chocolate.

Coffee flows through my veins like a wicked fuel, empowering me even as it causes my heart to detonate out of my chest. It is only natural that I top it off with a bit of chocolate. How better to enjoy the endorphin release?

The chemical skunk works have their noses to the grindstone in frantic endeavors to merge these two magnificent things into one utopian creation. A bit of synthetics here and a touch of synthetics there: bliss achieved.

Molecular recognition of xanthine alkaloids: First synthetic receptors for theobromine and a series of new receptors for caffeine

Synthetic receptors (H3, H4, H5 and H6) are designed and synthesised for the first time for theobromine, a xanthine alkaloid used as a diuretic. The synthesis of the receptor H6 is achieved by Co(PPh3)3Cl-mediated homocoupling of 3-(ethoxycarbonyl)benzyl bromide 12 under mild conditions. New caffeine receptors (H7, H8 and H9) are designed and synthesised. The binding results of theobromine and caffeine (both by NMR and UV studies) are reported.

My God! Is it not delightful?

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