I have heard of designer chemists that would take well known drugs, change a hydrogen to a methyl group, and then see what the effect would be in people.

So my question is, what happens in caffeine when these kinds of substitutions are done? What happens if you take the methyl group coming out of one of the nitrogens and make it an Ethyl, or if you change a methyl into a hydrogen? caffeine

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    $\begingroup$ Did you bother to google this a bit? Wikipedia perhaps? en.wikipedia.org/wiki/Theobromine $\endgroup$ – Karl Jan 7 '18 at 18:17
  • $\begingroup$ @Karl, how was I to know that Theobromine was the analog? Wikipedia does not have a search-by-structure feature. $\endgroup$ – vy32 Jan 25 '18 at 12:37
  • $\begingroup$ Really. The link in the first line in the wikipedia article about coffeine: en.wikipedia.org/wiki/Xanthine $\endgroup$ – Karl Jan 25 '18 at 16:59

Yes there actually a few analogs of caffeine (methylxanthines).

Other than caffeine, the naturally occurring methylxanthines are theophylline, and theobromine:

enter image description here

Caffeine is a widely used CNS stimulant. Theophylline has some medical use as a CNS stimulant, but its CNS stimulant properties are encountered more often as sometimes severe, and potentially life-threatening, side effects of its use in bronchial asthma therapy. Theobromine has very little CNS activity (probably because of poor physicochemical properties for distribution to the CNS).

  • $\begingroup$ Thanks! This is precisely the info that I was looking for. $\endgroup$ – vy32 Jan 25 '18 at 12:38

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