The plant Theobroma cacao is the source of chocolate, and theobromine is the primary purine derived from chocolate. Another related alkaloid is theophylline, which is an orally administered asthma drug.

Note that theobromine, theophylline, and caffeine differ by the location of two methyl groups-caffeine has both methyl groups, while theobromine and theophylline have a single methyl group on only one of the two nitrogens. Such minor changes in the chemical structure can provide significantly different biological responses.
a. What is the most basic nitrogen in theobromine and theophylline?
b. What is the most acidic hydrogen in theobromine and theophylline?
c. Do you expect theobromine and theophylline to form N-glycosides with sugars such as 2-deoxy-d-ribose?

Transcribed Image Text:

CHj H3C O N theobromine theophylline