Give Your Coffee or Chocolate a Boost with Grapefruit

Why on earth am I posting on this? My blog is titled Randomness, what do you expect? Really, it’s because @brampitoyo, @rachelrigg, & @donpdonp were talking about it on twitter and I caught wind of it. I had done some research into this in the past so I knew a little bit about what grapefruit does to your metabolism. I decided I should write it out somewhere. What follows may get a little bit technical, but don’t get scared away. Anyone should be able to get the gist of this even without fully understanding the chemistry. Please heed the warning at the bottom.

Grapefruit has a few compounds in it that alter the way you digest other foods. Namely, these are bergamottin and naringenin. These compounds temporarily stop certain enzymes in your digestive pathway and in your liver (in larger doses) from breaking down certain type of compounds. These compounds include estrogens, caffeine, certain anti-depressants, and many more found here, here, and at this list of drugs affected by grapefruit Note the first two list are technical, the column heading substrate is what you need to look at. Simply because and enzyme substrate is the molecule it breaks down or builds up.

So what happens when I eat a grapefruit?

When you eat a grapefruit everything in it goes into your stomach and then to you duodenum (the small intestine) and affects the rest of what is going on there. If not much is going on there it will get into your blood stream and circulate to your liver, where it can modify what’s going on there. If you have consumed some items from the above mentioned list, eating a grapefruit will keep it being broken down into its metabolites (literally, “things thrown away”, from Greek). Meaning it will stay active longer in your body.

So then if I Drink Caffeine or Eat Chocolate…

Yes, it should have a more lasting effect. Here’s why and where it can get technical.
Look at these pictures:
A picture of Xanthine, notice the benzene ring and a pyrrole ringA caffeine molecule, notice the benzene ring and pyrrole ringTheobromine, notice the benzene ring and pyrrole ring
Xanthine,Caffeine, & Theobromine
Here’s how Caffeine breaks down:

Caffeine breaks is metabolized by enzymes into paraxanthanine, theobromine, and theophylline.
Caffeine Metabolites

All of these are in the same family of compounds. Since they’re in the same family of compounds, they should all be affected by the same enzymes. So we lookup those enzymes, CYP3A4 & CYP1A2 and it looks like they do work on a lot of things with the same structure and same R-groups.


So there you have it. Just mix fresh squeezed grapefruit (or anything that has the bitter skin part) into a mocha and enjoy flying around the room and the added ability to create memories and remember things. Just beware of a minor caveat — theobromine poisoning. If you have too have too much of a good thing it’ll kill you. Another thing to keep in mind is that grapefruit juice has the potential to get you more drunk and keep you there longer if you drink enough of it. So don’t go drinking coffee, grapefruit juice and alcohol — it may or may not be pleasant depending on how you roll.