Why Isn’t Caffeine Called “Theoanaleptine”?

This question came to me as I read last week’s C&EN cover story by Dr. Lauren K. Wolf on caffeine toxicity entitled, “Caffeine Jitters.”

By the way, read it if you haven’t — it’s open-access on C&EN right now and remains the most-read (last 7 days), most-commented (last 30 days), and most-shared (last 30 days) article since it appeared. Lauren did a terrific job of sifting through decades of information on the physiological effects of caffeine to make sense out of the true health hazards of caffeine consumption at “normal” and excessive doses.

Caffeine, a natural alkaloid found predominantly in coffee beans, is 1,3,7-trimethylxanthine (not IUPAC, but you get it). In the body, the hepatic cytochrome P450 CYP1A2 catalyzes the N-demethylation of caffeine to theophylline, theobromine, and paraxanthine.

The cytochrome P450 CYP1A2 catalyzes the N-demethylation of caffeine to one of three dimethylxanthines, with paraxanthine predominating. Credit: C&EN

The cytochrome P450 CYP1A2 catalyzes the N-demethylation of caffeine to one of three dimethylxanthines, with paraxanthine predominating. Credit: C&EN

 

Divine chemicals

Of note, theobromine and theophylline also occur in nature. Theobromine is found in cacao beans. Because chocolate is heavenly, it was given the Greek name for “food of the gods”: theos – god; broma – food.

Correct, theobromine contains no bromine. Had it contained bromine, the name might have been the same but would have been derived from the Greek bromos, or “stench” – “stench of the gods,” which, clearly, it is not.

Stimulant of the Gods. Available now at the Pharmacopolis store at Zazzle.

Stimulant of the Gods. Available now at the Pharmacopolis store at Zazzle.

Theophylline also occurs naturally and had been extensively used as a bronchodilator for folks with asthma. Primatene tablets used to contain theophylline but today are ephedrine. Again, theophylline has the godly theo- prefix while the -phylline suffix indicated that it comes from leaves.

And apologies to paraxanthine. It’s known historically for having first been isolated from urine in 1883. Not until the 1980s was it shown to occur in some plants. In any case, the biosynthesis of the di- and tri-methylxanthines originate with xanthosine from purine metabolism.

So to my question. . .

Because caffeine is so widely worshiped, why is it not known as theoanaleptine? The Greek analeptikos means stimulant and the English term analeptic is defined as a stimulant drug.

So, why not?

My best guess is because caffeine was described in the literature prior to theophylline and theobromine. From M.J. Arnaud’s chapter in Caffeine (Springer, 1984):

The isolation of caffeine from green coffee beans was described in Germany in 1820 by Runge and confirmed the same year by von Giese. In France, Robiquet in 1823 and then Pelletier in 1826 independently discovered a white and volatile crystalline substance. The name “cofeina” appeared in 1823 in the “Dictionaire des termes de medécine” and the word “caffein” or “coffein” was used by Fechner in 1826.

Arnaud goes on to say that theobromine was discovered in cocoa beans in 1842 and theophylline in tea leaves in 1888.

So, caffeine had about a two-decade headstart in being named for its presence in coffee before related methylxanthines took on their divine monikers.

Sure, sure, caffeine is a well-recognized name that derives predictably from its source. But let’s live a little. Wouldn’t you rather be drinking the stimulant of the gods?

If you’re as excited about this as I am, you may purchase theoanaleptine coffee mugs here. They’ll set you apart from ever Tom, Dick, and Harriet who think they’re clever with their caffeine coffee mugs.

And even with accepting the new colloquial name of theoanaleptine, our friend Scicurious can still keep her tattoo unchanged.

 

 

Author: David Kroll

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6 Comments

  1. Zeus refers to Katy Perry as “theoanaleptine”, but don’t tell Hera.

  2. There’s never any rhyme or reason or consistency for the trivial names we assign to new natural products. The most usual course is to use the scientific name of the source organism, which is true enough for the xanthines. Another strategy is to use the location where the organism was located or purified (e.g. anatolioside from Anatolia or fredericamycin from Frederick, MD). Perhaps less felicitous is the practice of naming the compound after one’s wife, daughter or other relative (michellamine for Michelle) or movie stars (bissetone). Some of the most difficult to pronounce names have used Hawaiian names of the organism or location for marine natural products isolated in Hawaii (puupehenone) or Aztec names for plants (tonantizitlolone). It’s bad form, in general to create a new trivial name for the latest in a long series of similar compounds. I like a trivial name to be mellifluous, though sometimes it’s fun to go for tongue-tieing names.

  3. On the train to ScienceOnline, I talked to Deep Sea News’s Miriam Goldstein about the natural product I worked on in grad school– abyssomicin C. It was found in the Sea of Japan, but at a depth of only 200 meters or so. “That’s not very deep,” she said. I suppose not, I said, and wondered why the isolators picked abyss- maybe it seemed deep to them.

    • I believe it was named for the movie…..

  4. Or maybe I’m thinking of “The Deep”, which inspired bissetone…

  5. JAB, I love looking into the trivial names of drugs. Now that the USAN guidelines are so rigid in assigning generic names like sumadoobiptabanixmab, I long for the more colorful days.

    I believe that the topo I poison karenitecin was named for John Nitiss’ wife, Karen. Then there’s always good old warfarin from the Wisconsin Alumni Research Foundation.