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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.

 

 

Elion-Hitchings Building Tour: A Storify

  1. As discussed in my post last week, I had the opportunity on Saturday to tour the old Burroughs-Wellcome US headquarters building in Research Triangle Park, NC. Designed in 1969 by architect Paul Rudolph, the building was completed in 1972. The building became known as the Elion-Hitchings Building after BW scientists Trudy Elion and George Hitchings shared the 1988 Nobel Prize in Physiology or Medicinewith Sir James Black.The building was acquired by Glaxo when they merged with Wellcome in 1995 (Glaxo had built its US headquarters in RTP in 1983, just north of the BW property.).

    Now GlaxoSmithKline (GSK), the company began liquidating buildings and consumer products over the last two years. When they announced their intent to sell the Elion-Hitchings Building in April, 2011, I suggested that someone purchase it to fashion into hipster condominiums. My hopes were dashed when United Therapeutics purchased it and two other buildings for $17.5 million in late June of this year. United Therapeutics has a 55-acre lot adjacent to the GSK property where they’ve constructed a new headquarters building of their own.

    What follows is a Storify compilation of my tweets from Saturday with photos that I sent out. I’ll post other photos later.

HHMI and Duke Celebrate the Lefkowitz Chemistry Nobel

As discussed in my previous post, I took a personal day off from work yesterday to bask in the excitement of a university community celebrating a Nobel prize for one of its most beloved researchers, Dr. Robert “Bob” Lefkowitz, MD. He joined Duke in 1973 when, he says, “it was not the powerhouse it is today.”

Lefkowitz will share the prize with his former trainee, Brian Kobilka, MD, now at Stanford University.

I had the honor of joining his laboratory’s champagne celebration in the morning and the Duke University press conference in the early afternoon. (The full 47-minute press conference streamed live and is archived here at Duke.).

I live barely three miles from Duke and had no idea when or if I’d ever have the chance to be so close to such an event. The Lefkowitz prize is particularly meaningful to me as he is a biochemist physician-scientist who also considers himself a pharmacologist. So, I write this not so much as a journalist but rather — as Duke Research Communications Director Karl Leif Bates put it — a fan boy.

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L’Embarras Des Richesses: ScienceOnline2013 and ScienceWriters2012

In this quiet moment on a rainy Saturday evening in North Carolina Piedmont, I lie here in awe of the breadth of creative talent and boundless enthusiasm that this place attracts.

Tonight at 5:00 pm Eastern time, a couple hundred folks or so learned that they had not scored a slot in the lottery for the remaining spaces at ScienceOnline2013. I won’t be there this year either but I can certainly understand the disappointment. This simple idea of Bora Zivkovic along with Let’s-Get-Together-and-See-Where-This-Goes Guy, Anton Zuiker, has grown from a small gathering of likeminded online science enthusiasts to become the South-By-Southwest of science meetings, now under the exceptional leadership of Karyn Traphagen.

I encourage everyone to stay on or sign up for the waitlist. Lots of plans change between now and late January so registration slots will most certainly open up.

Y’all come! Click for details.

But in the meantime, you might consider another possibility that just happens to be available this year very near to the same GPS coordinates: ScienceWriters2012, the annual conference of the Council for the Advancement of Science Writing and the National Association of Science Writers.

Scheduled for October 26-30, 2012, ScienceWriters2012 will be headquartered at the very same hotel with a program crafted by a broad group of science communicators that include a subset of ScienceOnline folks. (For the record, we’re called Science Communicators of North Carolina, or SCONC.).

Here, look at the schedule yourself.

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Visualizing Chemistry Education with Untamed Science

Well, I’m coming up on 10 days on my new job at the North Carolina Museum of Natural Sciences working on science communications for our new wing, the Nature Research Center. Beyond my creative and uniformly brilliant co-workers, I’m blown away by how many remarkable people I’ve met from around the state and world by just being at the Museum.

Among those were the filmmakers from the visual science education operation, Untamed Science. Co-founders Rob Nelson and Jonas Stenstrom. I learned that I was very fortunate to get an audience with Jonas as he was visiting from Sweden where he coordinates the team’s international science education efforts. He first met Rob, a native Texan & Coloradan, while both were studying in Australia. Joining them was their local documentarian partner, the talented Michelle Lotker.

Fun, free, and scientifically accurate.

Untamed Science describe themselves as “a group of scientists and filmmakers that have united with one simple goal – communicate science in a fun way to the next generation.” Their portfolio of free video and text content covers the spectrum of biology, physics, chemistry, earth science and technology.

Their target audience began as middle-school students but many of the details are those that parents (yes, me) might not know. I had a fabulous time sitting with our nine-year-old daughter last night to go through about a dozen of their videos and podcasts. Bedtime was delayed significantly – thanks, folks.

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Reddit AMA with Neil deGrasse Tyson

Neil deGrasse Tyson. Credit: Patrick Queen/Columbia Magazine

I don’t know how many of you tune-in to these “Ask Me Anything” discussion threads at Reddit but I’ve been grooving on them since our colleague Derek Lowe did one back in March. In general, people of note can either propose their own session or be nominated to do so. Folks can ask them any question and the Reddit thread reflect their responses and discussion by others.

Neil deGrasse Tyson is one of the giants in public communication of science. An astrophysicist who has been been the Frederick P. Rose Director of the Hayden Planetarium for the last 15 years, Tyson will soon re-launch Carl Sagan’s Cosmos series. The complete thread of Tyson’s AMA can be found here.

Here’s one of his answers that may hold special appeal to our C&EN readers:

Question: If you think 5 and 10 years from now, what are you most looking forward to in science? Any expectations?

Tyson: Cure for Cancer. Fully funded space exploration. Physics recognized as the foundation of chemistry. Chemistry recognized as the foundation of biology. And free market structured in a way that brings these discoveries to market efficiently and effectively.

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Gooood morning, Santiiiiago!

My new Chilean colleagues: First-year medical students at the Universidad Finis Terrae in Santiago, Chile. Credit: Xaviera Cardenas

I love my blogs and my readers.

Last Friday morning, I had the delight of Skyping in to a medical school bioethics class at Universidad Finis Terrae to discuss the virtues and pitfalls of animal research. I was contacted earlier in the week by an email from Xaviera Cardenas, a first-year medical student at this university in Santiago, Chile, who was looking for an international scientist to hold forth on this topic.

Readers of CENtral Science know that any novel chemical you synthesize must undergo some animal testing before it can be used in people. This is not our choice as individuals but, instead, a requirement of our regulatory authorities. Despite advances with in vitro technologies, testing in a limited number of rodent and non-rodent species is absolutely required.
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Winners in The Henrietta Lacks Foundation design contest

First things first: Congratulations to Holly Gaskamp (hollycopter) and Michael Lombardi (Amoeba Mike)!

Let me explain. The last two weeks have been a whirlwind while planning for the 102nd Annual Meeting of the American Association for Cancer Research (AACR) held April 2-6 in Orlando, Florida. Having been invited by author Rebecca Skloot to serve on the board of The Henrietta Lacks Foundation, we used our recently-awarded 501(c)(3) status (non-profit charity) to host an exhibitor’s booth at the meeting.

Given the very short timeline between this IRS ruling and the meeting, I turned to you – dear readers – for graphic design expertise to fashion buttons and T-shirts to award at the meeting booth to promote the mission of the Foundation: “Helping those who’ve unknowingly made important contributions to science.”

Well, we were fortunate to receive a wave of entries into our contest and two designers were selected to imprint their designs on official HeLa Foundation paraphernalia.

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