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Category → Living with Chemistry

Colorado Marijuana Product Potency: Just Another Herbal Medicine

Bhana131210_ALTST_Edibles_Choco.jpg.CROP.promo-mediumlargeSince the beginning of the year, I’ve been watching Colorado’s burgeoning legal marijuana economy both as a natural products pharmacologist and science and health journalist and writing professor. And while the Colorado and Washington experiments are interesting to observe from afar, I’m amazed, but not surprised, by how much remains the same when it comes to the chemistry of what is essentially a botanical medicine consumer product.

The Denver Post has made a very concerted effort to treat the legal marijuana market as any economically- and culturally-important area of coverage, going so far as to establishing a focused, online publication called The Cannabist.

Over the past week, the section’s editor, Ricardo Baca, has been reporting on an aspect of recreational marijuana products where analytical chemistry reigns – and is putting some companies on the defensive. You won’t be surprised to hear of this episode if you read Bethany Halford’s article on marijuana product testing in the December 9, 2013 issue of C&EN.

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The Cinnamon Challenge: On Being Charged with #Chemophobia

Consider cinnamaldehyde.

Consider cinnamaldehyde.

As many of you are likely to have heard yesterday, a paper from Steven Lipshultz, MD, at the University of Miami appeared in the journal Pediatrics detailing poison control center reports on an adolescent misadventure called The Cinnamon Challenge. The challenge: to swallow a teaspoon of cinnamon powder in 60 seconds without any liquids.

The practice has been rummaging about the internet since 2001 but really took off on YouTube over the last three years. Lipshultz’s report discusses the risks of such tomfoolery, particularly due to the inhalation of cinnamon powder while one is choking.

I planned to write about this practice both here and at my Forbes.com blog since I thought both chemists and the general public would be interested in the topic. I wrote the Forbes post earlier this morning and drew a series of comments from a kindly San Diego-area chemist who took issue with my facetious comparison of cinnamaldehyde (cinnamic aldehyde) to formaldehyde.

While Lipshultz states that much of the acute pulmonary toxicity of cinnamon powder is likely due to the cellulose content, I submit that some damage could be due to protein adducts formed by cinnamaldehyde. Yes, yes, it’s not as dangerous as formaldehyde. But even at roughly 1% (w/w) in the powder, I hypothesize that the cinnamaldehyde could cause epithelial damage. Also note that cinnamaldehyde is not just any aldehyde but rather an unsaturated aldehyde. That makes me think of acrolein.

The experiments have not been done. But one animal study has been published showing that intratracheal administration of cinnamon powder — not pure cinnamaldehyde — can cause acute lung injury in rats and trigger pulmonary fibrosis within a month.

Alas, my concerns about cinnamaldehyde rubbed two commenters the wrong way and one, well, sought to chemsplain me.

I was originally trained in toxicology so I know the whole Paracelsan story that the dose makes the poison (to which I’d also add “route of administration”). But do you chemists, especially those in chemical toxicology, think that I’m overreacting (as it were) to the potentially reactive nature of cinnamaldehyde in inhaled cinnamon powder?

I’m willing to be corrected if I appear to suffer from #chemophobia. But I hypothesize that 1% (w/w) cinnamaldehyde can be cytotoxic.

Dr. Gina Stewart on Career Flexibility and Entrepreneurship

A cool idea! Photo: Arctic, Inc.

A cool idea! Photo: Arctic, Inc.

We’re about to close up the world headquarters of Terra Sigillata to head out and convene with the PharmFamily in points north for Easter (but, thankfully, not a Nor’easter.)

Before we do, I’d like to draw your attention to a short but astute editorial in The Chronicle of Higher Education by chemist Gina Stewart. Stewart launches her essay with a concise description of a dichotomy that’s giving all of us agita:

The STEM paradox: At a time when we have a national dialogue about the dearth of students pursuing these degrees, newly minted Ph.D.’s are having a harder time landing academic jobs.

She then talks about her career and what she considers to be the shortest postdoc on record (believe me, Gina, I know of many shorter) in the UNC-Chapel Hill laboratory of Joe DeSimone. There, the seeds were planted for entrepreurship and a fascination with the practical applications of carbon dioxide.

Years later, Stewart is now CEO of Arctic, Inc., a company that uses sustainable weed control methods by selectively freezing these nasty invasive threats to biodiversity – her company site is appropriately named frostkills.com.

Her experience is one example where one takes a different approach to a chemistry career than following in the traditional academic progression. The first commenter already admonished her for saying that she was pursuing an alternative career. Based on percentages, being a tenure-track faculty member is now the alternative.

It’s a great read so enjoy. I was also delighted to learn that she and her husband live just west of the Research Triangle and base their company in Clemmons, NC.

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.

 

 

Watch Twitter on Saturday for #Chemophobia

This week, the Research Triangle area is hosting ScienceOnline2013, an international science communications unconference that draws Pulitzer Prize-winning science writers, big media, graduate students, new media, science teachers, old media – pretty much anyone who’s involved in communicating science to diverse audiences via digital media.

The gathering began as the North Carolina Science Blogging Conference in 2007 (and probably before that) and has grown to be a highly-competitive ticket for 450 attendees. So popular are the conversations there that “watch parties” are being held in cities worldwide – London, Paris, Adelaide, Denver, Dublin, Belgrade, and others.

But the conversation can also be easily accessed via Twitter by following the hashtag #scio13.

I’d love to draw the C&EN and CENtral Science crowd to a superb session that will be held Saturday, 2 February, with our own Dr. Carmen Drahl and chemistry professor/former ACS intern Dr. Rubidium on chemophobia: the public aversion to anything that carries the label of “chemical.”

Here’s the description from the unconference wiki for tomorrow’s 10:30 am EST session:

Description: In today’s advertising and pop culture, words like “chemical”, “synthetic” and “artificial” are synonyms for harmful, toxic and carcinogenic, while words like “natural” and “organic” imply a product is wholesome and good for the environment. This widespread misconception colors public perceptions of chemistry and its role in the modern world. Chemophobia may not be as direct a threat to our future as, say, climate change denialism or the Israeli-Palestinian crisis, but it clouds public understanding of real and very important issues we face (e.g., how to boost agricultural productivity) and plays into the hands of quacks and cranks. How can bloggers and the media effectively combat chemophobia? How much chemistry does the public need to know to be well-informed and make good decisions, and what’s the most effective avenue for disseminating that kind of information? Proposed session hashtag: #chemophobia

Over the past year, several folks in the blogosphere and chemistry education realm have been providing folks like Carmen, DrR, and author Deborah Blum with examples of chemicals being portrayed as “bad.”

Yet, each of us are a glorious bag of chemicals (thankfully).

Where does the negative perception arise and how can we in chemistry-related fields better communicate with the public?

Carmen and DrRubidium have asked us to follow the #chemophobia hashtag on Saturday 10:30-11:30 am EST.

Here’s a world clock so you can plan when to follow the discussion on Twitter.

 

Lefkowitz and Kobilka win 2012 Chemistry Nobel for GPCRs

Defending the Chemistry Nobel for “biology” – again.

I’m near-certain that this is the first Nobel Prize in Chemistry given to two MDs. (10:31 am EDT: I was wrong, as per commenter Jonny below. Peter Agre, MD, and Roderick MacKinnon, MD, received the Nobel Prize in Chemistry 2003 for their work on aquaporins and other ion channels.)

Robert Lefkowitz, MD, of the Howard Hughes Medical Institute and Duke University Medical Center, and Brian Kobilka, MD, of Stanford University School of Medicine, will share the Nobel Prize in Chemistry 2012. The award recognizes a lifetime of work, certainly for Lefkowitz, in elucidating the action of the central chemical signal transducers of the human body.

This is a chemistry prize, albeit a biological chemistry prize.

The prize is being given for discovering how the body’s most important chemicals communicate their own chemical signals from outside the cell to inside. Without G-protein-coupled receptors, or GPCRs, our hearts would not beat, our lungs would not expand and contract, and our brains would be unable to regulate much of everything that runs in our bodies.

Moreover, the ubiquity of GPCRs have over history breathed tremendous life and stimulated innovation in chemistry to synthesize tools to modulate these receptors and thereby relieve human suffering. Chemists should revel in this prize – without G-protein coupled receptors, many chemists would not have been employed for the last few decades.

But I do agree that a case could be made for this prize to be given in Physiology or Medicine, particularly since GPCRs are central to physiology, “from plants to man.”

More later.

Feel free to vent your spleen in the comments below.

But do note that Derek Lowe, medicinal chemist and grand master of the chemblogosphere, has already decreed, “[M]y fellow chemists, cheer the hell up already.”

Disclosure: I hold an Adjunct Associate Professor appointment in the Duke University School of Medicine, Department of Medicine.

 

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Poisons and Policy: Arsenic and Aflatoxins

The other problem. Credit: Nakhonsawan Field Crop Research Center, Thailand.

In the past 24 hours, do you recall hearing anything about arsenic in rice? If you’re in the United States, the answer is very likely, “yes!”

A great many pixels were spilled yesterday when Consumer Reports and the US Food and Drug Administration released — almost simultaneously — analytical data on inorganic arsenic concentrations in 200 samples of commercial rice products, particularly those grown in the southern US.

You can’t do any better in understanding this story than reading, “Arsenic and Rice. Yes, again,” on Deborah Blum’s Elemental blog at Wired Science Blogs. Professor Blum has been discussing arsenic in the diet for a few years, an interest she developed while composing her superb book, The Poisoner’s Handbook: Murder and the Birth of Forensic Science in Jazz Age New York.

Deborah’s post puts in perspective the risks of inorganic (and organic) arsenic concentrations in food products such as rice relative to drinking water. Arsenic occurs in nature but exists in higher concentrations in water from areas where arsenical pesticides have been used in cotton farming or poultry deworming (the latter discussed in 2006 at NYTimes). While she closes in being critical of the FDA for lack of clear consumer guidance, let it suffice to say that no character in Blum’s book was killed by poisoning with rice from Louisiana.

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How Do You Like Your Caffeine?

Inhaled or oral?

Natural or synthetic?

Two interesting reports came across the interwebs over the last couple of days.

Earlier this week, the US Food and Drug Administration issued a warning letter (press release) to makers of Aeroshot brand of inhaled caffeine. No, it’s not an asthma medicine (although oral theophylline is). It’s billed as a non-caloric caffeine delivery system, 100 mg per hit. That’s roughly the amount in two 12 fl oz/355 mL cans of Mountain Dew or one gulp more than a 8.4 fl oz/250 mL can of Red Bull energy drink. However, the company claims that only 15-25 mg are delivered – perhaps half the amount in a Coca-Cola.

The FDA has concerns about the dual promotion of the product for swallowing and inhalation, the relative safety of inhaled caffeine, and the potential for children and adolescents to use the product in combination with alcohol. The company’s FAQ specifically notes that the product is not marketed for use in children. Readers will recall that Four Loko caffeinated alcohol drinks were withdrawn from the market in late 2010 and replaced with alcohol-only versions.

From Zhang et al., doi:10.1021/ac203197d

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Supporting chemistry education in public schools

Dear beloved, good-looking, and erudite readers of Terra Sigillata,

Our blog is once again participating in a drive for DonorsChoose, an online charity established to fund small, public schoolteacher-initiated projects that are not otherwise supported by their school districts. The annual DonorsChoose Blogger Challenge – Science Bloggers for Students – is a friendly competition among blogs and blog networks to use their reach to put our collective money where our mouths are.

Click on the graphic to go to the "Chemistry with Kroll" giving page. Thank you!

As public school budgets are cut and cut, we have to maintain the quality of scientific experiences for our young people. Your generosity can help!

How does it work?

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Compilation of synthetic marijuana posts (Spice, K2)

Welcome to readers arriving from Reddit – scroll down through the post for links to our more detailed discussions on cannabimimetics. (updated 8 October)

Recent media coverage of our writings on the chemistry, pharmacology, public health risks, and regulation of synthetic marijuana herbal incense products has led us to put together a compilation of posts we’ve written here on the topic over the last year-and-a-half.

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