Colorado Marijuana Product Potency: Just Another Herbal Medicine
Mar14

Colorado Marijuana Product Potency: Just Another Herbal Medicine

Since 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. Following a less-than-effective personal experience with an edible marijuana product, Baca wondered whether the amount of THC on product labels truly reflect the abundance of the psychoactive component. In Colorado, marijuana “edibles” – technically called marijuana-infused products, or MIPs – are limited to 100 mg of THC, with a recommendation of 10 mg per serving. Baca solicited the analytical chemistry assistance of one of three state-sanctioned cannabis laboratories, Steep Hill Halent’s Colorado laboratory, directed by chemist Joseph Evans. One particular brand, Dr. J’s, had several products that tested at less than 1 mg of THC despite being labeled at 100 mg. This JPG shows some of the other results. Some products did quite well – several were spot on at 100 +/- 6 mg – while others were a bit over. Baca’s reports were picked up widely this week and, as you might expect, received some pushback from companies whose products didn’t fare that well. But he followed up with some explanations from Evans in this article, as well as some additional replicate testing of products procured from a range of retail sites. But the companies making these products had better get their act together soon. An editorial in The Denver Post on Wednesday reminded manufacturers that Colorado’s potency labeling standards will go into effect on May 1st. The variation in active principles in each product reminds me of Consumer Reports‘ herbal quality analyses that I’ve used in pharmacy teaching since back in 1996, where they first showed ginsenoside content of U.S. ginseng products varying by two logs. Steep Hill Halent also provides other product quality testing that you’d want to see in any botanical medicinal product,...

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The Cinnamon Challenge: On Being Charged with #Chemophobia
Apr23

The Cinnamon Challenge: On Being Charged with #Chemophobia

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...

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Dr. Gina Stewart on Career Flexibility and Entrepreneurship
Mar28

Dr. Gina Stewart on Career Flexibility and Entrepreneurship

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,...

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Why Isn’t Caffeine Called “Theoanaleptine”?
Feb13

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.   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. 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...

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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....

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Lefkowitz and Kobilka win 2012 Chemistry Nobel for GPCRs
Oct10

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.     10:22 am EDT: Here’s an excellent 2011 C&EN article by Carmen Drahl that explains the relevance of GPCRs to chemistry. Cites Brian Kobilka’s work. Carmen also wrote the C&EN Online article that appeared just a bit ago.     11:30 am EDT: Went up to Dr. Lefkowitz’s office at Duke where he was holed up doing telephone interviews before he heads down to the lab’s champagne reception.   See my next post for discussion of the 1:30 pm EDT news conference and background on Lefkowitz’s dependence on chemical tools to launch this research.  ...

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