WWWTP? Operatic Chemistry in the Boston Globe

Has anyone seen the fantastic writeup by Carolyn Johnson in the Boston Globe today?

Johnson covers the J. Chem. Ed. recently penned by Prof. João Paulo André, of the Universidade de Minho to celebrate the storied use of poisons in opera. I hadn't realized, honestly, that this rich history involved poisons from such a wide variety of plants, minerals, and animals, or that specific references to each substance can be found in the libretti. Fascinating!

Unfortunately, the graphic that accompanies the story takes a few chemical liberties, which I've circled:

(Update 4/7/13 - I should point out that more structures are right than wrong here, which a commenter points out is more than you usually see in mainstream media. Kudos to the BG for covering the article the way they have)

I've written a short note to the author, reprinted below, and I will post any response I receive.

Dear Carolyn:

Good afternoon! My name is See Arr Oh (a pseudonym), and I blog at Just Like Cooking, a chemistry blog aimed at general-interest audiences.

http://justlikecooking.blogspot.com

I noticed your article in today's Globe, and I want to applaud you for your outreach. The article is well-written, and the science seems solid.

http://www.bostonglobe.com/ideas/2013/04/06/treasury-opera-poisonings/gKPw3zoiVNx7mZeRK1p0KL/story.html

However, the image that accompanies your article includes several inaccurate structures for the discussed poisons. For example, the structures of mannitol don't show explicit stereochemistry (3D structure); these might well be glucose drawn this way. 

Scheele's Green is actually a copper complex; trimethylarsine is the poisonous gas that evolves from the dye. Arsenic trioxide and mercuric sulfide aren't actually monomeric, as drawn, but adopt several different crystal forms involving multiple As and Hg atoms, respectively.

Finally, the neurotoxin shown in the "snake venom" box is not actually venom, rather, it's anatoxin-a, from blue-green algae. 

Please consider changes to the illustration. If you need anything further, don't hesitate to contact me at seearroh_AT_gmail.com

Sincerely,

See Arr Oh

Personal Log, Stardate: Mole Day

Well, I certainly 'fished my wish' for this carnival! Only two days in, and I've already compiled the requisite 10 entries for my own post. So, here goes...

Your current job: I'm a medicinal chemist at a (very) small startup company. How small? Let's just say that everyone at the company still fits around one table for lunch.

What you do in a standard work day: Like many folks at small companies, there's hardly a 'standard' day; I rapidly shift between lab and non-lab responsibilities. For instance, in the past month, I've written grants, met with vendors, fixed small equipment, scaled-up our final product, drafted provisional patents, tested new routes, and (nearly) finished our safety handbook. 

Never relaxing, but never boring.

What kind of schooling / training / experience helped you get there? Since I use the #phdlife hashtag from time-to-time, it shouldn't surprise you that I have my doctorate. But let me tell you why I went back to school. I had been working as an RA at a medium-sized biotech back in the "boom years." Every Friday, the Ph.D. chemists would meet in a conference room, and emerge with fresh data and synthetic ideas. 

Patriots coach Bill Belichick
attended Wesleyan around the time
Max Tishler became a chem professor

I wanted to be like them. 

[Soapbox Moment] - I can't recommend enough actual lab work as an intern or undergraduate assistant. Without that experience, I'd never have become a chemist.

How does chemistry inform your work? My nose often points into the pages of Aldrich, Alfa, Fisher, Green & Wuts, and Silverstein & Webster. Reaxys and the primary literature feel like best friends. Thick binders of NMR and HPLC data festoon my top shelves. I'm known to doodle structures on nearby scrap paper, so don't throw away anything on my desk, please!

Finally, a unique, interesting, or funny anecdote about your career: Gosh, lots of 'em. Moving shaky mercury-filled Schlenk lines on rusty old elevators (not recommended). Nearly catching myself and a balance on fire during my first week as an intern. Grading huge stacks of tests while blaring terrible pop music and noshing on pizza.

Here's one I suppose informed the theme of this carnival: my High School chem teacher was also one of our football coaches! So, periodic trends in class, linebacker drills on the field.

One more - Didja see the post title? I still recall one of my early "Aha!" moments as the ST:TNG episode "Night Terrors," where the alien race describes hydrogen as "eyes in the dark, one moon circles" (one proton and one electron). Must have really stuck with me!

"Pure Goodness" - Whirlpool's Chemophobic Water Ad

Last night, courtesy of Chemjobber, came this ridiculous sham ad interesting tidbit:

Here's the Whirlpool pop-up ad I saw that started it all: "Don't drink from the periodic table." #chemophobia http://t.co/M5MBCiKf

Done chuckling yet? I hope not, because you haven't seen the accompanying video, with cloying tagline "Pure Goodness." Apparently, for Whirlpool's target market - wealthy American moms with stupendously huge kitchens - the issue of anything in drinking water scares them silly. And that's the right word, because that pop-up ad above literally reads "don't Drink from the periodic table." Did I somehow miss the memo?

News Flash! Dateline: July 30, 2012 - Water officially no longer derived from hydrogen, oxygen; sources say it exists in new 'drink dimension,' far removed from natural world!

OK, I get it: filtering water removes certain trace metals and organic products you might not want to ordinarily consume - for the moment, we'll overlook fluoride, sodium salts, or relatively innocuous trace metals like iron and copper. If you believe the ad, every poured cup of tap water contains the following (~ 0:09 in the video): mercury, chlorine, lead, ethylbenzene, ortho-dichlorobenzene, lindane, atrazine, para-dichlorobenzene, endrin, MTBE, and benzene. Nevermind that two of the listed pesticides (lindane, endrin) are long-since banned from food crops, or that local water authorities test for most of the other potential contaminants.

What about those scary-looking chemical structures at 0:05? (see left). I checked 'em out: from left, moving clockwise, you have carbofuran, dinoseb, and alachlor (Picky pedagogical note: I've never seen a gem-dimethyl group drawn that way before...should I expect some sort of agostic bond?). Dinoseb and carbofuran are both banned pesticides, and alachlor, though common, lists as only a Class III (slightly toxic) toxin.

As with all chemophobic ads, realize that Whirlpool exaggerates the situation to sell more fancy refrigerators. The same effect can be achieved with any carbon filter: remember Pur, or Brita? Perhaps then you wouldn't have to worry about the other pressing concern (0:58)...


...deadly fridge fungus!

"Everyone run, it's got Timmy!"
Credit: whirlpool YouTube

Comic Homage

I've been a bit under the weather, so I've turned to an old stand-by: digging through the archives of my favorite webcomics. Bonus, when they contain scientific or chemical references.


So far today, I've made it through most of xkcd, and happened to finish Deborah Blum's Poisoner's Handbook last night. With some time on my hands, I figured a "mash-up" of the two might be in order.
(Cheat Sheet: check out this story about biochemistry, NASA, and "alien life" found here on Earth)

MESSAGE FROM THE FUTURE: BEWARE THE SUPER-TOXINS!

Chemistry Kits - Getting Your Hands Dirty

Many science bloggers bemoan the disappearance of the chemistry set, a seemingly anachronistic toy for the Millenials, who might rather Skype, LARP, Geocache, or Tweet (Note: All real activities with very little risk of injury or mess). Scientists especially detest the new “Chemical-Free Chemistry Kit” by Elenco, an educational products company that also sells models of Julius Caesar’s head, a color-in-the-countries globe, and an aluminum triceratops (who was real, btw).  JAYFK and Speakeasy Science jumped into the fray, suggesting that the Kit enhances public fears over the words “chemicals” and “chemistry,” making them synonymous with “evil.”

Should these fears deprive our youth of the chance to make beautiful alum crystals or basement fireworks?

Playing with dangerous things at an early age has a special place in my heart, a flame rekindled in a recent Collectors Weekly article by Lisa Hix. She recounts the laundry list of potentially dangerous compounds the pre-WWII generation could experiment with: potassium nitrate (explosives), sodium ferrocyanide (dyes), sulfuric acid (batteries), and even uranium ore (radioactivity). Most of the cases include hand-drawn images of young boys dressed in ties and lab coats, pouring liquids at eyeball-scorching closeness with no goggles.

Well, I may never have been that cavalier, but I was allowed a certain leniency to play with dangerous things as a child. Whenever thermometers would break, my brother and I would scoop the mercury (yup, mercury) into a little jar and play with it, watching the tiny spheres break apart and glom back together on the glass surface. Cyanoacrylate polymers (Superglue) could stick anything to anything, especially your hands to your face. When we learned that peroxide solution would make blood foam up, we would intentionally pour it on all sorts of things (much parental dismay) to see if we could duplicate the effect. A middle-school experiment to demonstrate how color of transition metals depended on ligation environment went horribly wrong, blasting bright green liquid all over the floor (and us), but I recall being fascinated how the metal complex color changed back to blue when it hit the floor (Readers: Can you guess the metal?). I also discovered that the same compound could permanently stain my lab apron and the concrete floor. Today, much of my current lab attire has holes, stains, and smudges that won't come out with any measure of bleach.

Perhaps my favorite example of theory - experiment - practice came from the day I discovered urushiol, one of the oily components of poison ivy leaves that produce an allergic skin response.  I had a theory based on “like dissolves like” that I could perhaps pick the poison ivy barehanded, and then wash away the urushiol with a suitable solvent, such as isopropyl alcohol (rubbing alcohol). Well, you can guess where this story goes: I went to the doctor with horrific, oozing, itchy bumps all up and down both hands. I had successfully taught myself about skin absorption of common chemicals, which I remember every time I accidentally get some methylene chloride on my lab gloves.

Update (July 30, 6:30PM) - Changed, at commenter gippgig's suggestion, the words "toxic and deadly" in para. 3 to "potentially dangerous." Gippgig correctly points out that potassium nitrate is not itself toxic (its danger comes from potential to construct explosives), and both uranium ore and thiocyanides are not themselves highly poisonous.