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Archive → October, 2010

WSJ Feature on “The Other Chemistry”

Jeanne Whalen, a Wall Street Journal

reporter based in London, had an article yesterday on the European aspects of a phenomenon we’ve been discussing here at Terra Sig since the beginning of the year: the adoption of academic chemistry to produce legal intoxicants that are just on this side of the law. Whalen spends the first half of her article talking with David Llewellyn, a middle-aged Scotsman in Belgium who works with a chemistry colleague to scour the literature for synthetic schemes and basic pharmacology to manufacture “legal highs.”

I’ve spoken before about Clemson University chemistry professor emeritus, John W. Huffman, and his cannabimimetic naphthoylindoles synthesized in the 1990s that are now creating a buzz, as it were, in the US in the form of herbal incense and synthetic marijuana products.

In Whalen’s article, Llewellyn is quoted as finding the work of Purdue University pharmacologist, Dr. David E. Nichols, as a particularly fruitful information source. Nichols, the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology in the Department of Medicinal Chemistry and Molecular Pharmacology in the College of Pharmacy is not particularly pleased:

“The drugs we make often end up on the black market, and it’s very troubling to me,” he says. Particularly worrying is that the drugs are rarely tested in humans before hitting the street. Random people sometimes write to him to ask for help in making certain chemicals, he says. He doesn’t reply out of caution.

“When people use this stuff chronically, on a weekly basis—suppose it produces liver cancer?” he asks. Also of concern are effects on the kidneys and bone marrow. Most of the designer drugs haven’t been tested in humans at all, let alone in large clinical trials. Dr. Nichols says he himself only ever carried out animal tests of the compounds that others are now copying and selling.

Whalen also speaks with St. George’s University of London toxicologist, Dr. John Ramsey, about his efforts to keep up a database from identification of street drugs as they appear.

It’s a fascinating article on an issue that chemists and law enforcement have been dealing with for decades.

Source:

Jeanne Whalen (with Kersten Zhang), In Quest for ‘Legal High,’ Chemists Outfox Law, Wall Street Journal, 30 October 2010.

Hat-tip: Aaron Rowe via Twitter.

Day-after-Friday round-up

Chemical health and safety news from the past week:

  • From the blogosphere: Chemjobber on employing mid-career scientists as safety officers
  • Souther Carolina researchers to study effects of chlorine gas exposure on lungs – following up on a train wreck, “in the first year after the train wreck and chemical leak, the lungs of some people who breathed chlorine were aging at about four times the rate that they were before the 2005 accident”
  • Toxic metals tied to work in prisons – recycling electronic waste, no health problems linked to the work
  • C&EN State groups plan registry for hydraulic fracturing fluids, EPA seeks input on limiting emissions of formaldehyde from composite wood products, CPSC revises its cadmium exposure standard (to 0.1 μg per kg per day and 11 μg per kg per day for acute exposures), and CSB calls for ban of natural gas ‘blows’

Fires and explosions:

  • A mixture of nitric and sulfuric acids and a mixture of ethylene glycol and ammonium chloride at the Materials Research Laboratory building at Penn State University Park – minor damage and no one hurt
  • Fire at India’s Presidency University destroys labs, years of research – no one was hurt, but “The flames, believed to have been sparked by a short circuit from a refrigerator in the organic chemistry laboratory on the third floor, singed all its three sections before leaping up vertically and destroying three lecture theatres on the fourth floor. As the tandava of destruction raged above, the heat generated partially damaged the physical and inorganic laboratories on the second floor.”
  • Flammable chemicals in a warehouse in Bangladesh

Leaks, spills, and other exposures:

  • Something at an alumina digestion plant in India when a safety valve exploded; two dead and four others seriously injured
  • Mercury poured into a drinking fountain at a school in Nebraska
  • Chlorine gas from sodium hypochlorite + hydrochloric acid at a power plant in Utah
  • Vapor of something at the Joint Manufacturing Technology Center on Arsenal Island in Illinois (“the only multi-purpose and vertically integrated metal manufacturer in the Department of Defense”)
  • Ammonia at a cold storage berry-packing plant in Oregon, a seafood-processing facility in Florida, a hospital in the U.K., and in the chemistry and physics building at Kansas University
  • Hydrogen peroxide at a plant in New Zealand
  • Sulfuric acid at Truth Hardware’s window and door hardware production facility in Minnesota
  • Xylenol on a cargo ship docked at the Port of Los Angeles
  • On the roads and railways – silver cyanide, silicon tetrafluoride, nitric acid, and hydrogen peroxide

FDA Rejects Vivus’s Obesity Drug Qnexa

As was widely expected, the Food and Drug Administration has rejected Vivus’s experimental weight-loss drug Qnexa, making it the second obesity drug in a week to be turned away by the agency. On Saturday, Arena Pharmaceuticals said it had received a complete response letter (CRL) for  its obesity drug Lorqess (lorcaserin), based largely on worries that the drug caused tumors in rats.

The biggest concerns in Vivus’ CRL were around birth defects and cardiovascular risk. Vivus had already submitted a plan to keep tabs on pregnancy and birth defects after the drug was approved, and the agency seems to want to continue evolving that monitoring strategy. FDA also wants data showing that the drug’s propensity to raise heart rate does not lead to an increased risk of cardiovascular events. If eventually approved, FDA said Qnexa would be considered a controlled substance along the lines of Xanax and Valium.

The good news  is that Vivus says it doesn’t believe it needs to generate any new clinical data to fulfill FDA’s requests. Further, the agency didn’t ask any questions about the drug’s ability to induce weight loss. In a conference call with investors this morning, Vivus CEO Leland Wilson said it would take the company about six weeks to prepare its response to the CRL, and depending on how FDA classifies the application, the drug could be reviewed two-to-six months after the submission. Shares of Vivus were up over 30% in pre-market trading.

As a reminder, Qnexa is the only drug in the three-way obesity race to lack a partner. Arena has licensed Lorqess to Esai, and Takeda has bought into Orexigen’s Contrave.

Qnexa is a combination of two drugs that are already FDA-approved: it’s a combination of topiramate, an antiseizure medication that enhances feelings of fullness, and phentermine, the “Phen” part of Fen-Phen, which was not linked to heart valve defects.

When FDA posted briefing documents in advance of the Qnexa panel meeting, we learned that the agency had no problem with Qnexa’s ability to help patients lose weight. But the committee had safety concerns in five areas: effects on pregnant women, cardiovascular risks, psychiatric events, cognitive events, and metabolic acidosis. Last July, an FDA panel thought that Vivus needed more long-term safety data on Qnexa and voted not to recommend the drug for approval. (Seven panel members voted for approval but nine recommended against approval.)

Braskem To Make Propylene From Ethanol

Brazil’s Braskem is taking another step in its efforts to derive chemicals from sugar cane. In September, it started up production of a 200,000-metric-ton plant in Brazil to make ethylene for subsequent conversion into  “green“ polyethene.

Now the company plans to invest $100 million to make 30,000 metric tons per year of propylene from ethanol by the end of 2013. The company will use the propylene to make polypropylene that will have same properties as conventional hydrocarbon-derived propylene.

Late last year, Braskem signed a deal with Novozymes to develop a biotech route to propylene. However, the 30,000-metric-ton plant will not be based on this technology. At a press conference at the K 2010 plastics fair, the company called the plant‘s technology “proprietary“ and would give few details. However, a possible route that company officials have alluded to in the past is to use ethanol derived ethylene to make butylene, and then through metathesis, convert ethylene and butylene into propylene.

The cost of the plant is staggering for a what amounts to semi-works scale production of polypropylene. However, Rui Chammas, executive vice president for polymers at Braskem, says that bio-based polymers have a completely different value proposition than regular polymers. “We are not in competition with fossil polymers,“ he says. He is also quick to add that 70% of the output from the polyethylene is already under contract.

Manoel Carnauba Cortez, vice president of Braskem’s based chemical unit, says the company also has its its sights set on another ethanol derivative, ethylene glycol. “We may be an ethylene supplier for EO production in the near future,“ he said.

There is strong interest in bio-based ethylene glycol. Coca Cola is beginning to use ethylene glycol as a co-monomer in its PET bottles, likely sourced from Asia. Japanese trading firm Toyota Tsusho, which incidentally is a green polyethylene distributor for Braskem, recently formed a Taiwanese joint venture to make ethanol-based ethylene glycol.

Chemist as cook

Hi ho there folks. This is the first of a two-part series about cooking and chemistry, a lovely guest post by the illustrious Chemjobber. So without further ado…

Imagine, setting stuff on fire and that not being a bad thing. Perk. Image by flickr user 7bikeframesweldedtogether.

Leigh’s profiles of people are typically folks who use the problem-solving or thinking skills they learned from being chemists and applying them to other equally cerebral tasks. But what about the equally important hand skills that chemists develop? The hands that can pull TLC spotters, poke them through a tiny 18-gauge needle into a reaction and spot them on a TLC plate can surely do something equally complex, no?

One of my favorite books of all time is Bill Buford’s Heat, where Buford tells about his adventures in being a prep and line cook at Babbo, the flagship restaurant of celebrity chef Mario Batali. In it, Buford goes from complete newbie (slicing himself while deboning duck leg quarters) to being able to hold his own in the middle of a rushed meal service; to me, that sounds like the process of becoming a chemist in a busy laboratory. Buford mentions a few things common to cooking and chemistry:

Repetition: “I was reminded of something Andy (a more senior chef) had told me. ‘You don’t learn knife schools in cooking school, because they only give you six onions, and no matter how hard you focus on those six onions there are only six, and you’re not going to learn as much as when you cut up a hundred.’ One day I was given a hundred and fifty lamb tongues. I had never held a lamb’s tongue, which I found greasy and unnervingly humanlike. But after cooking, trimming, peeling and slicing a hundred and fifty lamb’s tongues I was an expert.”

Complexity in combinations: Buford describes the grill station prep: “There were 33 different ingredients, and most had to be prepared before the service started, including red onions (cooked in beet juice and red wine vinegar), salsify (braised in sambuca), and farotta (cooked in a beet puree). There were six different squirter bottles, two balsamic vinegars, two olive oils, plus vin santo, vin cotto, and saba, not to mention the Brussels sprouts and braised fennel and rabbit pate – and damn! Today, I look at the map and am astonished I had any of it in my head.”

Image by flickr user staxnet.

The joy of creating: “I found, cooking on the line, that I got a quiet buzz every time I made a plate of food that looked exactly and aesthetically correct and then handed it over the pass to Andy. If, on a busy night, I made, say, fifty good-looking plates, I had fifty little buzz moments, and by the end of service I felt pretty good.”

Cooks, of course, need to please their customer’s tastes; chemists, I suspect, are subject to less pressure there. Batali mentions that in his explanation to Buford about what he’ll learn: “As a home cook, you can prepare anything any way anytime… Here people want exactly what they had last time. Consistency under pressure. And that’s the reality: a lot of pressure.”

Now I’m obviously not saying that a chemist could jump into a busy 3-star Manhattan kitchen and start pitching in. There are differences in the hours (can be brutal), the pay (may be really low) and the lifestyle — and you might have to go to culinary school. But I suspect that line cooking is something that would be familiar and even a bit homey to an experienced bench chemist.
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Super-duper thanks to CJ for both writing this post, and bringing up the topic. In part 2, I’ll be breaking down the sames and differents between a synthetic chemist and a line cook, via an in-depth exclusive interview with a self-taught chef with over 20 years in the biz. Stay tuned.

Photo Finish

First of all, a huge “Thank you!” to all who entered C&EN’s inaugural photo contest. We launched the photo contest on Flickr with the goal of creating a pool of chemistry images that anyone could benefit from (hence the Creative Commons requirement). I was excited when we had 50 entries. Then we had over 100. The final tally–235.  I’m absolutely thrilled by the enthusiastic response we received in the number and variety of submissions. So many of you truly have an appreciation for the art in your work. I hope people continue to contribute to the pool and submit entries to our future contests.

And now, without further ado, the envelope, please…

First place, and the winner of $250, is Jennifer Atchison’s SEM image of silicon nanocones:

Second Place ($150 prize): Robert D’Ordine’s water vortex:

And Third Place ($50 prize): Ryan O’Donnell’s colorful birefringence pattern:

Read more about these images and check out the honorable mentions on C&EN Online. All will be appearing in the November 1 issue of C&EN.

Extraordinary Opportunities: UNCF/Merck Science Initiative for African American Students

If you don’t get the hardcopy version of C&EN, you are likely to have missed the ad on pg. 36 (Oct 25) for a fantastic scholarship and fellowship opportunity benefiting African American undergrad, graduate students, and postdocs in the chemical or biological sciences.

The United Negro College Fund (UNCF) has partnered with Merck and the Merck Company Foundation to offer some comprehensive awards to create these unique awards. For example, the undergraduate award consists of scholarships up to $25,000 plus a paid internship at a Merck research facility. The graduate dissertation award is for up to $43,500 plus a $10,000 research and travel grant. The postdoc award consists of a fellowship of up to $92,000: $77K in salary for up to 24 months (but no more than $55K in one year) plus a $15,000 research and travel grant. Continue reading →

Cleaning up a middle school

A guest post by Russ Phifer, a consultant with WC Environmental and past chair of the ACS Division of Chemical Health & Safety.

As a volunteer for the EPA Schools Chemical Cleanout Campaign, I am frequently called to help schools manage their chemicals. This often involves disposing of chemicals they don’t want or shouldn’t have.

I was recently contacted by a teacher at a small, private middle school who was concerned about their chemicals. When I visited the school I found the usual kinds of chemicals you might expect to see in a middle school–vinegar, mineral ores, amino acids, sodium hydroxide, a number of solvents, and small quantities of a few alkali metals. There were also several old, decomposing containers of calcium carbide.

Now, CaC2 really only has one hazard–it generates acetylene gas when it comes into contact with water or moist air. As chemicals go, there are thousands of chemicals you might consider to be more hazardous. However, since the school doesn’t air condition the lab room in the summer, and southeast Pennsylvania has its share of summer humidity, this did seem like at least a slight concern. There were plenty of potential ignition sources in the room and the school doesn’t have any flammable storage cabinets or any other logical storage location for this material. It also doesn’t have a budget for chemical waste disposal.

I thought initially it would be easy to dispose or recycle this material. I first looked at recycling, since there are numerous firms advertising that they recycle carbides. However, after a couple of phone calls, I realized they really only wanted tungsten carbide. The first company I called said they’d never even heard of calcium carbide.

Next, I decided to get quotes for disposal. A local company that specializes in disposal of reactive chemicals quoted approximately $350 to dispose of the 60 g of calcium carbide, including transportation and labor. This is actually a pretty fair price when compared to what other companies might charge.

But it was still beyond the school’s budget.

According to my United States Dispensatory, 1926 edition, one pound of pure calcium carbide yields 5.9 cubic feet of acetylene gas at 180 ºC. (You might wonder why I even have a copy of this manual, or why I’d use it as a source for this information; it was actually the only source I could find in my library or on the internet that gave me the yield! The 1845 edition is available online.) Based on this, our 60 grams would produce approximately 0.13 cubic feet of acetylene. That doesn’t sound like an awful lot of gas to me, and certainly it doesn’t appear to represent a significant fire hazard.

I identified two methods for on-site treatment & disposal. The first, using small quantities (5 g) at a time, is essentially adding water and producing acetylene in small batches in a fume hood. The second is a more detailed laboratory operation for slightly larger quantities, requiring an ice bath, stirrer, dropping funnel, nitrogen gas and inlet, and a ventilation source.

While it seems evident that the 60 g could be treated fairly easily, both treatment methods called for laboratory equipment that this middle school doesn’t have. There is no fume hood and no appropriate or adequate ventilation source. Besides, the amount of time and labor required seemed excessive given the actual volume of acetylene that would be produced. Being prudent, however, it didn’t seem like a good idea to do the treatment in the school, given the potential liability.

So where do we go from here? I think what we’ll end up doing is dropping the sixty grams, a few grams at a time, into a bucket or water outside.

Sometimes the simplest solution is the best.