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...

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Extraordinary Opportunities: UNCF/Merck Science Initiative for African American Students
Oct28

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. But the program doesn’t only provide financial support. UNCF/Merck Scholars at all levels benefit from the networking opportunities through the collective association of scholars that number over 500 dating back to 1996. UNCF/Merck Scholars hold positions in academia, government, and industry – one even just flew on the Space Shuttle! Here’s a summary from the program’s “about” page but go there posthaste and apply! The deadline for applications is THE UNCF/MERCK SCIENCE INITIATIVE It’s a Chance of a Lifetime Through an Extraordinary Partnership UMSI brings together UNCF, the Merck Research Laboratories and The Merck Institute for Science Education to offer 37 annual awards to outstanding African American students and postdoctoral researchers: 15 undergraduate scholarships 12 graduate dissertation fellowships 10 postdoctoral research fellowships But besides funds for tuition, room and board and fees, there’s also institutional support through grants to the science departments of award recipients and research grants. And along with knowledge, you’ll develop a career, with hands-on research training, mentoring relationships and networking and career advancement through the Association of UNCF/Merck Fellows. African Americans hold less than two percent of PhDs in biology and chemistry today. But UMSI is creating opportunities for people in the biological and chemical sciences. Apply now, and get a jump on a rewarding and successful career! You cannot win if you do not apply – so get to it! Disclosure: An undergraduate student in my department received one of these awards last year. My family also donates monthly to UNCF because we believe so strongly in their mission, especially in chemistry and the pharmaceutical...

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“Wining” about corked Tylenol
Oct24

“Wining” about corked Tylenol

Things have not been going very well for Johnson & Johnson’s McNeil Consumer Healthcare division with regard to their now-closed Fort Washington, PA, manufacturing facility. Last week, they issued another recall for 8-Hour Tylenol products due to a musty smell caused by trace quantities of 2,4,6-tribromoanisole (TBA). I wrote about J&J’s issues at this blog’s old home back in May when some of our comments were included in a ABC News report by Dan Childs after a recall of 43 different products due to problems with potency, microbial contamination, and particulate matter in liquid dosage formulations. This past week’s story was covered extensively around the popular press but I was particularly taken by the article on TIME magazine’s Healthland site written last Wednesday by Meredith Melnick, a former fellow at Columbia University’s Digital Media program. In general, I’ve been really impressed with the quality of science writing at Healthland all around, a blog I’ve been following since an online writer friend, Maia Szalavitz, joined them. Beyond the high quality of her writing, Melnick won points from me in discussing the chemistry of the TBA contamination. The compound is believed to emanate from the wooden pallets upon which the products are stored and shipped. A commonly used wood preservative, 2,4,6-tribromophenol, can be O-methylated to TBA by microorganisms such as the filamentous fungi, Paecilomyces variotii, as detailed in this 1997 paper in the Journal of Food and Agricultural Chemistry. Within her article, Melnick made drew from another field that I had forgotten since my wine writing days. She linked to another Journal of Food and Agricultural Chemistry paper by Chatonnet et al., detailing that TBA is also the compound associated with the musty or “corked” smell of wines that had gone off. Among trained wine tasters, TBA has a sensory limit of detection in wine on the remarkable order of 4 ng/L. The compound does not appear to have any health risks at these concentrations but Dan Miller’s CellarNotes states that the musty smell is responsible for the contamination of 3% to 7% of wines, on average. Corks made from the bark of the aptly-named Cork Oak, Quercus suber, are most often associated with the unpleasant aroma of corked wines (hence the term). But just last month the same research group at the EXCELL Laboratorie in Merignac, France had another paper in the Journal revealing that oak barrels used to age wine could be a source of another halogenated anisole, 2,4,6-trichloroanisole (TCA).  These other oaks (the European oaks, Quercus robur Linn. and Q. petrae Liebl., and the American oaks, e.g., Q. alba and macrocarpa L.) have been extensively used in wineries around the world for aging. Chatonnet’s group now describes how the oak used for...

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British Chemists Hacked Off By Government’s “Lazy Stereotype”
Oct22

British Chemists Hacked Off By Government’s “Lazy Stereotype”

In discussing the chemistry of “legal highs” earlier this week, I was reminded of a dust-up last month in the UK following the launch of a government anti-drug campaign to warn young people that “legal” intoxicants are not necessarily “safe.” At issue was the Home Office’s “Crazy Chemist” campaign: Featuring an eye catching and menacing scientist, the campaign conveys the unscrupulous nature of people who create and sell substances with little concern for the health of those who consume them. (The UK Home Office is “the lead government department for immigration and passports, drugs policy, crime, counter-terrorism and police.”) Although Minister of Crime Prevention James Brookshire noted that the campaign resonated with young people, the Royal Society of Chemistry objected strongly: Jim Iley, director of science and education at the RSC, said: “This is a lazy stereotype of the chemist as unhinged scientist and it is totally irresponsible that the government has decided to use such an image for what is clearly an important campaign which we would whole heartedly endorse. Chemists in the UK and elsewhere invest significant amounts of time to use chemistry to solve health-related issue and, consequently, improving people’s lives. More information can be found at this BBC article and this RSC press release. Indeed, the graphic is not an attractive portrayal of the chemist, looking more like someone who was not paying attention to the content of The Safety Zone blog here at CENtral Science.  The Crazy Chemist poster can be downloaded as a 1MB PDF and a link to the postcard is here. The campaign also links to a rather good drug information site called FRANK with a video showing forensic scientist Dr Phil Yates using an Agilent 5893 GC/MS to analyze these legal chemical analogues of Class A drugs, the UK equivalent of US DEA Schedule I. My guess is that our readers would be far more interested in the accurate laboratory portrayal of the forensic chemist. But as far as educating young people about the dangers of God-knows-what that can be bought on the street or the internet, the Crazy Chemist might be a more effective campaign. The rest of FRANK does a good job without demonizing chemists but rather presenting information with Flash modules and catchy graphics. What do non-British chemists think? Are you okay with this representation of the clandestine chemist in the name of adolescent education? Or is any stereotypical promotion of the mad scientist harmful to the...

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Mephedrone in the U.S.
Oct20

Mephedrone in the U.S.

In a news item last week, two young men found dead in Hillsborough Raleigh, North Carolina, were described by police as having been taking the recreational drug, mephedrone. Known to chemists as 2-methylamino-1-p-tolylpropan-1-one, 4-methylmethcathinone (4-MMC), or 4-methylephedrone, the compound is a semi-synthetic derivative of the natural product cathinone found in the shrub, Catha edulis – better known as khat. My blogging colleague and substance abuse expert, DrugMonkey, has had an extensive series of posts on mephedrone since it became widely-used – and now outlawed – in much of Europe. Like amphetamine, these compounds are believed to enhance the release of dopamine in the brain but surprisingly little pharmacology is available in the literature. A PubMed search for “mephedrone” currently returns about two dozen papers that speak mostly to legality and use trends. Natural products have always figured prominently among drugs of abuse – alkaloids with central nervous system penetration have been used as intoxicants since ancient times and remain popular today. To stay ahead of drug enforcement regulatory authorities, clandestine chemists have endeavored to scour the scientific literature for old synthetic schemes – preferably in non-English journals – to make chemical analogs to create legal highs. In the US, the response of the Drug Enforcement Agency (DEA), was to promote within the Controlled Substances Act the Federal Analogue Act of 1986 that made illegal any “analog” of a known Schedule I substance (for those outside the US, Schedule I compounds are those forbidden for any medical use). In fact, the paper most often cited online for the first mephedrone synthesis is Bulletin de la Societé Chimique de France 1929;45: 284–286. Most recently, we have witnessed the circumvention of the Analogue Act with the popularity of K2, Spice, or other synthetic marijuana products that contain naphthoylindoles with activity toward cannabinoid receptors. These compounds emerged from work in the laboratory of John W. Huffman at Clemson in the 1990s and are important research chemicals because they have cannabimimetic activity while being structurally unrelated to cannabinoids. In fact, this structural dissimilarity is one reason for the popularity of synthetic marijuana products: they cannot be detected in most urinary drug screens for THC used in employment and probation monitoring. Huffman’s compounds, JWH-018 being the most popular, are illegal in most of Europe and are increasingly under scrutiny in the US, now illegal in 15 states with legislation pending elsewhere in municipalities and other states. Even where currently legal, local law enforcement officials are asking convenience store owners to take K2, Spice, and Black Mamba products off their shelves. And the US military has made such products illegal for use or possession. My K2 posts...

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