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From Blog: Terra Sigillata

RTI scientists solving forensic, designer drug mysteries

Kerstin Nordstrom, PhD, AAAS Mass Media Fellow, News & Observer. Credit: Losert Laboratory/Univ of Maryland.

Catching up on my reading this Sunday morning, I’m beaming with pride on the collective accomplishments and coverage of some old friends and colleagues.

Kerstin Nordstrom, a AAAS Mass Media Fellow with the Raleigh News & Observer, had a nice story on 3 September about the work of Dr. Peter Stout at RTI International. You old-timers will know this non-profit entity as Research Triangle Institute, home to the discoveries of Taxol and camptothecin by Wall and Wani and colleagues.

Kerstin, or Dr. Nordstrom I should say as she holds a PhD in physics, interviews RTI’s Dr. Peter Stout on the institute’s forensic analytical chemistry capabilities with regard to the “designer drug” industry. Yes, here we go again with my long-running commentary on the “synthetic marijuana,” “herbal incense,” “plant food,” and “bath salts” products that have recently taken a direct hit from “Operation Log Jam,” a coordinated, federal operation to shut down the industry.

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From Blog: Terra Sigillata

DEA jams synthetic marijuana and “bath salts” industry

With all the discord in Washington these days, it’s rare to see several US governmental organizations working together to address a significant public health problem.

This week, the US Drug Enforcement Agency (DEA) mobilized Operation Log Jam, an unusual and highly-coordinated action with six other federal agencies aimed to shut down the synthetic designer drug industry in 109 US cities. The products targeted were of two broad classes: 1) synthetic marijuana “incense” products comprised of naphthoylindole cannabimimetic compounds first synthesized by John W. Huffman’s lab at Clemson in the mid-1990s, and 2) “bath salts” or “plant food” products containing the stimulant/empathogen mephedrone (4-methylmethcathinone) or the stimulant MDPV (3,4-methylenedioxypyrovalerone).

This compilation of posts on synthetic marijuana and, to a lesser extent, “bath salts” serves as a good primer on the subject.

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From Blog: Terra Sigillata

K2 Synthetic Marijuana: Heart Attacks, Suicides, and Surveillance


Sixteen-year-old boys having heart attacks.

Blog reports of deaths and suicides.

And a little known chemistry and public health resource mobilized to identify “legal highs.”

The chemical and biological phenomenon that is “synthetic marijuana” continued to develop over the last week as we learn more about these products from the medical and public health communities.

Most notably, pediatric cardiologists reported in the journal Pediatrics on three cases of Texas teenagers who experienced myocardial infarctions – heart attacks – after using a synthetic marijuana product (DOI: 10.1542/peds.2010-3823).

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From Blog: Terra Sigillata

Synthetic marijuana for pharmacists

As a former pharmacy professor, I’m honored that a couple of our old and new blogposts have been picked up by colleagues at the University of Texas at Austin College of Pharmacy. Clinical Assistant Professor and drug information specialist, Jennifer Seltzer, PharmD, and her intern, Tiffany LaDow, PharmD, included us in their online durg information alert entitled, “‘Spice’ It Up – A New Way to Get High: What Pharmacists Need to Know.”

This type of distillation by LaDow and Seltzer is representative of exactly the kinds of briefs I used to enjoy writing for the Colorado Pharmacists’ Society and are what motivated my establishment of this blog when I was out of academia. I always found that practicing pharmacists appreciated these kinds of timely alerts complete with the basic science underlying these developments.

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From Blog: Terra Sigillata

Strong chemistry in NC bills banning legal highs

Carolina Chemistry. Source: Raven Maps/Medford, OR

On Wednesday, two bills passed unanimously in the North Carolina State Senate that would outlaw synthetic cannabimimetics and mephedrone. These compounds are currently sold as Spice incense (e.g., K2, Black Mamba) or “bath salts” (e.g., Ivory Wave), respectively. (Many thanks to WRAL-TV Capitol Bureau Chief Laura Leslie and fellow blogger DrugMonkey for alerting me to these bills via Twitter.).

Legislatively, similar bills have been passed and laws enacted in states and municipalities around the US while a proposed scheduling rule by the federal drug agency, the DEA, languishes in an administrative and legal morass.

The synthetic marijuana bill, House Bill 12 (Senate 9) and the mephedrone bill, House Bill 13 (Senate 7), were originally both put forth in the NC House by co-sponsors led by Representative George Cleveland (R, NC-14) of Jacksonville, North Carolina, home to the US Marine base Camp Lejeune. Cleveland himself is a retired, 25-year US Marine. The US military has been far ahead of other state and federal agencies in prohibiting use of these chemicals and associated products.

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From Blog: Terra Sigillata

Who decides what’s an analog of a controlled substance?

“We’re like a naughty Holland & Barrett”: John Clarke, a pharmacology graduate, and Jo Hall have been selling legal drugs (in the UK) since 2006. Photograph: Suki Dhanda/UK Observer magazine

In this quiet week of reflection around the blogosphere, it makes sense that I should put up one last post on the topic that has brought us the most attention this year: synthetic cannabimimetics that have been sold in herbal incense blends such as K2 Spice. While marketed as “not for human consumption,” these products exemplify the growing legal highs industry (Coffeesh0p.com, a UK company run by John & Jo, pictured right, is a well-known example.).

Let’s take a moment to re-hash (I can’t help myself) these marijuana mimics before getting to the question posed in the title.

This series of compounds first synthesized by the laboratory of John W. Huffman at Clemson were originally investigated to establish structure-activity relationships for non-cannabinoid agonists at CB1 and CB2 endocannabinoid receptors. (See this post for more background from us and others about these compounds.) That is, Huffman and his collaborator, the late Billy Martin, were testing what structures similar to or different from the naturally-occurring compounds in marijuana could still allow high potency binding and modulation of these receptors.

Endocannabinoid inverse agonists have been explored by several pharmaceutical companies as anti-obesity drugs via appetite reduction (the opposite effect of marijuana). Unfortunately, many of these compounds have failed – rimonabant (Acomplia), most notably – due to increased risk of depression and suicide. Carmen Drahl had an extensive 2009 C&EN cover story on these compounds and other anti-obesity strategies.

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From Blog: Terra Sigillata

DEA acts on naphthoylindoles and 3-phenylcyclohexanols in synthetic marijuana

Umm, not for long.

A slightly different version of this post appeared yesterday at my Take As Directed blog.

Just before we in the US took off for the holiday, the US Drug Enforcement Agency released notice of “emergency scheduling” of synthetic cannabimimetic compounds currently sold in herbal incense products. Products like K2, Spice, Black Mamba, and pure compounds such as JWH-018 have been a boon for convenience stores, head shops, and internet retailers (not to mention huge, sustained traffic benefits for bloggers.). The complete text of the rule can be found here at the DEA website.

Already outlawed in Europe and with various bans in 15 states, these products are now officially viewed by DEA as worthy of “schedul[ing] an abused, harmful, non-medical substance in order to avoid an imminent public health crisis while the formal rule-making procedures described in the CSA are being conducted.”

What this means is that the DEA is going to release within 30 days a notice of formal ban of five chemicals – JWH-018, JWH-073, JWH-200, CP-47,497, and cannabicyclohexanol – via temporary assignment to Schedule I, the US classification for drugs with no known medical benefit but that possess high abuse potential or are otherwise unduly harmful. This classification will then make these compounds temporarily illegal to sell or possess for one year (with a possibly six-month extension) while the DEA conducts studies and procedures for formal assignment to Schedule I.

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From Blog: Terra Sigillata

Mephedrone in the U.S.

The methcathinones, such as mephedrone (above), are based on the amphetamine structure with the exception of the ketone. Although more polar and with less propensity to cross the blood-brain-barrier, the additional 4-methyl substitution enhances lipophilicity.

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.

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From Blog: Terra Sigillata

What’s the buzz?: Synthetic marijuana, K2, Spice, JWH-018

The topic of one of our most popular posts of all time has been the synthetic marijuana products containing JWH compounds, naphthoylindole cannabimimetics synthesized in the 1990s in the Clemson University laboratory of John Huffman. This post first appeared at the ScienceBlogs home of Terra Sigillata on 9 Feb 2010 and gives you some background on the active components of K2, Spice, and other products.

ResearchBlogging.orgThis post was chosen as an Editor's Selection for ResearchBlogging.org

My field of natural products pharmacology was founded by indigenous cultures who recognized that plants and fungi contain compounds that produce altered states of consciousness, leading to their most common use in religious ceremonies. While we may most often associate these naturally-occurring drugs with hallucinogens, the arguably most common natural product in use today is marijuana or Cannabis sativa. Indigenous to India and China, Cannabis has been the subject of increasing decriminalization worldwide due in part to its clinical, medicinal effects in multiple sclerosis, cancer, and AIDS.

Over the last few months, I’ve seen reports of a so-called “synthetic marijuana” being sold on the internet with stories most commonly coming from England and Germany and, in the US, from Kansas, Missouri, and Arizona. In fact, the St. Louis Post-Dispatch reports today that a bill has been brought before the Missouri House Public Safety Committee seeking to add this product to the state’s list of illegal drugs.

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