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Category → Drugs of Abuse

Acetyl Fentanyl: Dangerous, Poorly-Named Street Drug

Acetyl fentanyl HCl, courtesy of Cayman Chemical Company. Click on the image to view the source page.

Acetyl fentanyl HCl, courtesy of Cayman Chemical Company. Click on the image to view the source page.

The U.S. Centers for Disease Control and Prevention has released a summary on a cluster of 14 deaths in Rhode Island earlier this year attributed to “acetyl fentanyl,” an analog of the potent, short-lived opioid used in pain management and outpatient anesthesia. The report, “Notes from the Field: Acetyl Fentanyl Overdose Fatalities — Rhode Island, March–May 2013,” appears in the August 30, 2013 issue of Morbidity and Mortality Weekly Report


The first 10 deaths were reported in the Providence Journal

on May 13, 2013, leading CDC officials to join the team in the investigation. A total of 14 deaths were identified. Samples from the decedents gave positive ELISA results for fentanyl but GC/MS revealed an analog that authorities are calling acetyl fentanyl. A CDC health advisory released in June briefly details the chromatographic pattern and mass spectra.

Cayman Chemical Company, who offers the reference material, also calls it acetyl fentanyl, but offers desmethyl fentanyl as an alternative. The IUPAC name is N-​phenyl-​N-​[1-​(2-​phenylethyl)-​4-​piperidinyl]-​acetamide; fentanyl has a propionamide instead of the acetamide.

A CBC news story described a late April series of drug busts in Montreal that included seizure of a compound they called desmethyl fentanyl. The current MMWR release also links to an alert from the Pennsylvania Department of Drug and Alcohol Problems that reports 50 acetyl fentanyl deaths in the state this year, through June 27th (PDF).

Most curious is that the compound has not been described before as a recreational drug. It’s not available as a prescription drug anywhere in the world and is only a minor side product (0.04%) found in prescription fentanyl (DOI: 10.1016/j.jpba.2010.04.004).

In a lengthy discussion on Twitter last night and this morning with Chemjobber, SeeArrOh, and others, I initially asked whether acetic anhydride could have been used to acetylate fentanyl, thinking — without looking at the structure — that it was truly acetylated. I found later that fentanyl is made from 4-anilino-N-phenethylpiperidine (ANPP) using either propionyl chloride or propionic anhydride. Hence, acetyl fentanyl could be made by reacting ANPP with either acetyl chloride or acetic anhydride (That’s the extent of my synthetic expertise, Dear Reader.).

The major problem with acetyl fentanyl — or fentanyl for that matter — is its high potency relative to natural opioids like morphine or the more potent synthetic, heroin. As a result, the CDC recommends that emergency rooms and other facilities providing substance misuse care services stock up on the opiate receptor antagonist naloxone in anticipation of an increase in overdoses across North America.

But it looks like we’re stuck with acetyl fentanyl as the name. Any thoughts?

Okay, Who’s Huffing Vicks VapoRub?

From the back end of this blog. What are you people doing out there? Credit: DJ Kroll

One of the fun things about having a blog is the traffic analytics feature on the dashboard of WordPress (although I really miss the features of SiteMeter that don’t run on WordPress because it doesn’t accept JavaScript. But I digress.)

Besides the addictive nature of looking at one’s traffic numbers, I always find it interesting to look at the search terms that bring people to our humble little corner of GlobCasino. I became hooked on this way back when I started the original version of Terra Sig on Blogger: in February 2006, I had an unusual spike in traffic originating from the UK via the search term “terra sigillata.” So, I posted this and learned this.

Usually, search term hits tell me that something has come up in the news. But, alas, I cannot find anything recent that would account for Vicks VapoRub to elicit much searching. Perhaps telling is that all 27 searches came via a misspelled search for “vicks vapor rub.”

North Carolina historical marker in Greensboro. Credit: DJ Kroll

(By the way, the search term brought folks here to read this post I wrote on Vicks VapoRub after a 2011 PR snafu with journalists like Ivan Oransky at Reuters Health. I ended up writing a bit more about the North Carolina pharmacy history that brought the world this lovely concoction.)

I do know that misguided youth will huff volatile chemicals for the acute high one might get. Vicks is most commonly used to enhance the experience of MDMA (ecstasy) – I’ve seen kids at raves wearing N95 facemasks inside which they have smeared the VapoRub.

So, what’s with you people wanting to know about Vicks VapoRub?

Smiles: 2C-I or not 2C-I?

Designer drugs in the news

This is tiring enough for a science writer. I cannot imagine being in law enforcement.

The pace at which psychoactive designer drugs are appearing on the street is about as challenging for me as keeping up with dietary supplement companies that adulterate their products with actual prescription drugs (an area I’ve been covering since 2007 but a practice that goes back decades.)

This week’s designer drug hullabaloo comes to us courtesy of last week’s frightful murder-suicide by Sons of Anarchy actor, the late Johnny Lewis. ABC News is reporting today that Lewis was reportedly taking “Smiles,” a street name for 2C-I, the phenethylamine hallucinogen first synthesized by Alexander Shulgin.

2C-I is more properly known as 2,5-dimethoxy-4-iodophenethylamine. This structural analog of mescaline (3,4,5-trimethoxyphenylethylamine) was among a litany of designer drugs that was criminalized in the US back in July with the Synthetic Drug Abuse Prevention Act of 2012 (Cheryl Hogue had a nice discussion of the Act, including some quotes from yours truly, in the 27 August 2012 issue of C&EN.).
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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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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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NIDA seeks SBIR/STTR apps on Spice, bath salts

C&EN senior business editor Melody Bomgardner dropped me a note yesterday about a new request for applications from NIH’s National Institute on Drug Abuse (NIDA) for small business grants.

Read the text below but here’s what I find interesting as a pharmacologist who plays well with chemists: the call for applications is not for analytical methods for designer drugs. Rather the announcement solicits novel methods for detecting some biochemical or pharmacological endpoint of these agents (a bioassay, in old-speak) that doesn’t require new method development every time a new structural analogue pops onto the market.

Other areas of substance abuse are also fair game but Melody thought the Spice and bath salts angle would be of greatest interest to our readers here at Terra Sig.

Here’s the text directly from NIDA – I can’t find an exact RFA to link to, however: (see update below)

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Was Demi Moore smoking synthetic marijuana?

My substance abuser writer and researcher friend DrugMonkey (@drugmonkeyblog) just tweeted a CNN story suggesting that actress Demi Moore may have suffered adverse reactions after smoking a synthetic cannabimimetic product:

A woman called 911 soliciting help for actress Demi Moore, whom she said was “convulsing” and “burning up” after “smoking something,” according to a recording of the call obtained Friday from the Los Angeles Fire Department.

[. . .]

“She smoked something — it’s not marijuana, but it’s similar to incense. And she seems to be having convulsions of some sort.”

Reports of tremors and seizures have been accumulating in association with synthetic marijuana products. These products are generally composed of an herbal material that is spiked with one or more synthetic compounds that act at cannabinoid CB1 receptors.

The “burning up” described by the 911 caller in the story would be consistent with some reports of serotonin-like syndrome associated with synthetic marijuana use.

The US Drug Enforcement Agency is currently regulating some of the psychoactive compounds as Schedule I substances, illegal for use or sale as they are deemed as having no medical value. Individual states have also issued bans on compounds containing even more related compounds in these products. However, marketers have been skirting laws by using compounds not expressly deemed illegal in state or federal statutes.

Moreover, analytical crime laboratories across the nation have suffered extensive budget cuts making it difficult to keep up with the demands in determinig which products are illicit.

On a personal note, the synthetic marijuana story that DrugMonkey, dr_leigh, and I have been writing about for two years is growing increasingly disturbing. I just received my second reader email in three months from a father whose son shot himself to death while allegedly addicted to synthetic marijuana products. We’ve been in touch with the US DEA to inquire as to whether similar cases are currently under investigation.

Just as DrugMonkey wrote awhile back (I have to find the post), adverse drug effects with celebrities are usually required before aggressive government action is taken against illicit drugs (death of University of Maryland basketball player Len Bias from cocaine and a congenital cardiac abnormality).

Drugs of Abuse Tag-Team at Skeptically Speaking

A brainy, free, and fun online and radio chat-type call-in show on all things science. Hosted by Desiree Schell and edited by K.O. Myers. Awesomesauce. From Canada, of course.

I recently had the pleasure of being interviewed by Canadian radio host Desiree Schell for her wildly-successful show, Skeptically Speaking. The episode on which yours truly appears can be accessed here.

Launched in March 2009, the show airs live on Sunday evenings at 6 pm Mountain Time on UStream where one can discuss the show and asks questions by live chat. The show also includes a previously recorded segment with another scientist and is then edited and distributed for rebroadcast to stations and networks across North America. The shorter pre-recorded segment where I appeared to speak about my most popular topic of the last two years on this blog, synthetic marijuana compounds.

I’m not entirely guilty of self-promotion here because I primarily wanted to mention that the first two-thirds of the show – the live part – was an interview with my neuropharmacologist friend, Scicurious, author of The Scicurious Brain blog at the Scientific American blog network and Neurotic Physiology at Scientopia. Sci has a gift for offering laser-sharp science in a hip, conversational manner.

Here’s how the Skeptically Speaking team describes the show:

With humour, enthusiasm and a lot of curiosity, Skeptically Speaking guides you through the fascinating world of science and critical thinking. We interview researchers, authors and experts to help listeners understand the evidence, arguments and science behind what’s in the news and on the shelves. A basic understanding of science, combined with a little bit of skepticism, goes a long way.

Note: The term “skepticism” may be new to you. If that’s the case, click here.

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