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. The first three compounds carry the eponym for Clemson University chemist emeritus, Dr. John W. Huffman. Neuroscience colleague dr. leigh has two nice posts (part I, part II) on her Neurodynamics blog at Scientopia explaining the action of JWH-018 and the related compounds classified as naphthoylindoles, a class of compounds unrelated structurally to cannabinoids that occur naturally in marijuana but that still bind to the cannabinoid receptors CB1 and CB2 to produce a qualitatively similar high. CP-47,497 is another cannabimimetic from another structural class that was actually developed by Pfizer in the 1980s. Cannabicyclohexanol is an analog of CP-47,497, often called CP-47,497 C8 analog, which differs by the length of the aliphatic side chain on the relatively simple 3-phenylcyclohexanol structure. The CP compounds were often found in Spice products sold across Europe before these were outlawed there. One assumes that even compounds not named explicitly will also be banned under the analogs provision (21 U.S.C. 813) of the Controlled Substances Act although this point was not made in the rule released Wednesday. The risk to public health defined in the rule is as follows:
JWH-018, JWH-073, JWH-200, CP-47,497, and cannabicyclohexanol share pharmacological similarities with the Schedule I substance THC. Health warnings have been issued by numerous state public health departments and poison control centers describing the adverse health effects associated with these synthetic cannabinoids and their related products including agitation, anxiety, vomiting, tachycardia, elevated blood pressure, seizures, hallucinations and non-responsiveness. Case reports describe psychotic episodes, withdrawal, and dependence associated with use of these synthetic cannabinoids, similar to syndromes observed in cannabis abuse. Emergency room physicians have reported admissions connected to the abuse of these synthetic cannabinoids. Additionally, when responding to incidents involving individuals who have reportedly smoked these synthetic cannabinoids, first responders report that these individuals suffer from intense hallucinations. Detailed chemical analysis by DEA and other investigators have found these synthetic cannabinoids spiked on plant material in products marketed to the general public. The risk of adverse health effects is further increased by the fact that similar products vary in the composition and concentration of synthetic cannabinoids(s) spiked on the plant material.
That it has taken me three days to bring this news to my readers tells me something about the timing of this announcement, although I'm not exactly sure how to take it. The rule was released on the Wednesday before Thanksgiving, the heaviest travel day in the United States. The 30-day window means that the ruling will be made final sometime around Christmas. Releasing the rule at such a distracting time does not seem to be the best way to maximize the dissemination of information on the ban. Such a release of information is akin to the propensity of political, business, and academic practices of releasing bad news late on a Friday afternoon so as to avoid robust discussion in the press. I would think that the DEA would want notice of this ban to get as much press attention as possible. However, not many of us had time to pump out blog posts over the last few days and much of the mainstream press seems to have only briefly mentioned this ruling. Even today, only about 30% of our regular readership will be viewing this post. The conspiracy theorists might contend that the DEA is trying to slip this ruling in so as to trap folks who are already in possession of synthetic cannabimimetic products. But I'm trying to look at this in a more positive light. Perhaps the fact that we have spent the weekend together as families, perhaps discussing recent news, and will then be together again in 30 days when the final ruling is issued might be one way to encourage discussions with the teenage and college folks in our social and family groups about the facts surrounding the safety of these products. I can certainly see the 60-ish-year-old aunts and uncles telling their young'uns - wink, wink - to just go out and buy some regular old weed like they did when they were in college - not that any of you 60-ish readers ever did such a thing. One last thing that I found interesting in the rule was wording to the effect that the banning of the compounds "will not have a significant economic impact on a substantial number of small entities," and won't unduly tax regulatory authorities as an unfunded mandate. I assume that "small entities" does not refer to local store owners, one of which in Victoria, Texas who noted in this article that they sell between $8,000 and $10,000 of these products per month.
"It's going big time. It's even surpassing porn and adult toys," said [Donna] Shook [D&D Novelties owner]. "I mainly sell it because there has been a huge request among my customers."
With that kind of cash on the table, I'm surprised that our colleague Chemjobber hasn't seized upon this previously-legal activity as an alternative career. In all seriousness, the demand for these compounds has been a boon for a few chemists out there judging by the prices at some internet retailers. With the DEA action, Chemjobber may have a few more readers on the chemistry job market. I'm sure there will be more discussion of this temporary scheduling of compounds in K2 Spice and other synthetic marijuana products. I'm just a little taken aback by the timing of this announcement.

Author: David Kroll

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  1. Not to be flippant, but isn’t low media coverage during US holidays the reason for some major drug companies (e.g. Sanofi-Aventis and AstraZeneca, IIRC) scheduling large layoffs at such times?

    My holiday wishes include fulfilling jobs (with benefits) for all who want/need them…

  2. Indeed, k, this will be a bad news month for many – you do indeed speak the truth.

    But back on-topic, I just received the following comment at one of my K2 posts at one of the old homes of this blog – those K2 posts continue to bring me a lot of Google traffic. This following account has many factors in common with others I’ve received over the last 6-8 months:

    I have just returned from dropping my son off at the hospital. Hullucinating, paranoid, seeing “colors”, feeling of extreme anxiety and a thankfully failed attempt at suicide. I knew he had tried Spice but thought nothing of it.
    I have smoked pot for 35 years. I believe in our dispensaries here in California and trust the product that is sold to me does not contain cemicals which are unknown.
    My concern, after much reading on this subject is that if your children mention that they are getting high legally using products such as Spice or Silvia LISTEN up. Educate them on the concerns and look at this as a warning sign that they may need treatment.
    I have never seen or experienced signs or symptoms such as my son is having today. My son graduated with top honors last June. He was ready to enter College this fall but was sidetracked by the side effects of this drug. Use of it has left him mentally disabled and unable to concentrate. I have brought him to the hospital several times in the last few months. No docter has taken this matter seriously. If you could see my son today you would not think it was the same person.
    Yes, I understand that dosage, strain and added cemicals contribute to the effects my son is experiening. Parents and friends please listen up if you see changes. This is an issue if it is abused. I believe that people who want to get high will use any method possible. so the supply and demand theory goes. Educate those who wish to continue using.

  3. You do know that this did not take place? It is in a battle in the courts, because of the way it was going to be inacted! Look it up, but the news will not broad cast it


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