28 January 2009

Cannabis Mimic

The February edition of Chemistry World (not yet online, but here is a link to the index) has a story, "Synthetic cannabis mimic found in herbal incense" by Ned Stafford.

The story explains how the synthetic substance is "being used by young people around the world to legally achieve a marijuana-like high".

Drawing done using ChemAxon's Marvin Sketch 2.9.12.


Smiles string

CCCCCN1C2=CC=CC=C2C(C(=O)C3=CC=CC(C=CC=C4)=C34)=C1

Checked using Daylsight's Depict.


The story goes on to explain that "[the substance] has been found in herbal mixtures sold legally"; the substance was added to the herbal mixtures, and this was only discovered by chance. I'll post more details when the original article appears on-line particularly about the finding by "chance".

The article is well worth reading, look out for it in a week or so.

The original article was published on the 15th January 2009, here's the link!
Other links: wikipedia; binding data (courtesy of Erowid); Spice Product (again, courtesy of Erowid).

29thJanuary 2009 - Thinking about the synthesis of the compound. If you look at this paper, "Acylation of indole under Friedel-Crafts conditions-an improved method to obtain 3-acylindoles regioselectively", the paper reports conditions for the acylation of indole, getting yields of up to 96 %. The authors argue that the order of addition of reagents is important: indole followed by SnCl4 in CH2Cl2 which forms a complex (work done reported in 1929 gave evidence of addition products between Lewis Acids and indoles). Subsequent addition of the acylating agent followed by nitromethane as a co-solvent lead to the desired product after work up. The conditions given are not suitable for scale-up (eg too dilute) but the paper is a useful start.
2nd Dec 2009, Synthetic cannabinoids and 'Spice', a link from the European Monitoring Centre.

Update 10th January 2011. Interesting comment to a post (More on homemade street drugs),
"I work for a contract outfit in the Midwest. We made alot of money these past two years off "legal high drugs".
When the projects started coming in a couple of years ago we were told by management it was shipped to Europe for making incense. Of course, something didn't quite ring true so we got online and discovered the true end use of what we were making.
Our boss, a complete jerk, believes he has no liability because he thinks he can hide behind one sentence on the label of these bottles: "not for human use".
I have to say that when I was growing up and studying to be a chemist I always thought I would use my synthetic knowledge for good. Cure cancer or something. Never in a million years did I think I would essentially become a drug dealer and worse, make a living off something that could kill people. The sad fact is these compounds have been the only thing standing between me (and my colleagues) and the unemployment line.
"
Update 18th May 2011.
Fascinating paper, Palladium-catalyzed synthesis of indoles via ammonia cross-coupling–alkyne cyclization, which could be used for the preparation of these cannabis mimics.
DOI: 10.1039/C1CC11874A

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