Deducing the structure of a new psychoactive substance

‘The new compound contains a cyclobutyl methyl group as a side chain and has not been described in any patent to our knowledge.’

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Illicit drug-makers are constantly looking to tweak the chemical structures of known psychoactive substances to avoid laws prohibiting their use. They are increasingly turning to one group of psychoactive substances called cannabinoid receptor agonists (SCRAs). These complex molecular structures can be modified in multiple ways and SCRAs are a source of many new illicit drugs. Originally developed for clinical research, they are now monitored by the European Monitoring Centre for Drug and Drug Addiction (EMCDDA).

German government legislation includes a law (called the NpSG) that restricts the use of novel psychoactive substances by defining certain chemical structures. The government amends the law when necessary to include new structural modifications designed to bypass restrictions.

Germany’s Adebar Plus project (co-funded with the EU) conducts a detailed structural analysis of any unidentifiable drugs for police and customs forensic laboratories, and international organizations. So when a novel SCRA was discovered in Germany in 2019, researchers at Adebar investigated samples of the herbal blend with a range of analytical chemistry techniques.

In particular, they used Liquid Chromatography quadrupole Time-of-Flight mass spectrometry (LC-qToF-MS) to confirm the proposed molecular formulas of the unknown substance and its most relevant fragments, as suggested by initial gas chromatography-mass spectrometry (GC-MS). This was undertaken on a Bruker impact II qToF instrument combined with a Bruker Elute HPLC system. Chromatographic separation was performed on a Bruker Intensity solo 1.8 C18-2 2.1 x 100 mm and a VanGuard BEH C18 1.7 µm guard-column.

Other techniques employed in the investigation were attenuated total reflection-infrared spectroscopy (ATR-IR), gas chromatography solid-state infrared spectroscopy (GC-sIR), Raman spectroscopy at 785 nm and 1064 nm, and nuclear magnetic resonance spectrometry (NMR).

The team found that the substance closely resembles a known SCRA called Cumyl-PICA, apart from one feature: a cyclobutyl methyl side chain. It appears that this time the drug-makers have modified the sidechain rather than the core structure of SCRA to make a new drug. The researchers called the new substance Cumyl-CBMICA (Cumyl-CycloButylMethyl-IndoleCarboxAmide), and predict it will have similar effects to cannabis, although there is no pharmacological data at present.

Many other cumyl derivatives have been reported in the scientific literature, but the researchers note that, to their knowledge, there are no compounds with the particular side chain found in Cumyl-CBMICA. This novelty meant the compound originally was not covered by German regulations, although this has since been rectified.

The team reported their findings to the Early Warning System of the EMCDDA. They warn that illicit drug-makers and retailers of SCRA products will continue to adapt known drugs as they attempt to produce novel substances that are not covered by legal restrictions. The scientists stress how important it is for forensic laboratories to monitor and analyze novel products as they appear on the market and for governments to amend legislation to include new substances as they are reported.

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References

  1. Auwaerter, V., et al. (2020) Drug Testing Analysis doi.org/10.1002/dta.2942
  2. Cumyl-CBMICA: A new synthetic cannabinoid receptor agonist containing a cyclobutyl methyl side chain, 
  3. Sebastian Halter,Benedikt Pulver,Maurice Wilde,Belal Haschimi,Folker Westphal,Jan Riedel,Michael Pütz,Torsten Schönberger,Stefanie Stoll,Jan Schäper,Volker Auwärter

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Last updated: Jul 7, 2022 at 3:57 AM

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