EMCDDA framework and practical guidance for naming synthetic cannabinoids

Abstract

Synthetic cannabinoids (SCs), often sold as “legal” replacements for cannabis, are the largest group of new psychoactive substances monitored by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). Currently, close to 240 structurally heterogeneous SCs are monitored through the European Union (EU) Early Warning System, and attributing consistent, informative, and user‐friendly names to SCs has been a challenge in the past. Over time, several naming conventions have been employed with the aim of making SCs more easily recognizable by non‐chemists, including regulators. To achieve this, the names assigned need to contain detailed information on the structural features present in the substance. This work provides a theoretical framework and a practical hands‐on guideline for consistent naming of SCs, which is easy to understand and can be applied by the forensic community, researchers, clinical practitioners, and policy‐makers. The proposed framework builds on the established letter code system for molecular building blocks (core, linker, linked group, and tail) implemented by the EMCDDA in 2013 and has been expanded to incorporate additional structural features through substitution. The scope of the issue of attributing semi‐systematic code names is illustrated, and earlier approaches used for naming SCs are discussed. The concepts and rules of the EMCDDA framework are described through a flowchart that provides a basis for naming new SCs, a graphical overview of the chemical diversity of SCs, and a detailed list of the SCs identified in the EU by the Early Warning System of the EMCDDA for reference.

From JWH‐018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day

“…The syntax uses code names for the four building blocks in the order: (1) Linked Group, (2) Tail, (3) Core, and (4) Linker, always preceded by (0) Tail Substitution. The EMCDDA naming system has recently been revised (“EMCDDA framework name”; Tables S1 and S2) and expanded upon to allow for increased consistency and additional flexibility to cover the substitution of each building block, which in turn better covers recently emerged SCs 12 . The same building blocks are retained in the same order from the original syntax, with prefixes for substituents added with hyphens where necessary; however, more specifically, substitution is now indicated in front of the modified building block.…”

Pharmacology, prevalence in Germany, and analytical data of cyclobutylmethyl‐ and norbornylmethyl‐type synthetic cannabinoid receptor agonists

“…27 The naming approach applied by the EMCDDA is currently being expanded and built upon further in collaboration with the ADEBAR project. 28 Following the detection of the indazole and γ-carbolinone NBM SCRAs, the semi-systematic names Cumyl-BC[2.2.1]HpMeGa-Clone and Cumyl-BC[2.2.1]HpMINACA were proposed. "BC[2.2.1]…”

“…Under the developed EMCDDA framework, the letter code NBM is used for the norbornyl methyl side chain, which is why it is used in the present work. 28 In the future, structurally similar side chain moieties will be assigned letter codes with adequate differentiators to remain unique. Preemptive differentiation from possible future building blocks is not considered.…”

“…“BC[2.2.1]Hp” was chosen as a detailed description of the side chain, allowing future similar side chains to be assigned a similar but unique name. Under the developed EMCDDA framework, the letter code NBM is used for the norbornyl methyl side chain, which is why it is used in the present work 28 . In the future, structurally similar side chain moieties will be assigned letter codes with adequate differentiators to remain unique.…”

In vitro cannabinoid activity profiling of generic ban‐evading brominated synthetic cannabinoid receptor agonists and their analogs

“…3 For instance, in Europe, over 230 SCRAs have been detected since 2008, and their number still increases. 4,5 These substances initially appeared on the market as legal alternatives to cannabis, in an attempt to produce compounds with effects similar to those of Δ 9 -tetrahydrocannabinol (Δ 9 -THC), its predominant psychotropic component. 6 The main target of SCRAs is the cannabinoid 1 receptor (CB 1 ), through which they exert their desired psychoactive effects such as euphoria, relaxation, and mood elevation, although most also interact with the cannabinoid 2 receptor (CB 2 ), present on cells associated with the immune system.…”