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. 2017;4(2):1040.
Epub 2017 Mar 21.

Synthetic Cathinones: A Brief Overview of Overviews With Applications to the Forensic Sciences

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Free PMC article

Synthetic Cathinones: A Brief Overview of Overviews With Applications to the Forensic Sciences

Richard A Glennon et al. Ann Forensic Res Anal. .
Free PMC article

Abstract

Catha edulis, the fresh leaves of which (i.e., khat) are used for their central stimulant actions, has been known for many hundreds of years. S(-)Cathinone was identified as a centrally-active khat constituents >30 years ago. Although khat use was a problem long localized to certain Middle Eastern and certain Eastern African nations, 'synthetic cathinones' (synthetic analogs of cathinone) represent a "new" class of abused substances with growing worldwide appeal. To date, about 150 synthetic cathinones have been identified on the clandestine market, and only a dozen or so have been controlled (U.S. Schedule I). Because these agents do not represent a pharmacologically (i.e., behavioral) or mechanistically homogeneous class of agents, synthetic cathinones are being investigated one agent at a time to understand their actions, mechanisms of action, metabolism, toxicity, and abuse potential - the latter to identify possible modes of overdose treatment and for Scheduling purposes. The available agents might represent only the 'tip of the iceberg'; the potential for many more new synthetic cathinones is very real. Investigation of these agents on an agent-by-agent basis is a daunting task. Attempts are being made to understand these agents as a class, by examination of their structure-activity relationships. Here, we provide an overview of review articles that attempts to shed light on these agents as a class, rather than on an agent-by-agent basis. This article is meant to be a reference resource that might expedite the work of those in this field by directing them to where they can find useful information.

Keywords: Forensics; Khat; Methcathinone; Psychoactive bath salts; Review; α-Aminopropiophenones; β-Ketoamphetamine.

Figures

Figure 1
Figure 1
Chemical structures of S(−)cathinone (1) and several structurally-related synthetic cathinones as their racemates: methcathinone (2), mephedrone (3), MDPV (4), and α-PVP (5).
Figure 2
Figure 2
In theory, synthetic cathinones (as well as other substances) can have one or more of multiple actions at the major monoamine transporters, DAT, NET, and SERT.a Several such actions are shown here; other scenarios are possible. aAgents might act as releasing agents (i.e., as substrates; ↓) or blockers (i.e., as inhibitors; ↑) of one or more transporters (i.e., Agents A-F). Some agents (e.g. Agent G) might be selective for one or more transporters as a substrate or inhibitor (only one example shown here); other scenarios are possible. Pharmacological action depends upon potency and function at each, as well as their selectivity.
Figure 3
Figure 3
General structure-activity relationships of synthetic cathinones with a primary focus on release or uptake inhibition at the dopamine transporter (DAT). Recognize that different actions are possible: i) release of DA, NE, and/or 5-HT at DAT, NET, and SET, respectively, ii) uptake inhibition at the same three transporters, and iii) different actions (release of one or more) and reuptake inhibition (of one or more) of these neurotransmitters, the latter being termed “hybrid” transporter agents. The information shown here is based on what has been learned so far, but additional studies are required for further elaboration. See Table 1 for reviews of SAR.
Figure 4
Figure 4
Positional (i.e., geometric) isomers of mephedrone (3; Figure 1): 2-methylmethcathinone (2-MMC; 6) and 3-methylmethcathinone (3-MMC; 7).
Figure 5
Figure 5
Four of 2,136 commercially available agents with an empirical formula identical to that of methcathinone (i.e. C10H13NO).

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