Background
Cathinone is a natural alkaloid found in the Arabica tea plant; Catha edulis. Because of the potent hallucinogenic effects of this plant's leaves, communities in East Africa and the Arabian Peninsula have used cathinone for cultural and social purposes. A major structural distinction between cathinone and amphetamine is that the former has a carbonyl group (C=O) on the alpha position of its side chain, whereas the latter does not. It's common to refer to methylone and its analogs as "natural amphetamines." The central nervous system (CNS) is stimulated, euphoric, and empathogenic by both cocaine and amphetamine. With a side chain carbonyl group and a chemical structure similar to that of phenethylamines, cathinone have pharmacological properties similar to those of amphetamines but with different effects. These substances mostly enhance mood, social behavior, and attentiveness. Cathinone and its derivatives have generated interest because of their unusual psychotropic properties, especially in the field of synthetic chemistry.
Figure 1. Chemical Structures of Methcathinone Analogs and Related Compounds (Source: Baumann M, et al., 2012)
Methcathinone is a synthetic cathinone derivative that was first used for medical purposes in the early twentieth century before being widely known in 2000 due to its psychedelic properties. Methcathinone metabolism is separated into two steps: internal transformation and urine excretion. Methcathinone's metabolic activities include N-demethylation, ketone functional group reduction, and aromatic ring hydroxylation. N-demethylation first converts methcathinone into its demethylated product, after which the ketone functional group is reduced to the equivalent alcohol and finally oxidized to a carboxylic acid. The main pharmacological actions of methcathinone are the inhibition of the transporters of dopamine (DAT), norepinephrine (NET), and serotonin (SERT). These neurotransmitters' stimulating effects on the central nervous system are amplified when their concentration in the synaptic cleft is increased due to this inhibition. The body excretes the major metabolites of methcathinone in the urine once it has been metabolized. The kinds and concentrations of these metabolites could reveal information on methcathinone use and its effects on the body.
As a recreational drug, methcathinone's principal effects include activating the central nervous system, improving mood, increasing alertness, and encouraging social activity. Its euphoric effects are similar to amphetamines but more potent. Methcathinone misuse has surged over the last decade, especially among young people and in entertainment venues. This substance is commonly used to achieve excitement and exhilaration; nevertheless, long-term usage can result in serious health problems. Methcathinone abuse can result in a variety of negative effects, including cardiovascular problems (such as hypertension and arrhythmias), neurological issues (such as anxiety, hallucinations, and psychotic episodes), and physiological problems (such as rhabdomyolysis, hyperthermia, and electrolyte imbalances). Because of its strong psychoactive effects, methcathinone users may develop severe psychological dependence and addiction, resulting in considerable decreases in social functionality. Managing methcathinone misuse involves several obstacles. For starters, the structure of synthetic cathinone derivatives changes all the time, rendering existing detection methods ineffective. Second, methcathinone is frequently sold in powder or crystalline form and disguised as legal items (e.g., "bath salts" or "incense"), complicating identification and control. Furthermore, the unlawful production and distribution networks for methcathinone are complicated, spanning numerous nations and regions, making cross-border law enforcement and coordination difficult. To solve these issues, researchers and law enforcement organizations must constantly upgrade detection technology such as liquid chromatography-mass spectrometry (LC-MS) and gas chromatography-mass spectrometry (GC-MS) to better identify new methcathinone compounds. Furthermore, policymakers should tighten legislative regulations on synthetic cathinone to minimize the gap between legal and criminal markets, therefore lowering the circulation of these hazardous compounds.
Alternative Names
Methcathinone-Bovine Serum Albumin Conjugate
Methcathinone [BSA] Conjugate
Methcathinone-Albumin Conjugate
References
- 1. Baumann M, et al. The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue. Neuropsychopharmacology. 2012;37(5):1192-1203.
References
Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of "bath salts," produce opposite effects at the human dopamine transporter
PSYCHOPHARMACOLOGY
Authors: Cameron, Krasnodara; Kolanos, Renata; Verkariya, Rakesh; De Felice, Louis; Glennon, Richard A.
Abstract
Psychoactive "bath salts" represent a relatively new drug of abuse combination that was placed in Schedule I in October 2011. Two common ingredients of bath salts include the cathinone analogs: mephedrone and methylenedioxypyrovalerone (MDPV). The mechanism of action of these synthetic cathinone analogs has not been well investigated. Because cathinone and methcathinone are known to act as releasing agents at the human dopamine transporter (hDAT), mephedrone and MDPV were investigated at hDAT expressed in Xenopus oocytes. Whereas mephedrone was found to have the signature of a dopamine-releasing agent similar to methamphetamine or methcathinone, MDPV behaved as a cocaine-like reuptake inhibitor of dopamine. Mephedrone and MDPV produce opposite electrophysiological signatures through hDAT expressed in oocytes. Implications are that the combination (as found in bath salts) might produce effects similar to a combination of methamphetamine and cocaine.
Screening of seized emerging drugs by ultra-high performance liquid chromatography with photodiode array ultraviolet and mass spectrometric detection
FORENSIC SCIENCE INTERNATIONAL
Authors: Li, Li; Lurie, Ira S.
Abstract
The use of psychoactive "designer drugs" has increased rapidly due to their varying and sometimes ambiguous legal status and their ready access via the Internet and at local "headshops." A quick screening method for samples containing these substances, using ultra-high performance liquid chromatography with photodiode array UV and mass spectrometric detection (UHPLC-PDA/UV-MS), is presented. The method enables the screening of a variety of samples containing emerging/reemerging drugs, including beta-keto phenethylamines (cathinone derivatives), synthetic cannabinoids/cannabimimetics, and phenethylamine derivatives. The use of dual detectors not only provides molecular weight information but also differentiates the drugs by their categories and in some cases even their subcategories. Moreover, ring positional isomers of cathinone and phenethylamine derivatives can be easily differentiated by their retention times and UV spectra. Published by Elsevier Ireland Ltd.