Khat and synthetic cathinones: a review

Abstract

For centuries, 'khat sessions' have played a key role in the social and cultural traditions among several communities around Saudi Arabia and most East African countries. The identification of cathinone as the main psychoactive compound of khat leaves, exhibiting amphetamine-like pharmacological properties, resulted in the synthesis of several derivatives structurally similar to this so-called natural amphetamine. Synthetic cathinones were primarily developed for therapeutic purposes, but promptly started being misused and extensively abused for their euphoric effects. In the mid-2000's, synthetic cathinones emerged in the recreational drug markets as legal alternatives ('legal highs') to amphetamine, 'ecstasy', or cocaine. Currently, they are sold as 'bath salts' or 'plant food', under ambiguous labels lacking information about their true contents. Cathinone derivatives are conveniently available online or at 'smartshops' and are much more affordable than the traditional illicit drugs. Despite the scarcity of scientific data on these 'legal highs', synthetic cathinones use became an increasingly popular practice worldwide. Additionally, criminalization of these derivatives is often useless since for each specific substance that gets legally controlled, one or more structurally modified analogs are introduced into the legal market. Chemically, these substances are structurally related to amphetamine. For this reason, cathinone derivatives share with this drug both central nervous system stimulating and sympathomimetic features. Reports of intoxication and deaths related to the use of 'bath salts' have been frequently described over the last years, and several attempts to apply a legislative control on synthetic cathinones have been made. However, further research on their pharmacological and toxicological properties is fully required in order to access the actual potential harm of synthetic cathinones to general public health. The present work provides a review on khat and synthetic cathinones, concerning their historical background, prevalence, patterns of use, legal status, chemistry, pharmacokinetics, pharmacodynamics, and their physiological and toxicological effects on animals and humans.

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

“…The product ratio of the diastereomers was determined by NMR spectroscopy. 1 To a solution of 6-bromo-1-hexanol in dimethylformamide (DMF) stirred at room temperature, tert-butyldimethylchlorosilane (TBSCl) was added, followed by an addition of imidazole. The mixture was stirred at room temperature for 3 h. The reaction was quenched by the addition of saturated ammonium chloride aqueous solution, and the mixture was extracted with ethyl acetate.…”

“…Various cathinone-derived designer drugs have recently appeared on the drug market in many countries, including Japan [1][2][3][4][5]. In particular, a-pyrrolidinophenones, including 3,4-methylenedioxypyrovalerone (MDPV) [6,7], apyrrolidinovalerophenone (a-PVP) [8][9][10][11][12][13], a-pyrrolidinobutiophenone (a-PBP) [13][14][15], 4-methyl-a-pyrrolidinohexanophenone (MPHP) [16,17], and 3,4-methylenedioxya-pyrrolidinobutiophenone (MDPBP) [18], have rapidly become a popular class of designer drugs.…”

Human Pharmacology of Mephedrone in Comparison with MDMA

“…NPS are defined as substances which are not prohibited by the United Nations Drug Conventions of 1961 and 1971, or by the Misuse of Drugs Act 1971, but which may pose a public health threat comparable with that presented by substances listed in these conventions (ACMD, 2015). Mephedrone (4-methylmethcathinone, 4-MMC), also known as 'M-Cat', 'MC', 'Meph' 'Drone', 'Bubbles', 'Meow Meow', and 'Meph' is a beta-keto analog of phenethylamine related to cathinone, the active stimulant present in khat leaves (Catha edulis) (Valente et al, 2014).…”

Las nuevas drogas: origen, mecanismos de acción y efectos. Una revisión de la literatura

“…La catinona, además de ser el precursor de la catina, es entre siete y 10 veces más potente que este compuesto. Los niveles de catinona presentes en la planta van decayendo a partir de que la hoja se corta, mientras que la concentración de catina permanece constante; esta diferencia explica por qué los usuarios prefieren las hojas frescas (Valente, Guedes de Pino, Bastos, Carvalho, & Carvalho, 2014).…”