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Exploring the synthesis of 2-FDCK: What is the chemical miracle behind this emerging drug?
2-Fluorodechlorone (2-FDCK) is a dissociative anesthetic related to ketamine. Although the pharmacological properties of this emerging drug are still unclear, 2-FDCK has been reported to have similar effects to its parent compound, ketamine. Its sale and use as designer drugs has emerged in various countries. In the molecular structure of 2-FDCK, chlorine atoms are replaced by fluorine atoms, showing its structural correlation with ketamine.
The synthesis and chemical structure of 2-FDCK involves a series of complex reaction steps, demonstrating the wonders of chemistry.
Historical background
The synthesis of 2-FDCK was first described in a 2013 paper, when researchers worked to synthesize and evaluate new anesthetics based on ketamine and its analogs. First introduced in 1964 and approved for clinical use in 1970, ketamine has become one of the most important general anesthetics. Over time, these emerging psychoactive substances (NPS) have emerged in the drug market to circumvent existing drug policies. In 2016, the European Monitoring Center for Drugs and Drug Addiction (EMCDDA) officially reported 2-FDCK for the first time and included it among 65 new substances. With insufficient research, this compound is still in the exploratory stage.
Chemical structure
The full name of 2-FDCK is 2-(2-fluorophenyl)-2-(methylamino)cyclohexanone, which is an aromatic cyclohexylamine compound and contains many other drugs, such as PCP and ketamine. . These compounds usually consist of a cyclohexylamine unit and an aromatic hydrocarbon group attached to the same carbon. Compared with ketamine, 2-FDCK only adds one fluorine atom to the phenyl group. Such structural changes may affect its pharmacological activity.
Synthesis process
The synthesis of 2-FDCK can be achieved through a five-step reaction process. First, 2-fluorobenzonitrile reacts with Grignard reagent cyclopentylmagnesium bromide, followed by bromination reaction to obtain α-bromocyclopentyl (2-fluorophenyl) ketone. Next, the resulting ketone is reacted with methylamine at -40°C to form α-hydroxycyclopentyl(2-fluorophenyl)N-methylamine. Finally, the five-membered ring cyclopentanol form was expanded to the cyclohexanone form through a thermal rearrangement reaction, and HCl was used to prepare a water-soluble 2-FDCK salt.
Detection method
The presence of 2-FDCK and its metabolites in urine can be detected using liquid chromatography mass spectrometry (LC/MS) technology.
Pharmacological properties
Metabolism
The metabolic pathway of 2-FDCK is similar to that of ketamine. It is metabolized by two enzymes, CYP2B6 and CYP3A4. The final product is Nor-2FDCK, which is further converted into other metabolites. Studies have shown that 2-FDCK has stronger binding strength to CYP2B6 in simulations, which may mean that it is metabolized more slowly in the body and has a longer duration of effect.
Pharmacodynamics
Although the structure of 2-FDCK is similar to ketamine, no studies have confirmed that it has a similar mechanism of action. The substituted fluorine atom of 2-FDCK affects the polarity of the molecule and may change its binding ability to NMDA receptors, which is the main target of ketamine.
Adverse reactions
According to reports in 2019, 2-FDCK was found in poisoning cases in Hong Kong and often appears together with other ketamine drugs, highlighting its potential dangers.
Legal status
Due to the rapid emergence of emerging psychoactive substances, new substances like 2-FDCK are not specifically listed in controlled drug legislation. Because of this, 2-FDCK is sometimes marketed as a "legal high." Currently, 2-FDCK is an illegal substance in Italy, Japan, Latvia, Singapore, Sweden, Switzerland and other places, and is subject to comprehensive bans in Canada, Belgium and the United Kingdom. With the strengthening of regulatory agencies, in October 2023, the United Nations Commission on Drugs and Psychotropic Substances recommended that 2-FDCK be included in the Class II substances of the 1971 Convention on Psychotropic Substances.
In the gray area between these emerging drugs and existing regulations, can we find effective solutions to clarify their scientific and legal status?
