Introduction

3-Chloromethcathinone (3-CMC), also known as clophedrone, CAS 1049677-59-9 is a synthetic cathinone derivative that has gained attention in recent years due to its psychoactive properties and presence in the recreational drug market. This compound belongs to the class of substituted cathinones, which are structurally related to the naturally occurring stimulant cathinone found in the Khat plant (Catha edulis).

The chemical structure of 3-chloromethcathinone features a chlorine atom at the meta position of the phenyl ring. As a chiral molecule, 3-chloromethcathinone exists in two enantiomeric forms: (R)-3-chloromethcathinone and (S)-3-chloromethcathinone.

From a pharmacological perspective, 3-chloromethcathinone acts as a stimulant, with effects reported to be similar to those of other synthetic cathinones like mephedrone, and to some extent, MDMA and cocaine. Its mechanism of action is believed to involve interactions with monoamine transporters, particularly the dopamine transporter (DAT).

The study of 3-chloromethcathinones properties, reactions, and potential applications is of significant interest to researchers in various fields, including toxicology and pharmacology.

Physical and Chemical Properties of 3-Chloromethcathinone

3-Chloromethcathinone, 1-(3-chlorophenyl)-2-(methylamino)-1-propanone, (3-CMC), CAS 1049677-59-9 free base form. The molecular formula is C₁₀H₁₂ClNO with a molecular weight of 197.66 g/mol. As a chiral molecule, 3-CMC exists as two enantiomers: (R)-3-chloromethcathinone and (S)-3-chloromethcathinone. It is moderately soluble in water and highly soluble in organic solvents such as ethanol, methanol, and dimethyl sulfoxide.

The hydrochloride salt of 3-chloromethcathinone (C₁₀H1₂ClNO * HCl) is more commonly encountered, with a molecular weight of 234.1 g/mol. It appears as white powder or small white crystals. The melting point of the hydrochloride salt has been reported as 182-183°C. Unlike the free base, the hydrochloride salt is readily soluble in water. It can also be dissolved in methanol, dimethyl sulfoxide or chloroform.

In terms of pharmacology, 3-chloromethcathinone acts as a stimulant, with effects similar to other synthetic cathinones. Its mechanism of action likely involves interactions with monoamine transporters, particularly the dopamine transporter (DAT). The hydrochloride salt form is preferred in pharmaceutical and research contexts due to its stability and solubility.

Cathinone: What You Need To Know

Synthesis of 3-Chloromethcathinone

The synthesis of 3-chloromethcathinone, CAS 1049677-59-9 involves multiple steps, typically starting from readily available precursor chemicals. The initial step in the synthesis of 3-chloromethcathinone is synthesis 2-bromo-1-(3-chlorophenyl) propan-1-one, that can be obtained by α-bromination of 1-(3-chlorophenyl)-1-propanone.

The second step in which 3-chloromethcathinone is obtained from 2-bromo-1-(3-chlorophenyl)propan-1-one by nucleophilic substitution with methylamine to give chloromethcathinone free base.

Another way of synthesis of 3-chloromethcathinone, the hydrolysis of N-acetyl-3-chloromethcathinone, it is an important process in the context of 3-chloromethcathinone synthesis. N-acetyl-3-chloromethcathinone can be considered a masked designer precursor for 3-chloromethcathinone. The hydrolysis of N-acetyl-3-chloromethcathinone can be achieved through acid or base hydrolysis. This process removes the acetyl group, revealing the primary amine of 3-chloromethcathinone. Reaction can be carried out using common acids (such as hydrochloric acid) or bases (such as sodium hydroxide) under mild heating conditions.

Each step in the synthesis is critical, requiring precise control of reaction conditions to ensure high purity and yield of the final product. The choice of reagents and conditions can significantly influence the efficiency and scalability of the synthesis process.

Chemical Reactions of 3-Chloromethcathinone

3-Chloromethcathinone CAS 1049677-59-9 chemical reactivity due to the presence of both a beta-ketone group and a chlorinated aromatic ring. These functional groups make 3-chloromethcathinone a compound involved in various organic reactions.

One of the main reactions involving 3-chloromethcathinone is the formation of the hydrochloride salt of 3-chloromethcathinone. This is an acid-base reaction that increases the solubility of the compound in water, making it more suitable for biological applications. In this reaction, the amino group of the free base form of 3-chloromethcathinone reacts with hydrochloric acid to form hydrochloride salt of 3-chloromethcathinone.

Another important reaction is the reduction of 3-chloromethcathinone, primarily targeting the beta-ketone group, converting it to an alcohol. This transformation is important because it changes the chemical and biological properties of the compound. A common reducing agent used for this purpose is sodium borohydride. For example, reduction of 3-chloromethcathinone with sodium borohydride in methanol produces 3-chloromethamphetamine.

Applications of 3-Chloromethcathinone

3-Chloromethcathinone (3-CMC) CAS 1049677-59-9, has applications in a variety of fields including pharmacological research, organic synthesis and recreational use.

Pharmacological Studies

3-Chloromethcathinone is being studied in pharmacological studies to understand its mechanism of action, potential therapeutic applications and side effects. Researchers are studying how 3-chloromethcathinone interacts with monoamine transporters, which leads to increased levels of neurotransmitters such as dopamine, norepinephrine and serotonin.

Organic Synthesis

In the field of organic synthesis, 3-chloromethcathinone serves as an intermediate for the creation of more complex molecules. Its reactivity, especially the presence of a beta-ketone group and a chlorinated aromatic ring, makes it suitable for a variety of chemical transformations. For example, 3-chloromethcathinone can be used to synthesize new derivatives with potential pharmaceutical applications, such as new psychoactive substances or compounds with unique therapeutic properties.

Recreational Use

3-Chloromethcathinone has also gained popularity as a recreational drug due to its stimulant and euphoric effects. Consumers often seek out synthetic cathinones for their ability to promote feelings of energy, sociability, and pleasure. Regulatory authorities in many countries have responded by classifying 3-chloromethcathinone as a controlled substance.

Health Effects of 3-Chloromethcathinone

Exposure to 3-chloromethcathinone CAS 1049677-59-9 can result in a variety of acute health effects, primarily due to its effects on the central nervous system. Synthetic cathinones such as 3-chloromethcathinones are known to increase the release and inhibit the reuptake of monoamines such as dopamine, norepinephrine and serotonin, resulting in increased central nervous system activity (CNS) activity.

• Cardiovascular effects: Rapid heartbeat (tachycardia), increased blood pressure (hypertension) and palpitations are common. In extreme cases, acute exposure can lead to arrhythmias and other serious cardiovascular events.
• Neurological effects: Users may experience agitation, confusion and severe headaches. At higher doses there is a risk of seizures, paranoia and hallucinations.
• Gastrointestinal effects: Nausea, vomiting and abdominal pain are common acute symptoms following ingestion or inhalation of 3-chloromethcathinone.
• Chronic Health Effects: The chronic health effects of 3-chloromethcathinone are less well documented, but long-term exposure and repeated use are associated with significant risks. Chronic use can lead to neurotoxicity, as evidenced by studies of synthetic cathinones that show damage to dopamine and serotonin neurons with long-term exposure.

Safety Precautions

Safety precautions are required when handling 3-chloromethcathinone (3-CMC), CAS 1049677-59-9 in a laboratory setting due to its strong psychoactive properties and potential health risks. Wearing appropriate PPE is the first line of defense against potential exposure to 3-chloromethcathinone.

The main PPE includes:

• – Gloves: Nitrile gloves should always be worn to prevent 3-chloromethcathinone from coming into contact with the skin.
• – Lab coats: Wearing lab coats or a chemical-resistant coats helps protect your skin and clothing from accidental spills or splashes.
• – Safety googles: To prevent contact with eyes, safety goggles or face shields should be worn.
• – Respiratory protection: When handling 3-chloromethcathinone powder or in situations where the risk of inhalation is high, it is recommended to use a respirator.
• Safe Handling Procedures
• Following safe handling procedures minimizes the risk of accidental exposure:
• – Fume hoods: Carry out all work with 3-chloromethcathinone in a fume hood to avoid inhalation of dust or fumes. The fume hood must function properly and have sufficient air flow.
• – Minimize the formation of dust and aerosols: Handle 3-chloromethcathinone in a manner that minimizes the formation of dust and aerosols.

Emergency Procedures

In the event of an accidental exposure or spill, immediate and appropriate action is critical:

• – Skin contact: In case of skin contact, immediately wash affected area with plenty of soap and water.
• – Eye contact: If 3-chloromethcathinone gets into your eyes, rinse immediately with plenty of water for at least 15 minutes, keeping your eyelids open. Seek medical attention immediately.
• – Inhalation: If inhaled, remove victim to fresh air immediately. If they have difficulty breathing, give oxygen and seek emergency medical attention.
• – Ingestion: If swallowed, do not induce vomiting. Rinse your mouth with water and seek medical attention immediately.

Conclusion

The study of 3-chloromethcathinone (3-CMC) CAS 1049677-59-9, reveals its diverse applications in pharmacological research and organic synthesis. Its chemical structure and properties make it a valuable compound for engineering and studying its interactions in biological systems. Its chemical reactions are important for the synthesis of new compounds with potential therapeutic applications, as well as for the modification of chemical structure to study various effects.

Bibliography

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• Critical review report: 3-Methylmethcathinone (3-MMC) Expert Committee on Drug Dependence Forty-fifth Meeting Geneva, 10–14 October 2022 https://researchonline.ljmu.ac.uk/id/eprint/18334/1/3-mmc_draft%20(accepted_uncorrected).pdf