4-Chloromethcathinone hydrochloride
[CAS# 2319878-22-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 4-Chloromethcathinone hydrochloride
• Synonyms: 1-(4-chlorophenyl)-2-(methylamino)propan-1-one;hydrochloride
• Protein Sequence: A
• Molecular Formula: C₁₀H₁₃Cl₂NO
• Molecular Weight: 234.12
• CAS Registry Number: 2319878-22-1
• EC Number: 874-137-7
• SMILES: CC(C(=O)C1=CC=C(C=C1)Cl)NC.Cl

Discovory and Applicatios

4-Chloromethcathinone hydrochloride, commonly abbreviated as 4-CMC HCl, is a synthetic cathinone that belongs to the class of substituted phenethylamines. It is a derivative of methcathinone, structurally characterized by a chlorine atom at the para position (4-position) of the phenyl ring, a ketone group on the side chain, and a hydrochloride salt form that enhances its stability and solubility. Its molecular formula in the hydrochloride form is C₁₀H₁₂ClNO·HCl.

The compound was first synthesized and reported in the chemical literature in the early 21st century, although its core structure as a cathinone analog has precedents dating back to the mid-20th century. Cathinones are beta-keto analogs of amphetamines and were initially developed for potential applications in medicine, particularly as stimulants or antidepressants. However, many synthetic cathinones, including 4-CMC, emerged outside traditional pharmaceutical development and became available through illicit markets.

4-Chloromethcathinone itself does not have approved medical use. Its appearance in forensic and toxicological studies is largely due to its classification as a "designer drug" or "new psychoactive substance" (NPS), where it was distributed for non-medical human consumption, particularly as a stimulant. Like other cathinones, it acts as a central nervous system stimulant, and its effects are believed to involve modulation of monoamine neurotransmitters, though precise pharmacodynamics and pharmacokinetics for 4-CMC have not been thoroughly characterized in the peer-reviewed literature.

Analytical identification of 4-chloromethcathinone hydrochloride in forensic settings relies on a combination of techniques. Gas chromatography–mass spectrometry (GC-MS) and liquid chromatography–mass spectrometry (LC-MS) are commonly used for detecting and quantifying the compound in biological and non-biological samples. Infrared (IR) spectroscopy can confirm functional groups such as the carbonyl (C=O) stretch from the ketone, while nuclear magnetic resonance (NMR) spectroscopy helps elucidate structural details, including substitution patterns on the aromatic ring and the position of the ketone moiety.

In its hydrochloride salt form, 4-CMC is usually a white to off-white crystalline powder. The hydrochloride salt increases water solubility and shelf stability compared to the free base form. The compound can be synthesized through standard organic reactions involving halogenation of methcathinone precursors, followed by salt formation with hydrochloric acid. This synthetic route, while straightforward, requires careful purification to ensure removal of impurities and positional isomers.

Due to its psychoactive effects and potential for abuse, 4-chloromethcathinone has been subject to regulation in various countries. It is classified as a controlled substance in many jurisdictions, meaning its manufacture, sale, or possession is restricted or prohibited. The legal control is primarily driven by public health concerns about its use in recreational contexts and the associated risks of toxicity, dependence, and adverse psychological or cardiovascular effects.

Toxicological data on 4-CMC remains limited but growing. Documented risks include tachycardia, agitation, psychosis, and, in some cases, severe toxicity. These effects are consistent with other synthetic cathinones, which can act as potent stimulants and produce adverse outcomes, especially when consumed in high doses or mixed with other substances.

In summary, 4-chloromethcathinone hydrochloride is a synthetic cathinone compound developed through chemical modifications of known stimulant structures. While it has no established therapeutic applications, it has gained attention in forensic and regulatory contexts due to its presence on the recreational drug market. It is subject to analytical study for identification and monitoring, and its use is legally restricted in many regions based on concerns about safety and public health.

References

2013. Asymmetric hydrogenation of �-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst. Organic & Biomolecular Chemistry, 11(23).
DOI: 10.1039/c3ob40481c

2020. Advances in biomedical and pharmaceutical applications of protein-stabilized gold nanoclusters. Journal of Materials Chemistry B, 8(39).
DOI: 10.1039/d0tb01393k