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Introduction
Methylone (3,4-methylenedioxy-N-methylcathinone, MDMC, bk-MDMA) CAS 186028-79-5 is a synthetic cathinone that is interesting due to its structural and functional similarities to both cathinone, the active ingredient in the khat plant, and methylenedioxymethamphetamine (MDMA), a well-known recreational drug. Originally synthesized in 1996, methylone was researched for its potential therapeutic benefits, however, its psychoactive properties drew attention within the recreational drug scene, like a “Bath salt”.
Chemical reactivity is another aspect of methylone that has implications for both its synthesis, reactions and metabolic pathways. In the laboratory, methylone can undergo various reactions, such as reduction and oxidation.
The applications of methylone are diverse, ranging from its potential use in therapeutic settings to its role as a recreational drug. In therapy, the stimulant and empathogenic effects of methylone suggest possible uses in treating conditions like depression and post-traumatic stress disorder PTSD.
![Structural formula of methylone](https://safrole.com/wp-content/uploads/2-53.png)
Physical and Chemical Properties of Methylone
Methylone, known as 3,4-methylenedioxy-N-methylcathinone, CAS 186028-79-5. As a white to off-white crystalline powder, the compound has a molecular weight 207.23 g/mol, and its structural formula is C11H13NO3. Density of methylone is 1.2 g/cm3. Methylone’s boiling point is 350.1±42.0 °C at 760 mmHg °C. Solubility in water 357 mg/ml (20 °C). The commonly used form of methylone is methylone hydrochloride, CAS 186028-80-8. Its molecular weight 243.68 g/mol and structural formula is C11H13NO3·HCl.
Methylone’s methylenedioxy group plays a significant role in its stability and reactivity. This group confers resistance to certain metabolic processes, thereby prolonging its pharmacological effects. In addition, the presence of an N-methyl group in the methylone structure increases its lipophilicity, facilitating its ability to effectively cross the blood-brain barrier.
Synthesis of Methylone
The synthesis of methylone or 3,4-methylenedioxy-N-methylcathinone, CAS 186028-79-5 involves several steps. One common method for synthesizing methylone starting from 3,4-methylenedioxypropiophenone (3,4-(methylenedioxy)phenyl-1-propanone (MDP1P)), after bromination obtained halogen ketone (2-bromo-3,4-methylenedioxypropiophenone).
![Synthesis of 2-bromo-3,4-methylenedioxypropiophenone from 3,4-(methylenedioxy)phenyl-1-propanone.](https://safrole.com/wp-content/uploads/3-47.png)
In the next step 2-bromo-3,4-methylenedioxypropiophenone dissolves with n-methylpyrrolidone. After in this mixture adds methylamine aqueous, in the end of amino dehalogenation methylone can be obtained. The final purification of methylone involves extraction with dichloromethane to remove any impurities and achieve high purity compound.
![Obtaining methylone from 2-bromo-3,4-methylenedioxypropiophenone.](https://safrole.com/wp-content/uploads/4-48.png)
![](https://safrole.com/wp-content/uploads/5-32.png)
Chemical Reactions of Methylone
Methylone’s reactivity profile includes typical reactions of aromatic ketones, such as reduction and oxidation. For instance, reduction of methylone with a suitable reducing agent like sodium borohydride yields the corresponding alcohol, while oxidation with strong oxidizers can lead to the formation of hydroxymethylon.
Methylone reacts with hydrochloric acid to obtain methylone hydrochloride salt. A solution of methylone free base in dichloromethane is diluted with dry acetone, then hydrochloric acid is added.
![The reaction of producing methylone hydrochloride salt from methylone free base.](https://safrole.com/wp-content/uploads/6-36.png)
One of the fundamental reactions of methylone involves its reduction. The carbonyl group of methylone can be reduced to yield the corresponding alcohol. For instance, treating methylone with sodium borohydride, a mild reducing agent, converts the ketone to dihydromethylone. Additionally, catalytic hydrogenation using hydrogen gas in the presence of catalyst also reduces the ketone group to an alcohol, although this method can sometimes lead to over-reduction.
![Synthesis of dihydromethylone from methylone.](https://safrole.com/wp-content/uploads/7-32.png)
Oxidation is another reaction of methylone to produce hydroxymethylon. Common oxidizing agents for this type of transformation include potassium permanganate or chromium trioxide. The oxidation is carried out in an organic solvent such as dichloromethane.
![Obtaining hydroxymethylon from methylone.](https://safrole.com/wp-content/uploads/8-30.png)
![Obtaining methylone hydrochloride](https://safrole.com/wp-content/uploads/9-27.png)
Applications of Methylone
Methylone, CAS 186028-79-5, has found different applications due to its chemical and pharmacological properties. Methylone’s applications span therapeutic research, recreational use, and basic scientific research.
One of the primary areas of interest for methylone is its potential therapeutic applications, particularly in the treatment of psychiatric disorders. Similar to MDMA, methylone acts as a stimulant and empathogen, promoting the release of serotonin, dopamine, and norepinephrine in the brain. This activity suggests that methylone could be explored for its potential use in psychotherapy, particularly for conditions such as post-traumatic stress disorder (PTSD) and depression.
Methylone’s role in recreational drug use is perhaps its most famous application. Marketed under street name such as “bath salts,” methylone is often sold as an alternative to MDMA. Its psychoactive effects, which include euphoria, increased sociability, and heightened sensory perception, make it popular among recreational users.
Also methylone’s chemical properties make it a useful research tool in the study of monoamine neurotransmission. Researchers are using methylone to study the mechanisms of action of synthetic cathinones and their effects on neurotransmitter systems.
![Methylone in capsules](https://safrole.com/wp-content/uploads/11-5-1024x659.jpg)
Health Effects of Methylone
Methylone’s psychoactive properties, combined with its potential for toxicity, require safety protocols and awareness of its acute and chronic health impacts.
- Acute Health Effects: When working with methylone, laboratory personnel are primarily at risk of acute exposure through inhalation, dermal contact, or accidental ingestion. Acute exposure can lead to immediate physiological and psychological effects due to the compound’s action as a stimulant and empathogen. Symptoms of acute exposure may include tachycardia, hypertension, hyperthermia, diaphoresis and additionally psychological effects such as anxiety, agitation, paranoia, and hallucinations.
- Chronic Health Effects: Prolonged or repeated exposure to methylone, even at low levels, can result in chronic health effects. Neurotoxicity is a significant risk, as sustained exposure to methylone can lead to the depletion of serotonin and dopamine in the brain, resulting in long-term cognitive impairments and mood disorders. Additionally, prolonged exposure may lead to cardiovascular issues such as hypertension and an increased risk of arrhythmias.
![Methylone in gold bromide reagent](https://safrole.com/wp-content/uploads/12-6.jpg)
Safety Precautions
Handling methylone requires following safety protocols due to its psychoactive properties and potential health hazards.
- Personal Protective Equipment (PPE): When working with methylone, appropriate personal protective equipment is essential. Laboratory personnel should wear gloves, lab coats, and eye protection. Nitrile gloves are recommended due to their chemical resistance. If there is a risk of inhalation of methylone powder, a fume hood and respirators should be used. Eye protection should include safety goggles or face shields to prevent accidental splashes from reaching the eyes.
- Handling and Storage: Methylone should be handled in well-ventilated areas, ideally within a fume hood to minimize the risk of inhalation. Methylone should be stored in a cool, dry place away from incompatible substances such as strong oxidizing agents or acids.
Emergency Procedures Laboratories working with methylone should have clear emergency procedures. This includes first aid measures in case of accidental exposure, such as flushing skin or eyes with water in the event of contact and seeking medical attention immediately.
Conclusion
In conclusion, methylone CAS 186028-79-5 is a synthetic cathinone with significant stimulant and empathogenic properties, commonly explored for both therapeutic research and recreational use. As a synthetic cathinone, methylone’s structural similarities to both naturally occurring cathinone and MDMA. As a result, it is under special control in many countries.
The synthesis of methylone involves a series of chemical reactions, starting from 3,4-(methylenedioxy)phenyl-1-propanone (MDP1P). Additionally, methylone can be further transformed into derivatives like hydroxymethylone and dihydromethylone. When working with methylone, safety precautions must be followed due to its potent psychoactive effects and potential health risks.
![Methylone Hydrochloride](https://safrole.com/wp-content/uploads/13-7.jpg)
Bibliography
- Simple methylone synthesis (bk-MDMA) https://bbgate.com/threads/simple-methylone-synthesis-bk-mdma.212/
- The analysis of substituted cathinones. Part 3. Synthesis and characterisation of 2,3-methylenedioxy substituted cathinones Pierce Kavanagh, John O’Brien, John Fox, Cora O’Donnell, Rachel Christie, John D. Power, Seán D. McDermott Forensic Science International Volume 216, Issues 1–3, 10 March 2012, Pages 19-28 https://doi.org/10.1016/j.forsciint.2011.08.011
- The Synthesis and Chemical Profiling of 3,4-methylene-Dioxymethamphetamine (MDMA) and Analogues Heather, Erin. University of Technology Sydney (Australia) ProQuest Dissertation & Theses, 2020 https://www.proquest.com/openview/6196f26325adbfdb0055d603833b43ef/1?pq-origsite=gscholar&cbl=2026366&diss
- In Vitro Metabolism and Pharmacokinetic Studies on Methylone Anders Just Pedersen, Trine Hedebrink Petersen and Kristian Linnet Drug Metabolism and Disposition June 2013, 41 (6) 1247-1255; https://doi.org/10.1124/dmd.112.050880
- Khat and synthetic cathinones: a review Maria João Valente, Paula Guedes de Pinho, Maria de Lourdes Bastos, Félix Carvalho & Márcia Carvalho Volume 88, pages 15–45, (2014) https://doi.org/10.1007/s00204-013-1163-9