3,4-Methylenedioxy-N-methylcathinone (Methylone)

Description

 3,4-Methylenedioxy-N-methylcathinone (Methylone)

3,4-Methylenedioxy-N-methylcathinone (also known as M1, MDMC, βk-MDMA, and Methylone) is an entactogenic and stimulant substance of the cathinone chemical class that produces a mixture of entactogenic, stimulating, and euphoric effects when administered. It was first synthesized by chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant.
This compound is often used as a substitute for MDMA due to similarities in their effects. Alexander Shulgin commented that the substances have “almost the same potency of MDMA, but it does not produce the same effects.” He also stated that it “has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA.

Chemistry

Methylone, or 3,4-methylenedioxy-N-methylcathinone, is a synthetic molecule of the cathinone family. Cathinones are structurally similar to amphetamines, they contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα. The Cathinones such as methylone are alpha-methylated phenethylamines. Cathinones differ from amphetamines by the addition of a ketone functional group, a carbonyl group at Rβ.
Methylone contains a methyl substitution at RN, a substitution that is shared with MDMA, mephedrone, and certain other stimulants. Methylone contains additional substitutions at R3 and R4 of the phenyl ring with oxygen groups. These oxygen groups are incorporated into a methylenedioxy ring through a methylene chain. Methylone shares this methylenedioxy ring with MDA, MDAI, and MDMA

What Is Methylone?

Methylone is a designer drug that acts on the brain much like MDMA or ecstasy. The substance releases a flood of dopamine and serotonin to increase alertness, excitability, and physical energy. However, according to the National Institute on Drug Abuse (NIDA), it may not have the same toxicity as the other amphetamine-based stimulants, meaning the drug may not have the same potential for addiction as MDMA.

Chemical structure of methylone

This was based on a study involving rats that monitored the levels of neurotransmitters released by the brain over time.

The study found that repeated, high doses of both and mephedrone, another synthetic cathinone, did not deplete serotonin in the brain in the same way that MDMA did. However, the initial studies on similarities between methylone, MDMA, and mephedrone are small and do not involve humans, so understanding how addictive and toxic new chemicals like methylone are can take time.

It is still unknown if methylone and related chemicals are addictive or predominantly toxic. The rats in the study mostly did not escalate their abuse of methylone. This makes the drug unique from other chemicals that could lead to bingeing behavior like meth or cocaine.

Because of the intensely energetic high it brings, methylone is one of the many chemicals that may be found in bath salts or sold on its own. It is made in a clandestine lab in large batches, so methylone is often much less expensive than cocaine, MDMA, or even methamphetamine.

Although methylone is not a well-understood substance of abuse, the drug has killed people because of its intense side effects when it has been accidentally taken instead of ecstasy at raves, concerts, or parties. When it is intentionally abused, methylone is abused as bath salts or Molly, a drug chemically similar to MDMA.

Who Abuses Methylone, and Is It Addictive?

The United Nations Office on Drugs and Crime (UNODC) reports that methylone has been found in Europe since 2005, a few years before the substance appeared in US illicit drug markets. The UNODC reported methylone as an analog for ecstasy or MDMA since it was a component in Molly.

The DEA reports that methylone was first found on the illicit drug market in the US in 2009, and it was placed on Schedule I in 2013. Before this chemical was banned, however, it was considered legal to import since it was not specifically controlled by the federal or many state governments until the DEA ban.

Because it was sold legally, young people had access to this potent stimulant, which led to many toxic side effects and overdoses. Although methylone is no longer legal in the US, other synthetic cathinones are legal at the federal level. After the devastating effects of bath salts on a few dozen people around the country, many states have moved to ban anything that could be considered a synthetic cathinone.

Although some older adults abuse synthetic cathinones like methylone, the market is predominantly adolescents who gain access to these drugs through convenience stores or the internet. Young adults may abuse them in social settings like at raves, concerts, or clubs.

A DEA lab first identified methylone as a harmful, intoxicating substance in 2009 in four drug reports. By 2012, there were 4,066 reports involving methylone intoxication. It is now an illegal chemical in the US, but adolescents continue to abuse this drug. A 2017 NIDA survey found that 0.5 percent of 8th grade students, 0.4 percent of 10th grade students, and 0.6 percent of 12th grade students in the US abused bath salts at some point in the past year, some of which may have contained this content.

The toxic effects reported include moderate symptoms like:

• Increased heart rate and blood pressure
• Changes in consciousness, leading to difficulty understanding reality
• Pupil dilation, leading to blurry vision
• Trouble focusing
• Restlessness
• Changes in perception of time
• Increase in body temperature
• Muscle tension and aches
• Grinding the teeth and clenching the jaw to the point of getting lockjaw
• Insomnia, also
• Sweating

Signs of severe side effects to the point of overdose include:

1. Hyperthermia, or extreme high body temperature that can damage internal organs
2. Dizziness and extreme confusion
3. Hallucinations
4. Depersonalization
5. Paranoid delusions or intense fear
6. Nausea, vomiting, or gastrointestinal discomfort, also
7. Skin rashes

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