Methylone

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BK-MDMA
The skeletal formula of BK-MDMA.
Dosage
Threshold	60mg
Light	100 - 150mg
Common	150 - 250mg
Strong	200 - 300mg
Heavy	300mg +
Duration
Onset / Initial effects	20 - 70 minutes
Coming up	10 - 15 minutes
Peak	2 - 4 hours
Coming down	1 hour
After effects	12 hours

Methylone, also known as M1, 3,4-methylenedioxy-N-methylcathinone, MDMC, bk-MDMA is an entactogen and stimulant of the phenethylamine, amphetamine and cathinone classes. It was first synthesized by chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant. Methylone is a close structural analog of MDMA, differing by the addition of a β-ketone group.

This compound is often used as a substitute for MDMA due to its similar range of subjective effects. However, in spite of behavioral and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin wrote of the former:

"[Methylone] has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA."

Chemistry

Methylone, also known as 3,4-methylenedioxy-N-methylamphetamine, is part of the phenethylamine and amphetamine families. There is a methylenedioxy ring attached to carbons R3 and R4, as well as methyl chains at Rα and RN.

Pharmacology

Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.[3][10] These are the neurotransmitters in charge of pleasure, motivation and focus. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, essentially allowing them to accumulate and be reused, causing physically stimulating and euphoric effects.

In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter, while its affinity for the norepinephrine and dopamine transporters is similar.[3][10] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA.[3] The results of these differences in pharmacology relative to MDMA are that methylone is less potent in terms of dose, has more balanced catecholaminergic effects relative to serotonergic, and behaves more like a reuptake inhibitor like methylphenidate than a releaser like amphetamine; however, methylone still has relatively robust releasing capabilities.[10]

Subjective effects

Template:EffectsStub The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely if ever occur all at once but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

The physical effects of MDMA can be broken down into six components all of which progressively intensify proportional to dosage. These are described below and generally include:

• Spontaneous tactile sensations - The "body high" of MDMA can be described as a moderate to extreme euphoric tingling sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher dosages. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
• Stimulation - In terms of its effects on the user's physical energy levels, MDMA is commonly considered to be extremely stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes MDMA a popular choice for musical events such as festivals and raves. The particular style of stimulation which MDMA presents can be described as forced. This means that at higher dosages, it becomes difficult or impossible to keep still, as jaw clenching and involuntarily bodily shakes and vibrations become present, resulting in an extreme unsteadiness of the hands and a general lack of motor control.
• Vibrating vision - At high dosages, a person's eyeballs may even begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus-- a condition known as nystagmus.
• Dehydration - Feelings of dry mouth and dehydration are a universal experience with MDMA; this effect is a product of an increased heart rate and an extreme motivation to engage in strenuous physical activities. While it is important to avoid becoming dehydrated, especially when out dancing in a hot environment, there have been a number of users suffering from water intoxication through over-drinking so it is advised that users simply sip at water and never over-drink.
• Difficulty urinating - Higher doses of MDMA result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless, due to MDMA’s promotion of the release of anti-diuretic hormone (ADH). ADH is responsible for regulating urination. This effect can be lessened by simply relaxing, but can be significantly relieved by placing a hot flannel over the genitals to warm them up and encourage blood flow.
• Tactile enhancement

Cognitive effects

The cognitive effects of MDMA can be broken down into six components all of which progressively intensify proportional to dosage. The general head space of MDMA is described by many as one of extreme mental stimulation, feelings of love or empathy and powerful euphoria. It contains a large number of typical psychedelic, entactogenic and stimulant cognitive effects.

The most prominent of these cognitive effects generally include:

• Euphoria - Strong emotional euphoria and feelings of happiness are present within MDMA and are likely a direct result of serotonin and dopamine release.
• Empathy, love and sociability enhancement - This particular effect is more pronounced, powerful and therapeutic with MDMA than any other known substance. It is the most obvious and noticeable effect within any MDMA experience and dominates the head space. With time and repeated use however, this effect becomes severely diminished as the perspective it instils becomes fully grounded and already in place, making people feel merely stimulated and euphoric with no new found urges to communicate with others. Some users report that MDMA 'loses its magic' with as few as 10 experiences, while others have reported hundreds of uses before the empathic qualities disappear. This does not appear to be true for all users, however, with many users reporting that they have not experienced any decrease in quality of the experience despite dozens or even hundreds of uses.
• Time distortion - Strong feelings of time compression are common within MDMA and speed up the experience of time quite noticeably.
• Unity and interconnectedness - Experiences of unity, oneness and interconnectedness between level 2 - 3 are common within MDMA. This component most consistently manifests itself at high dosages within large crowds at raves and musical events in the form of "becoming one with the crowd."
• Thought acceleration
• Mindfulness

Toxicity and Harm Potential

Lethal Dosage

The median lethal dosage of methylone within humans is unknown but considered to be far greater than its active dosage.

Legal issues

• Netherlands: In the Netherlands, methylone is covered under the medicine act. Because methylone is not registered officially, as such, it is forbidden to trade in methylone.
• New Zealand: In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an "amphetamine analogue" in the Misuse of Drugs Act, it is considered to be "substantially similar" to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug.
• United Kingdom: In the UK, methylone is illegal since the 16/04/2010 revision of the misuse of drugs act.
• Sweden: Methylone has been listed as a schedule I narcotics in Sweden as of Oct 1.
• Canada: Although not listed as a Schedule 1 substance, Health Canada reports that methylone falls under the scheduling as an analogue of amphetamine. However, Methylone bears the exact chemical difference between amphetamine and cathinone - and cathinone is listed as not being an analogue of amphetamine. Leading to imply that methylone is unscheduled in Canada.
• United States: As of October 21, 2011 the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.

Etymology

"Methylone" is also a trademarked brand name for an injectable form of methylprednisolone, a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. Aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug.

A proposed alternate name is bk-MDMA, or beta-keto-MDMA. While this nomenclature has not caught on because the name "methylone" became widely used before the conflicting Methylone trademark was noticed, the analogous names for related chemicals bk-MDEA and bk-MBDB have become the established names for those substances.