Methylone

Summary sheet: Methylone

Methylone
Chemical Nomenclature
Common names	Methylone, bk-MDMA, M1, MDMC
Substitutive name	3,4-Methylenedioxy-N-methylcathinone
Systematic name	(RS)-1-(Benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine
Class Membership
Psychoactive class	Stimulant / Entactogen
Chemical class	Cathinone / MDxx
Routes of Administration
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. ⇣ Oral Dosage Threshold 75 mg Light 75 - 150 mg Common 150 - 225 mg Strong 225 - 325 mg Heavy 325 mg + Duration Total 2.5 - 4 hours Onset 15 - 45 minutes Come up 15 - 45 minutes Peak 60 - 90 minutes Offset 60 - 90 minutes After effects 6 - 24 hours DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
Interactions
MAOIs
Serotonin releasers
SSRIs
5-HTP

Methylone (also known as M1, 3,4-methylenedioxy-N-methcathinone, MDMC and βk-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.

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 that the drug has "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 R_α. Cathinones such as methylone are alpha-methylated phenethylamines. Cathinones differ from amphetamines by the addition of a ketone functional group, a carbonyl group at R_β. Methylone contains an methyl substitution at R_N, a substitution which 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.

Pharmacology

Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine. 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(Ki=242.1 nM for methylone to Ki=72 nM for MDMA) while its affinity for the norepinephrine and dopamine transporters is similar. Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA. 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.

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

• Spontaneous physical sensations - The "body high" of methylone 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 doses. 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, methylone is commonly considered to be extremely stimulating and energetic. This encourages activities such as running, climbing and dancing in a way that makes methylone a popular choice for musical events such as festivals and raves. The particular style of stimulation which methylone presents can be described as forced. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, 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 doses, a person's eyeballs may begin to spontaneously wiggle back and forth in a rapid motion, causing the vision to become blurry and temporarily out of focus. This is a condition known as nystagmus.
• Dehydration - Feelings of dry mouth and dehydration are a universal experience with methylone; 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 methylone result in an overall difficulty when it comes to urination. This is an effect that is completely temporary and harmless. It is due to methylone’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.
• Temperature regulation suppression
• Tactile enhancement
• Increased heart rate
• Increased perspiration
• Increased blood pressure
• Teeth grinding - This component can be considered to be less intense when compared with that of MDMA.
• Increased music appreciation

Cognitive effects

The cognitive effects of methylone can be broken down into several components which progressively intensify proportional to dosage. The general head space of methylone 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:

• Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within methylone and are likely a direct result of serotonin and dopamine release. In comparison to MDMA, it is closer in effects to that of the euphoria felt within amphetamine and mephedrone.
• Empathy, love, and sociability enhancement - Although distinct and powerful in its effects, this particular feeling is less pronounced and therapeutic when compared to that of MDMA. It can be described as less forceful and more internal in its manifestation, resulting in feelings of love and empathy that are not necessarily felt as essential to express to others.
• Time distortion - Strong feelings of time compression are common within methylone and speed up the experience of time quite noticeably.
• Thought acceleration
• Analysis enhancement
• Mindfulness
• Increased libido
• Increased music appreciation

After effects

The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:

• Anxiety
• Cognitive fatigue
• Depression
• Irritability
• Motivation suppression
• Thought deceleration
• Wakefulness

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

• Erowid Experience Vaults: Methylone

Toxicity and harm potential

Further information: Research chemicals § Toxicity and harm potential

The toxicity and long-term health effects of recreational methylone use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because methylone has very little history of human usage. Anecdotal evidence from people who have tried methylone within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

As with other stimulants, the chronic use of methylone can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.

Tolerance to many of the effects of methylone develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). Methylone presents cross-tolerance with [[Cross-tolerance::all dopaminergic stimulants]], meaning that after the consumption of methylone all stimulants will have a reduced effect.

Psychosis

Main article: Stimulant psychosis

Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., paranoia, hallucinations, or delusions). A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis. Psychosis very rarely arises from therapeutic use.

Dangerous interactions

Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

• Stimulants - Methylone can be potentially dangerous in combination with other stimulants as it can increase one's heart rate and blood pressure to dangerous levels.
• "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] & "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 25x compounds are highly stimulating and physically straining. Combinations with Methylone should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
• "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
• "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
• "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
• "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
• "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
• "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Methylone may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
• "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is known to lower the seizure threshold and combinations with stimulants may further increase this risk.
• Cocaine - This combination may increase strain on the heart.

Serotonin syndrome risk

Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.

• MAOIs - Such as banisteriopsis caapi, syrian rue, phenelzine, selegiline, and moclobemide.
• Serotonin releasers - Such as MDMA, 4-FA, methamphetamine, methylone and αMT.
• SSRIs - Such as citalopram and sertraline
• [[Wikipedia:SNRIs|DangerousInteraction::SNRIs]] - Such as tramadol and venlafaxine
• 5-HTP

Legal issues

• Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.
• 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 U.K., methylone has been illegal since the 16/04/2010 revision of the Misuse of Drugs Act.
• Sweden: Methylone has been listed as a Schedule I narcotic in Sweden as of Oct 1 of 2010.
• 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; 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.
• Germany: On July 26, 2012, methylone was added to Germany's controlled substance act ("BtMG"), making it illegal to produce, sell or possess.

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.

See also

• Responsible use
• Entactogens
• Stimulants
• Phenethylamines
• Amphetamines
• Cathinones
• Mephedrone
• MDMA

External links

• Methylone (Wikipedia)
• Methylone (Erowid)
• Methylone experiences (Erowid)
• Methylone (TripSit)
• BK-MDMA (Bluelight)