Methylenedioxymethcathinone
Encyclopedia
Methylone, also known as "M1", 3,4-methylenedioxy-N-methylcathinone, bk-MDMA, is an entactogen and stimulant
of the phenethylamine
, amphetamine
, and cathinone
classes. It was originally patented by Nick Wald and Adam Fantoma in 1996 as an antidepressant. The more intuitive abbreviation MDMC unfortunately can not be used for this chemical, since it had already been given to another earlier Shulgin creation, 3,4-ethylenedioxymethamphetamine. Methylone is a close structural
analogue of MDMA, differing by the addition of a β-ketone
group
.
At the end of 2004, a new designer drug
called "Explosion" appeared in the Netherlands. This drug was sold as a liquid via the internet and in Dutch
"smartshops" (known as "headshops" in the United States and some other countries), stores selling at the time non-scheduled, usually becoming illegal within a year of becoming well-known, psychoactive substance
s such as Salvia divinorum
, Psilocybin mushrooms and other MDMA substitutes like BZP
and TFMPP
. The product is advertised as a "room odorizer" and is sold in plastic tubes containing 5 mL of liquid. The tubes cost between €10 and €15 ($13–$20) and do not present any information about the composition of Explosion; they contain only a label saying "Room odorizer Vanilla. Do not ingest" and "Keep away from children. Never use more than one bottle". Users have mentioned ingesting the liquid to reach euphoric stimulating effects similar to those of MDMA. The label circumvents Dutch regulations for illicit drugs and psychoactive substances when intentionally used for intoxication. Analysis of "Explosion" has confirmed that the active ingredient is methylone.
The effects of methylone may include the following:
Central Nervous System
Sympathomimetic
Most of these effects are very similar to those of other psychostimulants.
Methylone resembles MDMA in its behavioural profile, as it substitutes for MDMA in rats trained to discriminate MDMA from saline. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline. Further, also in common with MDMA, methylone acts on monoaminergic systems. In vitro, methylone has one third the potency of MDMA at inhibiting platelet serotonin accumulation and about the same in its inhibiting effects on the dopamine and noradrenaline transporters.
In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin
wrote of the former:
/releasing agent
of serotonin
, norepinephrine
, and dopamine
. In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter
, while its affinity for the norepinephrine
and dopamine transporter
s 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 has relatively robust releasing capabilities, perhaps due to its ability to phosphorylate the monoamine transporter
s being similar in potency relative to MDMA.
s in mammal
s for methylone are N-demethylation
to methylenedioxycathinone
(MDC), and demethylation
followed by O-methylation
of the 3- or 4-hydroxy
group
to 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). When 5 mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged).
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. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government.
In the UK, Methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the Misuse of Drugs Act
. In March 2010 plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the ACMD, the revision was rushed through by the government with little regard for the views of the ACMD. The importation of the compounds was banned immediately.
In Sweden, methylone was classed as a Harmful Substance since 2007, but since 21 September 2010 the drug was actively scheduled as a narcotic. In Sweden the name in the books for the substance classified is 3,4-metylendioximetkatinon (Metylon).
United States
, 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.
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
of the phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
, amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
, and cathinone
Substituted cathinone
Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions...
classes. It was originally patented by Nick Wald and Adam Fantoma in 1996 as an antidepressant. The more intuitive abbreviation MDMC unfortunately can not be used for this chemical, since it had already been given to another earlier Shulgin creation, 3,4-ethylenedioxymethamphetamine. Methylone is a close structural
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
analogue of MDMA, differing by the addition of a β-ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
.
Recreational use
Designer drug
Designer drug is a term used to describe drugs that are created to get around existing drug laws, usually by preparing analogs or derivatives of existing drugs by modifying their chemical structure to varying degrees, or less commonly by finding drugs with entirely different chemical structures...
called "Explosion" appeared in the Netherlands. This drug was sold as a liquid via the internet and in Dutch
Dutch language
Dutch is a West Germanic language and the native language of the majority of the population of the Netherlands, Belgium, and Suriname, the three member states of the Dutch Language Union. Most speakers live in the European Union, where it is a first language for about 23 million and a second...
"smartshops" (known as "headshops" in the United States and some other countries), stores selling at the time non-scheduled, usually becoming illegal within a year of becoming well-known, psychoactive substance
Chemical substance
In chemistry, a chemical substance is a form of matter that has constant chemical composition and characteristic properties. It cannot be separated into components by physical separation methods, i.e. without breaking chemical bonds. They can be solids, liquids or gases.Chemical substances are...
s such as Salvia divinorum
Salvia divinorum
Salvia divinorum is a psychoactive plant which can induce dissociative effects and is a potent producer of "visions" and other hallucinatory experiences...
, Psilocybin mushrooms and other MDMA substitutes like BZP
Benzylpiperazine
Benzylpiperazine is a recreational drug with euphoric, stimulant properties. The effects produced by BZP are comparable to those produced by amphetamine. Adverse effects have been reported following its use including acute psychosis, renal toxicity, and seizures...
and TFMPP
Trifluoromethylphenylpiperazine
3-Trifluoromethylphenylpiperazine is a recreational drug of the piperazine chemical class. Usually in combination with its analogue benzylpiperazine , it is sold as a legal alternative to the illicit drug MDMA under the name "Legal X".- Pharmacology :TFMPP has affinity for the 5-HT1A , 5-HT1B ,...
. The product is advertised as a "room odorizer" and is sold in plastic tubes containing 5 mL of liquid. The tubes cost between €10 and €15 ($13–$20) and do not present any information about the composition of Explosion; they contain only a label saying "Room odorizer Vanilla. Do not ingest" and "Keep away from children. Never use more than one bottle". Users have mentioned ingesting the liquid to reach euphoric stimulating effects similar to those of MDMA. The label circumvents Dutch regulations for illicit drugs and psychoactive substances when intentionally used for intoxication. Analysis of "Explosion" has confirmed that the active ingredient is methylone.
Effects
Reported dosages range from 100 to 250 mg orally. Some respondents say that increasing dose with methylone beyond 100–180 mg causes increased physical effects and does not substantially improve the empathic cognitive effects.The effects of methylone may include the following:
Central Nervous System
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...
- StimulationStimulantStimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
- EuphoriaEuphoriaEuphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...
or dysphoriaDysphoriaDysphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of depression, discontent and indifference to the world around them.Mood disorders can induce dysphoria, often with a heightened risk of suicide, especially in...
, and anxiolysis or anxiogenesis, depending on the individual. - An increase in sociability.
- InsomniaInsomniaInsomnia is most often defined by an individual's report of sleeping difficulties. While the term is sometimes used in sleep literature to describe a disorder demonstrated by polysomnographic evidence of disturbed sleep, insomnia is often defined as a positive response to either of two questions:...
and restlessness - DerealizationDerealizationDerealization is an alteration in the perception or experience of the external world so that it seems unreal. Other symptoms include feeling as though one's environment is lacking in spontaneity, emotional coloring and depth. It is a dissociative symptom of many conditions, such as psychiatric and...
/depersonalizationDepersonalizationDepersonalization is an anomaly of the mechanism by which an individual has self-awareness. It is a feeling of watching oneself act, while having no control over a situation. Sufferers feel they have changed, and the world has become less real, vague, dreamlike, or lacking in significance...
, hallucinationHallucinationA hallucination, in the broadest sense of the word, is a perception in the absence of a stimulus. In a stricter sense, hallucinations are defined as perceptions in a conscious and awake state in the absence of external stimuli which have qualities of real perception, in that they are vivid,...
s, and psychosisPsychosisPsychosis means abnormal condition of the mind, and is a generic psychiatric term for a mental state often described as involving a "loss of contact with reality"...
, depending on the individual, and in all individuals with high dosage or extended use.
Sympathomimetic
- TachycardiaTachycardiaTachycardia comes from the Greek words tachys and kardia . Tachycardia typically refers to a heart rate that exceeds the normal range for a resting heart rate...
and hypertensionHypertensionHypertension or high blood pressure is a cardiac chronic medical condition in which the systemic arterial blood pressure is elevated. What that means is that the heart is having to work harder than it should to pump the blood around the body. Blood pressure involves two measurements, systolic and... - HyperthermiaHyperthermiaHyperthermia is an elevated body temperature due to failed thermoregulation. Hyperthermia occurs when the body produces or absorbs more heat than it can dissipate...
and sweatingSweatingPerspiration is the production of a fluid consisting primarily of water as well as various dissolved solids , that is excreted by the sweat glands in the skin of mammals... - MydriasisMydriasisMydriasis is a dilation of the pupil due to disease, trauma or the use of drugs. Normally, the pupil dilates in the dark and constricts in the light to respectively improve vividity at night and to protect the retina from sunlight damage during the day...
and nystagmusNystagmusNystagmus is a condition of involuntary eye movement, acquired in infancy or later in life, that may result in reduced or limited vision.There are two key forms of Nystagmus: pathological and physiological, with variations within each type. Nystagmus may be caused by congenital disorders,... - TrismusTrismus-Common causes:*Pericoronitis is the most common cause of trismus.*Inflammation of muscles of mastication. It is a frequent sequel to surgical removal of mandibular third molars . The condition is usually resolved on its own in 10–14 days, during which time eating and oral hygiene are compromised...
and bruxismBruxismBruxism is characterized by the grinding of the teeth and typically includes the clenching of the jaw. It is an oral parafunctional activity that occurs in most humans at some time in their lives. In most people, bruxism is mild enough not to be a health problem... - AnorexiaAnorexia (symptom)Anorexia is the decreased sensation of appetite...
- NauseaNauseaNausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
and vomitingVomitingVomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
Most of these effects are very similar to those of other psychostimulants.
Resemblance to MDMA
In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
wrote of the former:
Pharmacodynamics
Methylone acts as a mixed reuptake inhibitorReuptake inhibitor
A reuptake inhibitor , also known as a transporter blocker, is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron, leading to an increase in the extracellular concentrations of the neurotransmitter and therefore an...
/releasing agent
Releasing agent
A releasing agent , or simply releaser, is a drug that induces the release of a neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs use neurotransmitter release to exert their psychological and...
of serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
, norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...
, and dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
. In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter
Serotonin transporter
The serotonin transporter is a monoamine transporter protein.This protein is an integral membrane protein that transports the neurotransmitter serotonin from synaptic spaces into presynaptic neurons. This transport of serotonin by the SERT protein terminates the action of serotonin and recycles it...
, while its affinity for the norepinephrine
Norepinephrine transporter
The norepinephrine transporter , also known as solute carrier family 6 member 2 , is a protein that in humans is encoded by the SLC6A2 gene....
and dopamine transporter
Dopamine transporter
The dopamine transporter is a membrane-spanning protein that pumps the neurotransmitter dopamine out of the synapse back into cytosol, from which other transporters sequester DA and NE into vesicles for later storage and release...
s 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
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...
in terms of dose
Dose (biochemistry)
A dose is a quantity of something that may impact an organism biologically; the greater the quantity, the larger the dose. In nutrition, the term is usually applied to how much of a specific nutrient is in a person's diet or in a particular food, meal, or dietary supplement...
, has more balanced catecholaminergic effects relative to serotonergic
Serotonergic
Serotonergic or serotoninergic means "related to the neurotransmitter serotonin". A synapse is serotonergic if it uses serotonin as its neurotransmitter...
, and behaves more like a reuptake inhibitor like methylphenidate
Methylphenidate
Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity...
than a releaser like amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
; however, methylone has relatively robust releasing capabilities, perhaps due to its ability to phosphorylate the monoamine transporter
Monoamine transporter
Monoamine transporters are protein structures that function as integral plasma membrane transporters to regulate concentrations of extracellular monoamine neurotransmitters. Three major classes of MATs are responsible for the reuptake of their associated amine neurotransmitters...
s being similar in potency relative to MDMA.
Pharmacokinetics
Little is currently known about the pharmacokinetics of methylone, aside from metabolism.Metabolism
The two major metabolic pathwayMetabolic pathway
In biochemistry, metabolic pathways are series of chemical reactions occurring within a cell. In each pathway, a principal chemical is modified by a series of chemical reactions. Enzymes catalyze these reactions, and often require dietary minerals, vitamins, and other cofactors in order to function...
s in mammal
Mammal
Mammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...
s for methylone are N-demethylation
Demethylation
Demethylation is the chemical process resulting in the removal a of methyl group from a molecule.A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms....
to methylenedioxycathinone
Methylenedioxycathinone
3,4-Methylenedioxycathinone, also called MDC or bk-MDA, is an entactogen and stimulant of the phenethylamine, amphetamine, and cathinone classes. It is the β-keto analogue of MDA....
(MDC), and demethylation
Demethylation
Demethylation is the chemical process resulting in the removal a of methyl group from a molecule.A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms....
followed by O-methylation
Methylation
In the chemical sciences, methylation denotes the addition of a methyl group to a substrate or the substitution of an atom or group by a methyl group. Methylation is a form of alkylation with, to be specific, a methyl group, rather than a larger carbon chain, replacing a hydrogen atom...
of the 3- or 4-hydroxy
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
to 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). When 5 mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged).
Legal status
In the Netherlands, methylone is not yet scheduled as a drug of abuse, but is considered to be a psychoactive medicine. Because methylone is not registered officially, as such, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group (CAM) to gather information about this substance, resulting possibly in an official risk assessment. Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug.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. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government.
In the UK, Methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the Misuse of Drugs Act
Misuse of Drugs Act 1971
The Misuse of Drugs Act 1971 is an Act of Parliament which represents UK action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic...
. In March 2010 plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the ACMD, the revision was rushed through by the government with little regard for the views of the ACMD. The importation of the compounds was banned immediately.
In Sweden, methylone was classed as a Harmful Substance since 2007, but since 21 September 2010 the drug was actively scheduled as a narcotic. In Sweden the name in the books for the substance classified is 3,4-metylendioximetkatinon (Metylon).
United States
- As of October 21, 2011 the DEA has issued an emergency ban on methylone. It is illegal to possess and distribute.
- Florida:
- In January 2011, it was reported that Florida Attorney General Pam Bondi issued an emergency ban on MDPV, Methylone, Mephedrone, 3-methoxymethcathinon, 3-fluoromethcathinone, and 4-fluoromethcathinone as media attention on products labeled as "bath salts" grew. These chemicals are now Schedule I under Florida law.
- Louisiana:
- In January 2011, the governor of Louisiana emergency scheduled 3,4-Methylenedioxymethcathinone (Methylone), 3,4-Methyenedioxypyrovalerone (MDPVMDPVMethylenedioxypyrovalerone is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor . Reportedly, it has been sold since around 2004 as a designer drug. It is also known as MDPK, MTV, Magic, Maddie, Black Rob, Super Coke and PV...
), 4-Methylmethcathinone (Mephedrone), 4-methoxymethcathinone (Methedrone), 4-Fluoromethcathinone (FlephedroneFlephedroneFlephedrone, also known as 4-fluoromethcathinone , is a stimulant drug of the cathinone chemical class.- History :Flephedrone started to be sold as a designer drug in 2008, along with its structural isomer 3-fluoromethcathinone .- Toxicity :Flephedrone has only a short history of human use and its...
), and 3-Fluoromethcathinone (3-FMC).- Tennessee:
- On May 5, 2011, Tennessee Governor Bill Haslam signed a law making it a crime to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-Methylenedioxymethcathinone (Methylone), 3,4-Methyenedioxypyrovalerone (MDPVMDPVMethylenedioxypyrovalerone is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor . Reportedly, it has been sold since around 2004 as a designer drug. It is also known as MDPK, MTV, Magic, Maddie, Black Rob, Super Coke and PV...
), 4-Methylmethcathinone (Mephedrone), 4-methoxymethcathinone (Methedrone), 4-Fluoromethcathinone (FlephedroneFlephedroneFlephedrone, also known as 4-fluoromethcathinone , is a stimulant drug of the cathinone chemical class.- History :Flephedrone started to be sold as a designer drug in 2008, along with its structural isomer 3-fluoromethcathinone .- Toxicity :Flephedrone has only a short history of human use and its...
), and 3-Fluoromethcathinone (3-FMC).
Etymology
"Methylone" is also a trademarked brand name for an injectable form of methylprednisoloneMethylprednisolone
Methylprednisolone is a synthetic glucocorticoid or corticosteroid drug. It is marketed in the USA and Canada under the brand names Medrol and Solu-Medrol. It is also available as a generic drug....
, 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
Bk-MDEA
Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone , is an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA . Ethylone has only a short history of human use and is reported to be less potent than...
and bk-MBDB
Bk-MBDB
Butylone, also known as β-keto-N-methylbenzodioxolylpropylamine , is an entactogen, psychedelic, and stimulant of the phenethylamine chemical class. It is the β-keto analogue of MBDB....
have become the established names for those substances.