Methcathinone
Encyclopedia
Methcathinone is a psychoactive stimulant
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...

, sometimes used as a recreational drug and considered addictive
Substance use disorder
Substance use disorders include substance abuse and substance dependence. In DSM-IV, the conditions are formally diagnosed as one or the other, but it has been proposed that DSM-5 combine the two into a single condition called "Substance-use disorder"....

. It is usually snorted
Nasal administration
Nasal administration can be used to deliver drugs for either local or systemic effect. Locally acting drugs are for example decongestants and allergy treatments...

, but can be smoked, injected, or taken orally. Methcathinone is currently a DEA
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...

 Schedule I controlled substance in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

.

The C=O bond
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...

 at the Rβ-position (directly right of the benzene ring) is slightly polar, and as a result the drug does not cross the lipid blood-brain barrier
Blood-brain barrier
The blood–brain barrier is a separation of circulating blood and the brain extracellular fluid in the central nervous system . It occurs along all capillaries and consists of tight junctions around the capillaries that do not exist in normal circulation. Endothelial cells restrict the diffusion...

 quite as well as 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,...

. Nevertheless, it is a potent CNS stimulant
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...

 and dopamine reuptake inhibitor
Dopamine reuptake inhibitor
A dopamine reuptake inhibitor is a type of drug that acts as a reuptake inhibitor for the neurotransmitter dopamine by blocking the action of the dopamine transporter...

. Chronic high dosage use may result in acute mental confusion ranging from mild paranoia
Paranoia
Paranoia [] is a thought process believed to be heavily influenced by anxiety or fear, often to the point of irrationality and delusion. Paranoid thinking typically includes persecutory beliefs, or beliefs of conspiracy concerning a perceived threat towards oneself...

 to psychosis
Psychosis
Psychosis 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"...

. These symptoms typically disappear quickly if use is stopped.

Unlike methamphetamine, methcathinone is not legal under any circumstances in the US due to its classification as a Schedule I substance. Conversely, methamphetamine has certain approved medical uses such as treatment of morbid obesity
Obesity
Obesity is a medical condition in which excess body fat has accumulated to the extent that it may have an adverse effect on health, leading to reduced life expectancy and/or increased health problems...

, narcolepsy
Narcolepsy
Narcolepsy is a chronic sleep disorder, or dyssomnia, characterized by excessive sleepiness and sleep attacks at inappropriate times, such as while at work. People with narcolepsy often experience disturbed nocturnal sleep and an abnormal daytime sleep pattern, which often is confused with insomnia...

 and ADHD.

History

Methcathinone was first synthesized in 1928 in the United States and finally patented by Parke Davis in 1957. It was used in the Soviet Union
Soviet Union
The Soviet Union , officially the Union of Soviet Socialist Republics , was a constitutionally socialist state that existed in Eurasia between 1922 and 1991....

 during the 1930s and 1940s as an anti-depressant. Since the 1960s, methcathinone has been used as a recreational drug in the (former) Soviet Union
Soviet Union
The Soviet Union , officially the Union of Soviet Socialist Republics , was a constitutionally socialist state that existed in Eurasia between 1922 and 1991....

.

Circa 1994, the United States government recommended to the UN Secretary-General that methcathinone should be added to Schedule I of the Convention on Psychotropic Substances
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...

.

Chemistry

Methcathinone is N-methylcathinone
Cathinone
Cathinone, or Benzoylethanamine, is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors. It is...

 whereas cathine
Cathine
Cathine, also known as d-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant...

 is N-demethylpseudoephedrine
Pseudoephedrine
Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It is used as a nasal/sinus decongestant and stimulant, or as a wakefulness-promoting agent....

 (SS), all of which are stimulant
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...

 alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s found in the shrub
Shrub
A shrub or bush is distinguished from a tree by its multiple stems and shorter height, usually under 5–6 m tall. A large number of plants may become either shrubs or trees, depending on the growing conditions they experience...

 Catha edulis (Khat
Khat
Khat, qat, gat or Waquish Spoken from true Yemeni, is a flowering plant native to tropical East Africa and the Arabian Peninsula....

). Stimulants such as meth/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,...

, and other phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

s are also similar in structure.

Methcathinone possesses a chiral carbon atom, and therefore two enantiomers are possible. When it is made semi-synethically from pseudo/ephedrine as a starting material, then only a single enantiomer is produced. Given that the chiral centre is adjacent to the carbonyl group, the molecule will racemise in solution.

Methcathinone is "most commonly" made by the oxidation of ephedrine
Ephedrine
Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....

. Oxidation of ephedrine
Ephedrine
Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....

 to methcathinone requires little chemistry
Chemistry
Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....

 experience, making it (relatively) easy to synthesize. Potassium permanganate
Potassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...

 (KMnO4) is most commonly used as the oxidant.

In clandestine laboratories, synthesizing methcathinone using either potassium permanganate or various chromate
Chromate
Chromate salts contain the chromate anion, CrO42−. Dichromate salts contain the dichromate anion, Cr2O72−. They are oxyanions of chromium in the oxidation state +6. They are moderately strong oxidizing agents.- Chemical properties :...

s is considered undesirable because of the low yields and the high toxicity of these oxidants. A method that yields more methcathinone is oxidizing ephedrine with sodium hypochlorite. If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.

Methcathinone as free base is very unstable; it easily loses its 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...

 and converts back into an alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

. Structurally, this occurs when the C=O bond at the Rβ-position is converted into a C-OH bond. In other words, basic methcathinone will turn into ephedrine
Ephedrine
Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....

, from which it was synthesized.

Effects

Methcathinone hydrochloride increases spontaneous rodent locomotor
Locomotor system
Locomotor system may mean:* Animal locomotion system* Human musculoskeletal system, also known simply as "the locomotor system"...

 activity, potentiates the release of 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...

 from dopaminergic
Dopaminergic
Dopaminergic means related to the neurotransmitter dopamine. For example, certain proteins such as the dopamine transporter , vesicular monoamine transporter 2 , and dopamine receptors can be classified as dopaminergic, and neurons which synthesize or contain dopamine and synapses with dopamine...

 nerve
Nerve
A peripheral nerve, or simply nerve, is an enclosed, cable-like bundle of peripheral axons . A nerve provides a common pathway for the electrochemical nerve impulses that are transmitted along each of the axons. Nerves are found only in the peripheral nervous system...

 terminals in the brain
Brain
The brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...

, and causes appetite suppression. Users can easily forget to consume fluids leading to increased thirst and dehydration. The effects of methcathinone are similar to those of methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

, initially deemed to be less intense by the inexperienced user, and often more euphoric. The effects have been compared to those of cocaine
Cocaine
Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...

, since it commonly causes hypertension
Hypertension
Hypertension 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...

 (elevated blood pressure) and tachycardia
Tachycardia
Tachycardia 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...

 (elevated heart rate). Reported effects include:
  • Feelings of euphoria
    Euphoria (emotion)
    Euphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of well-being, elation, happiness, ecstasy, excitement and joy...

  • Increased alertness
  • Dilated pupil
    Pupil
    The pupil is a hole located in the center of the iris of the eye that allows light to enter the retina. It appears black because most of the light entering the pupil is absorbed by the tissues inside the eye. In humans the pupil is round, but other species, such as some cats, have slit pupils. In...

    s
  • Slurred speech
  • Increased heart rate
  • Inability to stop talking
  • Increased empathy and sense of communication
  • Both decreased and increased sexual function and desire
  • Loss of cognitive ability relating to the distinction of relative importance of matters

The effects of methcathinone usually last from four to six hours.

Use and pharmacology

Methcathinone has very strong affinities for the dopamine transporter and the noradrenaline transporter. Its affinity for the serotonin transporter is less than that of methamphetamine.

Anecdotal reports have provided some information on patterns of methcathinone use. The most common route of administration
Route of administration
A route of administration in pharmacology and toxicology is the path by which a drug, fluid, poison, or other substance is taken into the body.-Classification:Routes of administration are usually classified by application location...

 is via nasal
Human nose
The visible part of the human nose is the protruding part of the face that bears the nostrils. The shape of the nose is determined by the ethmoid bone and the nasal septum, which consists mostly of cartilage and which separates the nostrils...

 insufflation (snorting). Other routes of administration include per os, IV injection and smoking
Tobacco smoking
Tobacco smoking is the practice where tobacco is burned and the resulting smoke is inhaled. The practice may have begun as early as 5000–3000 BCE. Tobacco was introduced to Eurasia in the late 16th century where it followed common trade routes...

.

Methcathinone binges resemble amphetamine binges in that the user may not sleep
Sleep
Sleep is a naturally recurring state characterized by reduced or absent consciousness, relatively suspended sensory activity, and inactivity of nearly all voluntary muscles. It is distinguished from quiet wakefulness by a decreased ability to react to stimuli, and is more easily reversible than...

 or eat
EAT
EAT or eat may refer to:* Eating, the process of consuming food, for the purpose of providing for the nutritional needs of an animal* To take a loss in a transaction. The one who absorbs the loss is said to eat the cost of that loss...

, and takes in little in the way of liquids. The methcathinone binge is followed by a "case of the Mondays" characterized by long periods of sleep, excess eating, long-lasting nosebleeds and, in some cases, depression
Clinical depression
Major depressive disorder is a mental disorder characterized by an all-encompassing low mood accompanied by low self-esteem, and by loss of interest or pleasure in normally enjoyable activities...

.

Injecting this substance has recently been associated with symptoms similar to those seen in patients with Parkinson's Disease (Manganism
Manganism
Manganism or manganese poisoning is a toxic condition resulting from chronic exposure to manganese and first identified in 1837 by James Couper.- Presentation :...

) due to the compound manganese dioxide which is a byproduct of synthesis with permanganate
Permanganate
A permanganate is the general name for a chemical compound containing the manganate ion, . Because manganese is in the +7 oxidation state, the permanganate ion is a strong oxidizing agent. The ion has tetrahedral geometry...

.

Street names

Street slang for methcathinone may be confused with methylmethcathinone (mephedrone) and terms may be used interchangeably and include terms such as MCat , Cat, Meow, Stroof, Katestroof, Jeff, Bathtub Speed, Wannabe-Speed, Kitty, Meth's Cat, Meth's Kitten or Marzipan (from smell during synthesis).

In Europe
Europe
Europe is, by convention, one of the world's seven continents. Comprising the westernmost peninsula of Eurasia, Europe is generally 'divided' from Asia to its east by the watershed divides of the Ural and Caucasus Mountains, the Ural River, the Caspian and Black Seas, and the waterways connecting...

, methcathinone is primarily known as Ephedrone.

In the United Kingdom
United Kingdom
The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...

, methcathinone may be known as M-cat (though this can also refer to the chemical 4-methylmethcathinone; known as mephedrone).

In Australia
Australia
Australia , officially the Commonwealth of Australia, is a country in the Southern Hemisphere comprising the mainland of the Australian continent, the island of Tasmania, and numerous smaller islands in the Indian and Pacific Oceans. It is the world's sixth-largest country by total area...

, methcathinone may be known as ketone or bk (beta ketone).

In South Africa
South Africa
The Republic of South Africa is a country in southern Africa. Located at the southern tip of Africa, it is divided into nine provinces, with of coastline on the Atlantic and Indian oceans...

 it is known as Cat, Ietsies kayo, gram or line. There, it is also confused (via name alone, not presentation) with Khat
Khat
Khat, qat, gat or Waquish Spoken from true Yemeni, is a flowering plant native to tropical East Africa and the Arabian Peninsula....

 (sometimes spelled Qat).

In Bulgaria
Bulgaria
Bulgaria , officially the Republic of Bulgaria , is a parliamentary democracy within a unitary constitutional republic in Southeast Europe. The country borders Romania to the north, Serbia and Macedonia to the west, Greece and Turkey to the south, as well as the Black Sea to the east...

 it is known as PIKO.

In Poland
Poland
Poland , officially the Republic of Poland , is a country in Central Europe bordered by Germany to the west; the Czech Republic and Slovakia to the south; Ukraine, Belarus and Lithuania to the east; and the Baltic Sea and Kaliningrad Oblast, a Russian exclave, to the north...

 it is known as Kot (cat)

Addiction

In preclinical studies, methcathinone hydrochloride
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

 produces an abuse potential similar to that of the amphetamines.

Methcathinone can be highly psychologically addictive, and can produce a methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

-like withdrawal, which is somewhat less in intensity than methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

. It is highly unlikely for a methcathinone user to experience addiction on their first or even several subsequent administrations of the drug.

In drug
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...

 discrimination
Discrimination
Discrimination is the prejudicial treatment of an individual based on their membership in a certain group or category. It involves the actual behaviors towards groups such as excluding or restricting members of one group from opportunities that are available to another group. The term began to be...

 studies, methcathinone hydrochloride evokes responses similar to those induced by both (+)-amphetamine sulfate
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,...

 and cocaine
Cocaine
Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...

 hydrochloride. When examined in particular pharmacological assays for psychomotor
Psychomotor
Psychomotor can refer to:* Psychomotor learning* Psychomotor retardation* Psychomotor agitation...

 stimulant
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...

-like activity, both the d and l enantiomeric forms of methcathinone hydrochloride have been found to be pharmacologically active. In these assays, the l-form of methcathinone is more active than either d-methcathinone or (+)-amphetamine.

Clinical use

In the US, methcathinone is listed as a Schedule I drug, for which there is no clinical use. Research in the United States without a specific DEA permit is also prohibited. In the Netherlands
Netherlands
The Netherlands is a constituent country of the Kingdom of the Netherlands, located mainly in North-West Europe and with several islands in the Caribbean. Mainland Netherlands borders the North Sea to the north and west, Belgium to the south, and Germany to the east, and shares maritime borders...

, methylcathinone is listed as a Level I substance of the Opium Law
Opium Law
The Opium Law is the section of the Dutch law which covers nearly all psychotropic drugs. All non-psychotropic, but prescription-only drugs are covered by the Medicine Act.- Origin and history :...

, for which there is no clinical use. In the UK, methcathinone is listed as a Class B drug, with no clinical uses.

External links

The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
x
OK