Methcathinone
Systematic (IUPAC) name
2-(methylamino)-1-phenyl-propan-1-one
Identifiers
CAS number	5650-44-2 49656-78-2 (HCL) 112117-24-5 (S form) 66514-93-0 ( S HCL)
ATC code	?
PubChem	1576
Chemical data
Formula	C10H13NO
Mol. mass	163.22 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	Urine
Therapeutic considerations
Pregnancy cat.	? Image File history File links This is a lossless scalable vector image. ... Image File history File links Size of this preview: 800 × 584 pixelsFull resolution (878 × 641 pixel, file size: 106 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Methcathinone User:Sbrools/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... This article or section is in need of attention from an expert on the subject. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	Schedule I(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Routes	Vaporized, insufflated, injected, taken orally

Methcathinone(2-(methylamino)-propiophenone, α-methylamino-propiophenone) is a psychoactive stimulant. It is sometimes used as a recreational drug and is considered to be addictive. It is usually snorted, but can be smoked, injected, or taken orally. Methcathinone is currently a DEA Schedule I controlled substance in the United States. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Evaporation is the process whereby atoms or molecules in a liquid state (or solid state if the substance sublimes) gain sufficient energy to enter the gaseous state. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behaviour. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... Addiction is an uncontrollable compulsion to repeat a behavior regardless of its negative consequences. ... The DEAs enforcement activities may take agents anywhere from distant countries to suburban U.S. homes. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ...

The C=O bond at the R_β-position (directly right of the benzene ring) is slightly polar, and as a result the drug does not cross the lipid blood-brain barrier quite as well as amphetamine. Its effects differ slightly from the amphetamines, especially in its ability to act as an serotonin reuptake inhibitor. Nevertheless, it is a potent CNS stimulant and dopamine reuptake inhibitor. Chronic high dosage abuse may result in acute mental confusion ranging from mild paranoia to psychosis. These symptoms typically disappear quickly if use is stopped. Freeze-fracture morphology of the blood-brain barrier of a rat The blood-brain barrier (abbreviated BBB, not to be confused with the blood-cerebrospinal fluid barrier, a function of the choroid plexus) is a membrane that controls the passage of substances from the blood into the central nervous system. ... Amphetamine or Amfetamine, also known as alpha-methyl-phenethylamine, phenyl-isopropylamine, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Selective serotonin reuptake inhibitors (SSRIs) are a class of antidepressants. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... This does not cite any references or sources. ... For other senses of this word, see paranoia (disambiguation). ... Psychosis is a generic psychiatric term for a mental state often described as involving a loss of contact with reality. Stedmans Medical Dictionary defines psychosis as a severe mental disorder, with or without organic damage, characterized by derangement of personality and loss of contact with reality and causing deterioration...

Unlike methamphetamine, methcathinone is flat-out illegal, being Schedule I, whereas methamphetamine has certain medical uses such as treatment of life-threatening obesity, narcolepsy, and ADHD. Narcolepsy is a neurological condition most characterized by Excessive Daytime Sleepiness (EDS). ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ...

History

Methcathinone was first synthesized in Germany in 1928. It was used in the Soviet Union 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. Year 1928 (MCMXXVIII) was a leap year starting on Sunday (link will display full calendar). ... Face The 1930s (years from 1930–1939) were described as an abrupt shift to more radical and conservative lifestyles, as countries were struggling to find a solution to the Great Depression, also known in Europe as the World Depression. ... This article or section does not cite any references or sources. ... ... The 1960s decade refers to the years from January 1, 1960 to December 31, 1969, inclusive. ... Recreational drug use is the use of psychoactive drugs for recreational rather than medical or spiritual purposes, although the distinction is not always clear. ...

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.^[1] 1994 (MCMXCIV) was a common year starting on Saturday of the Gregorian calendar, and was designated as the International Year of the Family and the International Year of the Sport and the Olympic Ideal by United Nations. ... The United Nations Secretary-General is the head of the Secretariat, one of the principal divisions of the United Nations. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ...

Chemistry

Methcathinone is very similar in structure to cathinone, a stimulant alkaloid occurring in the shrub Catha edulis (Khat), the synthetic stimulant methamphetamine, and other phenethylamines. Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... Diagram of Ephedrine An alkaloid, strictly speaking, is a naturally-occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... A broom shrub in flower A shrub or bush is a horticultural rather than strictly botanical category of woody plant, distinguished from a tree by its multiple stems and lower height, usually less than 6 m tall. ... Binomial name Catha edulis Khat (Catha edulis Forsk, family Celastraceae), pronounced cot and also known as qat, gat, tschat, and miraa, is a shrubby plant used for centuries in parts of Africa and the Arabian Peninsula. ... Binomial name Catha edulis (Vahl) Forssk. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... This article is about the psychostimulant, d-methamphetamine. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ...

Methcathinone has a single chiral carbon atom, thus yielding enantiomeric + and - forms. A stereocenter, or stereogenic centre, is any atom in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer [1]. In organic chemistry this usually refers to a carbon, phosphorus or sulfur atom, though it is also possible for other atoms to be stereocenters... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

Methcathinone is most commonly made by the oxidation of ephedrine. Oxidation of ephedrine to methcathinone requires little chemistry experience, making it easy to synthesize. Potassium permanganate (KMnO₄) is most commonly used as the oxidant.^[2] The most fundamental reactions in chemistry are the redox processes. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Chemistry - the study of atoms, made of nuclei (conglomeration of center particles) and electrons (outer particles), and the structures they form. ... Potassium permanganate is the chemical compound KMnO4. ...

Synthesizing methcathinone using either potassium permanganate or various chromates is considered undesirable because of the low yields. A method that yields more methcathinone is oxidizing ephedrine with sodium hypochlorite.^[3] If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.^[4] A sample of ammonium dichromate Chromates and dichromates are salts of chromic acid and dichromic acid, respectively. ... Sodium hypochlorite is a chemical compound with the formula NaClO. A solution of sodium hypochlorite is frequently used as a disinfectant and as a bleaching agent; indeed, often it is simply called bleach, though other chemicals are sometimes given that name as well. ...

Methcathinone as free base is very unstable; it easily loses its ketone status and converts back into an alcohol. 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, from which it was synthesized. Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... Functional group of an alcohol molecule. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ...

Methcathinone acts on the body and brain much like methamphetamines and amphetamines do.

Effects

Methcathinone hydrochloride increases spontaneous rodent locomotor activity, potentiates the release of dopamine from dopaminergic nerve terminals in the brain, and causes appetite suppression.^{[citation needed]} Users can easily forget to consume fluids and a state of thirst and dehydration is apparent. In a general sense, locomotion simply means active movement or travel, applying not just to biological individuals. ... Dopamine is a phenethylamine naturally produced by the human body. ... Dopamine is a chemical naturally produced in the body. ... Nerves (yellow) Nerves redirects here. ... In animals the brain, or encephalon (Greek for in the head), is the control center of the central nervous system, responsible for thought. ... Anorectics, anorexigenics or appetite suppressants are drugs that reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). // Used on a short term basis clinically to treat obesity, some appetite suppressants are also available over the counter. ...

The effects of methcathinone are similar to those of methamphetamine, initially deemed to be less intense by the inexperienced user, and often more euphoric. The effects have been compared to those of cocaine, since it commonly causes hypertension (elevated blood pressure) and tachycardia (elevated heart rate). Reported effects include: This article is about the psychostimulant, d-methamphetamine. ... Cocaine (see also: crack) is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. ... This article or section does not cite any references or sources. ... This article or section does not cite any references or sources. ...

• Feelings of euphoria
• Increased alertness
• Dilated pupils
• Rapid breathing
• 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 in relation to importances of matters (might spend days thinking that is being productive achieving something but later might realize that the product was not even necessary at all.)

The effects of methcathinone usually last from four to six hours. Look up euphoria in Wiktionary, the free dictionary. ... The human eye The pupil is the central transparent area (showing as black). ...

Methcathinone's effects differ in various characteristic ways to that of methamphetamine. The effects seem to be of somewhat similar intensity to methamphetamine, differing in the nature of the shiny white effect which characterises the first few methamphetamine uses, and the dopamine and serotonin effects are quite apparent and also produce a shiny white effect which is quite different to that of methamphetamine and is more localized to the head.^{[citation needed]}

The first time user often makes the mistake of thinking that methcathinone is less powerful than cocaine or methamphetamine. The experience is governed by factors such as quantity of dosing (initial build up) and the dose and interval used between maintenance. The effect of methcathinone has been described as somewhere between coffee and cocaine.^{[citation needed]} This comparison is completely inaccurate and might be expressed by the first time user or one who is converting from cocaine. The sudden burst of euphoria and then sudden fall as experienced by cocaine users does not occur on methcathinone causing some users to prefer cocaine.^{[citation needed]} The effects of methcathinone are closest to that of methamphetamine.

Another difference between methamphetamine and methcathinone is that tolerance seems to build up faster for methamphetamine than for methcathinone and the recovery period from methcathinone is faster, both in terms of physically recovery, and also in terms of magnitude of highs.^{[citation needed]}

Methcathinone has a mild yet distinct hallucinogenic quality especially at higher doses and when aggravated by sleep deprivation.^{[citation needed]}

Use and pharmacology

Anecdotal reports have provided some information on patterns of methcathinone abuse. The most common route of administration is via nasal insufflation (snorting).^{[citation needed]} Other routes of administration include oral ingestion, intravenous injection and smoking. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... For the article about nose in humans, see human nose Human nose in profile Elephants have prehensile noses Dogs have very sensitive noses Anatomically, a nose is a protuberance in vertebrates that houses the nostrils, or nares, which admit and expel air for respiration in conjunction with the mouth. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... The cigarette is the most common method of smoking tobacco. ...

Methcathinone is abused in binges lasting days and sometimes weeks. During binges experienced users will administer methcathinone at doses ranging from one-sixteenth to one-fourth of a gram. The interval between dosing varies between approximately 20 minutes and two hours. With such a dosing regimen, during a binge methcathinone may be administered in daily amounts exceeding 1 or 2 grams. The principal determinant defining the length of the binge is the amount of drug available; that is, the binge ends only when the available supply of drug runs out.^{[citation needed]} A binge is any behavior indulged to excess. ...

The methcathinone binge resembles amphetamine binges in that the abuser does not sleep or eat, and takes in little in the way of liquids. The methcathinone binge is followed by a "crash" characterized by long periods of sleep, excess eating and, in some cases, depression.^{[citation needed]} Sleep is the state of natural rest observed in most mammals, birds, fish, as well as invertebrates such as the fruitfly Drosophila. ... A meal is an instance of eating, specifically one that takes place at a specific time and includes specific, prepared foodstuffs. ... A liquid will assume the shape of its container. ... Clinical depression (also called major depressive disorder, or unipolar depression when compared to bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ...

Street names

Cat, Jeff, Bathtub Speed, Wannabe-Speed, Kitty, Meth's Cat, Meth's Kitten

In Europe, methcathinone is primarily known as Ephedrone. World map showing the location of Europe. ...

In (Australia): Goey, Speed, Gas, Go, Tweak (primarily distributed in a gel-like form measured in points(1/10 of a gram); although it can be "cut" -(mixed with) epsom salts and other products) which then usually turn the substance into a powder based form and/or to a liquid)-

In South Africa it is primarily know as CAT or occasionally KAT. There it is also confused (via name alone, not presentation) with Khat (and sometimes (under the confusion) spelt Qat). Another confusing name is that given to Tik - the local name for methamphetamine. Binomial name Catha edulis (Vahl) Forssk. ... This article is about the psychostimulant, d-methamphetamine. ...

Addiction

In preclinical studies, methcathinone hydrochloride produces an abuse potential similar to that of the amphetamines. In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... Amphetamine is a synthetic drug originally developed (and still used) as an appetite suppressant. ...

Methcathinone can be highly psychologically addictive, and can produce methamphetamine-like withdrawals, which is somewhat less in intensity than methamphetamine. It is highly unlikely for a methcathinone user to experience addiction on their first or even several subsequent administrations of the drug. Addiction is an uncontrollable compulsion to repeat a behavior regardless of its negative consequences. ... This article is about the psychostimulant, d-methamphetamine. ... This article is about the psychostimulant, d-methamphetamine. ...

In drug discrimination studies, methcathinone hydrochloride evokes responses similar to those induced by both (+)-amphetamine sulphate and cocaine hydrochloride. When examined in particular pharmacological assays for psychomotor stimulant-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. Racemic methcathinone hydrochloride is intravenously self-administered by baboons, thus indicating that methcathinone produces reinforcing effects in this laboratory animal, and suggesting that the drug has a potential for abuse in the human population. A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood, consciousness and behavior. ... Manifestations Slavery · Racial profiling · Lynching Hate speech · Hate crime · Hate groups Genocide · The Holocaust · Armenian Genocide · Pogrom Ethnocide · Ethnic cleansing · Race war Religious persecution · Gay bashing Blood libel · Black Legend Pedophobia · Ephebiphobia Movements Discriminatory Aryanism · Neo-Nazism · Ku Klux Klan National Party (South Africa) American Nazi Party Kahanism · Supremacism Anti... Amphetamine or Amfetamine, also known as alpha-methyl-phenethylamine, phenyl-isopropylamine, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Cocaine (see also: crack) is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Type species Simia hamadryas Linnaeus, 1758 Species Papio hamadryas Papio papio Papio anubis Papio cynocephalus Papio ursinus The five baboon species are some of the largest non-hominid members of the primate order; only the Mandrill and the Drill are larger. ... For other uses of lab, see Lab. ... Animalia redirects here. ...

Clinical use

As a Schedule-1 drug, there is no legal clinical use. Research without a specific DEA permit is prohibited.

Furthermore, anecdotal reports from USENET posts in the 1990s indicate that unlike many stimulants, Methcathinone probably doesn't have the inhibitory effects (mediated by norepinephrine) seen in other stimulants that make them useful as medications to treat Attention Deficit Hyperactivity Disorder. Usenet (USEr NETwork) is a global, distributed Internet discussion system that evolved from a general purpose UUCP network of the same name. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ...

See also

Other related phenethylamine drugs and plants:

• Khat (contains cathinone and cathine)
• Methamphetamine
• Phenethylamine
• Ephedrine
• Pseudoephedrine
• Phenylpropanolamine

Other CNS-active phenyl-ethylamino ketones (Drugs that contain the cathinone core structure): Binomial name Catha edulis (Vahl) Forssk. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... Cathine (β-hydroxyamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat). ... This article is about the psychostimulant, d-methamphetamine. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... Phenylpropanolamine (PPA) is a drug of the phenethylamine family used as a decongestant and also as an appetite suppressant. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ...

• Diethylcathinone (Tenuate)
• Dimethylcathinone
• Bupropion (Wellbutrin, Zyban)
• MDMC

Diethylcathinone, more commonly called Diethylpropion in the medical field (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ... Diethylpropion (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ... Dimethylcathinone is a phenethylamine that is synthesized from dichloromethane, bromopropiophenone, and dimethylamine. ... Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin, Zyban, Budeprion and Buproban) is an atypical antidepressant, which acts as a norepinephrine reuptake inhibitor and dopamine reuptake inhibitor[2], and a nicotinic antagonist. ... Explosion Methylone is a designer drug that is a beta-ketone analogue of MDMA (Ecstasy). ...

External links

• Cathinone & Methcathinone from Erowid
• Methcathinone from lycaeum

• Links to external chemical sources

References

1. ^ Erowid
2. ^ http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcatfaq.22.html
3. ^ http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcathinone.txt
4. ^ http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcatfaq.22.html

• International Drug Scheduling; Convention on Psychotropic Substances; Certain Stimulant/Hallucinogenic Drugs and Certain Nonbarbiturate Sedative Drugs, Food and Drug Administration, June 20, 1994.