Ethcathinone, also known as ethylpropion or ETH-CAT, is a
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
drug
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
of the
phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amin ...
,
amphetamine
Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
, and
cathinone
Cathinone (also known as benzoylethanamine, or β-keto-amphetamine) is a monoamine alkaloid found in the shrub '' Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the m ...
chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificat ...
es. It is an active
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
of the
prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
diethylcathinone
Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant. It is used in the short-term management of obesity, along with dietary and lifestyl ...
and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "
party pills
Party pills, also known as "herbal highs", "pep pills" "dance pills" and "natural power", is a colloquialism for a type of recreational drug whose main ingredient was originally benzylpiperazine (BZP), but has expanded to a wide range of compound ...
", and, along with
mephedrone
Mephedrone, also known as , , and , is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, , White Magic, meow meow, bubble, ''txomin'' and yurrpt. It is chemically similar to the cathinone compounds ...
, has also been reported as having been sold as "ecstasy" in the Australian city of
Cairns
Cairns (, ) is a city in Queensland, Australia, on the tropical north east coast of Far North Queensland. The population in June 2019 was 153,952, having grown on average 1.02% annually over the preceding five years. The city is the 5th-most-p ...
.
Pharmacology
The pharmacology for ethcathinone appeared alongside other psychostimulants in a paper by Rothman and Baumann in 2006.
The predominant two modes of action for ethcathinone is as a moderately active
releaser of
noradrenaline
Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad'', ...
(EC
50 = 99.3nM);
[ however it is only a relatively weak inhibitor of dopamine reuptake (Ki = 1,014nM).][
Since diethylcathinone appears to be an inactive ]prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
and only becomes active after it has been further metabolized to ethcathinone,[ it thereby would appear rational to consider that ethcathinone would also be expected to be ''N''-]dealkylated
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...
upon its consumption to the more active drug cathinone
Cathinone (also known as benzoylethanamine, or β-keto-amphetamine) is a monoamine alkaloid found in the shrub '' Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the m ...
that is more able to reliably stimulate the release of dopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...
. However, in contrast to diethylcathinone, ethcathinone is not universally considered to be a prodrug since (as is the case with tramadol, codeine, and MDMA) it is already active in its own right, therefore being excluded from the category by some of the more strict definitions.
Legal status
Ethcathinone, along with mephedrone
Mephedrone, also known as , , and , is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, , White Magic, meow meow, bubble, ''txomin'' and yurrpt. It is chemically similar to the cathinone compounds ...
and flephedrone
Flephedrone, also known as 4-fluoromethcathinone (4-FMC), is a stimulant drug of the cathinone chemical class that has been sold online as a designer drug starting in 2008.
Toxicity
Flephedrone has only a short history of human use and its tox ...
, was banned in Denmark
)
, song = ( en, "King Christian stood by the lofty mast")
, song_type = National and royal anthem
, image_map = EU-Denmark.svg
, map_caption =
, subdivision_type = Sovereign state
, subdivision_name = Danish Realm, Kingdom of Denmark
...
on December 18, 2008.
As of October 2015 Ethcathinone is a controlled substance in China.
This compound is banned in the United States, being a positional isomer of mephedrone
Mephedrone, also known as , , and , is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, , White Magic, meow meow, bubble, ''txomin'' and yurrpt. It is chemically similar to the cathinone compounds ...
.[DEA Controlled Substances Act listing dated 21-Jul-15]
See also
* 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 ...
* Etilamfetamine
Etilamfetamine (trade names Apetinil and Adiparthrol; also known as ''N''-ethylamphetamine) is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an ...
References
{{Phenethylamines
Cathinones
Designer drugs
Norepinephrine-dopamine releasing agents
Stimulants