Ethcathinone
Encyclopedia
Ethcathinone, also known as ethylpropion, is a stimulant
drug
of the phenethylamine
, amphetamine
, and cathinone
chemical classes. It is an active metabolite
of the prodrug
diethylcathinone
and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills
", and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns.
(Ki = 1,014nM).
Since diethylcathinone appears to be an inactive prodrug
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 upon its consumption to the more active drug cathinone
that is more able to reliably stimulate the release of dopamine
. However, in contrast to diethylcathinone, ethcathinone is not technically a prodrug since it is already active in its own right.
, was banned in Denmark
on December 18, 2008.
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...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
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...
chemical classes. It is an active metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of the prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
diethylcathinone
Diethylcathinone
Amfepramone , is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes that is used as an appetite suppressant.- Pharmacology :Amfepramone itself lacks any affinity for the...
and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills
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 , but has now expanded to a wide range of compounds with a variety of effects...
", and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns.
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 (EC50 = 99.3nM); however it is only a relatively weak inhibitor of dopamine reuptakeDopamine 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...
(Ki = 1,014nM).
Since diethylcathinone appears to be an inactive prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
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 upon its consumption to the more active drug cathinone
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...
that is more able to reliably stimulate 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...
. However, in contrast to diethylcathinone, ethcathinone is not technically a prodrug since it is already active in its own right.
Legal status
Ethcathinone, along with mephedrone and flephedroneFlephedrone
Flephedrone, 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...
, was banned in Denmark
Denmark
Denmark is a Scandinavian country in Northern Europe. The countries of Denmark and Greenland, as well as the Faroe Islands, constitute the Kingdom of Denmark . It is the southernmost of the Nordic countries, southwest of Sweden and south of Norway, and bordered to the south by Germany. Denmark...
on December 18, 2008.