Cathinone
Encyclopedia
Cathinone, or Benzoylethanamine, is a monoamine alkaloid
found in the shrub
Catha edulis (khat
) 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 probably the main contributor to the stimulant
effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a ketone
functional group
. Other amphetamines that share this structure include the antidepressant
bupropion
and the stimulant methcathinone
, among others.
Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances
. Circa 1993, the DEA
added cathinone to the Controlled Substances Act
's Schedule I.
The sale of khat
is legal in Israel
(although synthetic cathinone is not), and also in Oman
, in Yemen
, in the United Kingdom
and in the Horn of Africa
.
Cathinone is structurally related to methcathinone
, in much the same way as amphetamine
is related to methamphetamine
. Cathinone differs from amphetamine by possessing a ketone
oxygen
atom (C=O) on the β (beta) position of the side chain. The corresponding alcohol compound cathine
is a less powerful stimulant. The biophysiological conversion from cathinone to cathine
is to blame for the depotentiation of khat
leaves over time. Fresh leaves have a greater ratio of cathinone to cathine than dried ones, therefore having more psychoactive effects.
Cathinone can be extracted from Catha edulis, or synthesized from α-bromo
propiophenone
(which is easily made from propiophenone
).
, hence its use in party pills
as a "legal" replacement for MDMA
Persons driving under the influence of the drug have had their serum or urine tested for the presence of cathinone and norephedrine, a major metabolite.
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...
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....
) and is chemically similar to ephedrine
Ephedrine
Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....
, cathine
Cathine
Cathine, also known as d-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant...
and other amphetamines. Cathinone induces 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 striatal preparations that are prelabelled either with dopamine or its precursors. It is probably the main contributor to the 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...
effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a 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...
functional 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...
. Other amphetamines that share this structure include the antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...
bupropion
Bupropion
Bupropion is an atypical antidepressant and smoking cessation aid. The drug is a non-tricyclic antidepressant and differs from most commonly prescribed antidepressants such as SSRIs, as its primary pharmacological action is thought to be norepinephrine-dopamine reuptake inhibition...
and the stimulant methcathinone
Methcathinone
Methcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally...
, among others.
Internationally, cathinone is a Schedule I drug under 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...
. Circa 1993, the 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...
added cathinone to the Controlled Substances Act
Controlled Substances Act
The Controlled Substances Act 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 CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...
's Schedule I.
The sale of khat
Khat
Khat, qat, gat or Waquish Spoken from true Yemeni, is a flowering plant native to tropical East Africa and the Arabian Peninsula....
is legal in Israel
Israel
The State of Israel is a parliamentary republic located in the Middle East, along the eastern shore of the Mediterranean Sea...
(although synthetic cathinone is not), and also in Oman
Oman
Oman , officially called the Sultanate of Oman , is an Arab state in southwest Asia on the southeast coast of the Arabian Peninsula. It is bordered by the United Arab Emirates to the northwest, Saudi Arabia to the west, and Yemen to the southwest. The coast is formed by the Arabian Sea on the...
, in Yemen
Yemen
The Republic of Yemen , commonly known as Yemen , is a country located in the Middle East, occupying the southwestern to southern end of the Arabian Peninsula. It is bordered by Saudi Arabia to the north, the Red Sea to the west, and Oman to the east....
, 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...
and in the Horn of Africa
Horn of Africa
The Horn of Africa is a peninsula in East Africa that juts hundreds of kilometers into the Arabian Sea and lies along the southern side of the Gulf of Aden. It is the easternmost projection of the African continent...
.
Chemistry
Methcathinone
Methcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally...
, in much the same way 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,...
is related to methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
. Cathinone differs from amphetamine by possessing a 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...
oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
atom (C=O) on the β (beta) position of the side chain. The corresponding alcohol compound 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 a less powerful stimulant. The biophysiological conversion from cathinone to 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 to blame for the depotentiation of khat
Khat
Khat, qat, gat or Waquish Spoken from true Yemeni, is a flowering plant native to tropical East Africa and the Arabian Peninsula....
leaves over time. Fresh leaves have a greater ratio of cathinone to cathine than dried ones, therefore having more psychoactive effects.
Cathinone can be extracted from Catha edulis, or synthesized from α-bromo
Bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...
propiophenone
Propiophenone
Propiophenone is an aryl ketone. It is a clear liquid that is insoluble in water, but miscible with methanol, ethanol, diethyl ether, benzene and toluene....
(which is easily made from propiophenone
Propiophenone
Propiophenone is an aryl ketone. It is a clear liquid that is insoluble in water, but miscible with methanol, ethanol, diethyl ether, benzene and toluene....
).
Toxic effects
Excessive cathinone usage can cause loss of appetite, anxiety, irritability, insomnia, hallucinations and panic attacks. Chronic abusers are at risk of developing personality disorders and of sustaining myocardial infarction. Please note that the drug referred to in this article was actually the closely related mephedrone, a cathinone derivative which does not occur in nature. Mephedrone has more power as a releasing agent of serotonin than of cathinone or methcathinoneMethcathinone
Methcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally...
, hence its use in 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...
as a "legal" replacement for MDMA
Ecstasy
Ecstasy may refer to:* Ecstasy , a trance or trance-like state in which an individual transcends normal consciousness* Religious ecstasy, a state of consciousness characterized by expanded spiritual awareness, visions or absolute euphoria...
Persons driving under the influence of the drug have had their serum or urine tested for the presence of cathinone and norephedrine, a major metabolite.