Cathinone (
β-
ketoIn organic chemistry, a ketone is a type of compound that features a carbonyl group bonded to two other carbon atoms, i.e., R3CCO-CR3 where R can be a variety of atoms and groups of atoms...
amphetamineAmphetamine is a psychostimulant drug that is known to produce increased wakefulness and focus in association with decreased fatigue and appetite. Amphetamine is related to drugs such as methamphetamine and dextroamphetamine, which are a group of potent drugs that act by increasing levels of...
) is a monoamine
alkaloidAlkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of...
found in the
shrubA 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 5-6 m tall. A large number of plants can be either shrubs or trees, depending on the growing conditions they experience...
Catha edulis (
KhatKhat , also known as qat, qaat, quat, gat, jaad, chat, chad, chaad and miraa, is a flowering plant native to tropical East Africa and the Arabian Peninsula.Khat contains the alkaloid called cathinone, an amphetamine-like stimulant which is said to cause...
) and is chemically similar to
ephedrineEphedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia. Ephedrine is similar in structure to the synthetic derivatives amphetamine and methamphetamine...
,
cathineCathine, also known as d-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant...
and other amphetamines. Amphetamine induces the release of
dopamineDopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors — D
1, D
2, D
3, D
4, and...
from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this. It is probably the main contributor to the
stimulantStimulants, also sometimes called psychostimulants, 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 (
β-
ketoIn organic chemistry, a ketone is a type of compound that features a carbonyl group bonded to two other carbon atoms, i.e., R3CCO-CR3 where R can be a variety of atoms and groups of atoms...
amphetamineAmphetamine is a psychostimulant drug that is known to produce increased wakefulness and focus in association with decreased fatigue and appetite. Amphetamine is related to drugs such as methamphetamine and dextroamphetamine, which are a group of potent drugs that act by increasing levels of...
) is a monoamine
alkaloidAlkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of...
found in the
shrubA 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 5-6 m tall. A large number of plants can be either shrubs or trees, depending on the growing conditions they experience...
Catha edulis (
KhatKhat , also known as qat, qaat, quat, gat, jaad, chat, chad, chaad and miraa, is a flowering plant native to tropical East Africa and the Arabian Peninsula.Khat contains the alkaloid called cathinone, an amphetamine-like stimulant which is said to cause...
) and is chemically similar to
ephedrineEphedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia. Ephedrine is similar in structure to the synthetic derivatives amphetamine and methamphetamine...
,
cathineCathine, also known as d-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant...
and other amphetamines. Amphetamine induces the release of
dopamineDopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors — D
1, D
2, D
3, D
4, and...
from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this. It is probably the main contributor to the
stimulantStimulants, also sometimes called psychostimulants, 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
ketoneIn organic chemistry, a ketone is a type of compound that features a carbonyl group bonded to two other carbon atoms, i.e., R3CCO-CR3 where R can be a variety of atoms and groups of atoms...
functional groupIn 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...
. Other amphetamines that share this structure include the
antidepressantAn antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia. Drugs including the monoamine oxidase inhibitors , tricyclic antidepressants , tetracyclic antidepressants , selective serotonin reuptake inhibitors , and serotonin-norepinephrine...
bupropionBupropion is an atypical antidepressant that acts as a norepinephrine and dopamine reuptake inhibitor, and nicotinic antagonist...
and the stimulant
methcathinoneMethcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and is 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 SubstancesThe Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. During the 1960 such drugs became widely available. Government authorities opposed this for numerous reasons, arguing that along with...
. Circa 1993, the
DEAThe 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 U.S...
added cathinone to the
Controlled Substances ActThe 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 in order to fulfill the requirements of international law.
The sale of
khatKhat , also known as qat, qaat, quat, gat, jaad, chat, chad, chaad and miraa, is a flowering plant native to tropical East Africa and the Arabian Peninsula.Khat contains the alkaloid called cathinone, an amphetamine-like stimulant which is said to cause...
is legal in
IsraelIsrael officially the State of Israel , is a developed state in Western Asia located on the eastern shore of the Mediterranean Sea. It borders Lebanon in the north, Syria in the northeast, Jordan in the east, and Egypt on the southwest, and contains geographically diverse features within its...
(although synthetic cathinone is not), and also in
OmanOman , officially the Sultanate of Oman , is an Arab country in southwest Asia on the southeast coast of the Arabian Peninsula. It borders the United Arab Emirates on the northwest, Saudi Arabia on the west and Yemen on the southwest....
, in
YemenYemen , officially the Republic of Yemen is a country located on the Arabian Peninsula in Southwest Asia...
, in
United KingdomThe United Kingdom of Great Britain and Northern Ireland is a sovereign state located off the northwestern coast of continental Europe. It is an island country, spanning an archipelago including Great Britain, the northeastern part of Ireland, and many small islands...
and in the
Horn of AfricaThe Horn of Africa is a peninsula in East Africa that juts for 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
Cathinone is structurally related to
methcathinoneMethcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and is considered addictive. It is usually snorted, but can be smoked, injected, or taken orally...
, much like how
amphetamineAmphetamine is a psychostimulant drug that is known to produce increased wakefulness and focus in association with decreased fatigue and appetite. Amphetamine is related to drugs such as methamphetamine and dextroamphetamine, which are a group of potent drugs that act by increasing levels of...
is related to
methamphetamineMethamphetamine also known as metamfetamine , dextromethamphetamine, methylamphetamine, N-methylamphetamine, and desoxyephedrine) is a psychostimulant and sympathomimetic drug. Methamphetamine enters the brain and triggers a cascading release of dopamine, serotonin and norepinephrine...
. Cathinone differs from amphetamine by possessing a
ketoneIn organic chemistry, a ketone is a type of compound that features a carbonyl group bonded to two other carbon atoms, i.e., R3CCO-CR3 where R can be a variety of atoms and groups of atoms...
oxygenOxygen Oxygen Oxygen (acid, literally "sharp", from the taste of acids) and -γενής (-genēs) (producer, literally begetter) is the element with atomic number 8 and represented by the symbol O...
atom (C=O) on the
β (beta) position of the side chain. The corresponding alcohol compound
cathineCathine, 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
cathineCathine, 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
khatKhat , also known as qat, qaat, quat, gat, jaad, chat, chad, chaad and miraa, is a flowering plant native to tropical East Africa and the Arabian Peninsula.Khat contains the alkaloid called cathinone, an amphetamine-like stimulant which is said to cause...
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-
bromoBromine , is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown volatile liquid at standard room temperature that is intermediate in reactivity between chlorine and iodine. Bromine vapors are corrosive and toxic. Approximately 556,000 metric...
propiophenonePropiophenone 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
propiophenonePropiophenone is an aryl ketone. It is a clear liquid that is insoluble in water, but miscible with methanol, ethanol, diethyl ether, benzene and toluene....
).
External links