About Khat and Its Cathinone Nature

G.Patton

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What is Khat?

Khat, also known as qat (Amharic: ጫት ch’at; Oromo: Jimaa, Somali: qaad, khaad, khat or chat, Arabic: القات al-qāt), is an indigenous flowering plant found in eastern and southern Africa. Khat reaches heights from 10 feet to 20 feet and its scrawny leaves resemble withered basil. Khat leaves contain psychoactive ingredients known as cathinone, which is structurally and chemically similar to d-amphetamine, and cathine, a milder form of cathinone. Fresh leaves contain both ingredients; those left unrefrigerated beyond 48 hours would contain only cathine, which explains users' preference for fresh leaves.
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The cathinone alkaloid, a stimulant that induces increased sociability, excitement, reduced appetite, and mild euphoria. Khat-chewing has a long historical tradition in the regions where it naturally grows, particularly among men, and is comparable (though slightly different) to the use of coca leaves in South America's Andes Mountains or betel nut preparations in South Asia. It is often chewed socially in lounges, where it fosters conversations among groups of men, often while smoking hookah.

Fresh Khat leaves are crimson-brown and glossy but become yellow-green and leathery as they age. They also emit a strong smell. The most favored part of the leaves are the young shoots near the top of the plant. However, leaves and stems at the middle and lower sections are also used.
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The legal status of khat varies from place to place. In some regions, it may go relatively unnoticed as a botanical species and thus not be specifically regulated, but its recreational use could still be deemed illegal under more general laws. However, in many areas, khat is strictly controlled, and its possession, distribution, or use may be illegal. For example, it is classified as a controlled substance in countries such as Australia, Canada, the European Union, India, Jordan, New Zealand, Saudi Arabia, the United Arab Emirates (UAE), and the United Kingdom (UK). In the United States (US) and Turkey, the plant Catha edulis is not explicitly banned, but the consumption and distribution of harvested leaves for recreational purposes are illegal. On the other hand, in regions where khat holds cultural significance, such as Djibouti, Ethiopia, Kenya, Somalia, Sudan, Uganda, and Yemen, its production, sale, and consumption are entirely legal or not addressed in a legal context. In Israel, where there is a population of Yemenite Jews, only the consumption of the plant's leaves in its natural state is permitted.

Other names by which Khat is known include: Qat, Kat, Chat, Kus-es-Salahin, Mirra, Tohai, Tschat, Catha, Quat, Abyssinian Tea, African Tea, and African Salad.

Cathinone: What You Need To Know

Khat Chemistry

The stimulating properties of the plant were initially credited to "katin," or cathine, a substance of the phenethylamine type that was isolated from the plant. However, this attribution was challenged when reports indicated that fresh leaf extracts contained another compound with more noticeable behavioral effects than cathine. In 1975, researchers isolated the related alkaloid called cathinone, and its absolute configuration, (S)-2-Amino-1-phenylpropan-1-one, was established in 1978. Cathinone is not very stable and breaks down over time, transforming into cathine and norephedrine. These chemicals are part of the PPA (phenylpropanolamine) family, which is a subset of phenethylamines related to amphetamines and the catecholamines epinephrine and norepinephrine. In fact, cathinone and cathine share a very similar molecular structure with amphetamine. It is important to note that khat should not be confused with methcathinone (also known as cat), a Schedule I substance that possesses a similar chemical structure to the cathinone active component in the khat plant.
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When khat leaves dry out, the more potent cathinone decomposes within 48 hours, leaving behind the milder cathine. To preserve the potency of cathinone, harvesters package the fresh leaves and stems in plastic bags or wrap them in banana leaves to retain their moisture. It is also common for them to sprinkle the plant with water regularly or use refrigeration during transportation.

Upon chewing khat leaves, both cathine and cathinone are released and absorbed through the mouth's mucous membranes and the stomach lining. Studies on laboratory animals have shown that cathine and cathinone affect the reuptake of epinephrine and norepinephrine, causing the body to recycle these neurotransmitters more slowly, leading to wakefulness and insomnia associated with khat use.

Cathinone exhibits a high affinity for serotonin receptors, suggesting it is responsible for the euphoric feelings linked to chewing khat. In mice, cathinone induces nervous pacing and repetitive scratching behaviors akin to those associated with amphetamines. The effects of cathinone reach their peak within 15 to 30 minutes, with nearly 98% of the substance being metabolized into norephedrine by the liver.

On the other hand, cathine's mechanisms are not as well understood, but it is believed to act on adrenergic receptors, triggering the release of epinephrine and norepinephrine. In humans, cathine has a half-life of approximately three hours. The medication bromocriptine can be used to reduce cravings and withdrawal symptoms within 24 hours.

Khat Leaves Chewing After Effects

The impact experienced by a person who chews khat can be categorized as desirable effects (occurring within the first hour) and undesirable effects (manifesting towards the end of the desirable phase and lasting for several hours).

Khat chewers often report feelings of joy, increased energy, excitement, euphoria, heightened alertness, improved self-esteem, enhanced concentration, boosted libido, increased creativity, better communication skills, improved ability to associate ideas, and a subjective enhancement in work performance. However, there are also negative experiences associated with khat chewing, such as excessive talkativeness, hyperactivity, difficulty sleeping, irritability, anxiety, hostility, psychotic episodes, hysteria, and depression. Prolonged use of khat can lead to cardiac, neurological, psychological, and gastrointestinal issues. The consumption of khat leads to an increase in heart rate and blood pressure in humans due to the indirect sympathomimetic activity of cathinone, which persists for approximately 3-4 hours after use.

The presence of tannins in khat leaves causes astringency and may result in oesophagitis, gastritis, and oral mucosal keratosis. Studies have shown that around 50% of khat chewers develop oral mucosal keratosis, which can progress to oral cancer. Additionally, after consuming khat, cathinone acts as an appetite suppressant by affecting the hypothalamus, leading to delays in gastric emptying.
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Long-term khat users are prone to developing complications, including acute and chronic liver disease. Chronic use of khat can result in hepatitis, fibrosis, and cirrhosis. Khat use also affects human reproductive health, leading to lower sperm count and motility among addicts. Moreover, khat has teratogenic effects on pregnant women. In high doses, khat can induce manic illness characterized by grandiose delusions or schizophreniform psychosis with persecutory delusions. Fortunately, in most cases, these symptoms subside when khat is discontinued, and antipsychotic medications are administered. However, there is a likelihood of psychotic episodes reappearing upon resuming khat use. The short- and long-term physical effects of khat consumption have been thoroughly documented based on the physiological systems involved and are summarized in the accompanying image.

Conclusion

In conclusion, khat, an indigenous flowering plant found in eastern and southern Africa, contains psychoactive substances cathinone and cathine, leading to various desirable and undesirable effects upon chewing. While users may experience feelings of happiness, energy, and enhanced communication, there are potential negative consequences, including insomnia, anxiety, and health complications. As its legal status varies worldwide, awareness of khat's risks and effects is essential for responsible use.
 

Carlz

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It contains amphetamine. But how can it be extracted from it?
 

humax

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I read some years ago that people have tried but it was to unstable to get anything useful. I think there are write ups somewhere on the internet I can't remember where as it was a long time ago.
 
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Carlz

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Hi man if you remember tell me.
 

humax

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Not the one I read but done but found this with a quick search. There are also other articles when I searched the clear net
 

Carlz

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It was helpful good job
 

humax

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I read about the khat years ago. Ever since I have been keeping my eyes open for a khat tree which I read there are one or 2 that were grown years ago in old parts of my home city. Seems there are a few different varieties and if I ever suspect I found a khat tree I'd make sure to get it properly identified as many trees and plants are poisonous when ingested even in small quantities.

This is the most detailed write up of khat that I've ever seen.

I tried to grow some Betel Nut seeds I bought off ebay once. They spouted but ended up dying. They were the smaller of the betel nuts which were the closet variety that suited my climate. Maybe I'll try again and plant them at a different time of year one day.
 
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Batwing

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I have a plant, had it for years in a pot and chewing ok but is there any way to do a quick extraction to make a tea or something to drink the day of harvest? Ive blended some in the blender with lemon juice, then added some warm water then filtered, just did it as a test and didnt drink it because i was quiet sick with a cold at the time. Im going to try again this weekend to see if its better than chewing. But if anyone has a quick extraction or the best solvents to extract with then let me know. Thanks

heres a photo of the result, left is after running through a coffee filter, i put some bicarb solution in and it turned back to a green/brown mix from the red.
 
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G.Patton

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Hello. #Khat_Extraction
The bulk of the sample was left to dry in a brown paper bag that was kept at ambient temperature and protected from light.

Extraction
Approximately 5 to 6 g of plant material was cut into small pieces, dimensions of approximately 0.5 cm squares. The prepared sample was mixed with 15-20 mL of methanol, then sonicated for 15 min with intermittent shaking and stirring.


Concentration

The green methanolic extract was decanted into a breaker which was then condensed to near dryness (<1 mL) using a stream of air.

Cleanup
A very dilute solution of H2SO4 (approx. 0.02 N) was used to resuspend and acidify the plant residue. The acidified solution acquired a reddish hue. A chloroform extraction was performed to remove the neutral organic compounds as well as the remaining plant solids.


Base Extraction

A small amount of a saturated sodium bicarbonate (NaHCO3) solution was added to the aqueous solution to basify the extract. The pH change resulted in a light green solution. Methylene chloride was used to extract cathinone and cathine. A stream of air was used to reduce the extract to a minimal volume amount. (As a preventive measure, a solvent exchange to hexane is done to avoid degradation of the IRD light pipe.)
 
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Batwing

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So i extracted it to the redish solution again, so i can basify it again with NaHCO3 then just mix the solution in a mason jar with DCM, mix then seperate the layers and dry the dcm?
thanks for the help.
 

G.Patton

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Why do you ask this again? Do you need to repeat?
It looks very clear and understandable.

You're welcome.
 

Batwing

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Yeah sorry this is my first time extracting anything like this, wont rebasing it then washing in DCM leave me with the base of cathinone/cathine?
Ive heard its pretty unstable as a base from the plant?
Would i be better of washing the acidic solution to try keep the alkaloids as a hcl?
Please forgive my ignorance im just trying to learn. If this isnt the right site to learn let me know and ill move on. Thanks for helping so far.
 

G.Patton

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I can't answer you about this for sure.
You can try your way and compare. Then, share us your result.
 
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