Inhibiting the Decomposition of Cathinone in Catha edulis

[bigman23]

SWIM has a few Catha edulis seeds, and following countless hours of research, he is ready to plant them and let them thrive. However, he understands that Cathinone, the primary alkaloid in Catha edulis that SWIM is after, begins to break down only 48 hours after the cutting is removed from the plant. Given his prior research, SWIM does not expect this to be a simple problem to solve. Nonetheless, he would like to theorize and hypothesize with other like-minded thinks over the subject, in hopes of finding a way or procuring a method to retard or circumvent this seemingly inevitable decomposition of the plants most valuable alkaloid.

That said, SWIM's first theory is to Freeze-dry the leaves immediately after cutting them. The second, which is actually an option rather than a theory because it has been confirmed by many sources, is to put it in alcohol of some sort and allow for it to ferment for two weeks. However, SWIM knows none of the specifics involved with that. SWIM's other theory is to keep the leaves in the freezer. All of these would require testing, yet countless variables exist. Therefore, SWIM concludes that it may be best to find what actually causes the Cathinone to break down into Cathine.

Does anyone have any suggestions on how SWIM could go about retarding or inhibiting this process, or provide reasons as to what exactly leads to the biophysiological conversion from Cathinone to Cathine?

Thank you much!

 

[Alcyone]

SWIM has a few Catha edulis seeds...

As it happens, I did some research on this subject years ago. I suppose we can discuss it without violating the strict no-synthesis-discussion policy. This bloke who isn't you seems to have a fair grip on the science involved, but for all I know, you don't have a clue yourself. That's why I'm worried that if I post something here, vital information might get lost in the process where you try to understand and explain it to this other bloke who isn't you. I suggest that he posts his questions himself, and I'll try to answer him directly.

 

[nuke]

If he doesn't get it, someone else would.

It wouldn't be too hard, the problem is an enzyme in the plant that converts the benzyl ketone to the benzyl alcohol. Only the young plant seems to have high amounts of the cathinone. The big issue is that the sequence for the gene that codes for the enzyme is not known and would have to be search for using broad specificity methods. It probably wouldn't be that hard, maybe 3-9 months work if you're lucky and experienced.

Unfortunately, the plant (catha edulis) is already illegal most places. The major benefit to finding the gene/creating the knockout is that ephedra sinensis isn't and reduces the benzylic ketone is a homologous manner.

Not sure whether or not biosynthesis constitutes synthesis.

 

[bigman23]

Thank you for your responses; they are very much appreciated. As for my handle on the science, I've done lots of personal research and taken a few undergraduate level classes, but that is all. The more research I do, I find myself getting into more and more complex aspects of science that ultimately lead me to the chemical extraction of cathinone, which is NOT what I am attempting to do. I simply wish to inhibit the biophysiological breakdown of cathinone to cathine. For all intents and purposes, I will specify my questions since my initial requests were fairly ambiguous.

1. Will freezing the leaves retard or stop this process?
2. Will freeze-drying (lyophilization) retard or stop this process?

 

[kayenta]

When I was in a part of Africa where khat is very popular I was told many times that storing it in the fridge/freezer would keep it potent for a good while. I can't actually comment though as I just bought it on a need-to-use basis.

It's good stuff, I just hate the damn stomach aches when it wears off.

Only the young plant seems to have high amounts of the cathinone.

Yep, the young red-tinted leaves are the good stuff

 

[bigman23]

...the problem is an enzyme in the plant that converts the benzyl ketone to the benzyl alcohol...

In regards to what Nuke said, I suspect there must be a way to denature the enzyme. I researched and discovered several ways to control the enzymes. The methods I focused on in the article were those involving dry and moist heat. Do you think these methods may yield some success? In theory, the denaturation of the enzymes would prevent the oxidation and keep the Cathinone from breaking down. However, I fear the process would continue as soon as the temperature falls below the required level. Would freezing or sealing the khat in airtight containers immediately after work?

Source

 

[nuke]

Heat also expedites the dimerization of the compound, which also renders it inactive. You may be able to keep the product potent if you can figure out how to dessicate it extremely quickly and keep it completely dry. Simply freezing it should work, too.

As the amine is methylated in its product (methcathinone), ephedra sinensis doesn't have this problem.

 

[Alcyone]

I apologise for coming across as a cocky bitch in my above post. I can be one at times, believe me, but in this case my intention was to point out in a subtle way that SWIMming is discouraged on Bluelight, while at the same time calling upon the mods to decide whether or not the topic was in violation of the rules.

As pointed out by nuke, the conversion of cathinone to cathine is enzymatic, and the rate of conversion increases with time after the leaves are cut. The enzyme involved appears to be fairly robust and it exerts its activity across a wide temperature range. Hence, attemps at rendering it inactive by boiling or steaming the leaves or by drying them at high temperature have generally been unsuccessful. Freezing the leaves is a possibility, but there is definitely some loss of cathinone in the process. I'm not sure whether this happens in the actual freezing (and thawing) process, or if the enzyme exerts some activty even in the frozen material. Flash freezing in liquid nitrogen and storage at -70 °C might give better results, but I haven't looked into it.

Lyophilisation might actually work if you have access to equipment with sufficient capacity to process your amount of material quickly. For reasons stated above, time is of the essence and the material will need to be completely dry.

Conversion of cathinone to cathine is a reductive process, not an oxidative one, and the presence of oxygen is not critical in my opinion. The additional problem of dimerization becomes an issue only at higher cathinone concentrations, i.e. in extracts. It's also my impression that the dimerization is catalysed by UV(?) light.

My primary interest when I looked into Catha edulis some time ago was cathinone, and not the plant itself - which I personally find rather useless as a recreational drug. Cathinone can be extracted by steeping the plant material in ethanol, again with some loss to cathine. The yield can be improved if the fresh plant material is quickly and thoroughly homogenised immediately prior to the extraction. Without going into detail, addition of a protease, e.g. Subtilisin A, appears to increase the cathinone yield, probably by deactivating the enzyme. As usual with extracts of fresh plant material, getting rid of the chlorophyll is a bitch.

If cathinone is the substance of interest, an alternative approach - and perhaps the most practical one - is to accept that most of the cathinone is enzymatically reduced to cathine, and just isolate the alkaloid mixture. The subsequent chemical oxidation of cathine to cathinone is not as straightforward as the oxidation of ephedrine, in part due to the dimerization issue. It's still possible, and it has been described elsewhere.

 

[xxl]

It's also my impression that the dimerization is catalysed by UV(?) light.

This makes sense. In Addis Abebba they stock Cath freshly brought in from the mountains in cellars, possibly to keep them away from the light.