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chemical extraction of plants

anonymous Subject: Alkaliod extraction EXTRACTION: The method I use is a general one - I copied it from one used by some scientists to extract mescaline from peyote, but I have since seen close variations used on many plants.

. This procedure is followed, whenever a plant is studied for its alkaloids. A few ingredients and bits of equipment are necessary. I am a chemist, and have my own chemistry set.

. I have considered manufacture, but I find that there are enough interesting things to do just extracting natural compounds, which is much easier, indeed, possible in the home. You will need: A few flasks, glass containers, etc. of suitable sizes, depending on how large a volume you are playing with. A separating funnel is almost essential - this could be tricky to get without a little effort.

. If you don't know, it is an inverted conical flask with a hole at the top to pour stuff in , and a tap at the bottom to let the stuff out accurately . It is used for separating immiscible layers. A vacuum filtration apparatus would be very useful; I did have a bodgy one rigged up myself, but it was always difficult to use.

. Some kind of still, though, is pretty important to have, although conceivably for a once off you could get by without it, if you don't mind breathing in a lot of solvent. As far as still goes it is to recover solvent, and leave goodness as a residue at the bottom.

. I use a bit of quickfit I nicked: a round bottom flask, short column, thermometer on top, and a small condenser... takes for ever, but don't expect to follow this procedure in anything under a day.

. Other bits and pieces: A filtre of some sort is a necessity; preferably a good one, with a vacuum pump if you are filtring gluggy stuff (cactus is the worst, sticky goo, e.g., other things like seeds and bark are better).

. People have been known to use such devices as coffee filtres, t-shirts, tins with holes in the bottom (as a filtre press) and so on. Whatever you can scrounge. A lab buchner funnel, sidearm flask, and venturi pump are ideal.

. All this stuff is standard in any chemical lab, regardless of discipline. (cont'd in part ii) CTION part ii: Chemicals necessary: The paydirt (obviously) Some solvents: methanol (lots), and a non polar solvent.

. Some people use ether - this is dangerous and doesn't dissolve everything. Your best bet is probably something chlorinated - I use dichloromethane, although chloroform will do (don't breath too much - it is fun at first, but ends up making you feel ill). Drycleaning fluid... petrol.... I don't know what you have access to.

. Dichloromethane is good because it is non-toxic, volatile, and a good solvent. It has a major drawback: separation is often very difficult once you have placed your gluggy plant muck in there. The shot is to use large quantities of everything, and be patient.

. You will also need an acid (Hydrogen chloride is good) and a base/alkali (Sodium hydroxide is good - that way, if you stuff up, you end up synthesizing salt instead of something nasty.) Also useful: acid/base indicator paper, boiling chips (porcelain grains) and activated charcoal - see local chemist.

. The idea is this: Most fun compounds (the only exception is maybe THC, and alcohol if you count that) are basic - they contain nitrogen. So: in general, if you react them with hydrochloric acid, the form a water soluble chloride.

. If you react them with dilute base in the aqueous phase, they go back to being a base, which is insoluble in water, but soluble in organic non-polar solvents (like CH2Cl2). So, the theory is, that only a base will go from water to solvent and back to water etc. when changed from acidic to basic and back to acidic.

. This gives you a way of removing all the other crap which is not alkaloid from a sample. That is the theory. When I do this, if I can get down to some brown or green sludge that I can throw down or smoke, I am happy with a good days work.

. Ideally, you should end up with lovely white crystals, but I think that would require a lot of time and effort, and indeed a considerable loss of product in the process.

. Procedure: Get your stuff. Dry it as much as possible - this makes life easier later on. You will never get all the water out, but too bad. Chop it up as fine as possible: a blender comes in handy. You may wish to chop then dry.

. A word of caution : try to avoid exposing your stuff to excessive heat. I dry in low heat oven. Heat and air destroy good compounds from upwards of 100 degs C. All this bit will depend on exactly what you are extracting.

. Once it is finely divided - powdered if possible, put it in a big container, and cover it with methanol. Alternatives to methanol here are ethanol (not as good) and acetone (good solvent - rips the crap out of anything, but is more reactive - can react with your actives).

. Now, depending on what your stuff is, you have to let the methanol have time to remove it all. This is best done by leaving in a quiet warm place for a few days, even up to a week, and shaking it occasionally so it is mixed.

. Some papers recommend solvent extraction (soxhlet apparatus) and refluxing at the boiling point of the methanol (80 degs or so - I can't remember). I usually just rely on time to get the good stuff out. When you are ready (early in the morning), filtre the muck, to give you methanol+dissolved brown gunk, and a residue soaked with methanol.

. The residue still contains a lot of good stuff, so soak again for an hour, and repeat, and do a third time if you are feeling generous (3 is the magic number in extraction work).

. When you are done, there is another thing you can do finally, if desired: depending on what your stuff is, mix it up with dilute hydrochloric acid, 1M is appropriate.

. let stand for an hour, then filtre (this may be very difficult) That will get the last of the alkaloids out of the substrate. (continued in part iii) EXTRACTION part iii You now have a methanol-plant stuff mixture, and a dilute HCL-plant stuff mixture, if you bothered to do that part.

. Evaporate the methanol, to leave a small amount of goo. This will contain water, a bit of methanol, and all kinds of resins and muck, and if you are lucky, the alkaloids.

If a very quick and crude extraction was all that was desired, then after stripping the last of the methanol with vacuum if possible, this residue could be smoked eaten or whathaveyou.

. I leave that to your discretion. However, if a cleaner product is desired, the double layer extraction will need to be performed. Combine the evaporated methanol gunge with the hydrochloric acid filtrate if you have any.

. If you don't then mix the methanol stuff with an excess of dilute (1M) HCl. Feel free to filtre again at this point. Anything of marginal solubility here is no good to you.

. Get the stuff as clean as possible. Boiling with activated charcoal is another useful trick for removing gunge. Just boil it up, and filter off the charcoal for a cleaner brew.

. You should now have an acid aqueous solution of alkaloids and water solubles from the plant. Take your acidic solution, and bassify. This is done by mixing in dilute sodium hydroxide (I use up to 5M to save on total volume.

. Be careful with conc NaOH - apart from eating skin, it eats alkaloids) As you mix in the NaOH, you will see swirls of white precipitate form and redissolve. Continue until the white swirls stay, and until the solution is quite cloudy.

. Indicator paper is necessary to see that the solution is basic. If you can't get indicator paper, you can make an indicator by boiling up some purple flowers. The dyes in most flowers go bright red in acid, and green in strong alkali.

. Just a drop of dye and a drop of mixture should tell you what is acid or base. The white precipitate is the alkaloids. The more the better. Next, add equal volume of non-polar solvent (dichloromethane) to the mix. Place in separating funnel, and shake. Separate. This may be very difficult or slow.

. Adding more solvent, more basic water, etc. may help. Adding lots of salt to the water layer will help break an emulsion. Ideally you want it do this step 3 times - to extract as much as possible from the water layer into the organic.

. I find this part very difficult, and you have to accept that you will lose quite a lot of material here. It is, however probably easier with some plants that others: cactus is very difficult, barks and seeds would be easier.

. Use plenty of salt, and agitate to separate. When you have finished extraction, chuck the basic water layer. The solvent layer is kept, and can be backwashed with salty water for a cleaner mixture.

. The solvent can now be dried, (using salt or some dry powder, the filtred) (I don't usually bother with this - the old hairdryer at the end can remove some last solvent and water) then strip the solvent in a vacuum to get your final product - some kind of syrup could be expected.

. This is super concentrated, but may only be half the strength of the original. e.g. put in enough for 10 doses of morning glory seeds, get back 5 doses or more of concentrated alkaloids.

. If it is desired to take the process still further, you can do the obvious thing - mix your solvent layer with dilute acid again and extract back into water. Acid layer could be evaporated under vacuum to give salts of alkaloids.

. Alternatively, if the organic layer were scrupulously dry, bases could be salted out with some organic acid - a tartrate, oxalate could be formed. I have never bothered with such things - you would need a lot of pure extract to be bothered. The acid-base extraction process can be continued as many times as is desired.

. If a truly pure product is desired, the only way to go from here is chromatography. I have never used this at home, and wouldn't think it was worth the trouble, but there will be papers available on what was used for a particular extraction case. -----------------

. I can get some anyway. I'll see. First of all, you need either (a) a _lot_ of morning glory seeds or (b) some hawiian baby woodrose seeds. You also need petroleum ether, which is a petroleum refining byproduct, and some high proof drinkable ethanol. I'll explain the theory as I understand it so that you can understand the flexability in this recipe.

. There are two kinds of solvents, polar and nonpolar. Generally, the good stuff in seeds is polar soluable, and the bad stuff is nonpolar soluable. So the idea is to first make a nonpolar solution, which of course means that you take a nonpolar solvent and soak the ground up seeds in it.

. The result is a solution of garbage from the seeds and the nonpolar solvent. Petroleum is a nonpolar solvent, so it will function in this capacity. The down side is that petroleum is poisonous, so you don't want to drink it.

. The good news is that petroleum is extremely volatile, so it evaporates quickly and cleanly. So the first stage is to soak the ground up seeds in petroleum ether for a few days, and then filter the resulting cloudy solution through some coffee filters, throw away the solution, and keep the seed mush.

. The seed mush consists of nondisolved LSA's, fiber, and the remaining solution that didn't drip through the filter. This part can be iterated to get more and more garbage out of the mush.

. The final time, let the seed mush dry thoroughly so that the petroleum evaporates so that you don't have any poison in there. After the seed mush dries, the nest stage is to make a polar solution, which separates the alkaloids (the LSA'a) from the fiber of the seeds.

. This is done with alcohol. There are other polar solvents, but again, the key is to have one which easily evaporates, one which will not destroy the LSA's, and one which is not poisonous. Ethanol serves this purpose.

. Methanol will also work, but methanol causes blindness, so if you use methanol, make damn sure it's all evaporated before consuming the product. In some states ethanol is illegal, and California is such a state. In that case, using methanol is probably the way to go.

. Also keep in mind that there is such thing as denatured ethanol, which is ethanol which has been intentionally poisoned so that it is undrinkable. The reason for doing this is that drinkable ethanol is taxable under the Tobacco Alcohol and Firearms people, and denatured ethanol has uses in chemistry and cleaning.

. The point is that you should under no circumstances use denatured ethanol because it will make you sick or kill you or cause cancer or all three. So, make an alcohol solution of the seeds.

. Then filter the solution through filter paper, like before, except this time keep the liquid in a jar. Repeat this step 3 or 4 times, always keeping the liquid. When you've exhausted the seeds, throw them away.

. The liquid you have should be yellow and smelly. Put this in a shallow flat tray or pan or large bowl, and let it evaporate in a dark dry place for a day or two, or until there is no liquid. The pan should have a yellowish scum residue.

. That's the LSA gunk. Scrape that up with a razor blade or credit card or whatever works. It'll be sticky and gummy, and once it's all scraped up it will look dark brown. That's pretty much all there is to it.

. You can take this several steps further to get a more pure product. That would be to alternately make an acid solution and base salts from the LSA's, which would eventually leave you with a very pure white powder. This requires much more effort, and wastes some of the product, and the only reason for doing it would be to remove more garbage, but the amount of garbage left in the brown gunk is insignificant.

. Once you have this stuff as pure as you want it, you can ingest it in your favorite form. You can either swallow it as a lump, put it into a gelitain capsule, drink the ethanol solution, or dissolve it in some cool-aid. I recommend either capsules or swallow the lump if you can handle the taste.

. Other notes: Petroleum ether is in Naptha, which is available in hardware stores. That's what I've used, and it works fine. Other petroleum solvents would work like ethyl ether, which evaporates much more easily and is a better solvent, and something like gasoline, which has additives and does not evaporate as cleanly as naptha.

. If you can get petroleum ether from a chemical supplier, try it instead of naptha. A rule of thumb is that after making a solution with the nonpolar solvent, and after it dries, it should smell absolutely nothing at all like petroleum, or whatever solvent you used.

. If you use gasoline, you'll notice a strong gasoline smell, which means you're screwed. I know first hand from repeated experience that naptha works. Also, read the labels of whatever solvent you use.

. Make sure it contains no benzene. Benzene is the most evil carcinogen known, and even in trace amounts it can cause cancer. There is no safe amount of benzene. On the other hand benzene is everywhere, and if some chemical engineer points out to you that there is benzene in naptha even if it's not on the label keep in mind that there is an enormous amount of benzene in automobile exhaust.

. You're going to die anyway. If there is no mention of carcinogens or benzene on the label of the naptha, then there isn't enough such that you should not use it.

. The finer details of this recipe I can give you another time, but I just wanted to give you some theory and a general idea of what the procedure is. I can give you some things I have from off the net pertaining to this.

. : Extracting alkaloids from Tricocereus cacti.

. Instructions for purifying alkaloids from Tricocereus cacti. This is a general method for concentrating alkaloids, with emphasis on mescaline, but which may be adapted to other plants and alkaloids. It requires that the alkaloids be relatively basic and that the base form be less soluble in water.

. So it would work well for DMT, but not psilocybin of caffeine for example. The principle of alkaloid purification is to obtain from a plant only that fraction which is basic. This is achieved by a double layer extraction, relying on the principle that amines (as opposed to most of the other compounds in a plant) are soluble in acidic (the salt form) but insoluble in basic (the basic form) aqueous solution.

. However, the basic form is soluble in non-polar organic solvents whereas the acidic/salt form is not. Thus, by varying the pH, alkaloids can be taken from aqueous solution to organic solution or vice-versa, leaving behind other materials.

. Some chemicals and equipment are important for successful extraction of alkaloids from cactus. The chemicals include methanol, dichloromethane or chloroform, sodium hydroxide and hydrochloric acid. The equipment includes a distillation apparatus, a separating funnel, and various beakers and containers, pH tester, and filter.

. Alternatives can be found for each of these. Method: 1) Slice and dry the cactus. I haven't worked out the best way to do this; no matter how I do it, I am always afraid that I am destroying the alkaloids. In

. general, what seems to work is to slice it thinly, and run hot air over it overnight. The more water which can be removed from the cactus at this stage, the easier the process will be. 2) Pulverise the dried cactus.

. I have tried using a blender, and it seems to work moderately well. The cactus is tough so you will have to be patient. The finer the grinding, the better the extraction. 3) Extract dried cactus with methanol. Ideally this is done hot using solvent-extraction apparatus (soxhlet).

. Various makeshift methods may suffice for a hot extraction, but I have generally merely soaked the stuff for up to a week, cold. Ideally this step should be done three times, and the extracts concentrated. I have done it once for a week, and then washed out the absorbed methanol with fresh methanol once or twice over an hour or two.

. What you should end up with, after filtering out the bulk of the cactus, is a green methanol extract. Ethanol or acetone could be substituted for methanol, but neither of these is quite as effective. It is generally desirable to use several times the weight of the dried cactus for the methanol extraction, or at least enough to cover it well in a container.

. 4) Remove the methanol to leave just an extract residue. This is best done using vacuum distillation, but can be done using atmospheric distillation, to recover the solvent. If you don't mind losing several litres of methanol, you can merely boil the stuff into the atmosphere; just avoid starting a fire. ALWAYS no matter what use boiling chips (porcelain) to promote even boiling.

. Methanol superboils easily, as I have found :-(. Once most of the methanol is removed, you will be left with a hundred ml or so of watery, methanoly, green slime. If it weren't for the methanol and the bad taste, this could be consumed at this point. In general, I would say that it may be worth your while going to the next stage if you can manage it.

. 5) Add dilute hydrochloric acid. Sulfuric acid, etc. could be used instead, but I like to use HCl and NaOH, because the product is NaCl, which is of no consequence if it contaminates anything. HCl is not as oxidising as H2SO4. The HCl should be less than 1M, but not weaker than 0.1M (pH 0-1).

. Add a few times the reduced volume of liquid - e.g. take the stuff to 400 ml from 100 ml, etc. One good idea is to let the bulk cactus residue (post methanol) dry, and then soak it for a few hours in the acid you are going to use to add at this point. This will extract the last of the alkaloids. Unfortunately, cactus being what it is, will swell enormously, and removing the HCl is tricky.

. I have resorted to large quantities of HCl and a kind of press to squeeze out the acid from the bulk residue. This acid should then be filtered, and added to the methanol extract residue as above. 6) (optional) The stuff at this point will be a bit of a mess.

. Adding activated charcoal and boiling gently for 10 minutes will help to congeal the chlorophyll etc. which is gumming up the stuff. Do not add too much charcoal - less than a gram should be plenty. Too much will adsorb alkaloids.

. Don't use burnt wood, burnt toast, etc - get the proper stuff from the local pharmacist. Performing this step will make the next stages considerably easier.

. 7) Filter the HCl extract. This will remove a proportion of the gunge. This will be easier if charcoal was used. The more gunge that can be removed at this stage, the better.

. Washing the residue with fresh HCl before discarding, and adding this to the rest will ensure no loss of yield. 8) carefully basify the HCl solution with NaOH. I tend to use around a 5M solution for this, which is OK as long as you stir as it reacts. Take it well above pH 7.

. You should get white clouds of alkaloids forming in the solution, and the whole will become turbid as some of the acid soluble components precipitate. Ammonia or KOH should work for this purpose as well. I have had some difficulty with ammonia not being quite basic enough in other systems.

. 9) Add dichloromethane (or chloroform); be generous with the quantities if possible. Ideally, one would like to extract into CH2Cl2 3 times with equal volumes, but the amount of solvents gets huge. Ether is not all that good with mescaline extraction, I believe, even though it is easier to separate from water.

. CH2Cl2 is handy because it has a very low boiling point. It is at this point in the whole operation that the most care and patience is necessary. A separating funnel is really a must - one could plausibly separate the layers with a very tall thin jar and a syringe, but this would be difficult.

. Ideally, the basic solution and the CH2Cl2 will separate into 2 nice layers, the lower one (organic) containing the alkaloids. Unfortunately, while this is not difficult with most plants, it is very difficult with cactus extracts because the cacti contain so much resinous junk and natural surfactents (to retain water).

. The best way I have found to separate the layers once you have shaken them together is to add plenty of salt (NaCl) to the water/base layer. This is excellent for breaking the emulsions which form. Be prepared to use large quantities of salt. 10) Separate dichloromethane layer from mixture and put aside. Repeat steps 9-10 a few times: once is insufficient, three is good, four is excessive.

. Combine all the dichloromethane extracts together. This should be a slightly green solution. It will contain a bit of water, most likely. 11) Backwash the dichloromethane once with a solution of salt and NaOH (dilute).

. This will clean up the last of the junk from the organic solution. Separate the layers as before and discard all aqueous material. 12) Distill off the dichloromethane (or allow to escape to the atmosphere if you are rich and don't like the ozone layer). I have found that once you are down to maybe 20 ml of residue, the best option is to place the remainder in a petri dish (or some flat dish you are going to store it on) and hitting it with a hairdryer to remove any last CH2Cl2 and water.

. You should be left with a small quantity of moderately pure alkaloids. This can be easily consumed by dissolving in vodka, e.g., or should be stable for extended periods if refrigerated, frozen, kept airtight and away from moisture.

. Do not expect more than a 50% yield the first time you try this: theoretically if everything is done properly, the yield should approach 100%, but this is rarely the case.