Tue, 02 Mar 93 TOPICS Subject: Alkaliod extraction Subject: LSA extraction Subject: Extracting alkaloids from Tricocereus cacti. Subject: Re: Extracting alkaloids from Tricocereus cacti. Subject: Re: Extracting alkaloids from Tricocereus cacti. Subject: Extraction Refs Subject: Extraction info Subject: Extracting DMT from Acacia maidenii Subject: Extracting alkaloids from Psilocybe Subject: Myristicin and Safrol from Nutmeg / LSA from HBWR Subject: Re: Extracting LSA from HBWR Subject: Re: LSA Subject: BETA-CARBOLINES ---------------------------------------------------------------------- From: 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. ------------------------------ Date: 08 Aug 1992 17:53:37 -0500 (CDT) From: firstname.lastname@example.org Subject: LSA extraction The method is very simple, requires nothing you can't buy easily and legally, and it's not very expensive. There are refinements galore to this, and I might try them in order to purify this stuff, but the chemicals aren't as available, and it rewuires things like pH paper, which I don't know how to get. Maybe 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 soluble, and the bad stuff is nonpolar soluble. 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. ------------------------------ Date: Tue, 4 Aug 92 12:55:44 EST From: anonymous Subject: 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. ------------------------------ From: anonymous #2 Subject: Re: Extracting alkaloids from Tricocereus cacti. I've had a quick scan through that post, and it seems he's been pretty complete in his description. I can add the following information: - The initial extraction is very important. You only have as much alkaloid to play with as you extract at this point. Similarly, the more gunk you extract at this stage, the more you'll have to eliminate. Methanol is used because it's not too polar or non-polar, and it penetrates cell walls and membranes quite effectively. Acetone would be as effective, but it seems to pull much more gunk out along with it, and for this reason should probably be avoided. Also note that the better your mechanical mulching process is, the more effective the extraction will be. Also, note that a hot solvent extraction under reflux conditions, or using a soxhlet would be more effective, but bear in mind that some alkaloids may decompose with heat - it's probably worthwhile checking the physical characteristics of the alkaloid in question in your handy Merck index or CRC handbook. - With respect to the degree of acidity and basicity necessary for the extraction, this can only really be found by trial and error. Insufficient difference from neutrality will cause insufficient separation, extremes of pH (particulary too basic) may cause alkaloids to be degraded or other nasty things to happen. Also note that other compounds present may act as buffers - be sure to stir well, and measure the pH using indicator paper or somesuch. - The final product is a free base. Usually it's unneccessary to go further than this. Forming a salt can be tricky, and would also be wasteful. If you're ingesting the product orally, then it'll salt adequately with the HCl in your stomach. If you're concerned with oxidation by the air, well, use your better judgement (are you really going to wait that long before eating the stuff). Of course, if it's DMT and you're going to smoke it, forming the salt is a waste of time. Hope that's helpful. ------------------------------ From: anonymous #2 Subject: Re: Extracting alkaloids from Tricocereus cacti. One other question though which is on "backwashing"... what exactly is this procedure? Once you've extracted the goodies into the solvent layer, you attempt to remove any remaining non-alkaloid gunk that may have come along with it. So you wash the extract with basified water, which forms another layer which you discard. Jez describes this in the procedure. It's not always necessary, but once you've got that far, it's usually not difficult to do (i.e. you've got the layers to separate successfully once already) ------------------------------ From: anonymous #2 Subject: Extraction Refs Here are the references for the extraction procedures. I don't have the titles of the papers, but all are in readily available journals: Mescaline: JACS 88 p4218 (1966) Lloydia 29 p318 (1966) DMT from acacias: Aust. J. Chem 16 p246 (1963) ------------------------------ Date: Mon, 31 Aug 1992 16:30:46 EDT From: anonymous Subject: Extraction info >do you know what the following are: > >Et2O? diethyl ether, commonly called ether. less polar than water or alcohol, more polar than petroleum or toluene/benzene. I don't use it; dichloromethane is much safer, and easier to get, but is slightly more cosoluble with water. >THF? Tetrahydrofuran: O / \ H2C CH2 | | H2C___CH2 It is a cyclic ether, very similar to diethyl ether (obviously) but is perhaps a stronger solvent, and is even more dangerous. >IPA? H3C \ H-C-OH / H3C ispropanol. IPA could stand for anything, but this is a good chance. I'd call it iPrOH in writing, myself. It's a common alcohol - the next most commonly available after ethanol and methanol (not counting sugar etc.). It is still miscible with water. Butanol partly cosoluble with water. Higer alkanols are not. iPrOH has a similar boiling point to ethanol, and is quite volatile. It is less polar than ethanol, but much more polar than ether. Polarity and solubility is a nebulous concept. If you actually look at what is dissolved by what, you can only find vague general principles, and plenty of exceptions. Some authors have tried to make 3 and 4 dimensional polarity or solubility graphs, and put various solvents in various points as having a combination of different types of solvent power. >and how to do a distillation "at 2.0 mm/108-112 deg C, or at about 160 >deg C at the water pump"? You need special apparatus for both. If I were pushed, I could put together the latter (I have the necessary equipment lying around.) I wouldn't attempt the former, except in a lab, which is where I have done it. Both of them are, of course, low pressure distillation. At a low enough pressure, anything becomes gaseous. This is of course because every substances has a vapour pressure at a given temperature. By evaporating something under vacuum, you can turn it into a gas at a temperature lower than the temperature at which it oxidises or spontaneously decomposes. A water pump, or venturi pump, is a simple vacuum which can be attached to a fast flowing water source. The theoretical minimum pressure is the vapour pressure of water at whatever temperature (e.g. 15 mmhg at 20 degs or what have you), but in practive, this is never reached. A water trap between the pump and the distillation apparatus is essential, and if you wish to recover whatever you are distilling, you will need a special collecting vessel (often ice cooled) as well. A mechanical vacuum pump is just the same, except it is large and heavy and noisy and expensive and can achive a high vacuum, which is often necessary for the distillation and purification of organic compounds. ------------------------------ Date: Mon, 31 Aug 1992 16:31:22 EDT From: anonymous Subject: Extracting DMT from Acacia maidenii The following events are as far divorced from reality as the experience of the drug itself :-) I discovered that a local plant, Acacia maidenii, was reported to contain 0.6% alkaloids in the bark, of which 1/3 was N-methyl tryptamine, and 2/3 was Dimethyl Tryptamine (DMT). Alkaloids of The Australian Leguminosae - The Occurrence of Methylated Tryptamines in Acacia maidenii F. Muell. J.S. Fitzgerald and A.A. Sioumis Australian Journal of Chemistry, 1965, 18 433-4 Some research of old botany books suggested a nearby location, and to my surprise I found many hundred of the trees growing along creek gullys in a nearby national park. I took about half a kilo of vertical strips from a number of trees, trying to cause as little as possible permanent damage. The bark was thick, red, fibrous and resinous. Smoking the bark directly gave a mild hallucinogenic effect, on the limits of the detectable. That evening, I shredded the bark by hand. This was difficult and incomplete; mechanical milling would be far preferable. I placed the shreds about 3.5 litres of analytical grade methanol from Monday night until Friday afternoon. The methanol quickly took up colour from the bark and turned a deep red colour. As much as possible of the methanol was removed by filtering. I evaporated off the methanol using a fractionating column, a condenser, and a saucepan of boiling water as heating, for some hours, and recovered much of the methanol. I placed this methanol back with the bark and reextracted for some hours while evaporating the rest, then filtered the bark again and combined the extracts, and stripped as much as possible of the methanol, to leave a thick resinous brown liquid. A portion of the extract was evaporated using a hair-drier to give a thick brown resin. Attempts at smoking this using pipe and hot knife proved unpleasant and gave minimal effect. It was decided to perform further extraction. To the extract was added dilute hydrochloric acid (about 20 ml 10M, but well diluted). Immediately, a large amount of tar congealed and was removed, leaving a watery brown aqueous mixture. This was basified with NaOH, although on reflection, I would use NH3 next time as it is less likely to overbasify and react with any of the compounds present. White precipitations were seen on basification, which redissolved on stirring. The aqueous phase was extracted twice into CH2Cl2, and the solvent evaporated as before. The last stage of evaporation was accomplished with a hair drier, to leave about a gram or so of pale yellow liquid. On standing 24 hours, this liquid crystallised as circular arrangements of needles. Preliminary attempts at smoking small amounts of the alkaloids gave varying mild effects, and a friend and I decided to try a larger dose. He took a cone in one toke, and was immediately on the ground, making strange sounds and looking odd. He hugged me and told me to meet him in that place, and said it was very strong. I managed to finish a large cone in 3 tokes, and was instantly blown apart as if by a large brick through the head. I think I was temporarily blinded, and found myself on the ground grasping my friend, and coughing for air, as I watched all of my surroundings fragment into small pieces divided by lightning bolts, and feeling all the air in the universe escape through the holes. We were both totally astounded and scared shitless. 2 minutes later, the intense part was over. We staggered out into the open, and walked in the park until we calmed down. Pleasant mild hallucinations continued for about half an hour, and there were no after effects whatsoever. The experience was extemely intense, and the smoke has an unpleasant taste. Several other people have tried it since, and the most popular adjective is "wicked". Effects have ranged from mild to intense, and some people say that while it could not be described as "good" or "enjoyable", they would be happy to try it again. My subsequent trips were more bearable, as I was not under any anxiety about the duration or outcome of the trip. Nevertheless, the trip is still extremely intense, and also physically demanding: giving strong tactile hallucinations and stimulation. On a second occasion, I took 1.7 kg of bark, and pulverised it as best I could using a circular saw. The result was mostly a fibrous powder. Some pieces had to be shredded by hand. Methanol extraction was performed as before. Since the amount was larger on this occasion, the quantities were somewhat unwieldy. Stripping the five litres of solvent (aprx) took approximately 14 hours. On attempting to acidify, filter, and basify, considerable difficulty was experienced; the acidified residue seemed unfilterable, and when basified with NH3, a thick pink gel was formed which was impossible to extract. By a painful process of trial and error, I found that at very low pH, most of the resins became dissolved or suspended. At slightly low pH, the residue separated nicely into a tar and an aqueous phase. At slightly high pH, the mixture became a thick gelatinous solid. At very high pH, this solid redissolved. The result of this seems to be that much of the tar can be separated by successive extraction at moderately low pH (dilute HCl), and then that the addition of strong hydroxide will leave the amphoteric resins in solution, but make the alkaloids insoluble. These are then extracted into dichloromethane as before, and the organic layer is back extracted with salty NaOH solution to remove impurities. The dichloromethane is then stripped as before, to leave the alkaloids which crystallise in 24 hours or more. Myself and a friend experimented with repeat doses of DMT at close intervals. A base pipe was used for smoking the alkaloids. This pipe allows minimum combustion and maximum vaporisation, and thus is the most economical way to smoke DMT. Because there is little combustion, the smoke does not taste quite as bad, and also the base pipe allows more accurate metering of the dose. After the initial physical rush, it was found that taking small tokes at intervals of a few minutes was sufficient to maintain an extremely pleasant trip, not unlike that of psilocin. There was minimum physical discomfort associated with the cruise. However, while in this mild state, I took two large tokes of the substance, and a few seconds later, without warning, I was blown apart. I was walking, but staggered and choked, gasping for air. The effects were totally overwhelming, like being thrown out of the universe, and I watched my visual sphere being pixelated at successively lower resolutions, until I could see merely individual elements of colour. The intensity was such as to make it very unpleasant. A few more experiences should be related. It seems that the response of various people to this extract varies greatly, and even a single individual can have a variety of responses, from no effect to total dissociation. One girl tried a single toke for the first time, and was completely thrown out of the universe (from her description). She was begging for it to end; the duration was longer than usual: about 15 minutes of heavy peak, and at the end of it she vomited while gasping for air when beginning to return to some normality and bodliy control. On one occasion, I first ate a whole bottle of the 4:1 extract of Passiflora incarnata which is available over the counter in Australia. Each tablet contains 500 mg of extract, and I ate 60 tablets. Supposedly a single tablet is supposed to be a herbal sedative, but I was not sedated after consuming the 60. My reason for doing this was that Passiflora incarnata is supposed to contain a variety of beta-carbolines which are mono-amine-oxidase inhibitors, which have been used to potentiate the effects of DMT, and make it orally active. About 40 minutes later, I smoked some DMT, the effects of which were not greatly different from what I am used to. I then had a slightly larger amount, and without warning, felt an intense incredible rush of physical pleasure through my body. Within seconds, I was riding on the most intense unimaginable pure total body orgasm. I was unable to control myself, and I was screaming at the top of my voice until the effects subsided. The visual and auditory enhancement were mild, but the physical hallucination is was by far the most enjoyable thing I have ever experienced. Observers, who were taken aback by my behaviour, claim that I was in this state for about 10 minutes. Afterwards, I felt intensely euphoric, and both very excited and very relaxed. I tried eating a significant quantity of the DMT after this experience, and found no effect. This would indicate that the Sedacalm passionflower extract is insufficient to orally activate DMT at these doses. It may be that higher doses would have some effect, or that Sedacalm does not contain appreciable quantities of beta-carbolines. Harman, harmol, harmalol, harmaline, and harmine have all been reported in Passiflora incarnata over the years, but one paper claims that only harman, which is not particularly active, is the only alkaloid present. I intend to experiment further with this plant. I am planning to attempt to side-step the methanol extraction, simply by attempting to extract directly into hydrochloric acid. Freezing and thawing the bark might serve to burst the vesicles containing the alkaloids (if this is the case - I am not a biologist). The advantage of doing this would be decreased cost, easy availability of all raw materials, and decreased time involved. The disadvantage would most likely be a reduction in yield, but larger amounts could be processed. The acid extract would have to be boiled down from several litres to a few hundred mills, then filtered, and this process could destroy the alkaloid. Comments on this method would be welcomed. My references tell me that N-methyl tryptamine is most likely inactive at these doses. Does anyone have any information regarding the physical and psychological effects of this compound? Also any information regarding the hazards of DMT use would be appreciated. ------------------------------ Date: Mon, 31 Aug 1992 16:35:29 EDT From: anonymous Subject: Extracting alkaloids from Psilocybe Extraction Instructions for obtaining Psilocin and Psilocybin from Psilocybe or Panaeolus. I have not tried this method; it is taken from the classic volume (in French) and based on that used by Albert Hofmann. Le Genre Panaeolus: Essai taxinomique et physiologique par Gyorgy Miklos OLA'H Laboratoire De Cryptogamie du Museum National D'histoire Naturelle 12, rue de Buffon, Paris. Memoire hors-series No 10, 1970. Page 97. Dry the mushrooms. - This important step is most likely to cause the greatest loss of yield depending on how it is done. Crush or grind the dried carpophores or mycelium to a powder. Shake and allow to stand (e.g. 30 mins) in chloroform. Use maybe twice the dry weight in solvents at every step, or enough to well cover the powder. Filter and discard the chloroform. SHake the reidue and allow to stand with acetone. Filter and discard the acetone. Shake residue and allow to stand with methanol. Filter. Shake residue and allow to stand with methanol. Filter. Shake residue and allow to stand with methanol. Filter. Discard residue. Combine methanol extracts. Evaporate methanol to dryness, preferably in a vacuum, although low heat will do. This will yield a crude extract containing the active tryptamines, suitable for most purposes. This can be further chromatographed on cellulose etc. to give pure psilocin and psilocybin. The recommended solvents are n-Butanol saturated with water, and n-butanol:acetic acid:water (24:10:10). Anyone wishing to do chromatography should check the relevant texts for more detailed instructions. Contact me if you want further information - I may even be able to supply it. ------------------------------ Date: Tue, 01 Sep 1992 11:20:09 EDT From: anonymous Subject: Myristicin and Safrol from Nutmeg / LSA from HBWR >can you use an acid-base extraction for getting myristicin from >nutmeg or LSA from HBWR? (i.e. are either of those two chemicals both >polar soluble and soluble in acidic solution but not basic and >whatever the other condition was...) Ok: the former I have tried. The latter I haven't but hope to soon. Neither of these is really suitable for the kind of alkaloid extraction I have discussed before. In the former case, the allyl-benzenes are not alkaloids (as you should have realised). In the latter, the compounds are water soluble to some extent in the basic form, how much so, I don't know. If you look at the method I gave for psilocin, you will see it is different from that for mescaline and DMT. I got the psilocin recipe from an old book. II would have to go back to the original literature to make a proper recipe for LSA extraction. If you'd like to grab the reference for me (someone at Leri is sure to know) then I will go back and check it out; the Hofmann stuff where they first tested obliquhui (sp?). TO purify myrsiticin/elemicin/safrole from nutmeg, is a tricky process, but not impossible. The shot would be to soxhlet extract the oil from a few kilos of nutmegs, strip the solvent (pref. under vacuum) perhaps filter/press the oil at room temperature to remove the nutmeg fats (myristic acid and glycerides) Then fractionally distill at reduced pressure to obtain the correct fraction. The boiling temperature of these components might be a bit over a hundred degrees in a strong vacuum. This you could calculate from the Clapeyron equation (or a simplified Antione equation) and a knowledge of the distillation pressure and the boiling points of the compounds at two pressures either side of your distillation pressure. I did this using data from the Handbook of Physics and Chemistry. The equation to use is of the form ln(P/P*) = A/T + B (T in Kelvin). This process is quite a tricky one, and one which I would not be confident of performing succesfully myself. Double distilling would almost certainly be necessary to remove the last of the impurities. If I were to try to purify LSA from HBWR, my first instinct would be to grind it, soak or soxhlet (since the volume would be small enough to use the reflux equipment I have) with methanol, filter, strip the methanol, and consume. To go further, without accurate knowledge of the substance and its pH/solubility behaviour, would be tricky. Chromatography (e.g. TLC) may well be the required next step. ------------------------------ Date: Sun, 06 Sep 1992 21:34:20 EDT From: anonymous Subject: Re: Extracting LSA from HBWR Concerning the extraction and purification of LSA from HB**, The alkaloids are more polar than e.g. DMT or mescaline, and are probably water soluble to some extent. Thus, while a crude extraction can be performed with methanol, the next stage of purification may not be very good. Thus the general extraction method for alkaloids is quite possibly not applicable here. That is why I want to have a look at exactly what the original method was, although the journal seems obscure to say the least. Another day in the Chem Abs section, I fear. ------------------------------ From: email@example.com (Anthony Ankrom) Date: Tue, 22 Sep 92 15:41:10 GMT Newsgroups: alt.drugs Subject: Re: LSA In article 1992Sep22.034310.22075, Lamont Granquist (Lamont Granquist) writes: >>[is] there ... a relatively straightforward proceedure to extract the >>LSD and get it in a reasonably pure and consumable form? > >Yup. In a nutshell, you mix the HWBR powder in a nonpolar solvent, keep the >resultant gunk(I) and throw away the solution. Then dissolve the gunk(I) >into a polar solvent, throw away the new gunk(II) and evaporate the solution. >The final gunk (III) that comes out of the solution has LSA in it. > > gunk(I) = gunk(II) + gunk(III) > gunk(III) is the good stuff > gunk(II) is not > gunk(I+III) are therefore kept > >nonpolar solvent = petroleum ether >polar solvent = alcohol (methanol is better, but is a smidgin poisinous > so you've got to be damn sure its all evaporated). > >I don't have time to give a more detailed explanation than that right >now. For the layman: nonpolar solvent also = Zippo lighter fluid. St. Anthony -- CH3 O CH(CH3)2 | dadaMatrix >-P-S-CH2CH2-N< VX | CH3CH2O CH(CH3)2 | firstname.lastname@example.org | A kinder gentler lobotomy... ------------------------------ From: email@example.com (Pierre St. Hilaire) Date: Tue, 2 Mar 1993 19:53:02 GMT Subject: BETA-CARBOLINES >>Has anyone had a GOOD experience from moderate/large dosages of Syrian >>Rue seeds? Was the nausea because of the harmaline, or due to other things in >>the seeds? > >How did you prepare the seeds? Did you boil them and drink the extract? O.K., for all the poor souls who had to ingest those horrible seeds, here is an extraction than I think anyone on this newsgroup can do in their kitchen without blowing themselves up. From "The Alkaloids" Vol. II by Manske (p393). Printed without permission. ISOLATION OF HARMINE AND HARMALINE "The crushed seeds of Peganum Harmala are covered with three times their weight of water containing 30 g of acetic acid per liter of water [white vinegar is about 50g / l or 5 %]. The seeds swell as they absorb the liquid and form a thick dough which is pressed after 2-3 days. The pressed seeds are once more treated as above with twice their weight of dilute acetic acid and, after maceration, the liquid is again pressed out. To the combined liquors, sodium chloride [that's table salt, man] (100g. / liter of liquid) is added to transform the acetates of harmine and harmaline into the hydrochlorides which are insoluble in cold sodium chloride solutions and are precipitated during cooling. The supernatant liquid is siphoned off, the crystalline residue filtered with suction and redissolved in hot water. Addition of sodium chloride to the filtered solution causes the precipitation of the hydrochlorides as a crystalline mush and this process is repeated until the hydrochlorides have acquired a yellow color (for the purposes of this newsgroup, once is enough). The final product is then recovered by filtration." The paper then goes on to describe the separation of harmine from harmaline, but this procedure is slightly more complicated and not necessary for most purposes. Pierre St Hilaire MIT Media Lab P.S. While this procedure is legal in the U.S. (where harmine and harmaline are currently unscheduled), it is illegal in Canada where harmine and harmaline are Schedule I. These are extremely potent alkaloids. Misuse of them can result in serious, even fatal, consequences. Read the FAQ about MAO inhibitors. End of ftp.u.washington.edu:/public/alt.drugs/chemistry-extracting ******************************************************************
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