Lots of people are speculating about extracting oils, alkaloids and other stuff from plants. Strike has never been desperate enough (or is that smart enough) to go to the actual botanical sources for precursors. Lots of books talk about "steam extraction' of plant parts, but Strike don't know crap about that process. Strike has, however, had a few jobs here and there that have gained Strike a general idea of what can and cannot be done. See if you can envision a reasonable protocol for extracting a plant of your choice.

Strike's first recollections are by Strike's mommy's side as she worked over a pot of delicious vegetable beef soup. When Momma ain't around Strike takes a peak at the soup. "Say where'd all that oil come from that's pooling on the top of the water?" thinks Strike. Probably from the beef. Sometimes Momma would just make vegetable soup. "Hey! There's oil in this one, too!" noticed Strike. (Yes, Strike was a real genius).

Later on, Strike gets a job at a fancy French restaurant where they made consommes, stocks and demiglaces. They would chop up their bones and vegetables and then simmer them in water for a couple of days. What comes out is a pot that has all the nutrients and flavorings. In the water, all the oil floating at the top and the fibrous, insoluble matter sitting on the bottom. Gosh, that sounds a lot like extraction.

Even later on, Strike begins Strike's career as a chemist, and one of the first labs Strike works in is an enormous environmental testing facility. Talk about extraction! That's about all that organic testing labs do! You give these guys anything and they will extract it to test for any compound, poison or constituent. As it so happens, a lot of extraction protocols were for the removal and isolation of things like total fat content, total lipid content, vitamin assays, petroleum and hydrocarbons.

Sometimes we would get tissue samples such as fish from a river suspected of being polluted; sometimes plants for the same reason. No matter what kind of sample it was, be it leaves, dirt, fish, etc., they were all processed in the same way.

How we extracted these compounds was by using organic solvents. EPA protocols dictated that some compounds were extracted more exclusively by using one solvent as opposed to another. The most overriding factor in choosing a solvent for extraction was polarity. Some solvents are very polar, some so-so polar, and some very non-polar. Below is a partial list of solvents and their polarity.

Most Polar: Water, Methanol, Ethanol

So-So: DCM, Acetonitrile Ethyl Ether

Non-Polar: Freon, Pentane, Hexane

The key term here is "like dissolves like", which means if you want to extract a certain compound you use a solvent that is most similar to it. Water (the 'universal solvent') is the most preferred solvent for extracting (i.e. solvating, ie, ie, 'dissolving') highly polar compounds (i.e. water soluble compounds). Things like salts, sugars, other water molecules etc. all dissolve readily in water.

Methanol and ethanol are mostly polar due to their OH group. But that little methyl or ethyl group is sort of non-polar, meaning that both compounds dissolve water and oils equally well. This is why we use ethanol to isomerize safrole because it will dissolve the polar salt KOH and the nonpolar safrole. Get it?!

Moderately polar solvents like ether and DCM only absorb a little water and a lot of non-polar product. You can see that they are not at all polar like water because they won't mix with it and will form their own layer apart from water. After working a bazillion times with ether and DCM extractions Strike is all too familiar with requisite passing of the solvent thru sodium sulfate to rid it of the trace water it absorbs.

Now, let's take a look at a common leaf and vegetable extraction. Strike would place the stuff in a stainless steel blender and grind it up real good. Next, the ground-up stuff would be placed in a soxhlet (don't ask) or a jar. If Strike wanted to, Strike could pour a bunch of sodium sulfate into the jar and mix it with the ground-up plant. This will bind all the water without affecting any of the other constituents. (not necessary if desired, it's just a trick to exclude water for the detection efforts later on). Next Strike pours in some solvent (at least a 1:1 ratio), caps it and shakes for 5-l0 minutes.

After shaking, the contents are allowed to settle and the solvent decanted or removed. All that vegetable matter wants nothing to do with that solvent and will stay put in the jar. The vegetable matter will be extracted at least once more and the solvent extracts combined.

What essentially happens next is the solvent is boiled away leaving whatever was extracted behind in the bottom of the container. There is always oil in that residue no matter what solvent (aside of water) was used.

That's the key point here: No matter what solvent the method called for, Strike would always end up extracting all the oils out of a sample. Those solvents would ravage every pore of that tissue and leach out every last microgram of goodies, leaving behind all of the protein, fiber and cytoskeletal mass behind. As an environmental chemist, these constant oil yields were often an unavoidable pain that had to be removed by further purification so as to not hinder analysis. As an underground chemist, this selectivity is a godsend.

For petroleum and petroleum distillates (very much similar to drug oils) we used freon because of its lack of carbon-hydrogen bonds (don't ask). For grains and animal feed lipid and vitamin content we used ether. Any time we had a choice we used DCM. Sometimes acetonitrile was used on produce. In the case of acetonitrile we would shake it with NaCl to creat a separate water layer from which the solvent layer could be removed.

The list of applicable organic solvents is endless and almost all of them work. A good commercial example is the extraction of caffeine, a true alkaloid, from coffee. Until recently all coffee was decaffeinated using DCM. The coffee would be soaked, or continual extracted with DCM and that was it. That decaf stuff you see on the shelves is all that normal coffee is except it lacks caffeine. A remarkably selective outcome by careful solvent selection. (Personally, Strike feels that the coffee oils and flavorings would go with the DCM as well, and are probably readded after extraction) Nowadays we use the environmentally friendly CO2 under supercritical fluid conditions to get that caffeine out. (please don't ask!)

So now that you have a general idea of how professional extraction works (See? It's not very involved at all!), let's apply what we know to ephedrine extraction from an ephedra plant. The Merck Index says that the ephedrine molecule is soluble in water, ether, chloroform and ethanol. Yikes! That's quite a polarity range! Most likely it is due to the OH group which gives the mostly nonpolar molecule a little polarity (ie,gives it a little similarity to that HOH of water.

Since it's soluble in water, one can make ephedrine soup. That ephedrine will leach into the simmering water but so will a lot of other things. However, since ephedrine is also soluble in those organic solvents one can filter the broth of insoluble stuff, then extract it with the organic solvent. This will greatly narrow down the list because very few things, apart from ephedrine, will end up in that organic solvent.

"Wait a minute, Strike! If ephedrine is soluble in both water and the organic solvent how the hell can it go to one from one to the other?" Good point! Back in the professional organics labs Strike often had this dilemma.. In the situation of a solution with an aqueous layer and an organic layer one would often take advantage of the partial acidity or basicity of molecule to drive it into one layer or the other. By adding acid or base the water layer would become strongly so and either attract or repel the desired molecule..

How would we know which one (acid or base) to use? Well, the head investigating scientist would walk into the lab and tell us. Other than that we wouldn't have a clue. Still don't. This is to say if the acid/base trick even effects ephedrine. It may not. There also are some interesting carbonate salt separation techniques that work on alcohols which Strike is going to discuss in the upcoming MD-P2Pol page.

."Yeesh! This way doesn't sound too great, does it?" Shit no it doesn't! One best forget that water extracting crap and go straight for the gold: organic solvent extraction.

Again, the Merck lists ether, chloroform and ethanol. But Strike is relatively certain that DCM, acetone, benzene, tolvene, freon, methanol, ethanol, etc. will all work. Strike has extracted hundreds of different organic tissue matrices with almost every organic solvent. They are all relatively consistent in their interaction with tissue. And when it comes to drugs which are almost all oils or close enough to oil characteristics as to be negligibly different, the extraction with an organic solvent is pleasingly consistent as well.

Ground-up ephedra leaves shaken with an organic solvent will yield a clearish green, non-cloudy organic layer which can be decanted off, dried thru sodium sulfate if desired, then relieved of solvent by boiling it away. If the plant that was extracted is loaded with ephedrine then the resulting residue should be, with the exception of cell wall lipids and other requisite cellular oils, loaded with ephedrine concentrate.

OK, now. Let's have some more fun with this ephedra extract and learn at the same time. So we have an extract of ephedra, right? Let's assume we did it using either ether or chloroform. This means we'll have an ephedra colored liquid that's going to have ephedrine, contaminating cellular oils and alcoholic species, and probably some absorbed water. There is about a 99% probability that the ephedrine is going to be the only constituent of any consequential amount that will have an amine group. This means one could and dilute (l0% or so) HCi to the solvent and turn that ephedrine freebase into the hydrochloride.

All amines will submit to being precipitated as a hydrochloride (HCl) solid with HCl just like chemists do to their X or meth freebases, or by H2504 to give the sulpha-drug counterpart. If one does this to ephedrine in an organic solvent mix then it will separate to the acid water layer because as a hydrochloride it is now completely water soluble and ether or chloroform insoluble. ans the water layer can be separated and dried to yield relatively pure ephedrine-HCl.

If the chemist extracted using everclear (ethanol) then using a dilute HCl would be overkill because all that water of the HCl solution would merge with the ethanol extract and no second layer would form. The ethanol itself is a suitable medium to precipitate in, so the chemist would add straight-from-the-bottle 35% HCl or HCl gas until ephedrine-HCl crystals form. In this case there is not enough water for the hydrochloride to dissolve in so that it remains crystalline and is separated by filtration. Get it?!

The following are a few recipes for ephedrine extraction from our benefactor (Z):

Subject: Ephedrine base from Ma-huang

From: Fisherking <>

Date: 1997/03/11

Message-Id: <5g4hmu$>

Newsgroups: rec.drugs.chemistry[More Headers]

In a message of 26 Feb 97 wrote :ben> d <> wrote:

>> ma-huang contains roughly 6% ephedrine. ma-huang also contains roughly the same amount of p2p and psuedoephedrine. How might I go about extracting a solution containing p2p, ephedrine, and psuedoephedrine? Pseudo-ephedrine hydrochloride is soluble in chloroform where as ephedrine hydrochloride isn't. The 2 salts can be separated this way. I don't know what p2p could be.

>> Would an ethanol extraction work? I have boiled some ma huang in isopropanol and strained the remaining liquid. I came up with a black syrup which I dried. It somewhat tasted like the ma-huang, but to a lesser extent. It was also insoluble in water. Yuck. You will also have extracted the oils and chlorophyll by this method. I'm not trying to be a smartass, but why don't you just buy one of the pseudoephedrine generics at the store? Sounds like it would save you a lot of work and muck. Where's the fun of going to a shop and just buying what you need, this is a newsgroup with recreational in its name. A visit to the library is needed not to a shop :-]

Some of the properties of ephedra alkaloids that you should keep in mind, the bases are freely soluble in water which makes it necessary to saturate the alkaline aqueous extracts with sodium chloride before shaking with ether. Ephedrine base is volatilized when warmed, and it is therefore necessary to avoid evaporating its ethereal solution to dryness on the water bath. Ephedrine does not yield any precipitate when its acid solutions a treated with mayer's reagent. If a solution of a few milligrams of ephedrine or its salts in 1ml water is treated with a drop of copper sulphate solution followed by about 1ml of sodium hydroxide solution, a violet color is produced. When this liquid is shaken with a little ether and the immiscible liquids allowed to separate, the ethereal solution is coloured purple and the underlying aqueous portion becomes blue.

Isolation ephedrine from ephedra.

Small scale (determination of total alkaloids)

Take 20g powdered ephedra macerate for a few minutes with 200ml of a mixture of 3 volumes of ether and 1 volume of chloroform. About 10ml of 10% ammonia solution and 1g of anhydrous sodium carbonate are added and after shaking frequently during 4h, the mixture is allowed to stand overnight. It is then transferred to a percolator and extracted , first with 100ml of the ether-chloroform mixture, then with ether itself until all alkaloid has been removed. Above color test may be used to a few drops of percolate to ascertain when the powder is exhausted. The percolate is transferred to a separating funnel and shaken with four successive portions of dilute hydrochloric acid; the acid shakings are mixed together, filtered, and the filter washed with a little more dilute hydrochloric acid. The filtrate is nearly neutralized with sodium hydroxide solution, transferred to a separation funnel, 10g of anhydrous sodium carbonate and sufficient sodium chloride to saturate the liquid are added, and the mixture is shaken until the solids are dissolved. The aqueous solution is extracted with 5 separate portions of ether, the separated and combined ether extracts allowed to stand until clear, and then decanted through a pleated filter into a beaker. The ethereal solution of the alkaloids is warmed and poured off into a flask from the crystals of sodium chloride, which usually separate at this stage. The bulk of the ether is distilled off and the remainder allowed to evaporate spontaneously without the application of heat. The alkaloid residue is dissolved in excess of deci normal (0.100N) sulfuric acid, the solution diluted with a little water and titrated with decinormal sodium hydroxide using methyl red as indicator. Each (calculated) millilitre of decinormal acid is equivalent to 0.01651g of total alkaloids calculated as ephedrine. (safe liquid for next step)

Determination of ephedrine hydrochloride.

The alkaloid liquid, after being titrated, is transferred to a separating funnel, rendered alkaline with sodium carbonate and saturated with sodium chloride. The alkaloids are extracted with several portions of ether, and later evaporated to low bulk. The alkaloids in the ethereal solution are the precipitated as hydrochlorides by rendering just acid to litmus paper with alcoholic solution of hydrogen chloride gas. This acid liquid should be introduced from a capillary tube, the ether being agitated in the meantime, thus avoiding the addition of more than the slightest excess of acid. The precipitated alkaloidal hydrochlorides are filtered off on a sintered glass crucible, washed with saturated ethereal solution of ephedrine hydrochloride, and dried at 80C. The ephedrine hydrochloride is separated from the pseudo-ephedrine hydrochloride by macerating the dried mixture with dry chloroform, which dissolves the later salt, and collecting the insoluble ephedrine hydrochloride in a tarred Gooch crucible, drying at 80C, and weighing.

Large scale extraction

Macerate the powdered herb with 0.5% aqueous solution of hydrochloric acid for several hours and then pressing out the liquor and extracting the marc a second time with more acid. The mixed extracts are filtered, neutralized with sodium carbonate, evaporated to low bulk and rendered strongly alkaline with sodium carbonate and the mixture again filtered. The filtrate is saturated with sodium chloride, the alkaloids extracted with ether, and most of the solvent removed by distillation.

The concentrated ethereal solution is carefully acidified with alcoholic solution of hydrogen chloride, the precipitated alkaloidal hydrochlorides filtered off, and dried, The pseudo-ephedrine hydrochloride is removed be treatment with dry chloroform, leaving the ephedrine hydrochloride, which can be further purified by recrystalisation from alcohol.

And finally is this odd little simple extraction series from a couple that seemed to not be very particular about the highs they subject their brains to:


From: (Tailchaser)

Date: 1995/11/08

Message-Id: <47s1ti$>

Newsgroups: alt.drugs.chemistry

[More Headers]

Ephedrine from Ma Huang

(by the insane Tailchaser and Kirsty)

We used one pound of fresh Ma Huang to do these extractions. We also tried it with one pound of dried Ma Huang as well--details follow.


(1st process)

The Ma Huang was powdered in a flour mill. (this took about ten minutes, as the mill could only deal with four ounces of herb at one time) The fine powder was placed in a four quart pyrex pot. about 750ml of grain alcohol was used to cover the powder. (for this process, we used EverClear from our local spirit hut) The pot and alcohol was allowed to warm to 90 degrees F. (don't bring to a boil, as it will destroy the ephedrine) After allowing it to "steep" for ten minutes, the pot was removed from the stove. After fifteen minutes, we filtered the mush, through a #15 gold filter with a coffee filter inside the gold filter. The mush was then set aside. The filtered solution was poured into a 1" deep sponge cake pan, covered with a cheese cloth and allowed to dry. The solution dried in 12 hours, leaving only a fine white powder, (Which the GSA at my bud's job, showed to be 70% Ephedrine, and 30% misc. (Mostly oils that the alcohol couldn't break down.)) So we Trekked back to the herb shop, and purchased another two pounds of Ma Huang. They only had one fresh, so had to buy one that was dry.


2nd process

This time, we processed the Ma in the flour mill as we did the first time, and placed it in a four quart pyrex pot. To the pot, we added 750ml of Naptha and let it soak for three days. The mush was filtered through a #15 gold filter and coffee filter as we did earlier. The naptha solution was set aside for the second batch.The mush was allowed to dry for three days. (it dried into a fine powder.) The mush was then transfered to a fresh pyrex, and covered with 750ml of grain alcohol, and allowed to soak for two days. The mush was filtered as above, and the solution was marked solution "A." The mush was then placed back into the pyrex, and covered with another 750ml of grain alcohol. this time, it was allowed to soak for one day. The mush was filtered as above, and then was trashed. The second solution, was combined with the first, and was poured into a 1" sponge cake pan to dry. It dried in one day, leaving behind a fine white powder. The analyzer at school, showed 99% Ephedrine. The total Ephedrine extracted from one pound of Ma Huang was 96grams.

We used our ephedrine as one might, and it worked beyond our expectations!


3rd process with the dried Ma Huang

We used the same method as number 2, only after the naptha and filtration and drying, we just soaked the mush once in the alcohol. After that, we filtered the mush as earlier, and threw it out. We saved the alcohol mixture in a dark brown jug.... but first poured one shot glass full into 24oz of orange juice. The two of us split the juice. WOW! I thought my heart was going to burst. I heard some of the highest pitched sounds that I didn't think could even exist. My bud had a look on her face, that was like a little kid on her first roller coaster ride.... she was stoked. Neither of us slept for two days. (you can't believe how clean our house is! nothing like time for everything) We're going to try a little more "elixer" tonight, only .5 of a shot for both of us though.

peace and fast times,


"A Cube Full Of Sugar Helps The Medicine Go Down"

Alien Hunters, destroying the hearing of America--at a bar near you!

As far as safrole is concerned, Strike's extensive dealing with the substance lets Strike know that it, and indeed every one of the reaction products that can be made from it, are soluble in methanol, ethanol, acetone, DCM, ether, benzene, tolvene, hexane.....fuck it! Every solvent but water! Strike can certainly imagine the day when Strike will take an ax to a bunch of sassafras tree bark and plop them into a tub of solvent. And you can bet your ass it will work.

Indeed, there is enough benzyalkane character in almost all amphetmine precursors for similar extraction parameters to apply.

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