cerberus1983
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Alkaloid Extraction Confirmation?
Im an amateur chemist interested in learning the basics...
Id like confirmation that the post found below would be an effective alkaloid extraction technique. Pls note that i am aware that an acid/base
extraction would be a more comprehensive technique, but my question relateds specifically to whether or not THIS technique would go at least some way
towards purification
(id also like it to be known that i have no interest whatsoever in drug production, the post just happened to be related to LSA. To be honest i dont
even know what LSA is)
The full post can be found at totse.com
Thanks
Date: 08 Aug 1992 17:53:37 -0500 (CDT)
From: mike@penguin.gatech.edu
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.
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solo
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Totse is not known for a great information source.....try reading something from a more reputable place......solo
http://nepenthes.lycaeum.org/Extraction/extract1.html
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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not_important
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Also, in your case, the target materials are sensitive to strong acid, light, and oxygen. Foil wrapped around glassware, amber or opaque containers,
CO2 or N2 flow when evaporating, all might be needed.
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Sauron
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Well, he didn't really come out and say just what his alkaloid is, did he? He just threw down this half-assed lysergic acid extraction procedure as an
example of what he apparently things is appropriate.
Kind of silly when even Rhodium has better information on the subject, assuming that ergot alkaloids are what he has in mind.
He really ought to be reading the tale of the Brit chemist who DEA busted in an old missile silo in the midwest. Supplier to the Deadheads, now
serving a life sentence.
Crime doesn'y pay...enough.
Sic gorgeamus a los subjectatus nunc.
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Nicodem
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| Quote: | Originally posted by Sauron
Well, he didn't really come out and say just what his alkaloid is, did he? |
Well, actually in his previous posts he did say what alkaloids he is after. Assuming, his interests are still the same he is trying to extract the
mixture of pyrrolizidine-type toxins from Symphytum species.
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Sauron
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Right. That is why out of all the extraction procedures available in the lit. and on the net, he lighted on this one for LSA.
Curious, isn't it?
I'd advise him to go looking for a procedure much more akin to his target compound than morning glory seed extraction or that of Hawaiian woodrose
seeds. I mean, what's next, electric bananas? I was around for the morning glory seed thing. The 60s are dead. Half a century dead.
But now that you mention it, I recall a different thread about a plant with desirable medicinal properties that was unfortunately also containing this
same heterocyclic alkaloid, and the poster was looking for a way to detoxify the plant.
Sorry, I'm afraid that any pet.ether/ethanol sequence is likely to extract the baby along with the bathwater.
Any conceivable detoxification regime is going to involve, most likely, sophisticated high performance liquid chromatography on a prep scale for
anything from mgs to grams. That is after substantial investment of time in method development. It does not sound as if this fellow has the equipment
or the expertise required.
Am I mistaken that this is same poster?
[Edited on 19-2-2008 by Sauron]
Sic gorgeamus a los subjectatus nunc.
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chemrox
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The general procedure is outlined very simply in Orgnic Chemistry Survival Manual. The process there assumes nothing; that acids, bases (alkaloids)
and neutrals may be present.
If you're only interested in alkaloids, you have to decide whether to extract with acid or solvent first. It depends on the matrix and extraction
methods. Is the alkaloid temperature or light sensitive? Is it it in leafy, hard or fleshy material ? My firt inclination would be to use a more or
less 'universal' solvent like DCM or ether and a sohxlet extractor. Cruder approaches involve simply soaking in solvent. Once the material is in the
solvent, extract with acid, neutralize, extract again in solvent and isolate by removing the solvent.
Don't neglect critical fluid approaches- I'm really stoked on these.
If you're in the US you're in a police state. Act accordingly.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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Ephoton
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sorry sauron bear only did three years and is now free.
e3500 console login: root
bash-2.05#
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Rich_Insane
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LSA is an amine (lysergic acid amine). It's the good stuff in morning glory seeds. The structure doesn't contain too many polar-friendly areas. Its
mostly nitrogen and carbon. The amine might allow an A/B extracion. The LSA will probably be soluble in iPr alcohol or EtOH. I would use DCM or CHCl3
to get rid of all those lipid nasties that you don't want. I also know that celllulose can become soluble after being exposed to sulfuric acid
(apparently one person in the lab I work in solubilizes cellulose by exposing it to ~60% H2SO4, conc H2SO4 will likely cause dehydration of the
cellulose, as it is a polysaccharide). Avoid H2SO4. If you want to do an A/B extraction, use HCl (so you don't end up with charred cellulose in your
product).
To extract the LSA after DCM or CHCl3, I would use an alcohol like iPr, Et, or n-propyl alcohol to extract the LSA. Just blow a stream of nitrogen or
air over the mixture to evap. the solvent.
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zed
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Ah, Rich_Insane, it's been awhile since I've caught one of your posts. Alive! Good, good, good.
Rumor has it, that the highest content of Lysergic Acid type alkaloids, found in plants, is found in "Sleepy Grass". Grows wild, if you are in the
right part of the US, you can harvest it yourself. And, somewhere out there on the web, I found what looked like a Scientifically generated
extraction procedure.
Yield weren't super high. But as I recall, a few kilos (10?) of raw material, actually yielded a few grams of raw alkaloids.
Maybe I can relocate the paper........Yup! Found it. Isolated yield from the whole dried Grass......35 micrograms of ergonovine, LSA and isoLSA, from
each gram. That would only be 35,000 micrograms/Kilo, or 350,000 micrograms from 10 Kilos. Probably need ~30+ Kilos of dried grass to produce
1,000,000 micrograms lysergic acid. 1 gram. Though supposedly Alkaloids are much more concentrated in the seeds.
http://ddr.nal.usda.gov/bitstream/10113/25252/1/IND20401948....
[Edited on 9-9-2010 by zed]
[Edited on 9-9-2010 by zed]
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DDTea
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It's an amide. Lysergic Acid Amide. Unless I'm forgetting something, which I tend to do, Acid/Base extraction will not work.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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jon
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no it's an amine as well as an amide it has the piperidine nitrogen (amine) and in the same ring D and amide positioned at c-8
a little off topic but, how do these compounds respond to acids?
i was under the impression that in basic solution you have to worry about two thing well really 3 epimerization if the ph approaches 9 or there is
localized high ph, oxidation upon slight temperature increase and emphasize slight like 90 F
and addition of water to the 9-10 conjugated double bond.
on the topic of sleepy grass there is an asian variety stipa inebrieans which yeilds a gross of 3 grams of alkaloids per kilogram.
the reason for my inquiry is i was curious how these compounds stand up to mixtures of lewis acids at room temperature.
i suspect the 9-10 double bond is very labile and could add bronstead acids easily and lewis acids could possibly cause double bond rearrangement.
am i wrong?
[Edited on 6-10-2010 by jon]
[Edited on 6-10-2010 by jon]
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symboom
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Morning glories glow under blacklight
Lsa glows under backlight which is interesting
And useful as extraction
https://www.reddit.com/r/LSA/comments/4alzkj/500_hbwr_seeds_...
500 hawaiian baby wood rose seeds
Lsa glows under blacklight
[Edited on 6-2-2018 by symboom]
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