LSA Extraction

[eeroborroc]

Can the degradedation of the extracted LSA from air and light be stopped/slowed by redissolving it in another drinkable alcoholic solution and storing in a dark place? Or would the LSA degrade over time regardless of its environment?

[cookie-monster]

Actually water is considerably more polar than alcohols. The longer the carbon chain in the alcohol the less polar the solvent becomes.

Degradation would have to increase with increasing temp. So the higher the boiling point of the solvent the more degradation when evaporating. If you have enough apparatus to seal your evaporation vessel a cheap plastic water aspirator (10 bucks on ebay) would allow you to remove water at about 40 degrees.

Storage of extracts is just not worthwhile because of degradation and any solvent would probably speed this up. The losses are too extreme to justify the convienience. Better to prepare fresh as required. Instead of doing a full extraction what about simply preparing a tea when required?

[John_Barleycorn]

cookie-monster:

Acetone is excellent as a plant extraction solvent although it can be a little nonspecific, removing a lot more compounds from the plant tissue than ROHs or H2O. It is very clean in its industrial form, evaporating without residue and at low temperature. If the goal is simply to extract the LSAs it should be good. If you are processing the extract to a pure sample of LSA the array of compounds it extracts may make separation tedious.

I don't have a Merck in front of me, but asking amides to dissolve in a ketone is pushing things a little IMHO. Another reservation about acetone as a general-purpose solvent is the potential for a reaction between ketones and alkaloid base. I guess it all depends on what you have in your starting material, and any pH manipulations.

[John_Barleycorn]

d0tb0y/n00dle:

the denaturant is MIBK - methy isobutyl ketone i believe - it is pretty darn non toxic, i believe, and won't really effect you. Check an msds.

As I have speculated previously, it may be possible to remove ketones like MIBK and MEK from denatured EtOH using a metabisulphite reaction to drag them out of solution. A bit of playing around indicates that the filtered solution smells of SO2 - whether it also has some dissolved bisulphite is hard to tell. Whether that SO2 would still be there after a distillation is another interesting question.

OTOH, some SO2 may not be a bad thing to have - as it acts as an antioxidant. If you were to strip off the solvent in the presence of O2 and H20, you would ultimately wind up with a small amount of Na2SO4 in the product, which is reasonably innocuous.

[Torsten]

to remove SO2 it shoud work to simply add a *little* NaOH and redistill.

[Guest d0tb0y]

Just out of curiosity, what is a bottle of purish alcohol worth to you guys? Say, 95%/5%water (standard azeotrope) and 100% dry un-denatured EtOh.

[bloodbob]

Well the 100% is useless to me I don't have inert chamber to work in. Now when you say the azeotropic undenatured is that me with or without a ATO lisence

[Guest d0tb0y]

Just curious what'd you pay for say, 1L of 95% undenatured alcohol. Including if you bought it at a chem supply place.

[ 19. February 2005, 21:35: Message edited by: d0tb0y/n00dle ]

[teonanacatl]

ok i admit i just skimmed through all the posts but this maybe of use and may not be but its interesting. its from the road to eleusis by wasson hofmann and ruck.

wasson asked hofmann if early man in ancient greece could have found a simple method to extract from ergot alkaloids that would give the lsd experience without the side effects.

claviceps growing on wheat and barley contains ergotamine and ergotoine group, ergonovine and sometimes traces of lysergic acid amide. ergonivine and lysergic acid amide are both hallucinogenic and both are water soluble whilst the others are not. claviceps paspali growing on paspalum distichum contains only the alkaloids which are hallucinogenic meaning people could just use it in powder form.

ergonovine which is used now to stop post partum haemorrhage is also hallucinogenic and hofmann describes his experience in the book with 2mg ergonovine hydrogenmaleinate containing 1.5mg ergonovine base ingested in a glass of water. the effects last 10 hours. could be whats on acid blotters making them shit.

anyway the bit of interest. morning glory seeds were tested and the main constituents were lysergic acid amide ( ergine) and lysergic acid hydroxyethlamide, these are also the main alkaloids in ergot growing on paspalum distichum. this would appear to me that they are reletivly pure in mg seeds and a water extraction would be simple and effective. how long do mg seeds keep their potency??? was it ever concluded that the LSA in mg seeds was from a ergot releated fungus???

[Guest d0tb0y]

the best LSA extraction (in regards to purity, not yeilds) that i know of is simply placing the crushed seedpowder into water for exactly 120 seconds and then removing.

Apparently this is the best purity method. Not sure if you'd get a lot out of it though.

If you need pretty good purity but need high yeilds probably best to sort out some chromotography gear.

But if you're looking to extract LSA with that kind of purity, using chromo columns, you probably shouldn't be talking about it here.

[apothecary]

I doubt that the LSA in Ipomea spp. or Argyeria Nervosa is from ergot fungus.

Doesn't ergot fungus completely "consume" whatever it infects? That would imply that psychoactive Ipomea spp. seeds, etc wouldn't be viable for germination, which isn't true.

[mescalito]

Noodleboy-For us dumbasses out here why exactly 120 seconds?

I figure it's a kitchen tek based on solubilty vs time to get a reasonable extract without too much in unwanted chems vs a loss factor of actives...am I close?

[ 20. February 2005, 20:10: Message edited by: Maca ]

[teonanacatl]

hmm i shouldnt have said ergot. there was a post awhile ago by fractal saying that the lsa in seeds could be from a fungus. this will not nesserially mean unviable, symbiosis. but then it could also beproduced by the plant, im not backing either.

[2b]

Fractal posted this:

http://www.shaman-australis.com.au/cgi-bin...t=001805#000000

Pretty sure that LSA was not a result of some funi symbiotic relationship seems the plant just makes it.

[Zu]

d0tb0y/n00dle:

the best LSA extraction (in regards to purity, not yeilds) that i know of is simply placing the crushed seedpowder into water for exactly 120 seconds and then removing.

I've found that water extractions cause more sedation and a less intense experience than just grinding and swallowing the seeds (HBWR). So although it diminished some of the nausea it also diminished the experience.

[apothecary]

Zu, the above is definitely because not all the amides are water soluble, and if you throw away the seeds you end up with only the VERY water soluble ones.

[cookie-monster]

Lower amides are very soluble in water. The higher amides are sparingly soluble but the very high ratio of water to amide ensures they are extracted. The solvated lower amides also serve to encourage the higher amides into the solution. A little heat will also help their solubility.

Acetone is extremely effective at non-specific extractions provided it is compatible. If the material is dried a little water will help increase solubilities in the acetone. I have no idea if acetone reacts directly with LSAs but I doubt it would. The big advantage to using an alcohol or lower ketone is the rapid evaporation at room temp. Using heat to evaporate the water is going to create very harsh conditions for this and any other unstable amides.

Why does everyone doubt the purity of OTC methanol???? It is sold for high performance engines and needs to be very pure to prevent damage to the engines. It is dirt cheap too at around $33 per 20 litres. Anywhere that sells it will also supply you an MSDS that applies to the actual product being sold. This will confirm the purity.

Methylated spirits is not a formula set in stone. There are many different denaturants used. Most today contain MIBK only but the only way to know whats in a particular brand is to source the MSDS for that particular brand. An MSDS has to be available on request by law.

[Amulte]

I know this is an old thread but one small chemistry lession if i may.

there are three types of polar solvent. non-polar(petrolium ether[distilate]) Di-polar (isoprophenol alchol & distillates therof) and Polar (Water or drinking grade high proof alchol)

BTW the local hydroshop stocks 98%extraction ethanol(1%almond oil & 1%camomile oil)

Non-polar solvents are highly carcnagenic

Di-polar solvent are highly toxic

Both leave residue and i have seen results from poor extractions when i used to work in a ED. Toxicoligy of solvents varies whereas in polar solvents they are constant if any

[Fractalhead]

On a more general note regarding LEGAL alkaloid extractions... I think ion-exchange resin based alkaloid extractions could overcome the challenges encountered with many of the trickier (unstable) compounds. These systems allow the concentration of alkaloids in large volumes of aqueous solution without the need to use proportionally large volumes of nasty (hazardous) organic solvents, and all at low temps and potentially under an inert atmosphere. It is my guess that it is usually in this phase of alkaloid extractions that most of the alkaloid-degradation happens since it is common to boil the material for a long time to extract and then concentrate the aqueous extract down to a manageable volume. This is obviously a big no no for our more sensitive friends. Even the use of lower boiling solvents requires *some* heating.

I've seen some great designs for in-field alkaloid extractions of curare alkaloids, quinine, scopolamine and nicotine. In these systems the plant material is put into what is effectively a big tank with a filter at the bottom and (acidic) water percolated down through the plant material like a giant espresso machine. The filtrate containing some dissolved alkaloid salts is pumped through a column of cation exchange resin and when the water comes out the end, all the alkaloids have been adsorbed by the resin and hence the water only contains non-ionic and anionic compounds. This effluent is cycled back over the plant material and more alkaloids are extracted and the cycle goes round and round for a few hours until the plant material is exhausted or the resin becomes saturated. The column is then washed with an alkaline solution like NaOH or NH4OH to freebase the alkaloids which precipitate in the column. All the non cationic crap is then washed out with water and the clean alkaloids eluted with an appropriate organic solvent. Pretty cool, I thought

[apothecary]

Pretty cool, and I'd imagine fucking expensive

I'm not sure what started this thread, but goddamn has it turned into a compendium on LSA extraction hehehe.

[nabraxas]

fractalhead--ion-exchange resin based alkaloid extractions--never heard ov this before, but i think you're right, it does sound cool.

is this equipment expensive? do you have any links about its use?

[Torsten]

the best thing about these resins is that they are reusable after a bit of clean up. I think they will be the way ahead for difficult extractions like yohimbine and other alkaloids that are barely water soluble as salts.

[Fractalhead]

The actual plumbing wouldn't have to be expensive as you could probably build this yourself out of bits and pieces from the hardware store (nothing too complicated). A submersible water pump would probably suffice for the cycling of aqueous solutions. I'm beginning to look into various options for ion-exchange materials. Yes, some of the new synthetic resins have extremely high binding capacity, consistent properties and high purity but can get extremely expensive. I think you might be able to get away with the much cheaper option of some kind natural ion-exchange material like sulfonated coal or a zeolite based filter like the stuff used in water purification.

Maybe a good option would be to extract the bulk alkaloids on a cheap resin and then fractionate them on a smaller column of high quality resin using a pH gradient.

But yeah, like Torsten says, you can reuse these resins heaps of times by just converting them back to their protonated forms by washing with a cheap inorganic acid.

I guess this is one example of a situation where we can make an effort to embrace the principles of green chemistry while opening up feasible extraction pathways to a wider range of useful compounds (ie. legal ones).

[teonanacatl]

if your looking for somthing with a high cation exchange capacity you could try fulvic acid

[Auxin]

teonanacatl:

if your looking for somthing with a high cation exchange capacity you could try fulvic acid

Fulvic acid is water soluable, and hard to isolate in pure form, humic acid is insoluable in water (soluable as humate) and can be made very cheaply and easily (to someone who knows some basic chemistry techniques)... its a growth promoter/mineral chelator in plants, I make it from used potting soil, lye, ammonia, and hydrochloric acid. I admit the thought of using it to capture alkaloids never entered my mind- its a very interesting concept! I'm not sure if its strong enough of a acid to capture weak bases, but ammonium humate is stable- even as a solid obtained from evap of concentrated ammonium humate solution... so if you had a strongly basic alkaloid and extracted it with a acid weaker then humic acid the humic acid would capture the alkaloid- hopefully remaining non-water soluable, that might be the hard part- if it formed a water soluable compound with the alkaloid in question youd be in trouble... hmmm I got a buttload of quinine and a fair amount of humic acid- I might investigate this.