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Supercritical Butane Salv-A Extraction

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[This message has been edited by electro (edited 13 October 2002).]

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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alkaloids are generally present as salts in the plant (they don't move in oils, but in water), so you would need to basify the material before butane extracting it. this is not easy. you could powder the material and wet it with ammonia solution, then dry it and then butane extract. doesn't sound quite as attractive anymore wink.gif

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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salv A is not soluble in butane, butane is WAY too non-polar. Anything less polar than methanol is pushing it a bit. Same applies to the other compound. Also butane should be a VERY poor solvent for freebase DMT. DMT really is more polar than most people think. You also should remember that in those butane extractions the butane acts as a low order explosive that creeps around until it finds a spark and then KABOOOM, end of story.

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You also should remember that in those butane extractions the butane acts as a low order explosive that creeps around until it finds a spark and then KABOOOM, end of story.

Best to vent any solvent properly.

Acetone (& oxygen) makes a nasty explosive mixture.

When I was about seven I used about 30ml of acetone to help light an old pot belly fire.

Lucky for me I flicked the match in (like in the movies biggrin.gif )

BANG!

It literally blew the iron door off the hinges, several pieces of kindling & much ash into the room.

I almost pissed myself redface.gif

Butane extraction may clean some of the crap out of the salvia, athough it'd probably be a waste.

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Originally posted by Torsten:

alkaloids are generally present as salts in the plant (they don't move in oils, but in water),

(Just to avoid any confusion, salvinorin isn't an alkaloid, but cathinone and DMT are). Torsten, I think you may have your facts about the natural state of alkaloids back the front there. Otherwise, extraction would be all too easy - just boil up your herb/grass/bark/whatever in water! To complicate matters further, I believe that some substances such as morphine are found naturally as _both_ the base and the salt. Judicious use of a solvent such as an alcohol allows you to extract both at once, but this unfortunately doesn't apply to all alkaloids.

Another consideration is that even if you have got some natural salt in there, you might not necessarily like it on the grounds of storage stability. This is usually because the acid that the alkaloid is partnered with is organic and is too weak. This applies particularly to cathinone, which is notoriously unstable. I must admit that I am not even sure what the usual protocol is for extracting it.

 

so you would need to basify the material before butane extracting it. this is not easy. you could powder the material and wet it with ammonia solution, then dry it and then butane extract. doesn't sound quite as attractive anymore   wink.gif

I would add here that using ammonia to basify is not generally a great idea if you are trying to perform a _liquid_ acid-base extraction in a separating funnel (which is the most common method), because you then wind up with two amines in solution instead of the one that you want. It is more usual to use something like a bicarbonate solution (for a weak base) or a hydroxide solution (for a strong base). Both have their merits, depending on the characteristics and the stability of both the substance of interest, and any other junk that is likely to be in there that you wish to avoid.

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Originally posted by John_Barleycorn:

Torsten, I think you may have your facts about the natural state of alkaloids back the front there. Otherwise, extraction would be all too easy - just boil up your herb/grass/bark/whatever in water!

Na, haven't got things back to front. Most plants are just under pH 7 and their alkaloids are usually present in a mix of base and salt, but with salt being the majority in most cases. obviously there are some plants that are very alkaline and these woudl usually have mostly freebase. In many cases they also contain a latex which acts as the amine base carrier. The reason why most people add acid or base to the extraction is to make sure that ALL amine is one state or the other.

I would add here that using ammonia to basify is not generally a great idea if you are trying to perform a _liquid_ acid-base extraction in a separating funnel (which is the most common method), because you then wind up with two amines in solution instead of the one that you want.

ammonia is perfect unless you intend to separate the amine out of the acid phase. As ammonia is a gas it will be driven off in any process that involves evaporating solvent.

It is more usual to use something like a bicarbonate solution (for a weak base) or a hydroxide solution (for a strong base).

carbonates add a lot of salt loading to the procedure and can cause further problems (and will require further washings). But yes, for delicate alkaloids this is the way to go.

Hydroxide causes a whole other array of probems in liquid extractions, primarily unbreakable emulsion layers.

Both have their merits, depending on the characteristics

That's really what it boils down to. Each group (or even individual alkaloid) will have different needs.

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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"(following the principle that polar substances are soluble in non polar solvents & vice versa)"- electro

You got it backwards, polar is soluble in polar. Non-polar is soluble in non-polar.

Thats why oil (non-polar) is not soluble in water (polar). Just follow the rule that like dissolves like.

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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The salts in plants may not be very soluble, the phytates for example.

AND IT IS NOT SUPERCRITICAL BUTANE. You would need some heavy engineering to contain the pressures necessary for supercriticality not a can of lighter fluid. Liquid butane or butane under pressure or pressurised liquid butane. Supercritical sounds wonderful but is wrong.

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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Originally posted by electro:

Is anyone familiar with the solubility of Salv A and/or cathinone ?

If so this would make extraction of both these chemicals much simpler, and would produce a safer end product whilst still using readily available solvents.

Here's some entirely speculative ideas about a quick-and-dirty cathinone extract preparation which uses over-the-counter solvents and avoids messing around with separating funnels. Anyone with access to fresh plant material, please feel free to try it and report back.

The general principle here is that we don't want free-base cathinone sitting around by itself and deteriorating. In fact, that could be enough of a reason to avoid the acid-base extraction route altogether, provided that you are not after snorting-grade product. As always, only try this in countries where it does not contravene local laws.

1. Freeze fresh khat leaves overnight in order to rupture the cells and make extraction easier.

2. Puree the leaves up in some 100% ethanol (eg, metho) to which a very small amount of concentrated (35%)hydrochloric acid has been added (available from hardware or pool supply shops). The idea here is to steep the leaves for a couple of weeks whilst maintaining an acid environment - pH of about 5 or so. Alcohol is used instead of water because it probably penetrates the leaves more effectively, and also in order to reduce the extraction of green chlorophyll and other water-solubles. Obviously, the fresh leaves are going to contribute some water and that can't be avoided. Methanol for once is _not_ recommended because of its racemising effects on ketones such as cathinone. A generally wise strategy is to perform the extraction in a sealed vessel out of the light.

3. Strain and collect the product, then filter it through paper, and repeat the extraction process twice more. The steeping can probably go on for days instead of weeks the second time around. Also, you may find that you don't need to add too much acid the second time around. If the solution tastes tangy, it's acidic, but preferably use pH papers (available from pool supply or winemaking shops).

4. Combine all three extracts and let the liquid evaporate overnight. You will probably wind up with a resinous goo. Finish the drying process off with a hairdryer or a low (100C) oven in order to get rid of as much water as possible.

5. (This step is kind of optional, but recommended if you are conscientious. We are trying to lose more water solubles). Dry some 100% ethanol by adding some Epsom salts (MgSO4) which have been baked in the oven on high for a couple of hours, and allowed to steep overnight, with the odd shake. The salts should sink to the bottom of the bottle. Redissolve the product in the ethanol by giving it a couple of days to work in, in an airtight vessel, with the odd shake. Some mild heating could be applied to help the process, if you can work out a way of doing this. Discard anything which doesn't remain dissolved at room temperature, which may not necessarily be all that much. Evaporate the ethanol down again to yield a hopefully more refined product.

6. Dry some acetone by the same method as previously. The idea here is to use the acetone to (a) wash all the excess acid out of the product, and (B) hopefully pull out some of the organic tars as well, so that the consistency becomes more manageable. Once again, it may very well be that the acetone needs a couple of days to work in. But this time around, we want to keep the insoluble part, because that should contain the goodies. It could also be a good idea to keep the acetone fraction and evaporate that down, just to check whether there is anything useful in there.

The final product should be some viscous, off-coloured substance which contains HCl salts of cathinone, cathine and ephedrine. It could be eaten as is, or maybe redissolved in something like vodka. If the gods are smiling, the product could be smokable in a vapouriser. And if the gods are really smiling, the consistency could be more like a solid.

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"Dry some 100% ethanol by adding some Epsom salts (MgSO4)... baked... oven"- John_Barleycorn

BAD MOVE. Anhydrous magnesium sulfate is moderatly soluble in ethanol. Sure it would dry out the ethanol most the way, but after evaporating the ethanol the majority of your product would be magnesium sulfate! Very counterproductive.

Also MgSO4 signifies the anhydrous magnesium sulfate (ie. after baking). Epsom salts is MgSO4.7H2O. When baking this stuff watch out for boiling (start it at 300 F and crank it up to 450 F after an hour or so [to minimize splattering.])

"alcohol is used... to reduce the extraction of green chlorophyll and other water-solubles."- John_Barleycorn

Actually chlorophyll is soluble in alcohol and nearly insoluble in water, so you will be extracting FAR FAR more chlorophyll than if water were used.

"If the solution tastes tangy, it's acidic"

That rule only really applies to weak organic acids, not HCl. And even when weak organic acids are neutralized they can still taste quite tangy, so yeah- use pH indicator. Red cabbage juice is a great pH indicator that doesn't arouse suspicion, make little ice cubes out of it and it'll stay good for a long time.

Your idea needs a little work, but when you get the bugs worked out it could prove to be a useful procedure.

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Originally posted by Auxin:

BAD MOVE. Anhydrous magnesium sulfate is moderatly soluble in ethanol. Sure it would dry out the ethanol most the way, but after evaporating the ethanol the majority of your product would be magnesium sulfate! Very counterproductive.

Can you suggest a better, readily available drying agent for the casual shaman chemist? Note that I am only advocating drying comparatively small volumes of solvent, after the main plant material has been extracted. Calcium chloride (aka Damp Rid) is grossly unsuitable. All I can think of as an alternative is silica or polymer gels.

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Hey John_Barleycorn, maby the drying agent your looking for is plaster of paris (CaSO4.1/2H2O), you can find it in powdered form in many hardware stores. If you want to give it that extra little boost you can bake it above 165 C to make it into anhydrous CaSO4, thats also how you regenerate it after use (let any flammable solvents evaporate first). The cool thing about it is thats its insoluble in organic solvents, only slightly soluble in water (to the extent of about 0.25%), and it hardly reacts with anything- except water of course smile.gif

I personally try to avoid using the powder form, so I make a smooth paste with water, spread it out thin, let it dry, then crunch it up and bake it at 200 C for 4 hrs+.

It'll absorb about 20% its weight in water, maximum. Also it leaves less residual water than most others.

ALSO- After absorbing its fill in water it becomes gypsum (CaSO4.2H2O). Sometimes you can get pure gypsum granules or pebbles in the soil amendments isle in the hardware store. Just bake off the water ( around 200 C for 4 to 8 hrs) and you'll have the same thing with less trouble. Gypsum might be a little less pure, so you might want to soak it in water first to extract any chemical dust that might have found its way in.

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Cool, thanks for the tip on CaSO4.

As for putting a bit more work in on the process, it occurs to me that I probably stopped too early. All the goodies should be water soluble, so that means in principle that the product as described above could be stirred into a cup of coffee for that "extra wired" effect smile.gif In practice, it could possibly take a couple of days to dissolve, and that actually leads to a final refinement: dissolve viscous crude product in water (maybe with the aid of some boiling), let cool, filter, and evaporate. The odds of obtaining something reasonably solid this time around should be improved.

For those who have been intimated by the lengthy previous instructions, bear in mind that most of it is explanation of the reasoning. In concise terms, what I am suggesting is simply this:

1. Extract fresh frozen khat leaves into acidified ethanol.

2. Optionally, re-extract crude product into ethanol.

3. Wash crude product in acetone.

4. Re-extract crude product into water.

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More refinement of the process (don't you just love thought experiments)?

The optional step 2 above is a cludge. It is there to get around the problems caused by the water that is present in fresh leaves. But there is a simpler method than driving off the water by evaporation and then re-extracting into some alcohol. It would be far easier to take the initial, filtered ethanol extract, add some drying agent to cause the water solubles to crash out of solution, and then filter out the entire precipitate.

Like I kind of implied before, this may not necessarily achieve much. Almost all the candidate water solubles that I can think of (like sugars, starches, proteins and chlorophyll) are also soluble to a greater or lesser extent in alcohol. So dragging the water out is likely to boot a number of these substances into the ethanol. One variation might be to reduce the volume of the ethanol before applying the drying technique. The danger here, however, is that we don't want to reduce the volume to such an extent that the alkaloid salts themselves also start to crash out of solution. Clear as mud?

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Guest electro

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[This message has been edited by electro (edited 13 October 2002).]

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Vodka would do in a pinch if you don't like using denatured ethanol (metho). The 60% water content will pull out more water solubles though. Similarly, white vinegar could do as well, and you _might_ get away with not having to use HCl. I say "might" because I am not totally sure that vinegar would be a strong enough acid to react with the natural alkaloid bases and acids. And the salt formed from the vinegar, cathinone acetate, is probably not stable for storage.

Alcohol has the additional advantage that it might inhibit some of the fresh plant enzymes which lead to degradation of the goodies.

Naptha is OK as a defatter, but won't wash out any excess acid. It could be worth experimenting with washes of both naptha and acetone to see if that eliminates any more of the undesirables.

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Due to the instability of cathinone you would have to do this as quickly as possible. Two weeks sitting and soaking would not be an option. The fresh leaves liquidised with a powerful liquidiser with the solvents and filtered within minutes would be a better way.

Heat is also a bad idea. A huge volume of pressurised (dry) CO2 bubbled through an ethnaol/water mixture will, apparently, remove the ethanol at room temperature. This is purely theory, I haven't tried it.

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Originally posted by theobromos:

Due to the instability of cathinone you would have to do this as quickly as possible.  Two weeks sitting and soaking would not be an option.

But my speculation is that the moment the free base contacts the solvent, it will be converted into a strong acid salt, and hence will be more stable. Or am I missing something here, like that the alcohol won't penetrate the cells fast enough? Or that protic solvents are a problem?

I should add that this method could be adapted (possibly more successfully) for phalaris extraction, for those who don't wish to go the acid-base extraction route. Once again, there seems to be a suggestion that dried phalaris loses potency, and so extracting fresh material into an acidified, alcoholic medium could have some merit. At the very least, I would speculate that extraction into white vinegar (ie, 5% acetic acid) would be an improvement on the "boil it up with some lemon juice" method.

I suspect that one reason a lot of people are disappointed with phalaris is that they are leaving a good proportion of the goodies behind in the plant material. (This is apart from the bigger issue of whether phalaris, acacia, mimosa bark, etc, all contain the same active substances).

[This message has been edited by John_Barleycorn (edited 20 August 2002).]

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Originally posted by theobromos:

A huge volume of pressurised (dry) CO2 bubbled through an ethnaol/water mixture will, apparently, remove the ethanol at room temperature. This is purely theory, I haven't tried it. [/b]

would you be kind enough to expand upon this? ie theory, method/setup, etc.

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The dry salt may be more stable but imine formation occurs with salts of amines in solution as well as freebase, doesn't it?

The CO2 procedure needs a fine bubble of lots of CO2 and the liquid being heated continuously as the expanding gas cools it. Ideally the alcohol mixture needs to be at about room temperature. This would need a strong heater which is well-controlled, as the CO2 drags a lot of heat out very fast. Safety and efficiency are matters for the engineer, they need much thought. CO2 will asphyxiate one to death if not extracted from the workroom, for example.

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