Hypothetically, if one had done an acetone extraction followed by a few naptha washes to be left with a light green powder. BUT wanted to get white crystals (just to see if he can) could he return the powder to an acetone solution and run it through a DE or activated carbon to remove the remaining chlorophyll?

I found this paper that looks like it did benefit the cleaning process. Anyone more familiar with these types of papers care to verify that?

You might want to take a look at this thread.

The easiest way to remove the chlorophyll is via 99% IPA washes. Chlorophyll is very soluble in IPA, salvinorins are not (salvinorin A – 0.73mg/ml if I remember correctly). Wash the crude salvinorin A in a small quantity of IPA (less than 20ml or so), let it settle, then decant the IPA. Two or three washes yields a very clean product. (Save the IPA washes, combine them, evaporate and you can get a bit more salvinorin A out of it.)

I've done that in the past but always loose product. I was hoping to find a different way. It looks like in labs they filter it through AC/DE to get a very clean product. I'd assume with much less loss and work. Right?

If you’re processing a large enough quantity, then the loss is fairly small. It’s possible to clean a gram of salvinorin A (weight after cleaning) using about 60ml or less of IPA in 3 washes. This means a loss of about 44mg, or a percent loss of around 4%.

I assume that other methods of purification will involve some loss, but I can’t say what the percentages might be.

I read this sentence in the paper you posted:

"Compound 4 was triturated in diethyl ether, and
it was subsequently found that this is also effective for 1,
which could greatly reduce the decomposition accompany-
ing recrystallization from alcohols."

to indicate that simply washing the crude extract with diethyl ether would serve to get rid of the junk--which is essentially what gibran2 did.

I read something from Siebert (on the sagewisdom site, iirc) where quickly dipping whole leaves in chloroform resulted in >90% extraction of salvinorin-A. Since the compound is stored in trichomes on the leaf surface and chlorophyll is internal the result was a very clean product... definitely worth trying if you have chloroform.

Dipping leaves in chloroform may result in a fairly pure solution (not much chlorophyll), but I doubt that the yield would be very high (I find >90% hard to believe). So it’s a trade-off – higher purity or higher yield. The method I use involves extracting in ice-cold acetone. It pulls very little chlorophyll and (hopefully) more salvinorin A than a quick dip in chloroform.

A question: What is the solubility of salvinorin A in diethyl ether? Also, what is the solubility of chlorophyll in diethyl ether? The article makes no mention of this. Depending on solubilities, diethyl ether may be a better solvent choice over IPA, but we don’t know that for sure until someone gets solubility data.

It does sound pretty high. I guess we need someone with a stash of salvinorin-A and some chloroform to do a solubility experiment, or try it then do an acetone extraction.


Ya. I know that chlorophylls are soluble in diethyl ether, but not to what extent. Out of curiosity I compared the dipole moment of the four solvents commonly mentioned wrt salvinorin-A and noticed that a larger dipole moment corresponds (especially if you take into account that solubility in EtOH may be higher than commonly thought--Sigma-Aldrich says the solubility of salvinorin-A in EtOH is about 3mg/mL, close to the figure mentioned for MeOH and both Et and Me OH have a similar dipole moment) to higher solubility--that is unlikely to be the whole story though.

If dipole moment can be used as a guide to solubility in the light weight ketones, alcohols, and ethers the prediction would be that it is much less soluble in diethyl ether than IPA. (again) It will take someone with a big enough stash of salvinorin-A and the solvents to get more of a handle on it than guessing.

some dipole moments:
acetone 2.88D, MeOH 1.70D, EtOH 1.69D, IPA 1.56D, diethyl ether 1.14D

some others:
water 1.82D, chloroform 1.04D,
DMSO 3.96 ( salvinorin-A solubility >=10mg/mL, Sigma-Aldrich)

Thanks for the idea ThirdEyeVision. Can now report that activated carbon (AC) is effective at filtering chlorophyll out of acetone. This was tried on decanted chilled acetone crude extract (25g of microwave dried leaves which retain their green color). Used a mason jar PP funnel stuffed with AC in a nylon bag used for aquarium water filtering. Result after 1st pass through the filter:



Kept on filtering over and over and took some samples. Image below from left to right has 0x, 10x, 30x, 70x, and after a space, fresh reference acetone. After 70x passes extract looked like fresh acetone:



Bulk of the 70x filtered solution (minus the pictured partial filtered samples) is currently evaporating, along with a rinse of the filter in fresh acetone. The salvinorin may have been partially or totally filtered out too, don't know - but that is why we try. Will report back after evaporation.

PS: Don't use AC filter pads that can be cut out. The acetone destroyed them. The nylon bag held up very well.

After evaporation, white crystals where observed. Unfortunately there were also a small amount of black particles from the AC. Picture of the evaporate:



After scraping yield was low (~20mg measured, when at least 50mg were expected). Bottom line is that although the chlorophyll was removed this first attempt with AC is far from useful since we have an AC purity issue and low yield, presumably from some of the salvinorin being left in the AC filter.

Fortunately Mindlusion was in the chat and provided some ideas of what to try next. Powdered AC directly in the acetone extract followed by swirling, settling and decanting/filtering with celite. Also, trying Diatomaceous Earth to remove the chlorophyll itself.

More experiments to follow.

Chlorophyll filtration may be influenced by the sctuctures that chlorophyll (forms sometimes called micelles). Folks have studied these and proposed they can form cylinders, etc. Bellow is a proposed Chlorophyll a shape from an old paper (called P740 since it absorbed light at ~745nm). Looks large and "filterable",


Possible interpretation of P740 Chlorophyll a structure from 1986. Final understanding of the form is still being debated.

So P740 may be easier to filter out of the chilled acetone salvia crude extract if we can get it to form (I'm just guessing here, so feedback welcome). The interesting thing is that another paper studying Chlorophyll a structures in several solvent/water systems showed that P740 formed in acetone by adding water to get a 30% acetone solution and then waiting for a day,


30% Acetone/Chlorophyll a P740 formation (top) over time from a (t=0h) to d (t=24h)

Pending any feedback this may be worth trying. As usual the experiment will tell if this can ever be useful. Procedure would simply be to (partially) evaporate the acetone after the chilled extraction and decanting, then dilute with water to 30% (a guessing game if not evaporated completely since the chilled acetone will have absorbed some moisture after extraction, but I think the 30% may not have to be terribly exact), then wait for a day (color should change), then filter the larger P740 (that has hopefully formed) and hope Chlorophyll b also forms its own large structure in this environment so it is also filtered out.

Note: this is the 1st time I read these kind of papers. I'm a noob and doing a lot of guessing a here, so take the info with a grain of NaCl. Many thanks to any feedback/insights.

Papers from wich the above images are taken are shown below.

Looked into the possible color change during chlorophyll polymerization in acetone/water for easier filtration of the larger micelles. Poked at a random color applet on the net and tried to turn the acetone/water/chlorophyll absorption spectra from the last post into transmission. Result is below, looks like the color should change from green to a yellow-green if P740 forms (one of the papers above calls this the "polymer" regime)



I've got the experiment running on a small amount of crude extract (the samples taken for pictures during the 70x AC filtration experiment) with the initial pictures taken waiting to see if the color changes to something like what is shown above. Then will check if the filtration becomes easier or not.

Reading more on the subject, it seems like doing a centrifuge is a good separation technique once micelles form and is preferred over filtration. Anyone know how to build a centrifuge for quart Mason jars?.

Edit: These guys built a small centrifuge for $0.20. There may be hope for us yet.

I added water to the remaining crude extract. It was subtle, but it may have yellowed a little overtime (see attachment).

However, when I tried to filter the yellowish aged 30% acetone chlorophyll solution, it did not seem easier to filter using AC (kept on slowly getting clearer at a similar same pace as the crude acetone extract). I then tried a ghetto "centrifuge" with my bike tire, but that did not work. I think I only got to 400rpm, while labs use machines that go to 4000rpm or more (a quick search on had examples with 15000rpm) to separate chlorophyll.

So sorry to report that there is no positive progress when trying to separate the (supposedly) polymerized chlorophyll.

One thing left is the celite filtration. However, there is a risk of handling it if the dry dust is inhaled due to the crystallized silica I believe. There is also the boiling IPA re-x path discussed in gibran's purification thread which mindlusion suggested, I think I'll move to that next.