LSA extraction

[lycaeumblik]

Hello,

1) Extracted 500 HBWR in anhydrous MeOH for 7 days.
2) Evaporated filtrate under vacuum, resulting in orange oily substance and a bit of seed material
3) Redissolved in ddH20, easily dissolved with some shaking / agitation. Extract turned white-ish. When fully dissolved solution looked akin to a colloid of absinth and water with slight green hint.
4) Proceeded to filter this, and resulting solution was relatively clear but still retained green tint.
5) Solution was basified with 1ml of 1N NaOH
6) Solute was mixed with half the volume of chloroform
7) Organic layer was dried under vacuum to yield white crystals.

Now this is where SWIM had some what of a brain fart

8) tried to redissolve in ddH20 and absolute EtOH (2:1)
9) extract was almost completely insoluble.
10) acidified to try to increase solubility with 1N HCL, with no observable change in solubility
11) basified with 5N NaOH, and had a slight increase in solubility with the water layer developing a slight green tinge.
12) added xylene to extract freebase (1:2), and remaining extract easily dissolved in organic layer.

So at this point, SWIM thinks the actives are still in the organic phase. Any suggestions on next steps? I was going to isolate the organic phase, treat with dilute HCL, and evaporate off solvent. Im assuming that the result of which will be much more soluble in ddH20 and EtOH. What do you think?

 

[benzyme]

I think

a) quit SWIMming. this isn't 1999.
b) be wary of lumi-compound formation (hydroxylation at the 10-position..this occurs at high pH, >10).

kidding about a) (but not really. nexians tend to frown upon that acronym, it's just unnecessary, like YOLO).

 

[frobot]

I am here for exactly the same problem. I was going to make a post about it but figured I'd see if anyone else had this happen first.

My uncle's friend followed kash's tek. PH levels were right and measured with an accurate PH meter. He used toluene for the final step. This evaporated leaving very pure looking white crystals.
He wanted to dissolve them and drink them with peppermint oil but found that they would not dissolve in water or ethanol even after long periods of shaking it up.
Now he feels uncertain if he should ingest them.

 

[benzyme]

that doesn't seem like lsa.

try to dissolve it in ethanol again, and shine a blacklight on it. it should glow something like this

 

[frobot]

As far as I can see he followed the steps perfectly and the product glows just like that under blacklight, but will not dissolve in 151 proof everclear even when submerged and shook.

This is before being scraped up:

This is after being scraped:

He didn't send me a pic of it in liquid but said that it glowed just like the picture you posted.

 

[benzyme]

next step is characterization

when ehrlich's reagent is added to the analyte, it should leave a purplish-blue hue, something like this

a m.p. test may also be conducted. ergine melts/decomposes at 242C

 

[frobot]

Many thanks.
The only theories I have for it not being LSA is that the toluene was really impure and my uncles friend scraped up a bunch of residue. He thinks that is very unlikely though.
Also the steps that involved acidifying and basing the solutions were done over long periods of time because of a lack of separation funnel or proper syringe. They were done correctly, just took a long time. Could this result in some kind of "ultra super mega salt of doom"?

 

[Winemaker]

I'm sorry if this is a bit of a hijack, but if the seeds are active when chewed/swallowed, then why go to the trouble of extracting?

 

[frobot]

Three reasons I can think of
1. The seeds make most people very sick
2. The taste is pretty gnarly
3. Extractions are fun!

 

[Winemaker]

LOL okay yeah that makes sense.

 

[frobot]

Reporting back after he got some ehrlich's reagent, did a melting point test, and also did a 2nd extraction -
the product seemed to pass the melting point test (he only had an oven available to test this)
it also turned the bluish-purple color with the reagent, no doubt about it.
And last but not least, the ingestion test. He said it gave him the experience LSA usually does.

I might know what the solubility problem was though.
He added tartaric acid to the final product and unknowingly made LSA-tartrate.
Still might be odd though because from the small amount of info I can find on LSA-tartrate, it should be weakly soluble in alcohol.
He said he shook it up in alcohol for 30+ minutes and only got it partly dissolved.

The same process was repeated, this time without the tartaric acid in the final step.
The result was a much more familiar product that dissolved in water and/or alcohol.
This gave him an idea that he is going to try next time -

The LSA-tartrate crystals were pretty large and seemed very stable. They were easily filtered out of a solution.
I hear that lsa tartrate is not soluble in acetone, but tartaric acid and LSA freebase both are.
So i am thinking that adding acetone and tartaric acid to the freebase form and then left to freeze precipitate could make some very pretty crystals that could improve LSA's shelf life since the freebase form seems to degrade quickly outside of a solution.
This wold also make for an easy way to parachute it, since he doesn't like the taste of drinking it.

He is still new to chemistry as these are his first few extractions done, and would like to see if anyone has tried this first.
His only question, if this seems like a reasonable thing to try, is would this work using DCM or Toluene instead of acetone?
If so, you could just take the final step where LSA is in the DCM/Tol solution, add tartaric acid to it, and freeze precipitate for a faster and easier way to get LSA Tartrate.

 

[benzyme]

what you're describing is consistent with what I've encountered using a 2% alcoholic tartaric acid solution to salt lsa.
excess tartrate salts settled to the bottom of a dram vial, but a few drops of the solution, evaporated in a petri dish, yielded this

 

[frobot]

Yes that is exactly what he did and got a similar looking result.
He said he is going to make a large amount of freebase and try a few different methods of salting to see which one seems to work the best and report back again.

The ideas he has so far are-
-evaping half of the DCM + LSA solution in the final step of the process then adding tartaric acid acetone to try to precipitate.
-evaping DCM to freebase LSA, dissolving this in acetone, then adding tartaric acid acetone to precipitate.
-evaping DCM to freebase LSA, dissolving this in alcohol + tartaric acid, then evaping this (this is what was done originally and seemed to have a nice result)
-evaping DCM to freebase LSA, dissolving this in acetone, then adding tartaric acid toluene (I read somewhere that this might have a nice effect too)

Anyone have advice? Will adding things dropwise help him? Will freezing help crash LSA out?

Also, sorry for hijack but I don't think the OP has stuck around

 

[Oh-Hungee]

I'm very interested in this topic, and I'm just wondering if any progress has been made? If so, I encourage some more posting about this.

A while back I did try a very small Kash's advanced LSA extraction as a test run. I did try dissolving the freebase in acetone and adding an acetone/tartaric acid mixture. My memory of it has faded, but this is how I remember it behaving: The mixture of acetone and freebase ended up being cloudy, and when I added the tartaric acid/acetone, the mixture turned clearer with ever drop. I froze it overnight, and tiny crytals formed. The crystals didn't want to fall the bottom, and at the time I didn't really have a good way to filter them out. So I just evaporated the acetone, and dissolved everything in vodka. I pretty sure the acetone had a bit of water in it, and I'm not sure how much this might of effected things.

 

[frobot]

My uncles friend has been working on a big long report, typing up more and more every day, that summarizes all he has learned with LSA extractions.
I don't want to post his findings yet because he still has a couple things left to test.
It covers several extraction methods, tips and tricks, and has lots of pictures of all the things he has made.

I can tell you water in your acetone will keep things from precipitating though.

 

[Oh-Hungee]

Awesome. I will look forward to this report.

 

[Winemaker]

Definitely looking forward to that Frobot. I've been considering x'ing it eventually, but time is definitely on my side. Will you post it up in the LSA subsection?

 

[frobot]

I am not a member so my options are to post it in the welcome discussion or in the Plant Analysis and Substance Testing section. I think I will go with the latter.

 

[Uronam.345]

I am here for exactly the same problem. I was going to make a post about it but figured I'd see if anyone else had this happen first.

My uncle's friend followed kash's tek. PH levels were right and measured with an accurate PH meter. He used toluene for the final step. This evaporated leaving very pure looking white crystals.
He wanted to dissolve them and drink them with peppermint oil but found that they would not dissolve in water or ethanol even after long periods of shaking it up.
Now he feels uncertain if he should ingest them.

I know this is an old post but I'm now 100% sure this happened to me too. instead of using citric acid for acidifying the water layer I used tartaric acid and I got hard white lumps that were water insoluble. At first I thought my pH was to high and I based over some ergotamine, which isnt very water soluble. It glowed white, but wouldn't dissolve so I tosssd it. I think I know what to do now, this forum was a big help.

 

[Sore]

My uncles friend has been working on a big long report, typing up more and more every day, that summarizes all he has learned with LSA extractions.
I don't want to post his findings yet because he still has a couple things left to test.
It covers several extraction methods, tips and tricks, and has lots of pictures of all the things he has made.

I can tell you water in your acetone will keep things from precipitating though.

If you're still around and don't mind sharing their research or pointing me in the right direction I would be very appreciative



Sore.