This is for the Ethyl acetate approach thread by Loveall. I can't seem to post in there.

Great job on coming up with a greener and faster method that appears to give high purity product!

A few suggestions:
1) Dry the solvent before trying to precipitate the alkaloid salts:
- I saw some effort to dry the ethyl acetate, but CaCl2 is generally not compatible with amines or esters as they can form a complex with it, it can also be slow and finicky.
- K2CO3 is your best bet, compatible with both amines and ethyl acetate. Only use just enough and give it time to do its job. Molecular sieves are a possibility too.
- A dry solvent will make things more reproducible and will lead to faster crystallisation and also should avoid the formation of the biphasic "oil" some have seen. The "oil" appears to be a very saturated solution of alkaloid salt and acid, the addition of the acid in the presence of water in the solvent means the more polar compounds can form aggregates and eventually separate out due to the increase in polarity/ ionic nature. The fact they are in solution also means the stoichometry of the alkaloid salt could vary.

2) Dissolve the solid acid of choice (citric, fumaric etc) in ethyl acetate first, then add this to the ethyl acetate extract.
- This, providing the extraction solvent is dry enough, will mean the amount of acid can more accurately titrated (yes excess acid is soluble in ethyl acetate, but if a biphasic system develops it will also partition itself between the aqueous and organic layers complicating things).
- The ethyl acetate may need to be heated or sonicated to get more acid to dissolve but this is ok, just let it cool before adding to the extract.

3) Consider trying succinic acid:
- Fumaric acid is a Michael acceptor and there are cases in the literature recording amines reacting with it in this way. Probably fine most of the time, but should a solution need heat sterilisation that could be a problem.

4) Do an A/B extract on the residue to prove all alkaloids have been extracted.
- I think you should do this to confirm it gets all the alkaloids.

5) Melting point
- Do a melting point.This will tell you how pure it is.
- Popping or change in crystal structure prior to melting would indicate solvent or water or crystallisation/ hydrate.
- Otherwise more spectroscopic data to show it is clean and doesn't need recrystallisation. That Mass Spec you showed doesn't say how it was obtained, and doesn't tell the whole story. Im guessing it was run in positive mode only so no acids present?

6) Recrystallisation.
- Would be great to see some solubility information on the citrate/ fumarate/ succinate and also recrystallisation.

Hello and welcome!

Thanks for your considerations as a first post on the forum. I'll link it across to the main thread to ensure you get involved in the discussion. [EDIT: Here it is.] The main ethyl acetate thread is in a section of the forum that's only open to full members but your continued positive engagement with the forum would be the quickest way for you to ensure promotion to full membership.

You clearly have some appreciable level of chemistry knowledge, which is very welcome here. And that Ethyl Acetate Approach thread has grown to huge proportions so you may well have found it hard to go through the whole lot of it - the point being that several of your ideas have been touched upon already. They are still all valid points and what I would do is encourage you, if you have the means, to test them out yourself and report back to us. (That would practically guarantee you a promotion, btw.)

We are all willing volunteers here with limited time and resources so any further practical input is always gratefully received.

If you like, tell us a bit more about your interest and experience in matters psychedelic in the Introductory Essay section, or pop by and see what's going on in the Chat (all though you might need to be patient for a reply in there sometimes).

See you around!

Thank you that's a great list.

1) For drying, how about using Na2CO3? I believe arm and hammer super washing soda is the monohydrate that can do a good job at drying compatible solvents. That seemed to work well for me. I hear what you are saying about CaCl2, but in practice never saw a difference in yield with CaCl2. Dry with CaCl2, or Na2CO3, or no drying had no difference for me getting product. I do think it citrate granules take longer to dissolve after chemichally drying the solvent but that's it. Xtal formation time, etc is all the same when salting a dry/no-dry solvent split side to side in my limited testing. Could be different for others and drying is a good practice for consistency - agreed.

2) I wonder if this could help people that get oil.

3) Succinic sounds good. Someone published a paper saying that DMT succinate was very stable I believe. Would be interesting if someone tried it. I believe the WIKI has it as a suggestion on the list of untested acids soluble in EA.

4) Ok, if anyone does that would be great data. We did repeat the set EA extractions and showed that >90% of product is gotten in the first set vs. a second set. A data point to a full A/B on the spent paste would provide completeness and be completely to this.

5) Yep, I believe benzyme runs positive mode only, so all negative ions get curved away from the detector area. Further tests on purity are welcome.

Wish we could figure out the oil some people get. Did you see orchidist got xtals instead of oil with fumaric? I hope we figure the oil out soon.

Cheers and thanks for the info.