The teks don't say anything about optimal pH levels unfortunately so I am asking here.

With DMT, it is known that pH 12-12.5 is enough for getting over 95% of it freebased. How is it with harmalas?

According to this thread, harmine should precipitate from pH 7.0 and harmaline from pH 9.8. Is it possible to calculate pH at which, say, 95% harmaline gets freebased?

I have also recently tried harmine/harmaline separation but missed the pH 8.75 point and got to 8.9. I filtered the precipitate anyway and added more base. To my surprise, absolutely no precipitation occured even at pH 11.

I have calibrated the pH meter properly but maybe it doesn't work well or there was no or too little harmaline?? I though rue should contain these substances in about 1:1 ratio.

That thread is acurate.
You just borked it

The thread does not say anything about maximum and minimum pH that is sensible to reach (e.g. pH 4.0 to fully acidify and pH 11.0 to fully basify), only pH for separation (7.0), which is even different from what teks say (8.75). So I am confused.

Maybe I will look up some chemistry sources to calculate percentage of alkaloid precipitate vs pH - there must be a way to calculate it so I won't rely on confusing information on forums...

When extracting harmalas, I have somehow lost all the harmaline and don't know why. Maybe I have added too little base at one step and I don't want to lose many grams of product; I also don't want to add excess base just to be sure as this may contaminate the product and maybe even break it down (?).

BTW there are even inaccuracies in salt amount for Manske. One method (Phlux's) calls for adding same volume of saturated saline solution as there is harmala solution. This leads to widly different final salt content, depending on starting volume. This method should lead to "prettier crystals" though in my many trials it always lead to tiny crystals precipitating too fast.

The teks just don't seem to work as they say.

Welcome to the mystery that is rue extractions!

Don't expect everything to work out the first time (or nth time). Don't feel bad for loosing some product as you learn, it happens.

There cannot be one pH value that gives a % precipitation vs. pH. Why? Because solubility depends on pH and salt concentration (and the nature of the ionic salt). This is due to salting in (a little bit of salt increases solubility) and salting out effects (a lot of salt decreases solubility). When doing Manske other salts/ions are present besides NaCl (unless one is using purely NaOH and HCl) and the ratio of harmine/harmaline could influence crystal formation. Oh, and temperature also affects everything. If that is not enough, there are other alkaloids present, including rumors of harmalol in the literature whose presence can influence what happens during the extraction (colors, etc). If that is not enough, the target harmalas being extracted also influence pH and each-others solubility. Oh, and there are probably more variables I'm not aware of.

So with all these variables the teks are guidelines. With that being said...

If you don't have harmaline you probably did not base enough in one of the steps as you say.

Time to try again. When basing the pH will drop while harmalas crash out (I think that is because pronated harmalas are giving up their protons to become neutral/"free"?). The best way to know when harmine is done precipitating is to notice when the pH starts to go up again as was shown in the VDS protocol (which unfortunately gives a specific pH which seems "chemically incorrect" due to the reasons above).

If you want harmaline & dont seem to be getting any from your rue extractions why not take a portion of your harmine & convert to harmaline? The information is here somewhere that details the conversion process. Maybe jees or anikka can be of assistance?

Thanks for clarifying that. I now it seems more art than science

I have probably crystallized mostly one alkaloid while the other got lost in the extraction process.

I did about 6 harmala extractions so far but always want to make the method more controlled so the process will be a no brainer and I will now how much water use, how much acid/base (and how concentrated), what temperature to use etc. and just follow the formulas.



I will re-read the paper "A harm-reduction approach to the isolation of harmine and its hydrogenated derivatives from Peganum Harmala seed in low-tech settings" - it discusses the extraction and conversion processes in great detail.

Maybe I lost harmaline somewhere during the several A/B cycles. So I will try again being more careful about pH levels.