Man, how do you know the impurities aren't harmala red that formed? It looks like harmala red to me!

You need to do these tests with PURE HARMALINE like SWIM did. Only then will you know if harmala red formed or not. If it forms it WILL NOT PRECIPITATE OUT with the harmaline.

When SWIM did his IPA test, he used pure yellow harmaline hydrochloride dihydrate (made in water). Look at his pic above. Look at how pure it is in his pic above and see the red stuff growing from it. All the crystals that formed as harmaline hydrochloride anhydride became harmala red. The remaining yellow crystals are harmaline hydrochloride dihydrate.

Wow, nice info 69ron! We can nail the chemistry of those harmaloids once and for all!

So, about sticking to the facts:



It is therefore likely that incubation of the crude harmala alkaloids in hot ethanol



If the anhydrite is more susceptible to forming harmala red then one should be able to make it by incubating the anhydrite with hot ethanol for some time. I am very curious to test that!

As far as the right picture on my previous post is concerned, you are absolutely right, one does not know whether they are actually impurities or harmala red. My speculation is based on the fact that the initial Manske precipitation (which was repeated 3 times) gave a brownish material with few yellowish specks on that. Since the harmala alkaloids in their "clean" form are yellow, I assumed that a brownish substance is an impurity.

It should made clear at this point that the separation of the "brown" stuff from the "yellow" stuff was a happy accident. It just happened during the drying of the ethanol (which presumably contained harmine, brown impurities, and the elusive harmala red). As a matter of fact, there are three "zones" formed upon ethanol drying; the outer brownish one, the inner yellow and the middle with the reddish colour. Again I assumed that the reddish zone is a mixture of harmine and the brown impurities.

Again, the speculation about the nature of the brown (and reddish?) substance is purely based on its presence in the crude Manske precipitation that now happened to separate out. No other cues however about what this may be. Should there is any harmala red in the brown and reddish zones, how would one go about testing it? I am quite curious to find out. Had 69ron mentioned that harmala red is insoluble in water in a previous post? My brown and reddish zones are both soluble in water.

yeah.. he said it was insoluble in water. my red crystals are also soluble in water.

i aquired my crystals by taking the brownish powder which i had yielded from the manske method, dissolved them in 96.6% ethanol poured off the ethanol into a petri dish and left the crap which wouldn't dissolve at the bottom. then i evaporated from the petri dish in my oven at 50C. I was left with beautiful looking red translucent cystals. It would be very interesting to know what color they would have if I hadn't used pinkish himalaya salt but pure white salt.

gotta test that!

WHITERASTA.. please write us a step by step tech including measures and all. We need to know EXACTLY how you got those crystals to fall out.

OK....I need to apologise for some of the data and assumptions I have made so far. It is so easy to be carried over by experimental enthusiasm and "publish" any observations prematurely. The ultimate tests, such as bioactivities should be our guide and not and vague solubility data published here or there.

So, the white precipitate after ethanol washing of Manske precipitates was tested. To my great disappointment it was not only totally inactive to dose up to 1 gram, it also tasted very salty. In fact it IS pure salt, well done Infundibulum, you managed to separate salt contamination from harmala alkaloids... And it makes sense, since the Manske precipitation is bound to have plenty of residual sodium chloride when dried, which is fairly insoluble in ethanol...

is salt soluble in pure alcohol?

anb btw infund.. if the bioassay of the red stuff is done, please let us know, this is for sure very interesting information

That made me laugh. First laugh I had all day.

I can’t stop laughing.

That’s funny.

It’s good you tested it and posted your results.

You know this type of thing happens to all of us. We do some experiment, find some results, and then publish them, and then….oooops….Look at my thread on DMT Fumarate. The very first post in that has a tech from SWIM’s notes that doesn’t even work! I was so embarrassed by that one. Several people tried it and wrote me saying it didn’t work. Then SWIM tried it, and sure enough, it didn’t work! But SWIM tried it before and it worked, so SWIM apparently wrote down something wrong in his notes while doing the test, and then like an idiot I posted the notes without it being tested again. To this day I’m not sure what SWIM wrote down wrong in that tech.


Oh, if you don’t want much salt contamination from the Manske tech here’s what you do:

After extracting add 10% salt to your extraction. Bring it to a boil for about 30 seconds. Do NOT move it. Let it cool without touching it. When it cools down to room temperature, carefully move it to the refrigerator. That way the crystals grow more slowly and are far more pure. The difference can be dramatic. If you add salt and mix and don’t bring it to a boil, the harmaline and harmine start precipitating too quickly and form around pieces of salt and you can have your final product contaminated with as much as 50% salt! But if you follow my guide, salt contamination will go down to about 5% or less, especially if you re-crystallize a few times in salt water.

This works because harmaline HCl and harmine HCl are practically insoluble in cold 10% salt water, are somewhat insoluble in room temperature 10% salt water, but are quite soluble in boiling 10% salt water. If you don’t bring it to a boil after adding salt, some tiny harmala crystals form immediately after adding the salt. That’s a bad thing. When you bring it to a boil, all the salt dissolves, and all the harmaline HCl and harmine HCl dissolve. The boiling solution will have no crystals of salt or harmala alkaloids it in. The salt will stay completely dissolved as it cools, but the harmala alkaloids won’t. If you don’t move it, the molecules slowly navigate towards each other and form nearly perfect large crystals. If you move it, this causes tiny imperfect crystals to form that will have a lot of the solution trapped between them.

Unfortunately salt is slightly soluble in pure alcohol.

You can actually dry alcohol by adding salt because salt is highly soluble in water and will trap all the water, but then you need to distill the alcohol to remove the remaining salt. You can get highly pure alcohol that way.

I wrote an email to David Nichols about harmala red, see if he knows anything about it, what it is, pharmacological activity and so on.. Let's see if he will answer


btw ron.. couldnt one theoretically do the zinc dust technique to harmala red, if it was harmaline n-oxide, and get the harmaline crystals back, and in this way confirming if it is simply an oxide or not?

It should. But it seems like a lot of trouble when it’s creation can be so easily avoided.

But I’m not sure it’s an N-Oxide. What makes me think it’s an N-Oxide is how it looks, it’s red and many Oxide products are reddish. The other thing is that it forms in the presence of oxygen if it’s harmaline hydrochloride anhydride. However, what points in the direction of it not being an N-Oxide is the fact that it’s less water soluble than harmline is. That’s not usually the case for N-Oxides. So maybe it’s oxidizing at a different point and it isn't actually an N-Oxide.

SWIM would like to know what ron thinks is the best type of extraction for harmalas since he thinks that ethanol converts to harmala red. Mansake? or an A/B without ethanol like alcon was saying?

SWIM has just started an extraction on syrian rue.. 50g are soaking in glacial acetic acid water, will leave overnight.. tomorrow will filter, and add acidified water+boil 2x... then SWIM is wondering if maybe he will divide in 2, and with half will make an A/B, and with half make a manske + ammonia precipitation, and then compare.. But SWIM thinks its too little rue to make this, so maybe will just make it all manske+ammonia and then will post back the results

SWIM will skip the alcohol for now due to the still mysterious harmala red...

saturday results come

This was found on the Mycotopia forum if this helps anybody who isn't highly chem savy like SWIM.


"Success! 104 grams syrian rue seeds were ground in a coffee grinder and sifted through a course screen. I guestimate the screen to have 1/16th inch openings. The rue powder was added to everclear acidified with food grade citric acid. The container was put in a 140F water bath twice and cooled to room temperature. It then sat for a week getting shaken 1-2 times a day. The solution was separated from the seed via a silk screen and rinsed twice with everclear. The solution was then filtered through a coffee filter (with the help of a home made vacuum filter) The resulting solution was a reddish brown color. This was put in a dish and evaporated. Then water was added to the dish and agitated with a fork. There was a lot of reddish brown greasy gunk that wouldn't go into solution. The gunk was filtered out through a coffee filter. Then ammonia was added to the solution and put in the fridge. A dark freebase precipitated out over the course of 5-6 hours. This solution was filtered through a coffee filter. The freebase in the filter was washed off into a glass and decanted. Twice more water was added decanted. The freebase was then added to a HCL solution then neutralized with CaOH (pickling lime). Almost instantly the alkaloids precipitated out. They were filtered off the solution and allowed to dry in the filter. The final EtOH wasn't done. The result is a fine beige powder. The yield was 850mg. Here is a picture of the final product before it dried. Now the question is what is the proper dose? Is the dose different for oral DMT, smoked DMT and mushrooms? Any help on this front would be greatly appreciated."




SWIM figures that one could acidify the tan freebase obtained from a Mansake after the repeated ammonia washes then rebase and wash to obtain the white product if one was worried about the harmala red with the alcohol right? Obviously the yeild wouldn't be as good as the whiterasta method though. This guy was obviously following whiterasta's earlier version of the tech. It seems that the end product was beige instead of white probably because he did not use the alchy at the end or because he did not rebase and continue to wash like the tech says at the top of this thread.

It doesn't seem that whiterasta's method at the top of this page involves much evaporation of alcohol except of the "boil down to a heavy syrup" part. If one extracted in a jar like it says above and didn't use alot of alcohol in the extraction so it was already reduced and didn't have to be boiled down, there would be no evaporation of alcohol involved in the tech. Would this work good or if you use less alcohol would that mean that not as much harmalas would be soluble in the alchy?

sounds like a pretty weird thing what this dude did.. I mean, he got less than a gram alkaloids from 100 grams of rue ?!? thats a horrible yield!

did you look at the main harmala thread? Theres a sticky that has a link to it.. The first post is a tek that uses alcohol, and then in the second page, there's another tek by syzygypsy that uses ammonia.. this is what SWIM is gonna do

I think if one wants very pure stuff, then could do the manske precipitation over and over, and then do the ammonia washes... maybe even do an A/B on the final product... SWIM is gonna do just one manske precipitation and then ammonia and see what comes up... SWIM already filtered the 3x rue tea... tonight will add salt water and then fridge, and tomorrow will do the ammonia precipitation.. on sunday probably results come

It does seem quite horrible but possibly better than what SWIM has gotten from the same tech you are talking about posted by syzygypsy. SWIM just thinks that the process that this guy posted helps understand the steps in the whiterasta method a bit better. Let us know how SWIY's extraction goes and what yeild SWIY gets.

oh really? tell us more about it.. was the yield of the first manske step when the harmalas hcl precipitate also so low, or was it very low only once ammonia was added? is it possible not enough ammonia was added (or not enough salt in the first step?)?

The yeild actually seemed a lot higher and crystals were larger after the second salt precip. Then SWIM tried another precip and the crystals seemed to be smaller. SWIM is pretty sure enough ammonia was added. SWIM also thinks it's a good idea to do what 69ron was saying and bring the salt solution and extract to a boil for 30 seconds then let cool down to room temperature without touching it so it forms big crystals and doesn't have a lot of salt contamination. SWIM also did this for the 3rd precip but for some reason the crystals didn't form as big. He probably should have started washing after the second. SWIM is curious what kind of yeild you are supposed to get from this tech. He probably has around a gram from 100 grams of seed.

ammonia is definitely the nastiest smell I've ever smelled in my whole life! I had heard about it but had no idea... pffff.. Even my eyes started hurting a lot, and I was working outside!

so now gotta wait for alkaloids to precipitate and then separate.. problem is, with a 5ml pipette, sucking off the liquid at the top would take about a million years.. so will try pouring off and then filtering the last part

tomorrow process continues

SWIM uses a turkey baster to suck the liquid off of the top instead of pouring. Still takes quite a while but one can fit much more in it than a dropper or pipette.

For some reason SWIM's FOAF does not feel very happy washing freebased harmala alkaloids (from syrian rue) with basic water. The main reason is that the XlogP of harmaline is 0.6, that means that its freebase form is fairly water soluble. That roughly means that out of 10 parts of freebased harmaline 2 will be water soluble and will not precipitate.

This is not the case however with harmine (XlogP=2.5) or tetrahydroharmine (XlogP= 2.367) which are fairly non-water soluble in their freebase forms.

Whiterasta's approach for cleaning freebased harmaloids continually washing them with basic water gradually depletes harmaline after each washing step. This should not be a problem however in the case of banisteriopsis caapi (which contains mainly harmine and THH)

So, if syrian rue freebased alkaloids are washed a few times with basic water harmaline will be depleted from the yield. But it can easily be recovered from the washes if acidified again and Manske precipitated.

So SWIM tried the extraction the way that he said. With just enough alcohol to cover the seeds in a jar, giving heat baths, not boiling down. He got about a gram of off white/greyish product from 100 grams seeds. Would have probably been more white if he had done more washes at the end of the tech. He says 200mg doses holding under the tongue for a minute before swallowing work great with no nausea. He actually likes these harmaloids better than some caapi extracted harmaloids that he ordered online.