I hope it's alkaloids. If it clears and forms crystals, it probably is. I just remember reading somewhere around here that even white vinegar contains stuff other than just acetic acid and water. There's some pictures around here somewhere of the residue from evaporated vinegar.

And therefore I didn't mean sodium acetate(s) for that reason, but from what you've just said about crystals forming it's sounding fine. These things can take time, e.g. 5 days for a limonene/FASA precipitation to clear up, if you've seen my recent thread.

I think basically the volume of aqeous solution is too big for the amount of alks sitting in it...

Also I've come to the conclusion that I should warm the solution and heat the naphtha otherwise it reaches temperature equilibrium too soon...

Trying to pull from a solution that should be clear when not containing any alks is proving to be very educational... I've had good pulls and bad ones and I've learned from all of them...

At least I know what to do differently next time...or at least I think so

Well, I'm reasonably confident that there was something in there that didn't want to be pulled into hot naphtha, and it wasn't soluble in water either (some of it floated, some of it sank to the bottom)... It's white crystalline appearance seemed like an indication of it being alkaloids, but the fact that hot naphtha didn't pull it indicates the opposite...

I'll try another brand of vinegar next time, or try to find some fumaric acid...

To me it sounds like your overworking the solution. All it needs is time, the more you heat and agitate and move around the alkaloids the longer its going to take.


You mentioned when allowed to sit in the basic water for a period of time, it becomes clear with a white layer on the bottom. THESE ARE THE AKALOIDS, sodium acetate is a soluble salt.

This is the point where you want to separate the solution. Don't worry if it gets cloudy when you pick it up, just filter it, you can let it settle again later.

You forget the part where the vinegar was basefied with sodium hydroxide... If there's spice, it is freebase and non-soluble in aqeous solution...

I'm really pretty sure that the precipitation (after exhaustive pulling with nps) was due to vinegar-related impurities, the white crystals were an indication, but not proof, of it being alkaloids... There is something in vinegar which is only soluble in acidic conditions and it precipitates in basic conditions, we jsut don't notice this in a black soup full of organics - in a clear liquid however...

Next time...I'm going to give citric acid a try...

No I didn't forget, here Ill bold it.




I can't really say anything else that might help you, but doing something may help you in this situation.


If the precipitate REALLY is something else other then the alkaloids, why don't you take a sample and do a simple test to see if it is a tryptamine (A burn test, is an easy way to detect)

Otherwise your dismissing something without any evidence, and that is borderline pseudoscience.

You are right...

I jumped to conclusions because the precipitate didn't get pulled by hot naphtha - a tiny amount of it may be "recovered" during re-x as some of it did get into my pipette...

All alks that could be in there were pulled with naphtha in the first place, so why wouldn't naphtha pull them now - unless they're not alkaloids?

If I manage to recover some of the pysterious precipitate I'll surely examine it further, if not I'll do so during my next extraction...

I have left a sodium carbonate solution for a week that had been used to base vinegar and it grew thin needle crystals. They were not alkaloids and dissolved immediately in fresh water.

Lye and phosphoric acid can make glass shard crystals which are prob sodium phosphate and seemed insoluble in cold water.

Lye and vinegar made a fine white precipitate when left to stand this could be sodium acetate?

The combination of chemicals can make some things insoluble and push them out of solution when they would readily dissolve in plain water.

Always test things that precipitate out. I test solubility then put a bit on a old knife and heat it salts tend to sit there whereas DMT is obvious as it vaporises and smells of spice.

I do not see any problem so far, but just to make sure that we are on the right track, how do you know that naptha does not pull anything? Did you try fully evaporating the naphtha / fridge precitate it etc??

Obviously the persistent cloudiness could be due to all sorts of (unrelated?) reasons, but let's examine first if indeed the naphtha does not pull anything.

Well, the first naphtha pulls turned cloudy upon entering my pipette...
After this, pulls turned cloudy when sitting in precip vessel and blown upon...
At a certain point, the cloudiness of the solution did not change anymore - thinking it was alkaloids I did at least 5 more pulls without any change in cloudiness of the solution...
If anything had been pulled, the cloudiness/amount of precipitate should have changed, no?

Solubility of sodium acetate is way bigger (46.4 gr/100 ml H2O at 20°C) than the amounts of vinegar and sodium hydroxide that were used (<200 ml 7%, < 15 gr)...
I am still learning stoichiometry but I think "14 gr acetic acid + 15 gr NaOH > 46.4 gr sodium acetate" seems quite unlikely... Unless the addition of NaCl to raise the ionic strenght of the solution has contributed to the formation of sodium acetate, however the amount of acetic acid in the equation doesn't change... Perhaps the precipitation is more likely to be chlorine-related from the NaCl?

I am also wondering if reactants are to be chosen based on the properties they have on the left side of the equation or based on the properties of the molecules they form on the right side of the equaton... For instance, NaCl is added to raise the ionic strength of the solution, is this because NaCl has this property, or because of the properties of the ions after being dissolved in water, or of the properties of the molecules that are formed if and when reacting with the vinegar or the lye? Or is there no change in ionic strenght between the left and right side of the equation?

So you are yielding....that is good. Do you think that the yield you got so far from your naphtha pulls is anywhere close to what you'd normally expect?

I think you got yourself in an uphill fight with this cloudiness , thinking they are alkaloids, but as you suspect they may very well be something else. The important point is that if they are not pulled by naphtha then you may not want them in the first place.

As to what the remaining cloudiness in the basic solution may be, well your guess is as good as mine. I do not think that stoichiometries of acetic acid and NaOH or solubility of sodium acetate will help you solve the riddle. In my opinion, you might be seeing sodium acetate that is precipitating out because residual naphtha (yes, even traces) are present in the aqueous layer changing solubility parameters. Or it could be traces of alkaloids that are hold back in the aqueous layer because sodium acetate can behave, at least in some cases, like a soap molecule, holding or clathrating (see here and remember that sodium acetate is a the first in a series of chemicals that make soap molecules), or something totally irrelevant like impurities from the vinegar or a combination of many of the above things.

So, are you so far happy with your yield or do you think that a significant proportion of it is still trapped in the aqueous layer?

Thank you for this explanation... While shopping I remembered naphtha being partially soluble (0.75 gr/100 ml or so?) and how that may be related to my problem

I haven't weighed my yield yet, I'm going to do that just before and after re-x later today... I'm still too much of a neophyte to guesstimate amounts but I think it will be around 1% - but I've kept the basic soup so additional pulls are possible as soon as I have some toluene...

I do believe "wet" alkaloid crystals will have a hard time getting into naphtha. If the alkaloids have already precipitated from a mix and although not soluble in the water they can become coated in it. The water can act as a barrier to the NPS preventing contact where as normally they would go straight in.

You can test this with a small crystal in some basic water just drop it in leave for half an hour and then try and pull it with your NPS it won't work to well. Have you any way to filter and dry the precipitate then try pulling from it? Otherwise try heating the liquid right up above dmt's melting point so any crystals of melt and stick to the side or float to the top then they should dissolve more easily in the NPS or be able to be retrieved by pouring the water out leaving spice stuck to the side. Any salt by products should not turn to oil and stick with heating and should either dissolve or stay as is.

I had a similar issue recently and it was not spice floating in suspension just some byproduct from the acid / base. You could try mixing up a fairly saturated mix of your acid / base and salt if you used it with no spice and see if you get any precipitate and what it looks like compared to your mystery substance.

Thank you very much, this is very helpful indeed...

Unfortunately I got frustrated a couple of days ago and tossed most of the solution so some of the experiments you propose will have to wait until my next extraction... I am not sure that the bit I kept is enough to learn anything from...

For now, before re-x that is, my yield is 1,68% off-white crystals with some visible spots of discoloration - further clean-up of jars etc not taken into account yet
Perhaps toluene will be able to pull some more alks from the basic soup which has been sitting around for 2 weeks now - can it go off?
I have not yet decided how to proceed from here, simple re-x in naphtha, or mini-STB or water wash to get rid of vinegar-related impurities which I am sure of are in there...

At least 1.68% is nothing to be ashamed of for a second attempt...

With everything I've learned from this experiment and the knowledge obtained from my fellow Nexians I am pretty confident that the magic 2% barrier will be broken sooner or later

It's all about learning. You try all these different things some work and some don't but through that process you acquire far more knowledge.

Thank you... This has been a far more complicated yet rewarding experience than it would have been if I had stuck to a single tek and followed it to the absolute t...

I'll make a saturated solution of water and NaCl, add a pinch of sodium carbonate, put it in the fridge... Dissolve my spice in hot naphtha, mix with solution hard and fast (1 part solution for 4 parts of naphtha), let separate and decant naphtha asap, then a pull with warm naphtha just to make sure no alks are left behind... Are these amounts/ratios correct?
Some info on these pages says "pinch" of sodium carb, others say "sodium carb saturated solution" and also the ratio for solution/solvent seems to be different depending on the source... So I hope I got it right...and that it won't kill my yield

The water just needs to be basic so a pinch is fine.
Its just to pick up any lye and extract any organic plant matter back into basic water a quote from an expert JG92
" ,and the organic layer is back extracted with salty NaOH solution to remove impurities"
Will/can you get litmus papers?
As for yeild you cant go wrong at that stage the remainder can always be recovered you are correct in making a small solvent pull after.
As for solvent a good ball park ratio is 250ml of Naptha for every litre of solution, 250ml warm naptha should pull roughly 500mg of dmt give or take. So ratio is 4:1 or is it 3:1?

Are you referring to extracting or sodium carb wash?
Right now it's the ratio between solution/naphtha as in sodium carb salty water/naphtha with "dirty" spice I'd like confirmation for...

Also, does it matter what temperature the sodium carb solution is?

Sorry was for initial extraction..

For the wash room temp is fine.


Ratio for wash a third to half the volume of the naptha will do it.

One step I forgot to mention....


After separating the solvent from the vinegar, I ALWAYS stick the vinegar in a double boiler for 30-40 minutes.

It still smells strongly of solvent after separation, and it could very well the problem with your precipitation.