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DMT Oxalate precipitate from water?

M

modern

Titanium Teammate
So DMT oxalate has very limited information on the forum and only see references of it being precipitated from NP or from acetone? I had an idea of forming directly from the acid water pulls and would think it would precipitate directly from aqueous solution without the need for NP.

This is easy enough that I’ll test myself but how is the oxalate normally formed. I saw someone recently make 5-meo DMT oxalate from grasses but didn’t see the solvent used. If you have any references on solvents that work for oxalate salt formation please share. I would like to possibly skip NP or atleast skip total evaporation of water like I do with my isopropyl extraction requiring dry extract with sodium carbonate.

So my idea would be adding oxalic acid to the acid water pulls and it precipitate not an issue if other oxalates also precipitate. Maybe I would need to freebase with sodium carbonate before adding oxalic acid so it joins with freebase DMT?
 
Yes the oxalate salt can be crashed out from water. It has poor aqueous solubulity.... the crystals however may form instantaneously before you get the chance to separate your salted polar layer from you pulling solvent.

While i suceeded with oxalate for the extraction of 5-meo-dmt from phalaris, i haven't experimented further yet with this method.. DMT oxalate may dissolve better with added heat but haven't tried it yet to confirm..if true than recrystallization from water would be feasible.
 
Sidisheikh.mehriz said:
Yes the oxalate salt can be crashed out from water. It has poor aqueous solubulity.... the crystals however may form instantaneously before you get the chance to separate your salted polar layer from you pulling solvent.
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I wouldn’t have a pulling solvent. I would decant or filter off the water keeping the oxalate salts. If calcium of other salts also form this wouldn’t be an issue for my use case. Rather than using limonene or acetone or NP just pull from material with acid water. Then add oxalic acid.

I’ll give it a try… my reduced tea reached a point where it is starting to get too thick if reduced further maybe already too thick to I’ll make a saturated oxalic acid water soul it ion and add until I see something happen.

Do you know the solubility in isopropyl? Maybe 70% isopropyl will help lower solubility and help with separation. Ill report back my results but my more info would be helpful
 
modern said:
I wouldn’t have a pulling solvent. I would decant or filter off the water keeping the oxalate salts. If calcium of other salts also form this wouldn’t be an issue for my use case. Rather than using limonene or acetone or NP just pull from material with acid water. Then add oxalic acid.

I’ll give it a try… my reduced tea reached a point where it is starting to get too thick if reduced further maybe already too thick to I’ll make a saturated oxalic acid water soul it ion and add until I see something happen.

Do you know the solubility in isopropyl? Maybe 70% isopropyl will help lower solubility and help with separation. Ill report back my results but my more info would be helpful
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It's not that simple. Oxalic acid is no joke. While it's only a carboxylic acid it's still a pretty strong acid. I work with it often as a beekeeper as a treatment against varroa mites.. the stuff can easily cause blindness if mishandled and can cause skin burns.. the danger of oxalic acid is its silent action...you don't have feel it until it's too late...if it can cause skin burns imagine what it would do to your intestines!

How can you ensure there's no excess oxalic acid in your extract if you Crash your crude DMT oxalate from acidic solution?

On the other hand yes you can practically crash DMT oxalate from isopropyl but the ISO must be dry... Dissolve your spice in dry ISO... Saturate some ISO with dry oxalic acid and combine the two portions... DMT oxalate will crush out... But you'll have to extract your DMT first.

If you wanna skip the whole acid base step you're left with solid phase extraction cartridges but you'll need methanol, distilled water and acetic acid. Price of SPE cartridges is another disadvantage.
 
Yes I’m aware of the oxalic acid dangers. With the DMT oxalate due to possible issues with ingestion would be removed by breaking down the DMT oxalate with h2o2 so it should result in theory with freebase DMT, co2 and water? I’m sure there may be some side reactions and possible even complete breakdown of the DMT?

I wouldn’t want to ingest the DMT oxalate atleast not before the h2o2 oxidation. After that the h2o2 would break down with time.

I don’t have strong understanding of chemistry but from my research this may work in theory.
 
H2o2?! If you mean hydrogen peroxide it will simply oxidize DMT to n-oxide form nothing else rendering it inactive.

You want to use dmt oxalate only as a cleaning step and for storage. Freebase your oxalate once you want to smoke some or when you want to dissolve it as pharmahuasca.

If you dont want to use chemical solvents you can use olive or sunflower oil for extraction and base with sodium carbonate and salt with vinegar. Base your extract again and crash it with concentrated aqueous oxalic acid solution or crash it from dry isopropyl saturated with oxalic acid.
 
would the DMT oxalate become dmt n-oxide or freebase to oxide? Also didn’t know that oxide is inactive.

So I added oxalic acid to my concentrated tea and a precipitate formed. From the very dark purple it turned to a dark red. After a while the dark purple color returned and there is a precipitate layer on the bottom.

Will be a mix of oxalates I’ll filter off and test if DMT was removed by basing with lye and pulling with hexane.

Are all oxide alkaloids inactive?
 

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just adding to this I’ve read that at 200c you break down oxalate to co2 and co gases. With DMT idk if inhaling monoxide is a good idea but with mescaline freebase it should remain stable until 250c? So would heating mescaline oxalate at 200c for a while until no more gases are released yield mescaline freebase or an oxide?
 
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Sidisheikh.mehriz said:
H2o2?! If you mean hydrogen peroxide it will simply oxidize DMT to n-oxide form nothing else rendering it inactive.
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I was actually wondering about this - I think excess oxalic acid will probably get destroyed by the H2O2, but what exactly happens after that point, I'm not too sure. The DMT will be protonated in its oxalate form, making it more resistant to N-oxidation. Would the peroxide:
A) insert into the N-H bond to form the protonated equivalent of the N-oxide?
B) oxidise the oxalate dianion to two molecules of bicarbonate?
C) first form the N-oxidised compound, which itself goes on to oxidise the oxalate, i.e., a combination of A followed by B?

This is, of course, organic chemistry meaning we have an additional option:
D) forms a tarry mess.

All of these are likely to be dependent on the exact reaction conditions.
 
modern said:
So I added oxalic acid to my concentrated tea and a precipitate formed.
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This is almost certainly calcium oxalate, maybe with a few other largely inorganic cations mixed in.

You could try treating it with base and pulling with some kind of organic solvent; the procedure varies depending on the solvents to which you have access at the moment. (Otherwise, maybe it would be a candidate material for an initial H2O2 experiment.)
modern said:
just adding to this I’ve read that at 200c you break down oxalate with co2 and co gases. With DMT idk if inhaling monoxide is a good idea but with mescaline freebase it should remain stable until 250c? So would heating mescaline oxalate at 200c for a while until no more gases are released yield mescaline freebase or an oxide?
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I'd advise checking @Brennendes Wasser's work on the physical properties of classic psychedelics, which included some data on thermal decomposition. Flash vacuum pyrolysis of mescaline oxalate might leave you with some resublimed mescaline carbonate if you were to use a cold finger arrangement. I'd be disinclined to attempt this under an ordinary atmosphere.

link.springer.com

Decomposition of oxalate by hydrogen peroxide in aqueous solution - Journal of Radioanalytical and Nuclear Chemistry

The decomposition rate of oxalate by hydrogen peroxide has been investigated by a KMnO4 titration method. The rate equation for decomposition of hydrogen peroxide in the aqueous phase is 1n([H2O2]/[H2O2]0)=−k1·t, where k1=0.2, for [H+]<2M, k1=0.2+0.34([H+]−2), for [H+]>2M. As the acidity...
link.springer.com link.springer.com

Destruction of oxalate by reaction with hydrogen peroxide. [Hydrazine oxalate] (Technical Report) | OSTI.GOV

The U.S. Department of Energy's Office of Scientific and Technical Information
www.osti.gov www.osti.gov
 
Transform said:
This is almost certainly calcium oxalate, maybe with a few other largely inorganic cations mixed in.

You could try treating it with base and pulling with some kind of organic solvent; the procedure varies depending on the solvents to which you have access at the moment. (Otherwise, maybe it would be a candidate material for an initial H2O2 experiment.)

I'd advise checking @Brennendes Wasser's work on the physical properties of classic psychedelics, which included some data on thermal decomposition. Flash vacuum pyrolysis of mescaline oxalate might leave you with some resublimed mescaline carbonate if you were to use a cold finger arrangement. I'd be disinclined to attempt this under an ordinary atmosphere.
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I'll add lye and hexane to attempt to see if dmt is present in the oxalate precipitate.

The vacuum pyrolysis is beyond my accessibility currently so I'll forgo this or maybe just try it with some material I don't mind losing completely.

On the topic of dmt oxide activity has anyone tried with an MAOI? The report I saw was 80mg without an maoi had no activity. Also when converting back to DMT using vinegar and zinc dust... can the zinc be replaced with magnesium like with harmaline to THH? I'll probably attempt regardless but this is too many steps... I'll probably test the h202 results with an maoi to see activity of the dmt oxide.
 
This all sounds too complicated. Why not just cook your bark reduce your tea base and pull with your non polar solvent bof choice ..as per the usual acid base protocol.

And perform a mini acid base with oxalic acid you'll get some clean colourless sugar like DMT oxalate crystals. It worked perfectly for me with 5-meo-dmt.

The whole point from oxalic acid is the easier accessibility, cheaper price and better physical properties than the fumarate salt.
 
Sidisheikh.mehriz said:
This all sounds too complicated. Why not just cook your bark reduce your tea base and pull with your non polar solvent of choice ..as per the usual acid base protocol.

And perform a mini acid base with oxalic acid you'll get some clean colourless sugar like DMT oxalate crystals. It worked perfectly for me with 5-meo-dmt.

The whole point from oxalic acid is the easier accessibility, cheaper price and better physical properties than the fumarate salt.
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I had been meaning to talk to you about this periradial relocation assistance device that I've invented... ;)

@modern - if you have the lye and hexane why not just cut to the chase? Were you hoping to minimise your use of what are, for you, hard-to-obtain materials?
 
These are not hard to obtain for me however the smell is quite strong for these NP solvents... I could use limo but fairly expensive but not out of reach.

I wouldn't want to do this process if I need to convert back to freebase I would want a simple precipitate out of tea and maybe one more step to not have oxalate.

I don't want to just do extra steps but if dmt oxalate precipitates directly even with other oxalates if I could add sodium carbonate and dry and pull with isopropanol and add benzoic acid works well for me... Skipping the NP would be nice.

Is a carbonate salt possible with DMT?
 
I have access to most of the common solvents... heptane, hexane, limonene, xylene and isopropanol. But I do want to move away from hep/hex and xylene. I don't mind using lye and such but if I could get a fairly clean product using less it would be great. This is mostly for estimating content and NP is easy enough but another process would be nice.
 
modern said:
Is a carbonate salt possible with DMT?
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All the experimental evidence up to this point indicates that there are no stable, solid carbonates of DMT.

First things first, you'd better check whether the oxalate which you've directly precipitated from the tea contains any meaningful quantity of DMT. I'm definitely in favour of experimentation if there's even the slightest possibility that it may come up with a new alternative method of extraction.

[Not very practical, but I'd be willing to bet a small sum that refluxing anhydrous DMT oxalate *in the right solvent* with benzoic anhydride *and a suitable, yet-to-be-determined catalyst* would convert it directly to the benzoate, with the oxalate being driven off as CO and CO2. Maybe molten benzoic anhydride would do the job, it melts at 42°C and boils at about 360°C.]
 
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