CITLO DMT Benzoate [A CISLO® experiment]

[famine]

The assuming part made me laugh

Nexus is read by beginners, including visitors who search for "convert DMT benzoate to freebase" and click on links – sometimes years or even decades later. Stating assumptions saves them time and frustration. For instance, if you simply say "filter," people might try to filter the highly alkaline mixture through paper; if you mention "vacuum pump," those who don't have one will likely scroll past the comment, and so on.

I recommend using 15% NaOH not concentrated

Why 15%?

I prefer using more concentrated NaOH solutions because they don't increase the mixture's volume to the extent that a different beaker is required for further pH adjustment.

Just agitation is sufficient

Heating on a hotplate naturally comes with stirring. It prevents local overheating (when the freebase comes into contact with hot glass). It is effortless (as promised), and it is safer.

Understood about the beginner part. I just found it comedic. 15% is much safer to work with and a low quantity is needed nonetheless. I use 15% for basificiation, 5% for base washes. You really don't have to use conc OH- solutions for amines. Remember ph is logarithmic so even 5 times more concentrated. Doesn't do a big change in pH.

 

[merkin]

Did another round, with powder bark this time as recommended by Loveall so I used roughly the method outlined for the Limonene but with Toluene as solvent.

Still got a yellow/gold coloured solvent and there are definitely some coloured crystals too. I think my mistake was:
1. Either not waiting for the NaOH solution to cool properly before mixing with the bark? Or
2. Not letting the bark/NaOH mix rest until cool before adding solvent. There was definitely a dark yellow tint to the first pull and lighter as I went on.

Because Benzoic Acid does not dissolve very fast I was concerned that some of the crystals might contain Benzoic Acid which fell to the bottom. But after 24hrs the biggest growth seems to be around the edges (and a couple of cool crystal strands up the side) so I would say not Benzoic acid.

Next time I will wait for it all to cool before introducing solvent. I also got very faint clouding (close to zero) but this is not the best bark I have used. I was quite surprised to see as many crystals as I did after 24hr. The solvent was super clear too so definitely some clouding had been present. I added solvent from one more pull before taking the pics so the solvent is a bit cloudy again in the crystal photos.

Would anyone have a suggestion for a method to re-x this dmt-benzoate (candidate)?

 

[Toshido]

Side question.

I know that DMT fumarate lasts significantly longer than DMT free base and is edible only. Pretty convenient that DMT benzoate is smokeable and edible just like free base... but... do we know of the shelf life of benzoate yet? Or is this still new territory?

 

[Loveall]

Did another round, with powder bark this time as recommended by Loveall so I used roughly the method outlined for the Limonene but with Toluene as solvent.

Still got a yellow/gold coloured solvent and there are definitely some coloured crystals too. I think my mistake was:
1. Either not waiting for the NaOH solution to cool properly before mixing with the bark? Or
2. Not letting the bark/NaOH mix rest until cool before adding solvent. There was definitely a dark yellow tint to the first pull and lighter as I went on.

Because Benzoic Acid does not dissolve very fast I was concerned that some of the crystals might contain Benzoic Acid which fell to the bottom. But after 24hrs the biggest growth seems to be around the edges (and a couple of cool crystal strands up the side) so I would say not Benzoic acid.

Next time I will wait for it all to cool before introducing solvent. I also got very faint clouding (close to zero) but this is not the best bark I have used. I was quite surprised to see as many crystals as I did after 24hr. The solvent was super clear too so definitely some clouding had been present. I added solvent from one more pull before taking the pics so the solvent is a bit cloudy again in the crystal photos.

Would anyone have a suggestion for a method to re-x this dmt-benzoate (candidate)?

That may be quite white after filter/wash.

Did you rest the toluene before salting? Looks like stuff settled on top of the xtals?

 

[Brennendes Wasser]

If you are not satisfyed with colour maybe just try re-x with also Toluene. ~ 25 ml boiling for 1 g will be the best number. Only ~ 75 mg D Benzoate will be left behind upon freezing.

 

[merkin]

That may be quite white after filter/wash.
Did you rest the toluene before salting? Looks like stuff settled on top of the xtals?

I didn't really give it too long to settle at all tbh. I ran the Toluene through a double coffee filter twice before adding the Benzoic Acid. But no fridge rest and decant like CIELO.

You were right about the colour - no deep red stuff like my first try - the crystals came out a light tan colour with some clear ones sparkling in there.

If you are not satisfied with colour maybe just try re-x with also Toluene. ~ 25 ml boiling for 1 g will be the best number. Only ~ 75 mg D Benzoate will be left behind upon freezing.

Yes, thank you, I was reading through your posts on the properties and saw that and I think I will try it. I don't have any Amyl Acetate but obviously I have Toluene. Combining both sessions I have 4.5g of this now, so I was thinking about 120ml Toluene should be good?

 

[Loveall]

Looks good. My xtals where a bit smaller, but I agitated a bit.

Are you freezing the solution as BW suggests? I got a little bit more product from the freezer.

I think that if you rest the toluene in salting conditions (freezer) before salting, some unwanted stuff may settle out and give you a whiter product.

 

[merkin]

I did not freeze originally with the extraction. I saw those notes later so I will do that next time.

The re-x was not a great success!

I tried dissolving all in boiling Toluene (about 150ml). Maybe it was a bit too much. Even when stirring I still couldn't get a large portion dissolved. Ran it through a filter but it went very slowly (I think there was a lot of suspended product). As the solvent cooled this process got less and less efficient. Powder was already precipitating from the filtered Toluene while the rest was struggling to get through the filter. I am drying the two filter papers I used at moment and the beakers - there is a lot of fine particulate all over them. The Toluene that made it through the filter is in the freezer and had a (very fine) white layer already apparent on the bottom of the jar.

I think maybe the result will be a powder precipitation rather than a recrystalisation but maybe that is what I should be expecting.

So 4.64g of dmt-benzoate most definitely did not all dissolve in 50ml boiling Toluene. Maybe I should have used less of it. Anyway, I will dry all the residues and try and recover as much as I can while the rest precipitates in the freezer.

I had a small fan blowing fumes out of an adjacent window as I was not to keen on boiling Toluene! All in all an interesting operation! Quite frankly I don't think I had a clue what I was doing, lol.

 

[ijahdan]

Planning to try this dmt benzoate drytek soon, as I have a big bag of old rootbark, a gallon of fairly old limonene (hopefully not too degraded) and now some recently sourced benzoic acid. Also picked up a 25kg sack of NaOH from a local business who were chucking out several of these large sacks! Will report back. Just a quick question, though, will it be possible to convert to freebase using the 'paste and pull' method, which works for fumerate and acetate? ie., NaCO³ and water paste, dry and pull with alcohol/acetone. I know this was mentioned, albeit using naphtha for final pull, but was it successful? Hailstorm's method sounds elegant, but requires equipment and chemicals I dont have. I guess manual stirring, gravity filtering through paper (maybe not safe with NaOH?) and washing with household ammonia would be a cruder version of this...

 

[Hailstorm]

Would anyone have a suggestion for a method to re-x this dmt-benzoate (candidate)?

You can recrystallize DMT benzoate from distilled water. I much prefer amyl acetate, however – it can be hard to initiate recrystallization in water, and it takes long to dry.

do we know of the shelf life of benzoate yet? Or is this still new territory?

New territory. DMT benzoate is far more stable than DMT freebase in air, but nobody has compared different salts yet, AFAIK.

Because Benzoic Acid does not dissolve very fast I was concerned that some of the crystals might contain Benzoic Acid

Excess benzoic acid is easily removed if you wash DMT benzoate in heptane. The salt is insoluble in heptane, while benzoic acid is soluble.

Hailstorm's method sounds elegant, but requires equipment and chemicals I dont have. I guess manual stirring, gravity filtering through paper (maybe not safe with NaOH?)

Hydroxides quickly dissolve paper, which is why lye is an effective drain cleaner. If you are careful enough you can slowly decant (most of) the alkaline water after DMT freebase sediments, instead of filtering, and use the same technique after the cold ammonium hydroxide wash.

If you prefer filtering to decanting but cannot use a sintered glass filter, you can use K2CO3 instead of NaOH. Same procedure: dissolve DMT benzoate in a small amount of distilled water with a bit of heating, basify, quickly refrigerate, wait for DMT freebase to sediment, decant/filter, wash with cold aqueous ammonia, dry in a vacuum dryer.

 

[_Trip_]

Took some butyl acetate and dissolved FB DMT and then in another receptacle I dissolved some benozic acid in BA both dissolved very well, i then mixed both together. Unfortunately BA holds DMT benzoate (if it forms in BA) and no clouding occurred. ill check it in 24hrs and see if any crystals form, but I'm doubtful.

Unfortunately with other acids tested malic, fumaric, citric, tartaric, lactic, none dissolved well in BA except benzonic. So I don't know how much use it would have in DMT CITLO type teks. But thought it was worth reporting. I had little success with harmala either with BA but maybe 5-HO DMT?

 

[merkin]

Unfortunately BA holds DMT benzoate (if it forms in BA) and no clouding occurred. ill check it in 24hrs and see if any crystals form, but I'm doubtful.

Brennendes Wasser mentioned somewhere that clouding did not happen in Toluene with BA I think. During my last try at this tek-in-progress I got hardly any clouding at all - just the solvent got a little misty - and figured it was a bust since with CIELO that is a key event - and I knew it was not the best bark. But I was quite surprised after 24hr left alone to see what had accumulated! Hope for the best...

**EDIT** sorry I misread that _Trip_ you meant Butyl Acetate not Benzoic Acid! Well, maybe crystals come later anyway...

My first time I definitely did get clouding but I had gone a different route (via Cyb until the solvent part) due to it being shredded bark. Then I got clouding, but that bark is much better than my powdered bark.

As for my klutzy attempt at re-x I am back to a very fine slightly off-white powder. Lost about 663mg to filter papers, funnels and glassware sides/bottoms etc and probably some junk along the way. But I am keen to try this some more and get better, I really like the simplicity of the process and my yields are better than I get with my FB extractions (assuming FB=61% of Benzoate). The crystals/powder is far far easier to retrieve than fumarate as well as it doesnt glue itself to the glass.

Would it still be advisable to 'wash' the powder with heptane having gone through a toluene boil and freeze phase? Almost all of the colour has now gone.

So, I would like to learn more about washing and/or re-x if necessary and then after that see if I can create FB again from the Benzoate to close the loop. This is by all accounts a great way to store the spice.

Sincerely appreciate the suggestions and advice from Hailstorm, Brennendes, Loveall and y'all above (and in other threads) and I will definitely try the Amyl Acetate re-x. Anyone have some good clear steps about going about it? I flutzed my way through the Toluene version but would appreciate a model procedure to follow (solubility amounts, heat temps etc) - stuff you guys with an education in this may take for granted

 

[Hailstorm]

Took some butyl acetate and dissolved FB DMT and then in another receptacle I dissolved some benozic acid in BA both dissolved very well, i then mixed both together. Unfortunately BA holds DMT benzoate (if it forms in BA) and no clouding occurred. ill check it in 24hrs and see if any crystals form, but I'm doubtful.

Your DMT is still there. Don't pour it down the drain!

First, try magnetically stirring it. If enough crude DMT benzoate precipitates out, you can let it sediment, decant the excess solvent, and recrystallize the residue.

If nothing crashes out, you definitely have used too much solvent. You can evaporate some of it (mild heating, fan, etc.) to reduce the volume. After that, keep it in the freezer for a day and see what happens.

 

[Hailstorm]

Anyone have some good clear steps about going about it? I flutzed my way through the Toluene version but would appreciate a model procedure to follow (solubility amounts, heat temps etc)

An extract of ~3.7 g DMT in ~75 mL amyl acetate was magnetically stirred with 3 g (i.e. molar excess) benzoic acid for a few minutes; clouding began almost immediately. Stirring continued as the mixture was heated to ~100°C. After all solids redissolved and the mixture became transparent, the flask was stoppered, wrapped in a blanket, and left to cool down to room temperature. After several hours the flask was moved to the refrigerator for a few hours, and finally kept in the freezer overnight.

The DMT benzoate crystals were scraped off the walls of the flask with a spatula, the mixture was swirled and poured into a sintered glass filter funnel. Vacuum was applied to remove the solvent. Heptane was added to the filter, the crystals in heptane were thoroughly mixed and powderized with a glass rod, after which the vacuum was applied again to remove the heptane. After another heptane wash the powder was collected from the filter and dried in air while covered from dust with a piece of paper.

...While DMT benzoate is more resilient to degradation than DMT freebase, it is still essential not to overheat it. If it does not dissolve around 100°C it is better to add more amyl acetate than to continue increasing the temperature. Around ~120°C the thermal degradation of DMT benzoate becomes apparent as the previously yellow solution begins to darken rapidly.

Relatively pure DMT benzoate should be off-white (it does not seem to become snow-white even after multiple recrystallizations), but definitely not yellow or orange – strong coloration indicates degradation. The melting point is 166°C.

 

[merkin]

Thank you very much Hailstorm, the lesson/model is most appreciated and understood!

The results thus far from my first re-x attempt with boiling toluene is exactly what you describe: an ever so slightly off-white fine powder from a previously tan coloured mix of crystals and powder. Much of the original colour I had stemmed from my first attempt and I suspect that had more to do with following Cyb's tek with heat baths and such rather than Loveall's lazy O (the bark was shredded rather than powdered). All that colour seems to have stayed behind in the Toluene so I don't think I over did the heating thankfully.

I aim to repeat the entire process again soon with the powdered bark and I will try and source some amyl acetate too for the re-x. This should give me a bit of material for some trial and error in converting it to freebase at some later point too. I seem to get a superior yield from this mhrb powder than I get doing the 'standard' a/b or stb freebase teks so that makes me even more keen to get better at Loveall's process.

Another mistake with my toluene re-x attempt would have been to just keep it boiling and stirring vigorously rather than adding more solvent in case of residue not dissolving. It all got a bit hectic for a bit and I was kinda worried about fumes and flammability as well. Nice to have a cool and calm description to follow

 

[Twilight Person]

Another recrystallization could be:

> Dissolve in Ethyl Acetate or IPA or Ethanol

> As solubility is "too high" put it into a closed cupboard (slow evaporation) and check every day

> stop once you have many crystals and volume of liquid is pretty low, now place into freezer

> decant

That way maybe you could also get good crystals while ethal acetate (as a strong solvent) will hold back most of the colourants, if other methods did not work. But keeping it in a ventilated area would probably evaporate too fast, so you cant stop at the correct moment.

But can't be done with EA when directly using it in an extraction, as it contains a lot of water after mixing, so crystals will never form.

 

[Hailstorm]

Recrystallization via evaporation works, but results in some product covering the walls of the container, where the solvent was. That does not happen if you boil the solvent – the hot vapors will be condensing on the walls, washing any residue down.

The easiest way to evaporate a low-boiling solvent (without a rotary evaporator) is to heat it up while blowing a stream of air over it with a small USB fan (sideways and up, to avoid blowing too much dust into the mixture). Once enough of the solvent evaporates, the fan is removed to allow hot vapors to reflux and wash the walls of the container. The heat is then turned off to allow crystallization to begin.

 

[Loveall]

Thanks Merkin

A very important thing about the lazy STB methods is that the plant material needs to be ground very well. Otherwise the long acid heat treatments are needed.

I'm gonna try a conversion to free-base to make e-juice. Similar to the fumarate conversion TeKs:

- Make a paste with DMT benzoate and sodium carb
- Pull paste with heated naphtha
- Evap solvent. Naphtha should leave behind nice xtals I think

Then make a citrate salt e-juice.

If it works, this will be the way for me

I'm glad e-mesh works for some, and that DMT benzoate vapes cleanly at low temp, but I'm too lazy to deal with the loading of the spice on a narrow metal strip before every hit and get flustered when half of it falls off.

Carrying 2g of DMT in an 6ml e-juice tank ready to provide 200+ smooth hits at the push of a button is what a lazyman like me enjoys

Cheers

Weird, the sodium carbonate did not seem to work very well to move the dmt benzoate into naphtha.

Then, I spilled most of it

I soaked up the spill with paper towels and extracted them into waterbeith sone cigric acid (3x).

Ended up using lye and doing a mini liquid-liquid extraction into naphtha. It was very easy and clean.

Out of the 2g of FB dmt, got back 1.6g, so most was recovered despite the spill.

It came out very white (see image). Made an ejuice with the DMT part (3 parts 70/30 PG/VG) and made the pH neutral on pH paper with citric acid (~1/3 parts).

Juice is very smooth. Lovely and strong when vaped at 66.6W.

Cheers.

 

[Loveall]

The toluene jar that xtalized in the freezer was set aside for a few weeks and a small batch of xtals formed. Eyeballing maybe 10% more

Guess it takes time for all the DMT to crash in this system.

 

[Icon]

So based on that evaporation tests I already wrote I can only imagine DMT*H+ + Benzoate evaporating as a pair and while doing so keeping their ionic state as an explanation to the experiments. At the same time wrote this would go against my sense of physical chemistry, but well it is what it is :?

In case that this would be true and what we inhale would be DMT*H (+) and Benzoate (-) then it would also explain why it feels rather smooth: Neither component can react as a Base or as an Acid. Therefore no irritation. Probably the Amine is causing this at times unpleasant chemical-ginger-like burning at tongue and throat. Cannot react as a base if it is not in freebase-form obviously.

Something I never tried was the taste of DMT-Benzoate. Maybe it is also close to tasteless because of that? Just other amines like MDMA still taste absolutely terrible even when not being a Freebase ...



Also those DMT Benzoate crystals seem to always be pretty perfect in colour and shape. While freezing out Freebase from Hexane you might get first a fast precipitating yellow layer that will grow white crystals on top, the Benzoate always looks just perfect and voluminous. Probably the charge of the molecule pushing away too close neighbours, so no pi-stacking occurs which would be a main reason for yellow colour + different crystal geometry across the precipitate.

Has there been any more thought about whether vaped DMT benzoate breaks into its... could you call it conjugate base? (DMT*H+)
A tasteless, non-irritating DMT vapor sounds very attractive.

@Transform mentioned in this post that DMT in a basic solution may be more likely to polymerize over time due to deprotonation kicking off oligomerization (if I understand him correctly).

If that's true, would polymer DMT also vaporize into DMT*H+ ? Could DMT*H+ vapors polymerize in the air or in the lungs? Decreasing bioavailability perhaps?