The sad story of Bufotenin:

10 years ago 69ron wrote Bufotenin is the most colourful and least psychedelic cousin from the Trio of DMT, 5-MeO-DMT and 5-OH-DMT (Bufotenin). It would give strong CEV and OEV with patterns and colours and would not be harsh to smoke when pure. As it happened quite some times before that he made exaggerating reviews on a substance, this may have needed more verification by others. Many people tried, but reported to only extract amber to black stuff from A. colubrina seeds, which give a harsh vapor with strong vasoconstriction - also reported by 1950's early Bufotenin trials who stated them inactive. It had to come until Jonathan Ott reported some visionary effects of Bufotenin decades later, but still it was believed that you would mostly get unpleasant effects, as you'd more likely smoke an Alkaloid mix with a lot of nauseating substances.

So until now 69ron's praise of Bufotenin was not likely to be proven, but still his idea of extracting Bufotenin in its liquid form with Xylene seems like the final key to get a pure crystalline compound. So when I finally had some truly pure material I was excited to finally try it, but mostly ended up with nauseating vapor and vasoconstriction in the first trials, but still at any time being super harsh and non-smokable even with sper gentle vaporization. Back in the days he stated to use a test tube with a straw and heated from below. As the material collected at the bottom when heaten up, I guess this method would also produce a lot of charred products, making it far from enjoyable to smoke.

Therefore I believe probably many people who have smoked Bufotenin and gave it a bad review may have still smoked high purity Bufotenin and believed their dark Bufo may just have been full of 'plant poisons' due to the colour - somehow the same story like the belief a dark DMT fraction might hide a multitude of mysterious full-spectrum alkaloids.


Evaporation of Bufotenin Freebase

I measured the Vaporization Profile of Bufotenin some time ago and here we can directly see that vaporization of Bufotenin is really unconvient. Instead of Vaporizing to more than 90 % like DMT and 5-MeO-DMT something happens, which instead burns like 50 % of the Bufotenin. That reaction must be linked to the OH-group as seen here and is most likely the same reaction that Psilocin in Mushrooms can undergo, which causes their blue colouring and instability when not properly stored. The reaction is an oxygen mediated coupling of single Tryptamines to Oligo- to Polymers. In the case of Psilocin a bigger molecule conjugated with pi electrons (basically double bonds) extends its absorption from UV-only (being formerly colorless to our eyes) into the visible range, though becoming coloured = blue. The coupling positions of Bufotenin enable only a conjugation which is sterically more hindered than for Psilocin, that might be a reason why at room temperature Bufotenin stays stable forever. Furthermore Psilocin is also in touch with corresponding enzymes in the Fungi, that will promote this reaction even more at Room Temperature. As a consequence this reaction only takes place at high temperatures, like when vaporizing. It seems the threshold is reached at 170 °C, any Bufotenin will quickly become black above this point. The polymerization product will not vaporize anymore, hence the stop of any evaporation. Still traces of it might also vaporize upon heating, then if you inhale them they irritate your lungs like hell. That's why I can only hold 2 mg of properly vaporized Bufotenin for like 3 seconds, making it impossible to ever get any true Bufo experience. Now here you will see a picture of the vaporization of Bufotenin if you would just directly smoke it and the reaction that possibly makes evaporation so inefficient plus irritating. Keep in mind that is only a theory, but at least a quite reasonable one:



Bufotenin might be coupled like Psilocin, but 1 out of 3 positions are blocked. In case of a reaction a chinon-like polymer is created, which is coupled through a positioning which is labelled as 'ortho' in aromat nomenclature. Obviously there also could be mixes between the both Dimers shown above like 4+6 and 6+4. The position #3 would be 'para' and an enzyme-free and therefore thermodynamically-controlled coupling at this position would be the most likely. As that is not possible and the other 2 sites probably have a higher energy barrier due to steric hinderance from the Oxygen the corresponding reaction needs 170+ °C to occur, so only happens when vaping it. Maybe at first only Dimers are formed and then after 280 °C all that stuff is helplessly charred down to Polymers. But that would be just some speculation.

Now I guess in any way this cannot be prevented, hence I have no idea how to properly smoke Bufotenin ... Furthermore if eaten 100 mg only produce a weak effect (like 1 g Mushrooms) and also induce nausea. Seems pretty much like a dead end with Bufotenin becoming the unbeloved sibling out of the Trio. Bufotenin may be just a bitch in vaporization and also annoying to crystallize ... so what can be done now?




First I wanted to make an easy test how to get something like a proof that the problem is an oxygen-induced assembly of non-vaporizing, probably higher molecular weight substances, which is causing the whole trouble. Here is a super easy experiment I was doing: Just conduct the vaporization in Nitrogen. The oligomerization requires the Phenol to Oxidize to the Chinon-like structure. Oxygen is the go-to molecule to promote Oxidations (I guess that's where the name is from). By conducting the TGA experiment in an inert atmosphere, there is no possibility to promote the reaction at least with Oxygen. So here is the result:



Hooray!! FULL evaporation - only 2 % Bufotenin remaining. So we can directly see that removing the Oxygen all molecules will make their way into air. Now that is all cool and stuff, but I guess not many people here will fly to space to vaporize their Bufotenin in zero-G and vacuum (although temperatures for vaporization will be conveniently low). Therefore this is not more than a deeper look into the process in general. So what can we do to still experience this substance, if we know that the problem is an oxygen-promoted reaction, that blocks Bufotenin from vaporizing, while irritating the lungs with charred reaction products?




Many evidences recently came up that Tryptamine salts of a certain kind can be vaporized at actually just a few °C higher than the Freebase, being just a 10 % more temperature for DMT for example. A general discussion about this and which salts are working and why can be found here. The interesting thing here is even more that these dont seem to be too much more harsh than the freebase. Now you may ask: Ok ... cool so is this just some kind of scientific oddity or why else should I care? Indeed in the first place it is quite astonishing, but I admit it would normally not make too much of a difference to the Nexus' users. But now as there was some discussion about this general Bufotenin problem, consider this:

Considering that ALL salts of ALL tryptamines vaporize in the same pattern, which would then also be valid for Bufotenine

--> How about utilizing the salt formation to introduce a charge to the Bufotenin molecule, which will maybe stop polymerization by pushing away any molecules of similar charge? The impact of this on the initial problem is written further down. (Make yourself ready for some epic powerpoint showcase)



To see if that will make any difference I created some Bufotenin Benzoate and repeated the same Test ... here is the result:



So what you can see here: Quite a good vaporization of up to 70 %. Not bad actually, considering that for DMT and 5-MeO-DMT we are also just above 90 %. Maybe there is still a small chance for creating Oligomers. But highly-charged polymer-chains are a somewhat thermodynamically disfavored thing. In industry there is many stuff like sulfonated polystyrene, but in those cases probably not EVERY side chain carries a charge - like it would do here. High charge density on a small spot is disfavored in nature, therefore even if the reaction may still occur we might have only oligomers instead of polymers. Even better: Probably the charged side-products will not vaporize at all, so traces of them can't irritate your lungs. Will have to verify soon with a Bioassay (funny word). So just from the experimental results, I'm quite convinced that this method will actually render Bufotenin smokable to a drug than can be easily enjoyed finally.

See experimental results here.

So the key to all this evil is that Phenolic compounds can be oxidized to a keton state. That is also used in many anti-oxidants (they oxidize themself instead of the substances they protect), which are also often derived from phenols. Therefore any modification that will stop the 5-Oxygen from forming a double bond will effectively block this pathway. This can be demonstrated with 5-MeO-DMT: A demethylation would be needed and this requires fancy chemicals (H2/PtC or BBr3) instead of just heat. You may ask how is a true chemical conversion then still a solution to experience Bufotenin. The answer is you might use a substitutent for blocking, which is easily chipped off in the body like Acetic Acid = Ester formation. Therefore creating 5-Acetyl-DMT from 5-OH-DMT (Bufotenin) might be a way to block chinon-formation, while the (proposed) Pro-Drug will be transformed back to Bufotenin upon ingestion. See Scheme below (just ignore the quaternary Amine at MeO ):










Loveall has experimented a lot with E-Juice and also with some possible Tryptamin salts, which may have a better shelf life when stored in these mixtures than Freebase. A benefit of this might be to aerosolizing the Tryptamine in the E-Juice instead of vaporizing it directly. Therefore this method might even be performed with the picky Freebase. I dont have a suitable device for proofing, but if anybody else has they might report here:






Summary:

Even though being only a theory, experiments seem to show that Bufotenin might undergo the same oligomerization like Psilocin, but only oxygen mediated at > 170 °C. As it might seem impossible to conduct any vaporization for personal enjoyment without Oxygen, it looks like vaporization of the salt is shutting down this process by a decent amount. Also a chemical conversion blocking that pathway in general might also help to stop this reaction to occur, hence finally this compound could be vaporized just like other Tryptamines.

How about dissolving bufotenine or bufotenine salt in PG and vaping it (aerosolizing)?

Ah yes that would be also just super straight forward! So I'm not familiar with these devices, but when you say aeorosolizing it means they get transported with small liquid particles, hence to direct vaporization of that drug right?

That would be also great I guess. But sadly I dont have a device to test. I remember when we were both trying some efforts with the Crafty Vaporizer. Sadly it seems vaporization is just a little too slow and always just giving ~ 8 mg per big inhalation ... then I tossed all electronic devices alltogether. Also bought a handheld E-Nail (but dont remember the name) which also vaporizes too slow. But now you already have had many good results with E-Liquid, so maybe this one would work great too?

If you dont mind will also write it as a possible solution to that thread.

Correct, the e-juice becomes small dropplets can carries the drug still dissolved in it.

And yes, feel free to write it as a possible solution

Cool

Also I guess there is another possible practical conclusion of this. But only if that Benzoate salt indeed is more enjoyable.

Sadly I wasted all my Bufo for now, but maybe I will check soon again. Until then of course it's not even proven if it indeed is more enjoyable for smoking, but Trip has had some first impressions regarding this.



Regarding usage of Benzoic Acid for this TEK. At first I thought it would probably be more of just a personal decision to exchange Fumaric Acid with Benzoic Acid, because you still then need to do a purification step afterwards. These alkaloids still contain some more polar stuff, which is left as a tan powder in the next step, see here the RIGHT picture:



When keeping on extracting on this LEFT blob with Xylene you will end up with an Bufo-exhausted tan powder (RIGHT). Whatever this is, it seems to not be Bufotenin. Probably can't check with any Analysis, because dont want to buy any seeds anymore

But now if the Bufo Benzoate indeed would be easy to smoke, then a TEK could be made even more Kitchen Friendly, while also directly deliver a smokable product:

Step 4.) Extraction with Aceton

Extract as written with Aceton and then throw Benzoic Acid into it instead. For me it never made a direct precipitation, so I evaporated it in most cases and got the Salt. If you would indeed not do any decanting, it may make sense to not use too much excess of Benzoic Acid, maybe only like 1,2:1.

Now to purify it from the more polar alkaloids, it may work like this:

More polar DMT salts can be removed by re-x in Ethanol. Famine told me some more polar DMT-Oligomers can be actually dissolved in Ethanol, DMT benzoate will just (mostly) precipitate. Maybe this will work with the A. colubrina Alkaloids too. A risk would only be: Bufotenin itself is very polar, you may also loose some during this step? A verification and also optimization of Ethanol vollume to Alkaloid Benzoates would be necessary.

But if it works:

Step 5.) Recrystallization of Bufotenin-Benzoat

- Dissolve Bufo Alkaloid Benzoates in hot Ethanol
- Place that glass + an additional glass with Toluene in freezer
- at - 20 °C remove it and place Alkaloids in a funnel, pour freezer-cold Toluene on top until orange colour is gone

= that should give hopefully pure Bufotenin Benzoate, which maybe could readily be vaped?

If vaporization is convenient, will write it to that TEK, but sadly cannot verify on that Alkaloid-mix-Ethanol-re-x ...

You shouldn't have any issues with bufo benzoate forming in acetone but going off memory it may not be instant it may need a day or so to precipitate out. How long did you let it sit BW?

Everytime I gave FASA inside it precipitated directly, but with Benzoic Acid in DMT / Bufotenin it stayed clear for ~ 1 minute (ok ... not long time ) so I became nervous and just evaporated it down, which will then form the salt 100 %.

But if people at home cant be sure that air moisture will not be absorbed into their Aceton while evaporating, it should be indeed better let rest as long as it needs, as water will partially dissolve the salt again or be annoying in any potential next step.

So I experimented again a little bit and I just get short clouds when adding Benzoic Acid in Acetone into the DMT dissolved in Ethyl Acetate - but then these Clouds vanish.

So thats just the Benzoic Acid that needs 1-2 seconds to dissolve again in the mixed solvents. But then no precipitation for 10 min. As I did not want to wait during all trials I always distilled off the solvent and on the way to dryness the precipitation also started - I anways just rotavapped everything off.

So because of that I actually checked the solubility of DMT Benzoate in many solvents and actually needed to correct some statements:

The solubility is surprisingly high in medium-polar to polar organic solvents.

Now there are actually 2 sides of a medal

When recrystallizing Tryptamin salts people are just using Methanol or Ethanol. That works really well for Tryptamines*HCl (bubble HCl gas through Benzene and mix with Tryptamine), probably also for DMT Fumarate.
But DMT Benzoate is quite well soluble in Ethanol ... so you would loose up quite a lot when just decanting the liquid after recrystallization.
You can even dissolve quite a lot in boiling Aceton ...
Solubility in Ethyl Acetate is even less, but still not bad at boiling temp.

So even when probably waiting for longer in the freezer, there might be a much higher bunch of actives sitting still inside of the solvent when waiting for 1 night, compared to DMT Fumarate. Probably thats the reason why I never got any precipitation without removing the solvent?

Now thats the bad side, as you will need to be more cautios with this Salt to reduce material loss upon handling it, compared to the more traditional salt forms. Solution might be to just create this from Naphtha, I think Loveall found that you can even dissolve Benzoic Acid in Naphtha?




But at the other hand that may come handy for your other purpose, which is creating a non-degrading (= Salt) version of DMT that does not precipitate from PG to make an E-Juice?

Because this increased solubility even in organics will probably make the Benzoate salt much more suitable for E-Juices than Fumarate.

I believe Loveall first discovered DMT benzoate does not dissolve well in PG/VG https://www.dmt-nexus.me...spx?g=posts&t=98970

I have found this also to be the case.
Unfortunately from what I have tested, bufo benzoate has the same issue.

However, in terms of smoking it, it has been reported to be easier on the lungs by a few member (myself being one and for memory Dasein being another). In addition BW, as some of your test are indicating, it still may be a good salt form for storage and a safe candidate to smoke.
I should also note for anyone reading, Loveall found DMT benzoate to form very well in D-limo. D-limo holds benzoic acid well but not DMT benzoate (it precipitates fast), great way to easily store DMT long term. It also smells of citrus


Bufo lactate could be a good candidate for e-juice if the preliminary results for harmala and DMT lactate are anything to go off.

I have played around with benzoic acid a bit, it is fairly soluble in non polar solvents like naphtha and toluene. You can dissolve DMT in NPS and add benzoic acid dissolved in NPS, and DMT benzoate will start crashing out almost immediately. Adding benzoic acid crystals directly into naphtha also works but there are a few complications. I think the dmt benzoate forms a layer around the benzoic acid crystals and stops it from dissolving and thus crashing out more dmt benzoate, the finer the benzoic acid, the better it can directly dissolve in DMT-NPS solution, but benzoic acid dissolved in NPS works better!

In my last extraction, I used benzoic acid to salt out dmt benzoate from the pulls and then put the NPS back into the bark soup right away and continue pulling that way. Once the clouding stops, you know that the bark soup is exhausted and continue on with mini A/B.

Is bufotenine soluble in any form in any NPS?

No it is polar alkaloid. The exception is if the non-polar solvent is heated to boiling point, xylene and d-limo have been reported to work when brought to the boiling point. As for other salt forms of bufotenine. I could test bufo benzoate in other NPS. What are you thinking Dasein?

ok this one sounds funny... but wouldn't it be possible to salt out Bufo from water? DMT benzoate is much less soluble in water as compared to the other salts. Bufo being polar would be soluble in water no? and adding benzoic acid dissolved in hot water could at least partially crash it out, the rest could be obtained via evap. You'd have to use the minimum amount of water though.

Aside from that, alcohols could be an option, you could do it in different fractions. This could also help with purification, for example, dmt fumarate recrystallized at room temperature is more pure than that precipitated in the freezer. So I usually let it crash out at room temp, then pour off the mother liquor in another dish and freez precipitate the rest. You can also crash out one part, reduce the liquid, crash out another part, further reduce and so on, giving you different fractions of varying purities.

Finally, if it is soluble in xylene/toluene, than it can be easily crashed out since benzoic acid is fairly soluble in those, even more so than in naphtha. But... this is all based on things I have learned playing around with DMT. I will start working on Bufotenine in about... 4-5 months and will report my findings.

As for vaporizing benzoate, the trouble I had was that a) the vaporization was relatively slow and b) the vapor would recrystallize within the vape chamber... also, the vapor had a strong benzoic acid smell, so either there was some excess benzoic acid in there, or the benzoic acid got separated from the DMT during vaporization. Still... it was different from freebase and much easier on the lungs. Anyways, I only tried it once and need to run a few more experiments, try different temperatures etc. Hopefully, I will be able to report back soon.

Success!

I tried Solution #1 = creating the Bufo-Benzoate salt and it worked charmingly!

Bufotenin Benzoate was vaporized in the Spice Rotator at + 2 lego plates, which is - 6 mm reduced distance from the flame to the Banger compared to the optimal DMT distance. This is believed to be ~ 210 °C, which closely matches the vaporization start of Bufo Benzoate. That theory of Solution #1 seems right: Charged molecules (until the moment of vaporization) prevent aggregation by chemical bonds - or at least less of these are formed, so everything that gets into air will be unimolecular Bufotenin, free of neusating, irritating combustion products!


The vapor was

- absolutely NOT harsh
- absolutely NO nausea
- no flavor of roasted nuts anymore

As the material will be only ~ 62 % Bufotenin it means you need to load it up more, but still even with reduced mass fraction the potency seems to be above DMT.

I smoked like ~ 20 mg of Bufot Benzoate (~ 12,5 mg Bufotenin).

- it has a QUITE delayed onset, not just 5 seconds like DMT, but more like 20-30 seconds interestingly - you can already exhale and lay back to spectate how effects are rising

- bright CEVs with a lot of changing colours, interestingly changing faster and more colourful starting from ~ 5 mins after vaporization time

- whole effect lasted easily 20 mins with 10 min of strongest effects. Right now still not feeling sober at T + 30 min probably

- you will have slight vasoconstriction in forehead, arms and upper legs, but nothing that is truly distorting the experience. Much less than my first smoked Freebase Bufo in 2020. Also vasoconstriction only starts at t + 10 min and is gone at t + 20 min.

It will be very important to use a device with careful temperature control to not trigger the decomposition/polymerization reactions that Bufotenin still can undergo when being a salt at high enough temperatures! See yourself in the vaporization profile mentioned above. Just heat Bufo Benzoate to the absolute minimum temperature that still starts strong vapor formation, that seems just above 200 °C. Also use a device that induces strong ventilation to get as much Vapor in the shortest time possible.

Still the Benzoic Acid will decompose, but I promise you the vapor is FREE of benzoic acid. This is how the Banger of the Spice Rotator looked like after, charred Benzoic Acid and possibly traces of Bufotenin-Polymers, that are impossible to vaporize due to being cations:



Not pretty, but well there is still ~ 38 % of Benzoic acid in that mixture, which does not seem to vaporize. The vapor is a charm. And for ästethics, I guess that mess is a good friend of anybody who goes with the Bong anyways

Next step would be to measure the vaporization efficiency and check how much of the Bufotenin still decomposes to prove how efficient that cations stop polymerization at ~ 200 °C. Still I can say the effect of ~ 12 mg Bufo was easily matching 12 mg smoked DMT.

I think the ventilation problem was likely the reason why my trials with DMT-benzoate didn't go very well. I used divine crossing v5, it has two small holes through which the air flows in but yeah you need a really long steady toke. This is probably why dmt-benzoate kept resolidifying with in the chamber. I think I should give the spice rotator a try!

Seems like there is not such a big window like with DMT about temperature to get still pleasant hits? Probably overheating is still something to consider even with the benzoate salts. I just tried that method of vaping and even though vapor was charmingly smooth there was this ugly back tar inside the banger. I put some DMSO inside and that could undo most of that coloration. Still even considering that the vapor is not harsh it might be worthy to consider how easy a device can be cleaned of that mess.

So now I just checked how efficient that Bufo Benzoate vaping is:

> Weigh recorded of the Banger before Vaporization

> 20 mg Bufo Benzoate put inside

> Vaped at ~ 210 °C

> Weight afterwards with black tar recorded

Whole weight was + 6,5 mg

20 mg Bufo Benzoate are ~ 62,6 % Bufotenin ~ 12,5 mg Bufotenin

Therefore if perfectly vaped at that temperature you would expect + 7,5 mg remaining in the Banger. But a post about Tryptamine salts is nearly ready and this one also implies that there is always acid vaporizing together ... but in that case still nearly 70 % vaporized, which is also much better than Freebase and then also in pretty good accordance with the TGA of Bufotenin Benzoate, which stops at around ~ 70 %.

So _Trip_ that was a pretty cool find originally from you that the salt is quite smooth and so your idea of shortening that whole TEK down by 1 step might indeed come true, if your Alkaloid Benzoate of the separating step would be indeed already pure Bufotenin! So will be quite interesting what that analysis of yours will tell.

This is probably offtopic here, but 5-MeO-DMT is quite active when insufflated and sublingually. It would be good to know if bufotenine is. I expect it to be less effective than 5-MeO-DMT, but more effective than DMT, under the assumption that MAO will have respectively an easier and harder time breaking it down compared to those compounds.

Yes, bufotenine is active snorted and sublingually. Freebase bufotenine is, anyway. Salts i don't know.

Yopo (mostly bufotenine) is def active intranasally, as i've experienced myself. Not pleasant to have all that powder up one's nose but I def had visuals.

Not sure if you've ever read but there is a classic publication from Jonathan Ott called pharmañopo where he describes his experiments with bufotenine using different routes of administration.

Just as a sidenote I found an example where similar alkaloids also react in a way that is not too different to what might happen for Bufotenin.

Dopamin has also 2x OH-groups in 1,2-conjugation and it seems to also form polymers similar to the "Psilocybin-style Polymer" in the first picture:



Maybe we can learn something from here, as the process might not be too different. As Mindlusion and Loveall wrote for DMT it seems either Basic Conditions or a strong Oxidative Environment will do the job. Full paper can be found here. That Oxidation was achieved by light and therefore again UV-beams causing those polymerization to start.




Meanwhile I already have the 1H-NMR of Bufotenin which shows the 'regular state' with all the protons that might causing a reaction still unreacted (#4 + #2 + #8 + #5). Those are positions would likely decline in their integral, which means the average molecule will have less of these protons AKA those will have reacted in for example polymerization reactions. All my old NMRs were measured in Chloroform, but here in DMSO we also see the Signals #15 + #7.