Last night I weighed out & loaded up 10mg of my first Bufotenine extraction.
I used an oil vaporizer bulb, attached to a small bong & a torch lighter to heat it.
I don't know it the water filtering was such a good idea, it seemed to be a bit darker after use, so I wonder if some of the Bufo vapor ended up in the water.?.?
I have the gear necessary to put together one of 69ron's recommended test tube vaporizers coming sometime next week.

I took 3 tokes of the vapor over about 7 minutes time, it wasn't super harsh, but it definitely was not easy on the lungs either.
Tasted pretty bad, I could surely taste the D-Limonene orangeness!!
It was nearly impossible for me to hold the vapor in for more than a few seconds.

Soon after the first toke I could feel the tingling in my body, I felt just a little nauseous & I started to sweat a bit.
It was a little uncomfortable, but not too much so & it only lasted a couple of minutes.

The strongest effects I felt, were the body tinglings & my mind was very, very calm & peaceful.
I also felt that psychedelic vibration a tiny bit.
About 5 to 10 minutes in I could see the faint outline of some CEV trying to start forming behind my eye lids, but the fullest they got was to be faint squiggly outlines in my peripheral vision.

I would love to hear from those of you who have received the full effects from Bufotenine, on how you cleaned it up enough for easier smoking (if you did...).
Also, What device and/or smoking techniques were used to get the most efficient use of Bufo & how much do you usually use at a time?
Anyone ever try infusing some kind of herb with Bufotenine?
What herb? How much? How did you do it?


Thanks!!

WS

Could be a simple matter of underdosing...

I know that 10 mg's been thrown around as a very good dose, and from the report I received from SWIM, 15 mg is a nearly mind-blowing one. However, 69ron's SWIM seems to be a bit more sensitive than most, and the weirdo who's told me about his experience is both very light (40 kg), and very sensitive to visual effects (plain ol' weed gives him noticeable CEVs).

Said weirdo also didn't have much trouble holding the vapor in, though. He claims to have used the tek outlined in my post in the main Bufo extraction thread, where only one round of limonene purification was used

Can anybody verify whether or not, smoking Bufotiene using water filtering (I.E. a bong, water pipe, etc...) is a bad idea because of the Bufo being water soluble?
Or if it is OK, or bad to use some kind of water filtering smoking device for some other reason...

I am going to build one of the "test tube vaporizers" that 69ron has recommended.
I atch a pic at the bottom:
I like how it traps the vapor in the tube & I'm thinking it might be a nice smoking device for other vapors as well.

Although, I had thought about putting a vacuum flask with a bit of water in it, below the test tube set up & attaching the plastic tube from the "output" of the "test tube vaporizer", to a similar, 2-hole rubber stopper set up in the top of the vacuum flask.
One of the holes in the flask's stopper would have a glass tube attached that would reach down to the water, bong style. The other hole would have a small piece of glass tubing sticking out the top, to be used as a "thumb-carb".
Last, there would be a long plastic tube attached to the side tube hookup of the vacuum flask, that one would place in there mouth to inhale from.

*You would place a candle under the bottom of the test tube, were your dose of Bufo (or whatever) is, to heat it into vaporization.
*Once the crystals start to vaporize, you place your thumb on top of the "thumb-carb" on the flask & inhale through the plastic tube.
*This should pull the vapor out of the test tube & through the water in the bottom of the vacuum flask, where it should build up inside the body of the flask.
*When you are ready, take your thumb off of the carb, which will let you inhale the filtered & cooled vapor out of the flask.

I think I'll try this with some spice, as I like how the vapor remains trapped inside of the device, but I'm now wondering if the water filtering of Bufotiene vapor in particular, effects the potency of the vapor too much...


As always, thanks!!

WS

SWIM was wondering about the solubility of bufo in water making a difference for vapor bubbling. If so, perhaps raising the pH of the water in the flask could help (lime or sodium carbonate)?

I'm pretty sure bufo's somewhat soluble in water at all pHs (Though likely more so at both low and HIGH pH, don't forget that acidic phenolic hydrogen). Water filtration may be a no-go.

I'm not sure why one would want to filter one's bufo, though. One's extract should be pretty darn pure, so there wouldn't be any tars to filter out. If it's an issue of making the vapor less harsh, perhaps placing the tube one's inhaling from through some cold water will cool down the vapour. Ie, the vapour won't be itself go through the water, it'll just be passively cooled. However, then one may be risking having the bufo redeposit on the inside of the tube.

Putting the tubing in water to cool it...hmmmm...that's very interesting. That never occurred to SWIM. I'm sure some of the bufotenine would collect in the tubing, but maybe not as much as you might think.

Bufotenine is very water soluble. It's apparently the least water soluble between pH 8.5 and 9.5 according to SWIM's old tests. It would be poorly soluble in water that had sodium bicarbonate in it at pH 8.2. You could use another stronger base, but you'd need to be careful not to over shoot the pH. With sodium bicarbonate you can't overshoot the pH, but with sodium carbonate you can but I don't think it would matter.

Bufotenine decomposes at very high pH values into something that remains permanently water soluble. But this only seems to happen with hydroxides (sodium hydroxide, calcium hydroxide, ammonium hydroxide, etc.) and not with carbonates. I don't think bufotenine is soluble in highly alkaline carbonate solutions, even at pH 11. It's my understanding that hydroxides are required to make bufotenine soluble in alkali. This is not stated anyway in the literature but based on SWIM's own tests.

This is the case with harmalol, a phenolic compound like bufotenine. Harmalol is soluble in alkali hydroxides at a high pH but not carbonates. So I believe SWIM's tests are accurate.

Does a phenol-group within an indole-group behave as phenol? Is it even considered to be a phenol-group within an indole? SWIM's not quite that astute at o-chem yet.



This is a common misconception of using bubblers for vaporizing. The point isn't to filter it but to use the water as a heat-sink, as you suggest with cooling the tubing; except the bubbler would allow it to cool and expand at the same time.


Using sodium carbonate solution would probably be quite feasible for bufo and spice (for anyone worried about losing spice, though SWIM hasn't noticed any loss from pure water) from the sounds of it, but ultimately, only testing will determine that. Good info about the hydroxides, ron.

If you remember, the reason a phenolic hydroxide is more acidic than a normal hydroxide is because the aromatic ring permits delocalization of the negative charge on the oxygen when protonated. The indole provides even more "room" for the negative charge to be delocalized on, however the nitrogen inputs extra electron density on the ring. The net result is that it seems to be roughly as acidic as a phenol (The closest I've seen to a number is for 4-hydroxyindole, for which this prediction supposedly holds true (pka roughly 10, like phenol))

69ron, it doesn't make sense to me that the nature of an inorganic base should affect solubility beyond just pH. Do you have any idea of what mechanism could be behind that?

I'm not really sure. I’d like to see it explained. It’s a proven fact for harmalol that it’s soluble in alkali hydroxides but not alkali carbonates and it has nothing to do really with pH, and I can give references for that if you like. It’s not proven for bufotenine, but SWIM’s tests show that it’s soluble in hydroxides but not carbonates just like harmalol. I'll look into this a little more. There must be a good solid reason for this.

Here's something I found which backs that up:



They are talking about phenol itself, but this should apply to some phenolic alkaloids as well.

So basically they are saying that sodium carbonate can’t react with phenol because of the carbonate ion. I think this is why harmalol isn’t soluble at pH 11 if sodium carbonate is used, but IS soluble at pH 11 if ammonium hydroxide is used. The hydroxide ion is strong enough to take a hydrogen ion from the phenol, but the carbonate ion is not and so the solubility changes if a hydroxide is used because the molecular structure changes.

Make sense? That’s from this web site: http://www.chemguide.co....rops/phenol/acidity.html

Note that psilocin (4-OH-DMT) is very similar, so when freebasing psilocin, use sodium carbonate and not a hydroxide or you run the risk of damaging the molecule. It's my understanding that hydroxides decompose both psilocin and bufotenine at pH 11 and up, but sodium carbonate doesn’t. It’s likely that harmalol is also decomposed at pH 11 and up.

69ron,

I believe you're misreading the link. What that link is saying is that sodium carbonate is simply too weak of a base to generate a high enough pH to significantly react with phenols, not that there's some other factor. When sodium carbonate is solvated, it's not the carbonate ion that directly reacts with whatever acid happens to be there, it generates hydroxide ions just like calcium hydroxide or sodium hydroxide does when dissolved.

That we refer to ammonium hydroxide as ammonium hydroxide is simply a convention recognizing the fact that when ammonia is dissolved in water, it generates hydroxide ions by pulling protons off of water molecules. Following the same convention, one could refer to sodium carbonate as a mixture of sodium hydroxide and sodium bicarbonate (a solution of a stoichiometric mixture of sodium hydroxide + sodium bicarbonate would in fact be identical to the equivalent pH solution of sodium carbonate). Perhaps some other factor caused the results seen in your test, or perhaps they were simple happenstance.

Like I said, I don't know, I don't understand it, and I'd like someone to explain it.

For whatever reason, there's a big difference between sodium carbonate at pH 11 and ammonium hydroxide or calcium hydroxide at pH 11 despite your explanation. The sodium carbonate doesn't cause destruction, but the others do. If you can explain why, I’d like to know.

Look at the Merck Index for harmalol. It’s soluble in hydroxides but NOT carbonates. So try and explain that. Like bufotenine, it’s a phenolic alkaloid. I’m sure a similar principle is at play here.

I don't want to debate how this happens, because I have no idea. All I know is that sodium carbonate cannot destroy bufotenine at pH 11, while ammonium hydroxide and calcium hydroxide can. For whatever reason, that's what SWIM's tests have shown. If someone can explain how that is, I would be very grateful. As it is, I just don’t understand it.

NaOH and Ca(OH)2 are both strong bases, which means they completely dissociate in water (a straight reaction, rather than equilibrium) and completely deprotonate weak acids (such as phenolic compounds?). Does that help? Or did you already know that?

amor_fati, so how does that relate to sodium carbonate being unable to destroy bufotenine, but ammonium hydroxide being able to? Ca(OH)2, lime, is much stronger than sodium carbonate, and able to reach pH 12.4, so I get that somewhat. But ammonium hydroxide can only reach about pH 11.4, which is the same as sodium carbonate, so why would ammonium hydroxide be able to destroy bufotenine but sodium carbonate not be able to? Ammonium hydroxide is not a strong base right? I'm puzzled but this.

And I'm puzzled by why harmalol is soluble in carbonate solutions but not hydroxide solutions. Both bufotenine and harmalol are phenolic alkaloids. And SWIM found that bufotenine is more soluble in hydroxides as well. Why? I think if I could understand that a little more it might help me to see the whole picture a little more clearly.

Are harmalol and bufotenine forming salts with these bases?

What can we rule out?
I agree with other posters that hydroxide ion alone cannot be causing this effect. The OH- concentration in any simple aqueous solution with pH=11.4 will be identical regardless of the base used. The strength of the base will just determine the number of base molecules needed to achieve pH=11.4.

So maybe it is an effect caused by the positive ion. The positive ion for sodium carbonate is sodium, just like sodium hydroxide. Carbonic acid decomposes rapidly into water and CO2. This is why marine aquarists love it. It raises pH without affecting calcium levels. If you aerate a sodium carbonate solution well you will have a slightly watered down sodium hydroxide solution.




I guess we can predict that a NaOH solution at pH=11.4 will not degrade bufo.

What could be destructive about NH4+, and Ca++? Maybe it does form some kind of salt.

69ron, would it be possible to copy-paste the Merck entry for harmalol?

I love chewing on scientific problems like this.

Well, I'll take a swing at it.

It's not the pH so much as the reaction itself that probably makes the difference. With sodium carbonate (and other weak bases), all potential species of the solutes can exist within the solution at equilibrium: the sodium carbonate itself, its conjugate acid ions, its conjugate base ions, the bufotenine salt and its ions, the bufotenine freebase, and probably some amount of dehydrobufotenine (I would guess but don't really know for sure). Infundiblum seems to make an accurate assessment here about how the ionic balance likely buffers this reaction.

NH3 has a higher pKb than sodium carbonate, the equilibrium balance probably shifts more toward the products in the equilibrium reaction that results in dehydrobufotenine (meaning dehydorbufotenine is favored over bufotenine). I can't explain how it would shift so drastically though except with the following hypothesis:

In terms of extractions utilizing sodium carbonate, perhaps the fact that your pulling out so much freebase with your target solvent, combined with an equilibrium favoring bufotenine over dehydrobufotenine, would continually shift equilibrium to the point of having an almost insignificant amount of dehydrobufotenine left in the solution. But with ammonia, it would simply require far more pulls to extract the expected amount of bufotenine since equilibrium favors dehydrobufotenine, which is less soluble in the target solvent.

This is the best way I know of to understand this, but there's still much I need to learn.

Maybe drying the basified material would affect the outcome of this as well? As in, if equilibrium favors bufotenine (in the case of sodium carbonate) the bufotenine will continue to precipitate out of the solution as less and less water is available to dissolve until only a very small amount of bufotenine is left dissolved and an even smaller amount of of dehydrobufotenine is left dissolved. In such a case, dehydorbufotenine would only remain as long as bufotenine can dissolve. The amount of dehydrobufotenine present will be limited to the amount of bufotenine dissolved.

In the case of ammonia, perhaps the dehydrobufotenine would precipitate out along with only a very small amount of of bufotenine. As the the dehydrobufotenine precipitated out, less and less bufotenine would be able to. The amount of bufotenine would be greatly limited by the amount of dehydrobufotenine dissolved and the amount of water left. It probably wouldn't even precipitate til late in the drying process.

Perhaps the solubility of the base itself would make a difference in this as well?

The significance of this would be that while it's possibly still available in a solution with NH3, though in small amounts, it's availability from dry material would be limited and small. If my assessment is accurate, this would affect the research regarding this.

Wait a minute, isn't the Na+ a spectator ion? NaOH can't exist in aqueous, as it completely dissociates into Na+ and OH-.

Edit:
I'm mistaken, NaOH can exist in sodium carbonate solutions, but occurs in this way:
Na2CO3 + H2O <-> NaOH + NaHCO3(Sodium Bicarbonate)
And isn't it generally insignificant except in special conditions?

Yeah the sodium ion doesn't usually do anything and it isn't associated with the hydroxide ions at all in solution. The reactions are just drawn this way for convenience.

Ca++ ions on the other hand form many insoluble salts and ammonium ions can participate in many reactions.