Tryptamines The Big & Dandy Bufotenine (5-HO-DMT) Thread - The Truth is Out There

[Anadenanthera]

^^^All the same, the plants do contain DMT and 5-meo-DMT, just in extremely small concentrations.

I'm just tired of all the crap out there.

If you look at all the places selling these seeds, they claim Yopo's effects are from DMT and 5-MeO-DMT. This is money talking, not the facts. People believe this crap too and spread it all over. I've seen this on Wiki too for a long time. But recently someone updated it so it doesn't say it anymore.

Yes, many tests prove Yopo and Vilca contain DMT and 5-MeO-DMT in small amounts. So do our brains for that matter, but people aren't tripping on that either. A. peregrina usually contains more DMT and 5-MeO-DMT than A. colubrina does. The most DMT A. peregrina has been found to contain is a mere 0.16 %! Its been found to contain up to 7.4% bufotenine. You also must remember that bufotenine is as active as DMT when used as snuff. A typical A. peregrina seed contains much less DMT than 0.16 % and the DMT content is quickly lost as the seeds age. They usually contain 1% or more bufotenine and bufotenine lasts a long time. Even very old seeds that no longer contain any DMT at all will still contain bufotenin. On average A. peregrina contains 30-40 times as much bufotenine as DMT and 5-MeO-DMT combined. People just aren't having DMT or 5-MeO-DMT trips from any Anadenanthera seeds. Its just not possible, unless people isolate these chemicals from the seeds and use them that way.


Anyone who's used both Yopo and Vilca very extensively over many decades will tell you, other than Vilca being about twice as strong, there are pretty much no differences in the effects of the two. Most long time snuff users prefer Vilca because it’s cheaper and stronger. Why pay the extra money for Yopo just to know that it contains more DMT and 5-MeO-DMT when its still not enough to do anything? I don’t know. People are suckers I guess. As long as people are willing to pay more for less, there’ll always be salesmen taking advantage of them.

Don’t waste your money on Yopo thinking you’re getting a good source for DMT or 5-MeO-DMT. If you want DMT, get Mimosa or some other plant with DMT in better quantities. Yopo often contains less that 0.01% DMT and older seeds tested often contain NONE AT ALL. You’re VERY LUCKY to find any Yopo that contains any more than 0.05% DMT.

 

[cognosis]

I'm just tired of all the crap out there.

Yes, many tests prove Yopo and Vilca contain DMT and 5-MeO-DMT in small amounts. So do our brains for that matter, but people aren't tripping on that either. A. peregrina usually contains more DMT and 5-MeO-DMT than A. colubrina does. The most DMT A. peregrina has been found to contain is a mere 0.16 %! Its been found to contain up to 7.4% bufotenine. You also must remember that bufotenine is as active as DMT when used as snuff. A typical A. peregrina seed contains much less DMT than 0.16 % and the DMT content is quickly lost as the seeds age. They usually contain 1% or more bufotenine and bufotenine lasts a long time. Even very old seeds that no longer contain any DMT at all will still contain bufotenin. On average A. peregrina contains 30-40 times as much bufotenine as DMT and 5-MeO-DMT combined. People just aren't having DMT or 5-MeO-DMT trips from any Anadenanthera seeds. Its just not possible, unless people isolate these chemicals from the seeds and use them that way.

I'm confused as to what exactly I said was a rumor or "crap".

~Maybe I made a mistake by saying yopo had DMT and 5/DMT as the primary active compounds; however, I'm sure too if you've done any sort of experimentation with the snuffs and also smoked the seeds you will have noticed a difference.

Isn't the calcinated lime used to, like, get the dmt to cross the brain-blood barrier? I mean, isn't bufotenin already orally active? Why blow a wad of crushed shells and seeds up your nose if eating or smoking it would be just as effective? When I smoked the seeds I smoked like two or three; whereas, when I made the snuff, I used 10-20 seeds. Yeah, I know there's minuscule amounts of dmt and 5-meo-dmt in yopo and vilca, but it seems to me that the experience one has with the snuffs differs significantly enough to assume that it isn't solely 5-ho-dmt that's coloring the trip.

BAM

 

[swilow]

I have two questions- why is this often written as 5-OH-DMT- what does OH stand for?

And secondly- can any of the pharmacollogically inclined let me know if A. Colubrina has significant MAOI properties and will ineract badly with the Zoloft I take?

 

[stirfry]

I have two questions- why is this often written as 5-OH-DMT- what does OH stand for?

5-HO-DMT=5-OH-DMT=5-hydroxy-dimethyltryptamine

 

[swilow]

^^Confusing, I did think it stood for hydroxy- but why is it written OH? Oh well, it probably doesn't matter. Just something I've always wondered.

 

[Morninggloryseed]

^^Confusing, I did think it stood for hydroxy- but why is it written OH? Oh well, it probably doesn't matter. Just something I've always wondered.

Because DMT has an OH sticking off the 4 position. An oxygen connected to the indole with one hydrogen filling in the other end.

HO is a contraction of the name, HydrOxy.

 

[swilow]

^So OH and HO are interchangeable terms for HydrOxy?

Anyway, I'm bumping this I have some culubrina seeds in the pipelines, and would really like to ascertain if this would be safe with Zoloft 75mg/day. I am concerned that, as with other tryptamines, this may have MAOI effects....I have smoked 5-meO-DMT on anti-depressants (Prozac) with really quite awful physical symptoms- though that was a one off, when the 5-meo-DMT was mixed with DMT, the experience became almost safe feeling. This is something I really need to know, as I am definteily going to consume the seeds within a week, I DO NOT want to do anything that could induce seratonin sydrome and death. If someone is able to give me a basixally definiteve answer, I would be much obliged. As far as I can tell Bufotenine (I prefer calling it UFOtenine ) doesn't appear to effect monamineoxidase enzymes. But I ahve to be sure. I'm thinking a light smoke of the substance may be advisable initially....

Anyone.....please??

 

[Coolio]

Yeah, it depends on what nomenclature you're using. I think the proper way to write it is OH, because you put the elements with higher atomic weights preceding the elements with lower atomic weights.

 

[Solipsis]

Yeah, it depends on what nomenclature you're using. I think the proper way to write it is OH, because you put the elements with higher atomic weights preceding the elements with lower atomic weights.

That's true, however I think there is a rightly tendency to put the atoms or moieties in ordered sequence. The O is always in between DMT and H/Me - to form 5-HO-DMT and 5-MeO-DMT resp.
The order by atomic mass you are referring to is properly used when dealing with actual structural formulas. Those would be C12H16N2O and C13H18N2O in this case.
I am describing my personal view on this matter, while both nomenclatures are correct this would technically be best (clear when comparing use of terms).

 

[vecktor]

This common shorthand used to describe molecules works from left to right so it is better sometimes to write HO-something rather than OH-something if the thing sticks out of the left of the molecule as described.

it is obvious with something as simple as bufotenine that the O is attached to the ring. hydrogen can only form one bond so is essentially a dead end, oxygen usually forms two bonds so it is a fairly safe bet that oxygen is the link atom between the Hydrogen and the rest of the molecule.
other ones often written backwards are carboxylic acids and their derivatives.
HOOC-CH2CH2-COOH is succinnic acid, a dicarboxylic acid where HOOC is the same as COOH.

there are plenty of examples where this shorthand falls over but they tend to be more complex.

 

[swilow]

Well, I've found the answer to my 5-0h-dmt/maoi qeury:

Bufotenin was found to have mild MAO inhibiting effects and should not be used with other drugs known to interact dangerously with MAO inhibitors.
Anadenanthera: Visionary Plant Of Ancient South America By Constantino Manuel Torres, David B. Repke, 2006, Page 168

How potent an effect I'm not sure, though I doubt I'll be smoking these fat seeds for a while. What to do with them?

 

[egor]

^So OH and HO are interchangeable terms for HydrOxy?

Anyway, I'm bumping this I have some culubrina seeds in the pipelines, and would really like to ascertain if this would be safe with Zoloft 75mg/day. I am concerned that, as with other tryptamines, this may have MAOI effects....I have smoked 5-meO-DMT on anti-depressants (Prozac) with really quite awful physical symptoms- though that was a one off, when the 5-meo-DMT was mixed with DMT, the experience became almost safe feeling. This is something I really need to know, as I am definteily going to consume the seeds within a week, I DO NOT want to do anything that could induce seratonin sydrome and death. If someone is able to give me a basixally definiteve answer, I would be much obliged. As far as I can tell Bufotenine (I prefer calling it UFOtenine ) doesn't appear to effect monamineoxidase enzymes. But I ahve to be sure. I'm thinking a light smoke of the substance may be advisable initially....

Anyone.....please??

My brother has done them on mirtazipine, though he got sicker than the rest of us. I think mirtazipine is a pretty fart cry from zoloft, so I dont know how much it will help. I just know he woulnd't do them again until he was off the remerom

I also did a line of snuff (amongst an assload of other things) on remeron and didnt have nearly as bad of a reaction.




Oh, I found this bit on pubmed, though the entire paper would be better>

Ott J.
Phantastica, Barcelona, España.

Summarized are psychonautic bioassays (human self-experiments) of pharmañopo--crystalline bufotenine (5-HO-DMT; 5-hydroxy-N,N-dimethyltryptamine; dimethylserotonine), at times combined with harmaline or harmine-via intranasal, sublingual, intrarectal, pulmonary (inhaled vapor) and oral routes. This is done by way of pharmacological modeling of diverse South American shamanic inebriants, principally the snuffs ñopolyopo and cebílhaáj, prepared from seeds of Anadenanthera peregrina var. peregrina and A. colubrina var. Cebil, respectively. Psychoptic (visionary) activity of bufotenine has been established and the 1967 Holmstedt-Lindgren hypothesis of the paricá effect-intranasal potentiation of tryptamines by concomitant administration of monoamine-oxidase-inhibiting (MAOI) beta-carbolines from stems of Banisteriopsis caapi admixed with the snuffs-has been confirmed by 25 psychonautic bioassays. Salient phytochemical and psychonautic literature is reviewed, and isolation of bufotenine from Anadenanthera seeds detailed (with one table and eight references).

PMID: 11718320 [PubMed - indexed for MEDLINE]

 

[Anadenanthera]

I'm confused as to what exactly I said was a rumor or "crap".

Sorry...I should be more clear. Its a rumor that any Anadenanthera seeds out there contain DMT or 5-MeO-DMT in large enough amounts to have much affects at all. Even Anadenanthera peregrina only has minute amounts of DMT and 5-MeO-DMT, less than 0.05% normally, and almost always over 1% bufotenin. Its more DMT than A. colubrina, but its SO SMALL as to have almost no effects at all. The experience is from bufotenin.

~Maybe I made a mistake by saying yopo had DMT and 5/DMT as the primary active compounds; however, I'm sure too if you've done any sort of experimentation with the snuffs and also smoked the seeds you will have noticed a difference.

The only difference we've noticed here is that A. colubrina is usually about twice as strong. If you make snuff with A. colubrina and A. peregrina, and use the same amount of lime, there will be a difference in the effects because A. colubrina usually requires more lime and A. peregrina requires less lime.

My friends in Brazil have extensive experience with both and they all prefer A. colubrina because its stronger. There's really no difference in effects other than potency.

You may be having placebo effects because you believe one is different from the other. If you really do notice a difference, you're the only person I've met that does.

Isn't the calcinated lime used to, like, get the dmt to cross the brain-blood barrier?

No, its used to make bufotenin cross the blood brain barrier. Without the lime, bufotenin has a hard time crossing the blood brain barrier, DMT doesn't need to be in free base form to cross the blood brain barrier. Neither does psilocybin, LSD, mescaline, etc. This only applies to bufotenin. DMT in acid salt form is actually better for taking as snuff because it dissolves better. Try adding an acid to your snuff. It will make a bufotenin acid salt that will make you really sick. That's why shamans don't add any acids to the snuff. They know what they are doing. You do know that cocaine works better as a snuff if made into a water soluble acid salt form right? The same thing applies to DMT. But NOT to bufotenin, because it changes the effects of bufotenin and makes it very toxic.

I mean, isn't bufotenin already orally active?

Yes, but it becomes bufotenin hydrochloride when it enters the digestive system which is VERY TOXIC and not very hallucinogenic. Try it out. You'll get really sick if you take enough of it.

Why blow a wad of crushed shells and seeds up your nose if eating or smoking it would be just as effective?

Like I said above. You don't want to eat bufotenin. It becomes very toxic and can easily kill you if you take too much of it orally. It causes lots of nausea, tension, high blood pressure, etc. VERY TOXIC that way. That's why shamans use it as a snuff. They know what they're doing.

When I smoked the seeds I smoked like two or three; whereas, when I made the snuff, I used 10-20 seeds. Yeah, I know there's minuscule amounts of dmt and 5-meo-dmt in yopo and vilca, but it seems to me that the experience one has with the snuffs differs significantly enough to assume that it isn't solely 5-ho-dmt that's coloring the trip.

BAM

The snuff is different from smoking it because of sevaral factors. First, you mix the snuff with lime. This changes the bufotenin in the seeds to calcium bufotenate, which has more hallucinogenic effects than whats in the seeds. Secondly, the effects of bufotenin differ if smoked, snuffed, or taken orally. If smoked, the effects are primarily visual. If taken orally, the effects are primarily toxic because it gets converted to bufotenin hydrochloride. If taken as snuff, the effects are more "psychedelic"...its hard to explain, but its very different from smoking it.

Pure free base bufotenin smoked is VERY DIFFERENT than when taken as a snuff. If smoked, it only produces visual effects. If taken as a snuff, its a beautiful full blown psychedelic experience. If ingested it converts to bufotenin hydrochloride which REALLY SUCKS. Its a little bit hallucinogenic, but mostly causes lots of side effects which get really bad and deadly at high doses. A high dose of it orally can cause a little hallucinogenic effects, and can kill you. Don't take it orally.

 

[Anadenanthera]

^So OH and HO are interchangeable terms for HydrOxy?

Anyway, I'm bumping this I have some culubrina seeds in the pipelines, and would really like to ascertain if this would be safe with Zoloft 75mg/day. I am concerned that, as with other tryptamines, this may have MAOI effects....I have smoked 5-meO-DMT on anti-depressants (Prozac) with really quite awful physical symptoms- though that was a one off, when the 5-meo-DMT was mixed with DMT, the experience became almost safe feeling. This is something I really need to know, as I am definteily going to consume the seeds within a week, I DO NOT want to do anything that could induce seratonin sydrome and death. If someone is able to give me a basixally definiteve answer, I would be much obliged. As far as I can tell Bufotenine (I prefer calling it UFOtenine ) doesn't appear to effect monamineoxidase enzymes. But I ahve to be sure. I'm thinking a light smoke of the substance may be advisable initially....

Anyone.....please??

I hate to tell you that both Bufotenin and 5-MeO-DMT are known to be mild MAOIs. And it doesn't matter if they are in free base or salt form. I don't know how mild though. Be careful.

 

[swilow]

^See above. That has been ascertained. I'd just like some sort of anecdotal report on it, as 5-Meo-DMT didn't effect me too negatively.... I mean, passionflower spp. is a mild MAOI, that has no detrimental effect when used; but that has little to do with the topic. Best to err on the side of caution.

 

[Anadenanthera]

Isn't the calcinated lime used to, like, get the dmt to cross the brain-blood barrier?

No, its used to make bufotenin cross the blood brain barrier. Without the lime, bufotenin has a hard time crossing the blood brain barrier, DMT doesn't need to be in free base form to cross the blood brain barrier. Neither does psilocybin, LSD, mescaline, etc. This only applies to bufotenin. DMT in acid salt form is actually better for taking as snuff because it dissolves better. Try adding an acid to your snuff. It will make a bufotenin acid salt that will make you really sick. That's why shamans don't add any acids to the snuff. They know what they are doing. You do know that cocaine works better as a snuff if made into a water soluble acid salt form right? The same thing applies to DMT. But NOT to bufotenin, because it changes the effects of bufotenin and makes it very toxic.

I mean, isn't bufotenin already orally active?

Yes, but it becomes bufotenin hydrochloride when it enters the digestive system which is VERY TOXIC and not very hallucinogenic. Try it out. You'll get really sick if you take enough of it.

Why blow a wad of crushed shells and seeds up your nose if eating or smoking it would be just as effective?

Like I said above. You don't want to eat bufotenin. It becomes very toxic and can easily kill you if you take too much of it orally. It causes lots of nausea, tension, high blood pressure, etc. VERY TOXIC that way. That's why shamans use it as a snuff. They know what they're doing.

When I smoked the seeds I smoked like two or three; whereas, when I made the snuff, I used 10-20 seeds. Yeah, I know there's minuscule amounts of dmt and 5-meo-dmt in yopo and vilca, but it seems to me that the experience one has with the snuffs differs significantly enough to assume that it isn't solely 5-ho-dmt that's coloring the trip.

BAM

The snuff is different from smoking it because of sevaral factors. First, you mix the snuff with lime. This changes the bufotenin in the seeds to calcium bufotenate, which has more hallucinogenic effects than whats in the seeds. Secondly, the effects of bufotenin differ if smoked, snuffed, or taken orally. If smoked, the effects are primarily visual. If taken orally, the effects are primarily toxic because it gets converted to bufotenin hydrochloride. If taken as snuff, the effects are more "psychedelic"...its hard to explain, but its very different from smoking it.

Pure free base bufotenin smoked is VERY DIFFERENT than when taken as a snuff. If smoked, it only produces visual effects. If taken as a snuff, its a beautiful full blown psychedelic experience. If ingested it converts to bufotenin hydrochloride which REALLY SUCKS. Its a little bit hallucinogenic, but mostly causes lots of side effects which get really bad and deadly at high doses. A high dose of it orally can cause a little hallucinogenic effects, and can kill you. Don't take it orally.

I want to elaborate on this and explain a little more in detail of why this is the case for all the chemists out there.

As you probably know, free base DMT and free base 5-MeO-DMT are both non-polar molecules that are basic (with a pH above 7) and are both not water soluble. If you add calcium hydroxide or any other strong base, they will not react with it because they are not acids. They are weak basis, and they can only react with acids, not other bases. So, they will only form salts with acids (hydrochloric acid, acetic acid, citric acid, etc) and not with bases. Also, they are hallucinogenic no matter which form they are in because they primarily affect central 5-HT receptors, and have little effects on peripheral 5-HT receptors whether in acidic salt form or free base form. Only when in acidic salt form can they react with strong bases, in which case they form free base compounds and not basic salts.

5-OH-DMT (bufotenin) is very different from the other two. The exposed OH group changes everything and gives it polarity. So unlike free base DMT and free base 5-MeO-DMT, free base 5-OH-DMT is polar, weakly acidic (with a pH below 7) and somewhat water soluble. Like DMT and 5-MeO-DMT, it can form a salt with acids. This is unusual though as 5-OH-DMT is itself a weak acid. Its amide side is able to bond with acids. It’s able to form a free base compound at pH 8-9. Like 4-OH-DMT (psilocin), its close relative, 5-OH-DMT also decomposes at hi pH levels.

Unlike DMT and 5-MeO-DMT, 5-OH-DMT affects both central 5-HT receptors and peripheral 5-HT receptors. If it’s in a very water soluble form, it affects more peripheral 5-HT receptors. If it’s in a poor water soluble form, it affects more central 5-HT receptors in the brain. That’s why water soluble forms, like bufotenin hydrochloride, produce toxic effects, and poorly water soluble forms, like free base bufotenin, produce more hallucinogenic effects. This is pretty unique to 5-OH-DMT. Even 4-OH-DMT (psilocin) is hallucinogenic no matter what form it’s in.

To make things more interesting, 5-OH-DMT has an exposed OH group that decomposes at very hi pH levels. This is the KEY to Yopo and Vilca. If you react 5-OH-DMT with any strong base at pH 12 or so, it will free base then decompose, lose the H atom, and become 5-O-DMT. At this point it’s NO LONGER BUFOTENIN. Bufotenin is defined as 5-OH-DMT, and this compound is 5-O-DMT, a new compound. 5-O-DMT is able to form a salt with the base. However, because it’s a salt of the base used in the reaction, the polarity is governed by whatever base was used in the reaction. For example, calcium hydroxide is notorious for producing salts with poor water solubility. So if you react 5-OH-DMT with the strong base calcium hydroxide at pH 12 (as is done when making Yopo or Vilca snuff), it becomes the calcium salt of 5-O-DMT (currently being called calcium bufotenate, but perhaps calcium bufotenoxide is more appropriate?). It becomes a salt with very poor water solubility, much like other calcium salts. However, if you use sodium hydroxide, it becomes the sodium salt of 5-O-DMT, which I’ve heard is very water soluble and toxic. I have no experience with sodium bufotenate, so please don’t quote me on that. Is anyone out there willing to test sodium bufotenate (or sodium bufotenoxide, whatever you want to call it)?

What’s even more interesting is that because 5-O-DMT is not bufotenin, it should be legal in nearly all countries, even in the US.:D However, if you react 5-O-DMT with an acid, like the acid in your stomach, hydrochloric acid, the reaction is reversed and it becomes 5-OH-DMT hydrochloride (bufotenine hydrochloride), which is illegal only in the US (as far as I know).

 

[Anadenanthera]

That's true, however I think there is a rightly tendency to put the atoms or moieties in ordered sequence. The O is always in between DMT and H/Me - to form 5-HO-DMT and 5-MeO-DMT resp.
The order by atomic mass you are referring to is properly used when dealing with actual structural formulas. Those would be C12H16N2O and C13H18N2O in this case.
I am describing my personal view on this matter, while both nomenclatures are correct this would technically be best (clear when comparing use of terms).

Bufotenin is commonly written as 5-OH-DMT and 5-HO-DMT. Google found about 230 pages for 5-OH-DMT and about 240 for 5-HO-DMT, so 5-HO-DMT is slightly more popular.

With bufotenin the O is attached to the DMT and the H is attached to the O. When mixed with calcium hydroxide it decomposes to 5-O-DMT. I agree that 5-HO-DMT is more clear than 5-OH-DMT. But with so many publications out there written as 5-OH-DMT, I find myself typing that by habit. Even the book TiHKAL by Alexander & Ann Shulgin shows both OH and HO in use all over the place! 8(

And then there's the spelling of bufotenin. It’s spelled as both bufotenin and bufotenine all over the place! Google found about 48,500 for bufotenin and about 57,400 for bufotenine. So the spelling bufotenine is slightly more popular. What consufion! 8(

 

[Morninggloryseed]

I don't see how it would lose the H without forming a double bond, which it can't do on an aromatic ring. Any chem guys want to explain this one? F&B?

To make things more interesting, 5-OH-DMT has an exposed OH group that decomposes at very hi pH levels. This is the KEY to Yopo and Vilca. If you react 5-OH-DMT with any strong base at pH 12 or so, it will free base then decompose, lose the H atom, and become 5-O-DMT. ).

 

[Anadenanthera]

Bufotenin is commonly written as 5-OH-DMT and 5-HO-DMT. Google found about 230 pages for 5-OH-DMT and about 240 for 5-HO-DMT, so 5-HO-DMT is slightly more popular.

With bufotenin the O is attached to the DMT and the H is attached to the O. When mixed with calcium hydroxide it decomposes to 5-O-DMT. I agree that 5-HO-DMT is more clear than 5-OH-DMT. But with so many publications out there written as 5-OH-DMT, I find myself typing that by habit. Even the book TiHKAL by Alexander & Ann Shulgin shows both OH and HO in use all over the place! 8(

And then there's the spelling of bufotenin. It’s spelled as both bufotenin and bufotenine all over the place! Google found about 48,500 for bufotenin and about 57,400 for bufotenine. So the spelling bufotenine is slightly more popular. What consufion! 8(

Here's even more confusion:

* Anadenanthera peregrina is commonly said to contain DMT as its main active chemical, when in fact it is bufotenin for both A. colubrina and A. peregrina!

* Anadenanthera colubrina is often sold as Anadenanthera peregrina due to misidentification.

* Anadenanthera legumes are commonly called beans and seeds! Seems no one can make up theirs minds! Are they beans or seeds? What is it?

* Bufotenin is commonly misrepresented as being the main toxin in toad venom, when its in fact only present in very small amounts in some venom and is clearly not the main active compound in any of them.

* Tests with injected bufotenin sulfate and oxalate, have made people think bufotenin is not hallucinogenic, but a toxin. This is true for THESE FORMS, but not free base bufotenin. This has been proven many years ago, but most people still think it’s a toxin!

There are so many misleading "facts" out there about bufotenin. Its going to be a long time before this mess is cleaned up. Maybe it’s a good thing? Maybe its better that people think it’s a toxin and not a hallucinogen? That way no one will buy the seeds/beans/legumes/whatever and they’ll remain out of the spot light and relatively easy to get for the few people who know about them.

 

[Anadenanthera]

I don't see how it would lose the H without forming a double bond, which it can't do on an aromatic ring. Any chem guys want to explain this one? F&B?

It’s a well known fact that phenolic compounds behave like this. You do know about phenol right? Bufotenin is based on phenol. If you react calcium hydroxide with phenol, you get calcium phenoxide. It loses the H and forms a salt with calcium. The same thing happens with morphine, psilocin, and bufotenin is no exception to this rule. Look up phenoxide and phenol, and you'll see what I'm talking about.

How is it possible for this rule not to apply with bufotenine when it clearly applies to phenol, morphine and psilocin? Can someone please explain how bufotenine could be the one exception to this rule?