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

[yoyoman]

Interesting.

I had a little extract a long time ago and smoked it with DMT, the visuals were awesome - everything was made of 'lego blocks', went to the bathroom pissed out rectangles/squares.

I did a DMT style extraction (i'd get the freebase), didn't notice any side effects and didn't get that much out of the amount of seeds but it did work.

 

[Heyoka]

I'm still hopeing to stumble into a source for reasonably priced seeds that are reliable performers (I'm not asking for a source). There is just too much involved in the process that may go wrong to bother with it unless I'm confident in the potency of the starting seeds.

I am still very interested in these seeds !

 

[FormerlyHeyoka]

Well, I recently recieved another batch from the same supplier. The new batch was shipped as a replacement for the first shitty batch. The supplier actually said that they were delayed shipping on account of the time they took to dry after harvest. Well the seeds are cracker dry and clearly not very fresh. I actually think the replacement seeds are from the same batch as the original seeds. Well, at least they were free but I wonder if they are worth the time and effort to extract?

Either way, another supplier shipped a batch of nice fresh anadenanthera colubrina seeds and I extracted 20 grams by boiling in water acidified with muriatic acid and then after mixing in calcinated lime (Mrs. Dash) and evaporating I hoped to extract bufotenine from the tar with IPA 91%. As the alcohol evaporated a layer of irridescent syrup formed as a skin atop the extract. I took that as a good sign and continued evaporating. A orange/red/brown syrup remained after complete evaporation. This syrup was added to a glass pipe and an attempt to vaporize the material was made. The stuff didn't vaporize or produce much smoke and no effects were noted from the extract. I do believe based on the smell that this syrup should be active, it just doesn't want to smoke well so I'll likely refine the syrup a bit and hope to increase potency.

 

[hamhurricane]

^^^
never underestimate the importance of defatting, i remember my first salvia extraction was not defatted and was totally useless. it was like trying to smoke a puddle of molasses. i hope you have some luck with this though, i gave up hope in the fall after the anadenanthera debacle. but the truth is out there. and as soon as someone else has some reliable results, ill begin investigating again.

 

[swilow]

i gave up hope in the fall after the anadenanthera debacle

Likewise really. Isn't it stupid that the Anadenanthera guy, who was trying to promote the product, has actually turned us away?

I have several seeds that I will probably just hold for aesthetic purposes ie. no reason at all

 

[FormerlyHeyoka]

I think that the idea behind the extraction that I did was that by doing a acidified water extract, the alkaloid is pulled from the plant material while the fat is left behind.

Perhaps something closer to Otts extraction would work better. Really, though I think that the crux of this issue is high variability in the potency of seeds.

Allthough there is enough of the book online to make the hardcopy practically irrelevent, I recently bought Otts "Shamanic Snuffs or Entheogenic Errhines". For those familiar with Ott's bufotenine psychonautica, it's clear that there is enough positive info reguarding these seeds to warrant exploration independent of the reports of Erick Smythe or Anadenanthera. Very positive reports from Christian Ratsch and J. Ott are enough for me. Really, all Anadenanthera/Smythe did was promote a certain type of extraction and promote the ca-bufo thing. The ca-bufo thing was ONLY an interpretation of the reasoning behind native preparation of these seeds using certain type of lime.

There is enough info from Ott's self experimentation as well as from Torres and Repke's study of ancient use of these seeds to make investigation worthwhile.

 

[FormerlyHeyoka]

I just noticed that Erick Smythe, sounds about the same as "Erics Myth".

 

[Entropymancer]

As someone with a bit of chemistry background, I figured I'd chime in on the whole calcium bufotenate issue.

I know that many are put off by the fact that he was duplicitous in spreading the information. For that reason I don't really trust anything he said. It's also clear that he lacked understanding in some of the chemistry he was discussing... for example, he always referred to Ca(5-O-DMT) and was surprised when someone wrote Ca(5-O-DMT)2. If this salt forms, the latter formula is correct; Calcium cation bears a +2 charge, while bufotenate anion bears a -1; to form a neutral salt, we need two equivalents of bufotenate anion per calcium cation.

Another comment he made that I'm a bit suspect of is the claim that snuffing bufotenine in the form of an acid salt produces the unpleasant facial flushing and nausea. This could be true, and I certainly am not recommending anyone try it; all the ethnographic literature deals with alkaline snuffs; snuffing of water-soluble salts is by and large unknown (with respect to bufotenine, water-soluble salts = bufotenine cation + acid anion). The reason that I draw attention to this point is the following quote from Isbell (1956):

"No subjective or objective effects were observed after spraying with as much as 40 mg bufotenine".

This is significant for a couple of reasons. First, the word "spraying" to describe nasal administration of bufotenine very very strongly indicates that it was prepared as a soluble salt. The lack of effects at 40 mg also indicates it was not the freebase (at least based on Ott's bioassays)... it could well be that rather than being terribly unpleasant, snuffing an acidic salt of bufotenine would simply be ineffective (being a salt of a polar molecule, it's not apt to be very good at passing through your nasal mucosa).

That said, I don't feel comfortable dismissing calcium bufotenate as an entirely bunk claim. Certainly it's very much lacking in evidence, but there is sound reasoning behind it (which Anadenanthera appeared to be attempting to explain, in a jumbled confused sort of way. I wrote a summary of how the issue looked to me a few months ago, starting with an accurate representation of the chemistry behind why this salt might form. I also discuss a particular preparation method that piqued my interest as potentially indicating the formation of this water-insoluble alkaline salt of bufotenine:

My reasoning:

- The 5-OH group on bufotenine is weakly acidic. Based on the trends for other aromatic alcohols (phenol, naphthol), it's likely that the pKa of this group is somewhere between 9 and 10. It seems utterly inconcievable that it'd be higher than 10.5.

- Calcium hydroxide (slaked lime) is a pretty alkaline material, capable of getting water up to pH 12. Furthermore, as a metal hydroxide, it's capable of participating in neutralization chemistry (acid + metal hydroxide = metal salt + water).

Obviously the question then is simply whether bufotenine and calcium hydroxide have a sufficient affinity for one another to perform such chemistry. I turned up a reference to calcium phenolate in Handbook of Inorganic Compounds, which indicates that this sort of salt is plausible. And the Standard Methods of Chemical Analysis indicates that the phenolate forms by reaction with calcium carbonate, another neutralization reaction ("acid + metal carbonate = metal salt + water + carbon dioxide" ). Since calcium hydroxide is more alkaline than calcium carbonate, this pretty well substantiates the idea that bufotenine might be able to form a calcium salt.

Also, if you look into the ethnographic literature on South American natives, different tribes use/used a variety of bufotenin-containing preparations. In a very large number of these cases, the tribe places a strong emphasis on a preparation ritual where the bufotenin-containing material is mixed with slaked lime. It seems strange for such similar traditions to rise around such diverse materials, among totally unrelated tribes, unless the lime played some role in enhancing the effects. Of course, Jonathan Ott's bioassays indicate that bufotenine freebase is entirely capable of accounting for the effects of the shamanic snuffs (and clysters ).

There are various and sundry claims on the internet about different procedures, but many of them are lacking in substance or detail. I was able to find some very good information by a poster on the ayahuasca forums, druiddream, who I've found to be a very reliable poster in the past. Consider the following:

If you were to do this one day, you could soak the snuff in an appropriate amount of acidified water, filter out the seed material, then basify it with calcium hydroxide until you get a fluffy precipitate at the bottom of your vessel. Then you can either pour this preparation (liquid + precipitate, but with no seed material in it) in a nasal sprayer after pouring out the saline solution that comes in it, or you can simply use a small 1/8tsp measuring spoon and insufflate the liquid, paying special attention to getting some of the fluffy precipitate in your spoon each time.

And some more detail on a method used to alleviate sciatic nerve pain:

What she found so exceptionally effective was a 2g cold-water phosphoric-acid infusion of the seeds just as outlined in the recent LSA thread, leaving a practically CLEAR liquid with minimal nasty seed oils. She then boiled this down from 8 oz. to 2oz. and basified with edible lyme to ph10. Then, before working with this liquid, she drank *without any revulsion* 2g of a similarly prepared cold-water infusion of Syrian Rue, but with no basification and sweetened to taste. (The cold infusion came out very light yellow without the characteristic foul, nauseating smell or taste of hot water Syrian rue extractions, she said). She then took a 1/8tsp. measuring spoon and began insufflating the equivalent of 1 tsp. of the LIQUID form of the basified yopo infusion over a 5 minute period. The small amount of liquid was easily snuffed up and there was no spillage or leakage. If liquid came down the nasal passage into the mouth, she just held the liquid sublingually and spat it out as need be (she said that surprisingly it didn't taste nasty like the hot water infusion of yopo does).

First off: Yes, it was ingested potentiated by an MAOI, so the effects she recieved may be different than those that are typically encountered. This is irrelavent; I'm not concerned with the specific effects right now (and the effects described did not include nausea, which would be expected from a typical rue+yopo mix).

Here's what interests me: A precipitate froms at pH 9-10. This would not be remarkable in itself, since this was made with a crude extract, that precipitate could be the result of any phytochemical soluble in acidic water. What interests me is the emphasis on making sure to get some of the precipitate in every sniff, implying that the precipitate is psychoactive. Bear in mind this is something that swidruiddream has done repeatedly, as she apparently finds it to be an effective remedy for sciatic nerve pain, not just a one-time report.

So when an acidic extract of yopo is treated with calcium hydroxide, a precipitate forms, and this precipitate appears to be centrally active. This is very interesting, because it's not possible that this precipitate is bufotenin freebase. Bufotenin freebase is sufficiently polar to be somewhat soluble in water; if it weren't, Jonathan Ott would have seem a precipitate in the ammonia step of his extraction, and been saved the trouble of recrystallization.


A couple of other things. I asked druiddream if this experimentor had tried collecting the precipitate, and using that material dry, without the liquid. Apparently she had not, as the liquid adminitration was found to be plenty effective. I should mention that it's entirely possible calcium bufotenin is unstable in the presence of air at atmospheric conditions; calcium phenoxide was found to be unstable under these conditions. So if SWIy decides to try this method, they ought to confirm psychoactivity of the precipitate before collecting it out of the water and drying it.

But of course shamanic snuffs were traditionally left to dry for a substantial period of time. There are three possibilities to my mind in this issue:

-The first is that they weren't preparing calcium bufotenate, just bufotenin freebase. Ott's published bioassays confirm that bufotenin freebase is capable of producing substantial visionary effects. (This is the currently accepted hypothesis)

-The second is that they were preparing calcium bufotenate, but it's unstable to environmental conditions and decomposed into bufotenin freebase and calcium (oxide? hydroxide? carbonate?). Again, the bufotenin freebase can entirely account for the shamanic effects of the snuff.

-The third possibility is that they were preparing calcium bufotenate, and that the material was at least semi-stable in their preparation. This is concievable; consider: when they left the snuff to dry, it's been reported that the excess calcium hydroxide (which is pretty alkaline for the nasal cavity) reacts with atmospheric carbon dioxide to make calcium carbonate (chalk). This material is less uncomfortable on the nasal passages than lime, but it's still alkaline. It's possible that being mixed thoroughly with an alkaline material prevents atmospheric moisture from dissociating the salt so easily.

Of course, it's entirely possible that the precipitate which was observed to form was some other basic organic compound (basic like an amine, not basic like baking cookies) and that the recommendation to get some of it in each snuff just a coincidence.

I should also mention that the basic principles of pharmacodynamics could also explain the use of the lime just fine; the closer the pKa of a molecule to the pH of the membrane, the more effectively it can cross (brief explanation); thus adjusting the pH of the nasal mucosa to about 10-11 (right around the presumed pKa of the aromatic hydroxyl group) could fairly be expected to increase the absorption and efficacy of the drug.

It would seem the best way to test this would be to isolate a sample of pure bufotenine, and with a portion of that attempt to make the calcium salt (dissolve bufotenine in a minimal amount of water and add calcium hydroxide... calcium bufotenate should be insoluble and precipitate).

From a chemical aspect this is interesting, but not really from the perspective of using the material. Whether or not calcium bufotenate forms, you still want to add lime to make the snuff alkaline and make bufotenine free base.

 

[Entropymancer]

And how about a little more bufotenine info for this big dandy thread (unrelated to the debatable calcium bufotenate theory).

I've read that ethno vendors are notorious for having the seed species mislabelled, so you can't tell always tell which species you're getting. There's also reports of occasional batches of bunk seeds (there's at least one inactive species which is difficult to distinguish from A colubrina/peregrina and can form an identical-looking seedpod according to Raetsch). This seems to have been the case with Heyoka's batch... upwards of a gram, either species ought to be discernably active. And a quote from a bufo extractor:

Last year I got a batch of seeds that was only 0.06% alkaloids. That's very unusual. These seeds didn't even produce effects when smoked. Normally, you can smoke the seeds in a water bong if you grind them in a coffee grinder. With average potency seeds you should get very noticeable effects after about 5 strong hits. If you don't, you're seeds aren't any good. There are some seeds that look like A. peregrina and A.colubrina, but have no active alkaloids in them. Sometimes these are mistakenly sold as A. peregrina or A.colubrina.

I read somewhere (don't recall the source, sorry) that the seeds sold to vendors are identified by their location since the species are difficult to distinguish botanically. Since there are certain regions (perticularly in Brazil) inhabitted by both species, this could be responsible for some misidentification.

Anyway, I found some info on this subject from sources I find to be botanically reliable (Ott and Raetsch):

In a published interview (Entheogen Review 8 (1) : 28.) talking about Anadenathera peregrina and colubrina, Ott indicates that both himself and another ethnobotanist (Rob Montgomery) had found insufflation of A peregrina preparations to produce an intense burning sensation in the entire head. Such sensations weren't typically noted with A colubrina. (Of course erowid experience reports associate this effect with both varieties, but as we've noted, vendors aren't the best at distinguishing the two). A colubrina also tends to be higher in its concentration of bufotenine. So it looks like that pretty well settles which sort you want; A colubrina are the way to go.

But if the vendors don't know, how do we tell them apart? Well, relying on Christian Raetsch's Encyclopedia of Psychoactive Plants, it appears that the seeds of A colubrina are lighter, many of them almost a reddish brown ("reddish brown" is in fact the exact phrase used to describe the seeds, now that I look at the "Appearance" section). A pergrina on the other hand appears to have darker seeds, they seem to be typically somewhat smaller. I recall some years ago when I bought a small sample of each from a vendor, that these same characteristics distinguished the two sorts of seeds. It appears the lighter ones are more likely to be A colubrina, and thus are probably more desirable.



And for those interested in an extraction, here's one that was posted by a SWIMer (69Ron) who is well-versed in chemistry, and whose information I've always found to be reliable:

RebBaron's Yopo Extraction

Here’s what’s needed:

* Acetone: available at most hardware stores. This solvent is actually present in the human body in small amounts. It’s best to use distilled acetone that you distilled yourself if you’re at all worried about contaminants. KleanStrip acetone is pure acetone and 100.0 % volatile according to their MSDS, so there will be no residue left behind after evaporating it. SWIM uses this brand, always distills it, and never finds any left over residue. It seems to be very clean.

* Pickling Lime: available at some grocery stores. It’s used to make pickles crispier. It’s not as poisonous or dangerous as the sodium hydroxide commonly used to extract DMT. Pickling lime is edible but only if greatly diluted.

* Citric acid: available as “sour salt” in some grocery stores. It’s often used in canning. It’s available from many health food or vitamin shops. This is found naturally in fruit.

* Filtering system: coffee filters aren’t that good but will work. For best filtering results it’s better to use a lab filtering system (glass micro-fiber filters, a vacuum pump, and a filtering flask, Buchner funnel, etc.)

Here's the extraction steps:

1) Prepare citric acid solution by adding 1 gram of citric acid to 10 ml of acetone. We’ll use it later so put this aside, go onto step 2, but mix the citric acid solution occasionally. It will eventually all dissolve after about an hour or so.

2) Mix 100 grams of crushed Anadenanthera seeds (either peregrina or colubrina works) with and equal volume of pickling lime (calcium hydroxide) and add enough water to form a paste. Let it sit for about 1 hour, mixing it a few times. Dry it completely in an oven at 150 F.

3) Break apart the dried materal. Add 500 ml of acetone. Mix for about 5 minutes. Let the dry material settle to the bottom. The acetone should be reddish amber in color. Pour the acetone through a good quality filter.

4) Add 10 ml of citric acid solution (from step 1) to the filtered acetone and mix. Tiny crystals will form which look like yellow dust. Let the crystals settle to the bottom. Poor off the acetone, being careful not to pour off the crystals. Discard the acetone. Wash the crystals by adding 100 ml of fresh acetone, mix, let the crystals settle, and then carefully pour off the acetone and discard it (EDIT: you might want to let the acetone evaporate down to about 50 ml before discarding, as more precipitates might form. Keep in mind that a small amount of the alkaloids won’t precipitate out of the acetone. A small portion of this contains the tiny amount of DMT present in the seeds. If you save the acetone, you could extract the last bit of alkaloids using an A/B extraction, but It’s not really worth the trouble). Let all the acetone evaporate off the crystals. They’ll start absorbing water from the air and become dark brown goo once all the acetone has evaporated.

5) Mix the crystal goo with an equal volume of pickling lime. Add enough water to form a thin watery paste. Let it sit for about 1 hour while mixing a few times. Dry in an oven at 150 F.

6) Break apart the dried material. Dissolve in 100 ml acetone for about 5 minutes, mixing a few times. Filter off the pickling time. Evaporate the acetone leaving behind 5-HO-DMT freebase as a single solid mass of amber micro-crystals (and a few other active freebase alkaloids). It looks like amber candy, not crystals. It’s very difficult to form large crystals, so don’t bother. Just scrape it up and store in an air tight container away from light.

You can repeat steps 3-6 with the same seed mix up to 4 more times to recover nearly all the alkaloids if you like, but since the seeds are so cheap, it’s probably not worth the effort.

Comments on the effects:

The resulting product is active at 5-15 mg vaporized and is mostly 5-HO-DMT freebase. The effects are unique without all the side effects of Yopo/Vilca snuff. The onset after inhaling a large dose is about 3-5 minutes, peaking after 10-15 minutes, lasting a total of 1-2 hours. At 10 mg, there are both visual and auditory hallucinations. The auditory hallucinations are quite fascinating and unique to this alkaloid mix. It's got the visuals but almost none of the "mind-fuck" of most other psychedelics. It's not nearly as alien feeling as DMT. It's a more relaxed visionary experience. It's often said to be much more friendly than DMT.

What’s nice about this extraction is that it’s final product is more potent than DMT, cheaper, uses less toxic ingredients, doesn’t require a separatory funnel, and it can’t have those nasty problems with emulsions because it’s not a liquid/liquid extraction like most DMT extraction techs. It based on precipitating the desired alkaloids with is less trouble and less labor intensive than liquid/liquid extractions.

And a warning:

Don’t smoke this extract like its DMT. When smoking this extract, it's best to take several smaller inhalations spread out rather that one big inhalation. It’s more pleasant that way.

When smoked, the effects take a few minutes to come on and peak after 10-15 minutes. So as long as you smoke the entire dose before the peak hits, very little tolerance is developed.

If you smoke a 15 mg dose all at once as if smoking DMT, it is going to hit you REALLY HARD, and the first minute of the trip is going to be unpleasant with some side effects felt (a little nausea, possible tension, and strong tingling sensations) before the psychedelic effects start. These side effects will pass in a minute or so, but the entire first portion of the trip will not be as nice if taken this way.

Instead, you want to smoke the 15 mg dose spaced out in smaller doses so that you take about 5 minutes to smoke the entire dose. This will bypass the side effects altogether and the trip will be much more pleasant.

And some more notes on the product, and on the idea behind the extraction process:

These seeds have TONS OF FAT. If doing a typical A/B extraction, you’ll spend all day defatting the seeds. It’s a real pain in the ass. That’s why most of the extraction techs for these seeds are not A/B extractions.

I've used this and similar techs many times. This is the easiest and most reliable one. The part where the acetone is acidified with citric acid is unique to this tech. It’s the most important part. When the alkaloids are in the acetone in step 3, there’s also a lot of fats, oils, and waxes present. When citric acid is added, it causes most of the alkaloids (except DMT and a few other minor alkaloids present) to precipitate out of the acetone leaving all the fats, oils, and waxes in the acetone. This is the magic of this tech. It very efficiently de-fats the extract in one shot, so you don’t spend all day de-fatting the extract as you would with an A/B extraction.

The result of this tech is an amber crystalline solid material that is easy to break apart, completely dry, and easily made into a powder. Its not oily, waxy, tarry, it’s a dry solid material. It’s active at 2-15 mg smoked. The taste of the smoke is almost coffee like, bitter, completely unlike the plastic taste of DMT.

I’ve done many A/B extractions on these seeds. They all take more work and usually you end up with a pretty impure result that’s sticky.

If you follow Jonathan Ott’s famous extraction tech, it looks easy but it’s a lot of work, it has really nasty emulsion problems during the de-fat steps that take all day to perform, the solvents are hard to obtain (chloroform, ethyl acetate), but you do end up with nearly pure freebase bufotenine crystals and almost nothing else.

Ott’s tech is found on Erowid: http://www.erowid.org/archive/sonoran_desert_toad/ott.htm

An A/B tech, like the naphtha based ones for Mimosa hostilis, will produce extremely poor yields because most of the alkaloids present in these seeds are insoluble in naphtha. Such a tech will only extract very tiny amounts of DMT and a few other minor alkaloids. Since DMT is only a very small amount of the alkaloids present, you’ll end up with an extremely small yield.

If you like, you can get pure freebase bufotenine crystals from this tech too, but you need to dissolve the final product in ethyl acetate and crystallize the freebase bufotenine in that solvent. A lot of people don’t have access to ethyl acetate, so I didn’t bother posting about that. It’s very difficult to crystallize freebase bufotenine. It will not crystallize in acetone, alcohol, DCM, MEK, etc., the only solvent that seems to work well is ethyl acetate, the crystallization solvent Ott used.




Here are some additional info:

Pickling lime (calcium hydroxide) can be substituted with equal portions of baking soda (sodium bicarbonate) without any other modifications to the tech. Baking soda is a strong enough base to freebase bufotenine in these seeds, making it extractable by acetone. The only problem is that, unlike pickling lime, baking soda is slightly soluble in acetone so you’ll end up with a tiny bit in your final product, but the results are still very potent, and actually easier to grind to a powder. Baking soda is difficult to work with though. It tends to splatter from the release of carbon dioxide gas bubbles. If using it, make sure to put your stuff in a very tall container so that when it does splatter is doesn’t end up coming out of the container.

You should not use an acid other that citric acid. None of the other acids tested worked in this tech. This tech is all about changing the solubility of the alkaloids in acetone. Citric acid is soluble in acetone, but many citrate salts are not. The freebase alkaloids are pretty much all soluble in acetone (bufotenine, bufotenine n-oxide, DMT, DMT n- oxide, 5-MeO-DMT, 5-MeO-DMT n-oxide, etc.). Bufotenine citrate (and the n-oxide) is insoluble in acetone and I believe that the 5-MeO-DMT citrate (and the n-oxide) is also insoluble in acetone. DMT citrate (and probably the n-oxide) is soluble in acetone. This is why this tech loses the small amount of DMT present in the seeds. This doesn’t matter because these seeds contain mostly just bufotenine and bufotenine n-oxide and very tiny amounts of the other alkaloids. This seems to be the case for both A. peregrina and A. colubrina.

Another note, in the oven drying steps, a temperature of 150 F (65 C) is hot enough to vaporize freebase DMT. But since this tech wouldn’t extract it anyway, it doesn’t matter. Freebase bufotenine vaporizes at 608 F (320 C), so that temperature is safe for the target alkaloid.

What about bufotenine n-oxide? These seeds sometimes contain a lot of this compound. This is said to be a very water soluble form of bufotenine. Some people say it produces a lot of side effects and is visually much weaker than bufotenine. Over time bufotenine can oxidize into bufotenine n-oxide. I’m not sure what to do about this. I have little knowledge of bufotenine n-oxide. I think crystallizing the bufotenine in ethyl acetate is probably the best way to remove it.

Lately since bufotenine has been bouncing around the back of my head lately, I've tracked down all the primary ethnographic and chemical literature that I could find in english relating to Anadenanthera use. If I find interesting info on traditional preparations beyond what we usually hear, I'll be sure to share.

 

[Entropymancer]

Well now, I didn't have to go any further than reviewing the Pharmanopo-Psychonautics article to find something extremely interesting:

While Jonathan Ott's bioassays are surely conclusive in extablishing 5-HO-DMT as a psychoptic tryptamine, his results DO NOT yet demonstrate definitively that insufflation of pure bufotenine adequately models the psychoactivity of the snuff! I don't know why it didn't set off an alarm when I first read the article.

Check out the timeline that his intranasal experiences:

The following pharmacodynamics are characteristic at 40 mg (0.57 mg/kg): first sign of activity, acouasm (tinnitus) at five minutes; clear tryptaminic body effects at 25 minutes; peak between 35 and 40 minutes; unmistakable diminution by 50 minutes; and evanescent after effects up to 90 minutes.

Five minutes to first effect, peaking at the 35 minute mark for a 15 minute plateau, and about 40 minutes of deminishing afterglow (to put it in plainer English).

Okay, now lets take a look at a handful of reports where the seeds were prepared with calcium hydroxide, sodium bicarbonate, or calcium carbonate: Experience 1, Experience 2, Experience 3, Experience 4, Experience 5.

In these cases, the first indications of activity came within the first minute, building up to a peak within TWO MINUTES! The peak was reported to plateau for 15-20 minutes, and dimish to baseline over the course of another 25-40, typically with the same sort of afterglow as Ott decribed.

So the peak appears to last the same duration. And the comedown proceeds along the same timeline. But look at the difference in onset!! There's a tremendous difference between taking 35 minutes to build to a peak, versus 2 minutes. That's not an issue of individual variability; that's an issue of different pharmacokinetics.

Recall that Ott's assays were done with the pure alkaloid. He did not add any alkali to the snuff, but simply snuffed the plain freebase. All of the experiences I've linked above used substantially alkaline mixtures. If we accept Ott's hypothesis that bufotenine is the only significant psychoptic chemical in the seeds (and let me be clear, I do accept this hypothesis), then clearly the alkaline additive is playing a very substantive role in the pharmacology of the substance.

I do not regard this information as evidence for the existence of calcium bufotenate. Sure, that could explain it, but that would be wild speculation without substantiation. As I've mentioned, our current understanding of membrane diffusion indicates that raising the pH of the nasal mucosa could account for a drastic difference in effect, without having to invoke the formation of an alkali salt.

In that light, someone who has a sample of pure bufotenine (NOT a crude extract) could potentially resolve this issue by psychonautic bioassay. First I'd try insufflating the pure freebase to see whether Ott's effect timeline is replicated. Next, to establish the role of nasal pH, they could pretreat with an alkaline nasal douche (I didn't know such things existed before I typed "alkaline+nasal" into google) to adjust the nasal pH immediate prior to snuffing. If the effect timeline is shortened to that of the above reports, then pH is almost certainly the only thing at work here. If such an attempt doesn't shorten the effects, then this little headscratcher might point toward a more effective alkali salt.

I'm not encouraging people to try this, expecially if it's illegal where you live. I'm simply outlining the an anomaly I've found, and what experimentation might shed light on it.

It's also worth commenting on another substantial discrepency between Ott's assays and the erowid reports with Anadenanthera snuffs. In every one of the above reports (which were characterized by the rapid onset of the peak), nausea and vomiting was also reported. Since whole seed preparations were used in all these accounts, it's entirely possible that this effect was due to another constituent of the seed which wasn't present in Ott's assay. Considering the obvious pharmacokinetic differences between the pure bufotenine and alkaline Anadenanthera, it's also very possible that the nausea results from a more rapid change in serum concentrations of the drug. This certainly has piqued my interest though.

 

[Entropymancer]

As I recall, this thread so far has included a lot of allusions to the early work on bufotenin that's responsible for the allegations of its toxicity. For those who aren't familiar, it seems germane to summarize these studies. As has been mentioned, the frequent use of bufotenin salts limits the applicability of some of these findings to the actual use of the drug by typical routes (intranasal, vaporized, etc. administration of the free-base).


Fabing & Hawkins (1955)

These two have the dubious honor of having been the first to explore bufotenine's activity. They injected it intravenously into four inmates at the Ohio State Penitentiary, in doses ranging up to 16 mg of bufotenine creatinine sulfate. The higher doses in this study caused the subjects faces to turn "the color of an egglant." These subjects apparently also experienced minor short-duration visual phenomena, leading Fabing & Hawkins to classify the drug as "hallucinogenic". (Fabing & Hawkins 1956, Ott 1996)


Isbell (1955)

Working under the auspices of the CIA's infamous project MKULTRA, Isbell administered both bufotenin and cohoba snuff to inmates at the Lexington, Kentucky Federal Narcotics Farm (at this facility, nominally a drug rehab center, incarcerated addicts were offered heroin in exchange for cooperation in the experiments). The snuff was found to be inactive at doses up to a gram (the quality of the snuff is unknown, as this report comes secondhand through Turner and Merliss). Doses of up to 40 mg of bufotenine creatine sulfate were found to be inactive when administered intranasally. With 10-12.5 mg of the same salt administered intramuscularly, subjects experienced "visual hallucinations... a play of colors, lights, and patterns." (Turner & Merliss 1959, Ott 1996).


Turner & Merliss (1959)

Having the leisure of captive subjects in a New York mental institution, Turner and Merliss investigated the effects of both bufotenin and DMT in 14 schizophrenics (their trials with the latter drug will be relevant to the discussion of bufotenin's reported toxicity). They reported dramatic physical symptoms following the intravenous administration of 10 mg bufotenin.

It must be recalled that the subjects in these trials were almost certainly on other medications which could have played a role. In some of the cases, bufotenin injections were administered as "[the 'patients'] were coming out of insulin coma or following EST" (electroshock therapy). In their own words, "each of these injections almost proved fatal in small amounts (between 2.5 and 5.0 mg)," with cessation of breathing and the developement of a "plum-colored" face. They note that "the patients become frightened to an extreme degree," which prompts Ott to wonders "whether this 'paranoia' may have conttributed to their continued incarceration and 'treatment' for 'schizophrenia'."

After finsihing their work with bufotenin, Turner and Merliss concluded that bufotenine was not capable of producing the snuff intoxication.

Next, dynamic duo went on to experiment with the human effects of DMT, finding it quite active when 25 mg or more was administered intravenously. In one case, a female patient suffered cardiac arrest and nearly died after the intravenous administration of 40 mg DMT (not bufotenin, which only caused respiratory arrest). This has been reported mistakenly in the literature as a case of "bufotenine toxicity". Based on the work of Dr. Rick Strassman, it would appear that interactions with other medications must have played a role in this instance. (Turner & Merliss 1959, Ott 1996).


Bonhour et al (1967)

Intravenous injection of 12-16 mg bufotenin (again as a water-soluble salt) essentially confirmed the fidings of Fabing & Hawkins. (Bonhour et al 1967, Ott 1996).




In the bufotenin entry of TiHKAL, Dr. Shulgin presents a couple of quotes from patients exemplifying the somatic and visual effects typically encountered with lower-dose IV administration. At higher doses, the unpleasant somatic effects from intravenous administration appear to largely drown out the psychoactive effects.

(with 4 mg, intravenously, over a 3 minute period) "During the injection, I first felt a burning sensation in my face, then a load pressing down from above, and then a numbness of the entire body. I saw red and black spots -- a vivid orange-red -- moving around. Apparently my purplish face color lasted some 15 minutes, well after my visual things had disappeared."

(with 8 mg, intravenously, over a 3 minute period) "I became lightheaded as soon as the injection started, and then my face turned purple and I became nauseated and I felt I couldn't breathe. I see white, straight lines with a black background. I can't trace a pattern. Now there are red, green and yellow dots, very bright like they were made out of fluorescent cloth, moving like blood cells through capillaries, weaving in and out of the white lines. I another two minutes, everything was pretty much gone."

This was essentially the state of the inquiry into bufotenin's activity prior to the pbulication of Jonathan Ott's landmark Pharmanopo Psychonautics. Shulgin summed up the state of the literature with respect to the activity in bufotenin in the late 1990s:

Some clinicians demand that the compound is unquestionably a psychotomimetic and it must be catalogued right up there along with LSD and psilocybin. Others, equally sincere, present human trials that suggest only peripheral toxicity and conclude that there is no central action to be seen. And there are many who state that there are no effects for it at all, either inside or outside the CNS. The psychopharmacological status of bufotenine... may be essentially unanswerable... At the bottom line, I do not really know if bufotenine is a psychedelic drug. Maybe yes and maybe no.

However, he also notes a very compelling bit of evidence for bufotenin's role in the psychoactivity of Anadenanthera snuffs:

A study of the use of the seeds of a South American legume, Anadenanthera colubrina var. Cebil by the Argentine Shamans in Chaco Central, shows then to be dramatically psychedelic. And yet, extremely sophisticated spectroscopic analysis has shown them to contain bufotenine and only bufotenine as their alkaloid component.

Referencing this fact (and the bulk of older literature which confirms bufotenin to be the primary alkaloid in the seeds), Ott points to psychonautic bioassays by himself, CM Torres, Christian Raetsch, Pages Laraya, and Castillo, which clearly indicate the seeds to be a psychoptic (psychoactive visonary) agent. He then details his experiences with a range of doses by various routes of administration, both in the presence and absence of an MAOI (read the article if you haven't). This work seems to definitively establish that the concerning somatic effects of IV bufotenin salts don't appear to be so much of an issue when administering the free-base orally, buccally, parenterally as vapor, or intrarectally.

Ott's bioassays would firmly establish bufotenine as the chemical reponsible for the psychoptic effects of Anadenanthera snuffs, were it not for the tremendous disparity between the timeline of his intranasal bufotenin freebase experiences (peaking around 35 minutes in), compared to SWIM and many others' experiences with Anadenanthera snuffs (peaking 3 to 5 minutes in).

And so that's how it stands today: Anadenanthera seeds are without a doubt a psychoptic agent. Bufotenin is without a doubt a psychoptic agent. All the literature suggest bufotenin is the only alkaloid present in the seeds at a high enough concentration to account for psychoactive effects. And yet, the fundamental question, whether bufotenin is solely responsible for the psychoptic effects of the seed snuff, has still not been answered to a satisfactory extent.

Kind of ironic, when we consider the words of Safford, in his 1916 article providing a definitive botanical identification of the source of the snuff:

The most remarkable fact associated with this narcotic [sic] is that... the source of its intoxicating properties still remains unknown.

 

[Entropymancer]

69Ron and I have been mulling over the question of why lime seems to be so important to the snuff, and have bumped into an interesting possibility. And it's entirely consistent with the idea that [Anadenanthera/Adam Smyth] had absolutely no idea what he was talking about (which, to my eyes, is a plus).

Vecktor mentioned it several pages ago:

one possibility is that adding lime and heating causes the formation of dehydrobufoetenine a three ring compound where the amino tail ends up joined back to the phenyl ring, this supposedly is active. I am not certain how dehydrobuftenine arises it is quite common in analysis, I think it might be heat and base.

I don't think i really registered that comment when I read it, but it must have been in the back of my mind, smushed together with some comments from TiHKAL:

Dehydrobufotenine: There is a covalent bond formed between the dimethylated nitrogen atom and the indolic 4-position, by the theoretical removal of a molecule of hydrogen. It is no longer a simple tryptamine but as it is a commonly found component of the chemistry of several toads, and a few giant reeds as well, it is included here. It is, by definition, a quaternary amine salt. The original structure assigned it was that of a vinylamine (with the loss of a hydrogen molecule from the alpha/beta chain positions. This was shown to be incorrect.

I mentioned my garbled recollections with regard to dehydrobufotenine, and 69Ron turned up the quotes I was recalling, as well as another quote from Vecktor.

There has been plenty of confusion regarding dehydrobufotenine which is an extraction artifact of bufotenine and which is believed to be psychoactive rather than a violent poison

Here are 69Ron's comments on the subject:

This shows the structure of dehydrobufotenine.

This is the page for bufotenine

Dehydrobufotenine exists in nature and is commonly found where bufotenine is found.

Maybe dehydrobufotenine is being made when bufotenine is mixed with lime and water for a few hours? Maybe at the high pH of 12.4, the H is pulled off bufotenine’s HO at the 5 position, and then the amine side is attracted to the O, but can’t reach it and instead attaches to the indole ring? Is that even possible?

I can’t find an XlogP for dehydrobufotenine. I’m sure its solubility is very different from bufotenine. It might be very lipid soluble.

I ran across a report that states that dehydrobufotenine lacks the pressor activity of bufotenine. I can't find anything that talks about hallucinogenic activity for it though. But that doesn’t mean its not hallucinogenic...

According to TiKHAL, it is theorized that removing hydrogen, as would happen when bufotenine is exposed to pH 12 and above, is what causes dehydrobufotenine to form. If this is right and dehydrobufotenine is indeed more psychedelic than bufotenine then this would sure answer the mystery of Yopo! It looks pretty logical to SWIM.

It seems like a lot of people are thinking this happens.

Can anyone test this? All you should need is to put pure bufotenine in pH 12 solution for maybe a few hours. Maybe the reaction also requires heat (the natives usually heat the Yopo both before and after mixing it). Then when done have the results analyzed to see if indeed dehydrobufotenine is created.

From a chemical perspective, this makes sense. We know that psilocin and bufotenin decompose at high pH... but we don't know what they decompose into (AFAIK). It's entirely possible that with bufotenin, deprotonation of the 5-position would activate the adjascent 4 position for attack by the dimethyl(alkindole)amine.



Generating improved psychoactivity may be a little trickier than just mixing lime and bufotenine, however. How much the snuff improves with lime seems to vary from report to report. 69Ron reported SWIM's attempt at making calcium bufotenate: he found that he recoved 100% of the lime at the end of the process, eliminating the possibility that a calcium salt had formed. But he also reported different and improved effects from the treated bufotenine. Later, he editted this post noting that SWIM was having difficulty repeating the process successfully. So the conversion seems pretty finnicky... a quote from TiHKAL could potentially explain that

O-Methylnordehydrobufotenine, is a rearrangement product of dehydrobufotenine, which may be a natural product or it may be an artifact of analysis.

But the bottom line is, I'm very curious where Vecktor got his info that dehydrobufotenine is an extraction artifact? This seems like an entirely plausible solution to the calcium hydroxide + bufotenine mystery.

Also (shifting back towards the issue of how Ott's bufotenine experience differs from mine and others' experience with the seeds), anyone who's had experiences with the snuff, do you recall how long it took you to peak?

 

[Entropymancer]

Here's some information that, while still inconclusive, goes a very long way towards putting "Eric's myth" in its grave.

Below are two independent account of attempts to convert bufotenin freebase + calcium hydroxide to calcium bufotenate. Both came to the conclusion that if calcium bufotenate forms, it is only very transiently. In both cases, all the calcium hydroxide was recovered seperately from the treated bufotenin. This process does appear to affect a chemical change in the bufotenin (as speculated above, this may be dehydrobufotenine; or there could be more than one degradation product). However, the author of the first report indicates that it is very inconsistent in the results; there seems to be an unidentified variable in the process. The bufotenin has always chemically reacted, but whether it retains psychoactivity is apparently variable from batch to batch.

“I mixed 10 grams of pure bufotenine freebase with 10 grams of pure calcium hydroxide in just enough 50% alcohol to make it easily mixed by the electric stirrer. This was stirred continuously for 12 hours. I evaporated the alcohol completely. I dissolved the resulting powder in 99% alcohol. The alcohol absorbed roughly 50% of the material. It left behind pure calcium hydroxide. The test seemed to be a failure.

I tested 10 mg of the bufotenine which should be bufotenine freebase because the reaction of forming calcium bufotenate seemed to have failed and I wanted to see for sure that the bufotenine was simple freebase bufotenine. So, I vaporized it, and the taste was very different. It was sort of soapy tasting. After about 5 minutes it produced euphoria and some light visuals effects. It wasn’t anything like bufotenine. The effects were too mild and consisted of mostly euphoria and little else. I thought maybe it got partially decomposed and was just weaker because of it.

The following day I vaporized 30 mg of this material in one large inhalation. Pure bufotenine freebase tastes a little like bit like very mild coffee to me. The taste was again soapy and not like bufotenine. The smoke was milder also. After I exhaled, I immediately started feeling a strange prickling sensation in the back of my head. Within seconds it traveled down to the rest of my body light a bunch of tiny needles jabbing me lightly. I was a bit startled by the prickling sensation. I get this from bufotenine for the minute or so, but never this strong. About 1 minute after that, the prickling sensation was replaced by a euphoric tingling sensation as I started experiencing visuals of such intensity that I cannot compare it to anything else. Everything in the room was vibrating and changing color, but the room still looked the same. After about 2 minutes colors were flying all around the room, like colorful fireworks, but the room still looked the same only it was vibrating and constantly changing color. My body felt relaxed. There were no side effects, not even slight nausea. After about 5 minutes the visual effects were really strong. With my eyes closed I saw all sorts of visions. These were actual visions of places, not just a bunch of visual patterns. The experience peaked in about 10 minutes and lasted at least 2 hours. The visuals with the eyes opened or closed were much stronger than any other psychedelic I’ve tested (bufotenine, DMT, 5-MeO-DMT, LSD, psilocin, salvinorin A) and were very unique. The euphoria was also stronger than I’ve felt from any other psychedelic. These were the only effects felts other than the prickling that quickly changed to a tingling sensation in the body. It wasn’t mentally psychedelic at all. There were no effects on the mind. There was no sense of disorientation, no clouding of thoughts. There were just very strong visual effects and euphoria. This was psychedelically inactive on a mental level, but visually more powerful than any other hallucinogenic alkaloid I’ve tried. It also did not seem to have the auditory hallucinogenic effects that bufotenine has.

After many other tests I came to the conclusion that this alkaloid is no longer bufotenine. And it can’t be calcium bufotenate either because all of the calcium was recovered after the reaction took place.

I believe the 5-HO-DMT (bufotenine) reacted with the calcium hydroxide, probably forming Ca + -5-O-DMT (calcium bufotenate), but then after drying the calcium went back to form calcium hydroxide and left behind 5-O-DMT. With the missing H at the 5 position the molecule is highly reactive just waiting for something to react with. The negatively charged O needed something to bond to. With nothing available I think the positively charged N at the end of the amine side change of -5-O-DMT became attracted to the negatively charged O at the 5 position forming a ring like alkaloid. This is the only plausible explanation.”

OK

5 HO-DMT Bufotenine to 5 O-DMT' or Ca+ 5 O-DMT as a compound'

Calcium hydroxide does not bond with Bufotenine'


“Swim took one gram of bufotenine with one gram of calcium hydroxide in a little water to make a paste'
This paste was left at room temp for 14 hours' It had almost dried'
Swim then took the paste and dissolved it in acetone'

The calcium hydroxide falls out of the acetone and pressipitates at the bottom'
The mole we are seeking dissolves in the acetone'
Swim evaped the acetone and got back 940mg of the new mole' don't know of where the 60mg went' maybe left in the sludge at the bottom of the flask'


Swim vapourised 20mg

It is not bufotenine or Calcium Bufotenate' there is no calcium in the final product cos it stays in the bottom of the flask insoluble in acetone'

Prickly sensation' like Bufo' much stronger though'~
After 3 minutes the room is collidoscoping'~
The peak in about ten minutes' the whole experience about two hours'
Extremely visual and euphoric'

The 5-HO-DMT (bufotenine) react with the calcium hydroxide, to form a compound Ca + 5 O-DMT (calcium bufotenate), but splits in the acetone solution leaving 5-O-DMT in solution'
So basically calcium bufotenate only exists in solution' or as of when Bufotenine is in physical contact with calcium hydroxide' as a compound'

Calcium Bufotenine/nate is only existent within the reaction'

The end product is 5 O-DMT'~

As in the snuff' the calcium does not enter the blood stream' but the 5 O-DMT does' so the compound calcium Bufotenine/Bufotinate does not exist as a tryptamine molecule' only as a compound of the tryptamine Bufotenine and calcium hydroxide' Ca+ 5 O-DMT'
The calcium hydroxide knocks out the H' from the 5 HO-DMT' leaving 5 O- DMT'~

Take the seeds' roast them' split them' grind the pip into a fine dust' mix it's own weight with the same amount of Calcium Hydroxide' and a little water into a paste' leave to stand until the acrid fishy smell has gone'
Take the paste and dissolve it in acetone'
The calcium hydroxide does not dissolve in the acetone' actually it is quite insoluble' the mole we are seeking does' 5 O-DMT'
Decant the acetone and evap it'
Of what is left is a sticky brown goo'

Vapourise 20-30mg of this' 5 O-DMT'

Calcium Bufotenine does not really exist'
only in the process of the side chain reaction that forces out the H' of the 5HO-DMT' it only exists in solution or as of when in physical contact with calcium hydroxide' as a compound'~

 

[psychedelicious]

*slips sandals on and takes off for the hardware store*

will let you guys know how it turns out

 

[IGNVS]

oooo yes! i will be waiting

 

[swilow]

*slips sandals on and takes off for the hardware store*

will let you guys know how it turns out

Nice, you wear sandals- very christ-like

Entropymance, much thanks for the info here- it will be of much interest I believe. Old erik/anadnanthera certainly put a bit of a dampner on 5-Ho-DMT for many here I think. Peace!

 

[psychedelicious]

Left the goop over night to do whatever magic happens. About to do a couple pulls with acetone.

Entropymancer, thank you for compiling and thinking and posting. I've had a handful of A. peregrina seeds sitting around for like a year, not knowing how to properly prepare or even expect!

 

[Entropymancer]

My only experiences have been with a snuff made from the whole roasted seed, but looking into bufotenin recently got me back interested in a big way.

I'm definitely going to be playing around with this stuff in the near future.

It's a shame about erik/anaden putting people off the seeds. Whoever he is, that twerp is still putting his crap up on wikipedia as fact (I've removed it a couple times now). On another board, I was accused of being him, simply for talking about yopo and bufotenine

 

[IGNVS]

pdlishus- what are your plans for consuption? smokin it rite?

 

[psychedelicious]

yup, vaping/smoking.

So my friends B and A came over to experiment. Both had previously tried some of the n,n-DMT I found in some rootbark a while back and really took a liking to it. I ended up with a dark red, crystal-ish goo. It smelled very much like morning glory seeds.

I took a hit, but the taste made me very, very nauseous. I refrained from going any further, however, I did feel some tingles, which, while DMT-esque, were definitely different than DMT. I was definitely not completely sober for about 45 minutes. Everything looked a bit different. The normal static seen behind my eyelids was organizing itself into subtle but noticeable patterns. All in all, most similar to low dose DMT. Definitely an easy-going psychedelic in terms of the mental alteration - the only mental change I felt was a slight mood lift and minor tip-of-the-tongue syndrome (with DMT at a visually similar dose, I am far more affected mentally than I was with bufo).

B and A don't have the same taste/smell aversions as I, and were happy to smoke more than I. It was mostly B doing the tokage over the next several hours.

He felt a tingling not unlike the DMT tingles, a bit of euphoria, and some visual alterations. He described it summarily as very low-dose DMT. Mind you, B is not very experienced in these things, so don't take that as bufotenin/5-O-DMT/whatever this chemical is = DMT. Things began to "swirl" and "move way more than they ever should" and become more saturated/bright. He noticed no closed-eye visuals. We smoked some herb that night as well, and B said his pot high was a bit more intense and classically psychedelic: brighter colors, stationary things moving about a bit, buzzing body high. If B stared at something for a few seconds, it would "swirl" or jiggle or become animated.

A was nodding on oxycontin and didn't have much to say about the bufo-whateveritis. He didn't have much to say at all, in fact, lol

I think my seeds were pretty low potency, not to mention that they are A. peregrina (as opposed to A. colubrina, the more potent seed). I have more seeds left, but I think I'll save those for the collection and invest in a fresher batch of both varieties in the near future and further experiment.

I do still have my seed goop from which more alkaloid may be pulled via acetone, and about half of the yield from the first pull. More reports will come as more experiments are had.

Another note: we attempted to vape in a standard glass pipe. Further experimentation will utilize a lightbulb vape and hopefully we'll be able to get more vapour into our lungs more efficiently than with a pipe.