The Yopo Transformation Theory


Shamans prepare yopo snuff from the toasted pulverized seeds of either Anadenanthera colubrina or Anadenanthera peregrina which is then mixed with water and a source of a calcium carbonate. Calcined shells are often used as the source of calcium carbonate. The mixture is kneaded while wet and allowed to sit and react, often overnight. Before use it is toasted again to dry it, and it is again ground to produce a fine powder.

Many anecdotal reports indicate that authentic yopo prepared by skilled shamans in South America has hallucinogenic effects that differ dramatically from those of bufotenine and swear that some reaction must be taking place when the recipe is followed properly.

Clearly the shamans would not do this extended procedure if it did not enhance the effects. By adding calcium carbonate, they are greatly increasing the quantity of material needed for use. The calcium also makes the snuff more alkaline and more irritating to the nasal passages.

Anadenanthera colubrina and Anadenanthera peregrina seed only contain bufotenine in quantities large enough to elicit effects. The special yopo snuff preparation used by shamans uses aqueous calcium carbonate, a specific alkali which will theoretically slowly dehydrogenate bufotenine into dehydrobufotenine. The dehydrogenation process is claimed to be slow, taking many hours. Most authentic yopo snuff is allowed to "react" for 24 hours before use. This should be enough time to dehydrogenate a good portion of bufotenine into dehydrobufotenine.

Bufotenine is itself a phenol. What’s happening is that calcium carbonate is reacting with the acidic phenolic hydroxyl group at the 5 position of bufotenine, deprotonating it. This kind of reaction is a very well known reaction that's possible for phenols. This should create the unstable phenoxide of bufotenine with a negatively charged oxygen atom at the 5 position. The negatively charged oxygen atom in this case will be highly reactive, causing the molecule to be unstable, and could theoretically cause the positively charged amine side chain of bufotenine to bend towards the negatively charged oxygen atom in order to stabilize the molecule, producing dehydrobufotenine.

For the skeptical, it is a known fact that phenoxide ions form from phenols exposed to aqueous alkali. This means that the phenolic OH group on the benzene ring becomes a negatively charged O atom. Bufotenine is itself a phenol, and should definitely form a phenoxide-like ion in aqueous alkali, but unlike phenol bufotenine in this form is a bit unstable (just as the case is for the closely related phenol psilicin[2]), potentially leading to dehydrogenation and other reactions if kept in alkali for extended periods of time.

Dehydrobufotenine has a higher XLogP3 of 1.6 compared to 1.2 for bufotenine and 1.5 for 5-MeO-DMT. If it is hallucinogenic, it's likely to have stronger hallucinogenic activity than bufotenine. However, there is some conflict concerning the lipid solubility of dehydrobufotenine. Some prediction software gives high water solubility for dehydrobufotenine. ACD/Labs Percepta Platform gives a prediction of -3.71 for it's lipid solubility. If correct, dehydrobufotenine should have extreme difficulty entering the brain.

Yopo Transformation Theory Possibly Verified

Tests performed by an anonymous researcher claim to have been able to replicate this classic yopo transformation using pure bufotenine rather than the seeds. The steps used are outlined below:

  1. Add 1 part bufotenine freebase to 2 parts aqueous calcium carbonate (thin enough to stir easily)
  2. Mix continuously for 24 hours at room temperature.
  3. Evaporate off the water at 150 F.
  4. Extract with acetone and filter off the calcium carbonate.
  5. Evaporate the acetone to produce the extremely stable end product.

It's important to note that the researcher states the results could not be replicated easily using calcium hydroxide. Substituting other bases for calcium carbonate is not advised. When using calcium hydroxide instead of calcium carbonate, after mixing for 24 hours, the end product is inactive. However, if mixed for only a few hours using calcium hydroxide, the results were occasionally partially successful. Calcium hydroxide is likely too strong of a base, leading to additional decomposition, making the end result inactive when mixed for 24 hours. Consistent results were only seen when using calcium carbonate.

The researcher also states that shortening the mixing time can reduce successful transformation when using calcium carbonate. Mixing for just 1-2 hours was not sufficient. Mixing for 24 hours produced consistent results in every test.

The end product is believed by the researcher to be primarily dehydrobufotenine or something similar with some impurities present. Unfortunately, the end product could not be positively identified as dehydrobufotenine because of a lack of reference material.

The shelf life of the end product is reported as over 4 years without noticeable degradation.

The end product was tested for activity by the researcher. Potency was approximately the same as bufotenine but more "hallucinogenic" (see the dosage warning below). The researcher indicates that the hallucinogenic effects differ substantially from that of bufotenine, being more in-line with the effects of DMT, but lasting for several hours. Oral use should probably be avoided. Yopo snuff is not known to be used orally. When used orally, like bufotenine, the end product unfortunately causes nausea from agonizing 5-HT3 sites in the body. If used orally, nausea can be alleviated by taking it 30 minutes after using a potent 5-HT3 inhibitor (5-10 drops of lemon essential oil for example).

WARNING! Two other anonymous sources claim to have duplicated this reaction. One source used pure bufotenine and is stating that the end result is indeed dehydrobufotenine. This source gives the oral dose starting at 1.5 mg, producing effects similar to 50 micrograms of LSD, and very unlike the effects of a tryptamine. The other source did the reaction with the seed material first (4 parts calcium carbonate, some water, mixed for 24 hours), and then extracted the unknown alkaloid from the results, but this source was unable to identify the end product. This source gives the starting oral dose at 4 mg for the freebase (which is stated to be an oil that will not crystallize), and also states that his starting oral dose of the alkaloid extract from the same collection of seeds not processed with calcium carbonate is 100 mg, indicating that the potency increased by 25 times. This means the dosage of the end product could be much higher than that of bufotenine in some individuals. Researchers attempting this simple reaction should use EXTREME caution testing the results for human activity.

This illustrates the theoretical chemical reaction taking place.

Bufotenine Mix in aqueous calcium carbonate Immediately the unstable deprotonated bufotenine forms After 24 hours the stabilized dehydrobufotenine forms (along with some impurities)
Bufotenine.png Calcium_Carbonate.png Bufotenoxide.png Dehydrobufotenine.png

See Also


1. The Alkaloids: Chemistry and Pharmacology V43: Chemistry and Pharmacology, Volume 43
Contributor Gerard Meurant; Publisher Academic Press, 1993; ISBN 0080865674, 9780080865676
2. Clarke, E. G. C., Isolation and Identification of Drugs, Pharmaceutical Press, London, 1974, p. 526.
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