There are many plants that contain 5-HO-DMT (bufotenin) along with DMT and often 5-MeO-DMT (methoxybufotenin). Examples include:
* Anadenanthera colubrina
* Anadenanthera peregrina
* Anadenanthera macrocarpa
* Phalaris Aquatica
* Phalaris Arundinacea
* Arundo donax
* Desmodium caudatum
* Mucuna pruriens

I often see people on these forums expressing a desire to remove 5-HO-DMT (bufotenin) from their plant alkaloid extracts. It’s actually quite simple to do. Both freebase DMT and freebase 5-MeO-DMT are soluble in naphtha or heptane. Freebase 5-HO-DMT is very polar and is completely insoluble in naphtha or heptane. It is soluble in more polar solvents like DCM, ether, chloroform, water, acetone, alcohol, etc. Because of its different solubility profile, it can be easily separated from DMT and 5-MeO-DMT.

Here are two methods that SWIM tested which work very well.

Selective Solvent A/B Extraction
During the freebase phase of an A/B extraction, first extract the freebase DMT and 5-MeO-DMT with naphtha, heptane, xylene, or d-limonene. The freebase 5-HO-DMT will not get extracted because it’s insoluble in those solvents. Next extract the freebase 5-HO-DMT with DCM (dichloromethane), ether, or chloroform. Evaporate to give freebase 5-HO-DMT (and other similar plant compounds).

Citrate Acetone Precipitation
Dissolve the mixed alkaloids in acetone. Add 10% citric acid solution (pre-dissolved in acetone). This causes a cloud to form. Continue adding the citric acid solution and precipitates start falling out of the acetone. Stop adding citric acid solution when no more precipitates form. The precipitates will contain the 5-HO-DMT citrate (and 5-MeO-DMT citrate if there was any). The acetone will contain DMT citrate. Pour off the acetone through a filter and wash the precipitates with acetone to obtain 5-HO-DMT citrate. NOTE: Before vaporizing 5-HO-DMT, it needs to be freebased.

Comments
People often think that 5-HO-DMT (bufotenin) is to blame for the side effects felt from various alkaloid extractions and usually want it removed. While it does produce some side effects (especially if injected or taken orally), it’s usually not responsible for most of the side effects felt, but it usually gets all the blame for them because its known to cause serious side effects when injected in certain salt forms. However, that’s not the case when vaporizing it as freebase.

Freebase 5-HO-DMT (bufotenin) is actually a heavy duty psychedelic when vaporized. It’s much stronger than DMT (active at 2-10 mg). When vaporized it’s about as strong as 5-MeO-DMT (methoxybufotenin) but much more visual. When snorted, or taken sublingually, it’s about as potent as DMT. Like 5-MeO-DMT, it produces some minor side effects in some people so it’s not for everyone. Injecting it or taking it orally produces a lot of side effects, so that’s not recommended. It’s not something you want in an ayahuasca brew. As far as vaporizing goes, SWIM likes it more than DMT or 5-MeO-DMT, and finds that vaporizing 10 mg produces an ayahuasca like trip that is more visual than DMT, longer lasting, and more auditory than any other psychedelic SWIM knows of.

Often people are disappointed after they remove the 5-HO-DMT from their alkaloid extract, especially if they were vaporizing their extract. They are usually expecting the side effects to vanish, but that’s usually not the case. Instead they usually find that their extract is less visual. 5-HO-DMT adds a unique dimension to the effects of vaporized DMT and 5-MeO-DMT. It increases the visuals and adds an auditory effect that is otherwise usually absent. The side effects from vaporized freebase 5-HO-DMT only last about 2 minutes and may include very light nausea and strong tingling sensations. The psychedelic phase occurs after the side effects and peaks after about 15-30 minutes with the overall effects lasting up to 1-3 hours (depending on the dose taken).

Do you have a good cebil or yopo extraction?

Would a standard A/B (w/ multiple defats) using DCM as the np work?

Yes it will, but you need to do about 10 defats for really good results because they contain lots of fats and oils. Also most of the alkaloids are quite water soluble and so you’ll need to do at least 5 pulls at pH 9.5 to get most of the alkaloids.

If someone wants a full spectrum Yopo/Cebil extraction, they’d use DCM (dichloromethane), ethyl ether, or chloroform as the non-polar solvent. This will extract all the alkaloids giving the most authentic Yopo/Cebil experience.

When freebasing, you don’t want a high pH because some of the alkaloids get destroyed. The pKa of bufotenine (the main alkaloid) is 9.67. SWIM’s tests found 9.5 works well for all the alkaloids present. 8.5 is about as low of a pH as you should go (pH 8.5-9.0 is what Jonathan Ott uses). Don’t take the pH up to 10 and beyond for more than a few hours or many of the Yopo/Vilca alkaloids start coming apart. According to SWIM’s tests, about 50% will be lost if kept in pH 12 water for about 4 hours.

Keep in mind that both Cebil and Yopo mostly contain 5-HO-DMT, 5-HO-DMT n-oxide, and quite a bit of other unusual alkaloids, along with some DMT and 5-MeO-DMT and their N-oxides. Yopo usually contains more DMT, but not that much. The alkaloid content is still usually more than half 5-HO-DMT in both varieties. There are some batches that contain mostly DMT, but these are very rare to come by.

Here are the calculated XlogP’s of various alkaloids present in Yopo/Vilca (lower mean more non-polar soluble, higher means more water soluble): [EDIT: <-- Wow, that's a very confusing sentence!!! I meant lower ON THE LIST means more non-polar soluble, higher ON THE LIST means more water soluble. Lower XlogP values are more water soluble, and higher XlogP values are more non-polar soluble. Sorry for the confusion. I should have read that more clearly before posting it!]


0.1 - 6-methoxy-2-methyl-beta-Carboline
0.7 - Beta-carboline, 6-methoxy-1,2-dimethyl-1,2-Dimethyl-2H-beta-carbolin-6-yl methyl ether
1.0 - 5-HO-Tryptamine (serotonin)
1.3 - 5-HO-DMT N-oxide (Bufotenine N-oxide)
1.6 - 5-HO-DMT (bufotenine)
1.7 - N-Methylserotonin
1.7 - DMT N-oxide (Dimethyltryptamine N-oxide)
1.7 - 5-MeO-NMT (5-Methoxy-N-methyltryptamine)
1.7 - 2-Methyl-1,2,3,4-tetrahydro-beta-carboline
1.8 - NMT (N-Methyltryptamine)
1.9 - 5-MeO-DMT (methoxybufotenin)
2.0 - DMT (Dimethyltryptamine)

As you can see, most of the alkaloids in bold have an XlogP of 1.7 or lower. NMT, 5-MeO-DMT, and DMT are the only alkaloids that can be extracted with naphtha or heptane. The rest need more polar solvents. So if you’re using naphtha or heptane you’re throwing away most of the Yopo/Vilca alkaloids. When it comes to DMT and 5-MeO-DMT, Yopo/Vilca usually contains more of their N-Oxides than the parent alkaloids and those would be lost. Plus Yopo/Vilca contains many other unusual alkaloids that affect the experience, including some beta carbolines (MAOIs). This is why a typical A/B extraction using naphtha or heptane produces very poor results for Yopo/Vilca.

Here are some XlogP’s of various common solvents:

-0.7 - DMSO
-0.5 - Methanol
-0.1 - Ethyl Alcohol
0.2 - Acetone
0.4 - IPA
0.4 - MEK (Methyl Ethyl Ketone)
0.7 - Ethyl Acetate
0.9 - Ethyl Ether
1.5 - DCM
2.1 - Chloroform
2.5 - Toluene
2.5 - Xylene
3.7 - Limonene
4.3 - Heptane (similar to naphtha)

You see how the solvents from ethyl ether to chloroform are in bold? These are the non-polar solvents that will best extract all the alkaloids. [EDIT: Toluene and xylene, will only usually extract alkaloids with an XlogP of about 1.7 or higher. Heptane/naphtha will only extract the highly non-polar alkaloids with an XlogP of about 1.8 or higher (5-MeO-DMT, DMT, and NMT). As the solvent gets more non-polar, it extracts less and less alkaloids. XlogP calculations are never completely accurate and there are always exceptions to these solubility guides.]

I know of some non A/B extractions that work for Yopo/Vilca that are simple. I’ve posted them elsewhere on other forums.

That is excellent info. Thank you, I feel like I kinda understand a little more about solvents and polar vs non polar.

If you could, please, post a link to one of those extractions or PM me the link.

I would be very grateful.

I have been wanting to do an extraction on my cebil for a while.

Which do you prefer, the full spectrum or isolated of 5-HO-DMT

Thanks for the very valuable infos. Your knowledge of alkaloids and extractions is impressive !



Waoh, seems really interresting. There is what look likes a good yopo extraction on erowid (http://www.erowid.org/experiences/exp.php?ID=64707). But I'm also very keen about a link in PM about a possible other methods.

what do you know about extracting freebase 5-HO-DMT from mushrooms

This tek has been added to the Wiki:

Separating 5-HO-DMT (bufotenin) from DMT


Kind regards,

The Traveler