Research The Caapi Analysis Thread

[endlessness]

This thread will grow as more analysis is gathered.

Related Threads:

Harmala and other less known B carbolines - Ongoing research thread with pharmacology, plant sources, chemical and physical data, analysis info, etc on different beta carbolines

Why talking about different ayahuasca varieties (yellow/black/cielo/boa/tukunaka etc etc) is almost meaningless. Post with some ideas on the classification of ayahuasca varieties.

Poorly understood family of Ayahuasca vines (thread with plenty of info on different ayahuasca varieties, ayahuasca "colors" and unknown ayahuasca plants of the Banisteriopsis, Alicia and Tetrapterys genus, possible vendor misidentifications, etc)

Conversion of Harmine->Harmaline->THH by simple boiling (and storage?)


Literature:


Schwarz et al 2003 Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism

Kawanishi et al 1982 Shihunine and Dihydroshihunine From Banisteriopsis caapi

Callaway 2005 Various alkaloid profiles in decoctions of Banisteriopsis caapi

Mckenna et al 1984. Monoamine oxidase inhibitors in South American hallucinogenic plants: Tryptamine and β-carboline constituents of Ayahuasca

Hashimoto & Hashimoto 1976 New alkaloids from Banisteriopsis caapi

Samoylenko et al 2010. Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease

Hashimoto & Kawanishi 1975 New organic bases from amazonian Banisteriopsis caapi.

Chemical profile described so far in literature:

Harmine (Mean: 4.79 mg/g) (Santos et al 2020)
Harmaline (Mean: 0.451 mg/g) (Santos et al 2020)
THH (Mean: 2.18 mg/g) (Santos et al 2020)
Banistenoside A
Banistenoside B
Shihunine
Dihydroshihunine
Harmic acid methylester
Harmalinic acid
Harmic amide
Acetyl norharmine
Ketotetrahydronorharmine
Tetrahydronorharmine
β-d-fructofuranosyl-(2 → 5)-fructopyranose


Nexus Analysis:

(newer analysis from 2022-2024) Thanks to Kykeon Analytics
LC-MS

#5 Banisteriopsis muricata VINE (Peru - Red)

Harmine 0.094%

Tetrahydroharmine 0.0031%




#6 Banisteriopsis caapi VINE (Brazil - Yellow)


Harmine 0.06%

Tetrahydroharmine 0.0025%



#9 Banisteriopsis caapi VINE (Peru - Trueno)


Traces harmine



#63 Banisteriopsis caapi VINE (Yellow)


Harmine 0.22%

Tetrahydroharmine 0.024%

Harmaline traces



#64 Banisteriopsis caapi VINE (Red)


Harmine 0.48%

Tetrahydroharmine 0.056%

Harmaline traces


#65 Banisteriopsis muricata VINE


Harmine 0.2%

Tetrahydroharmine 0.05%

Harmaline traces



#66 Banisteriopsis spp. ? LEAF


Harmine 0.09%

Tetrahydroharmine 0.03%

Harmaline traces



#68 Banisteriopsis caapi (Brazil - Tucunaca)


Harmine 0.007%



#69 Banisteriopsis caapi VINE (Ecuador)


Harmine 0.3%

Tetrahydroharmine 0.12%

Harmaline traces



#70 Banisteriopsis caapi VINE (Peru - Huitoto)


Harmine 0.19%

Tetrahydroharmine 0.13%

Harmaline Traces




#71 Banisteriopsis caapi VINE (Peru - Red Napo)


Harmine 0.21%

Tetrahydroharmine 0.06%

Harmaline traces



#72 Banisteriopsis caapi VINE (Peru - Red vine)


Harmine 0.36%

Tetrahydroharmine 0.05%

Harmaline traces



#73 Banisteriopsis caapi VINE (Peru - Black)


Harmine 0.25%

Tetrahydroharmine 0.05%

Harmaline traces



#74 Banisteriopsis caapi VINE (Peru - Shipibo)


Harmine 0.34%

Tetrahydroharmine 0.23%

Harmaline traces




#75 Banisteriopsis caapi VINE (Brazil - Ourinho)


Harmine 0.12%

Tetrahydroharmine 0.01%




#76 Banisteriopsis caapi VINE (Peru - Cielo)


Harmine 0.49%

Tetrahydroharmine 0.08%

Harmaline traces




#77 Banisteriopsis caapi VINE (Brazil - Caupuri)


Harmine 0.14%

Tetrahydroharmine 0.14%




#78 Banisteriopsis caapi VINE (Peru - White)


Harmine 0.11%

Tetrahydroharmine 0.009%




#79 Banisteriopsis caapi VINE (Yellow)


Harmine 0.23%

Tetrahydroharmine 0.02%

Harmaline traces




#80 Banisteriopsis caapi VINE (Colombia - Tigre)


Harmine 0.065%

Tetrahydroharmine 0.04%

Harmaline traces




#81 Banisteriopsis caapi VINE (Peru - Cielo)


Harmine 0.13%

Tetrahydroharmine 0.02%

Harmaline traces




#82 Banisteriopsis caapi LEAF (Peru - Yellow)


Harmine 0.03%

Tetrahydroharmine 0.02%




#168 Banisteriopsis caapi VINE (Colombia - Pilde)


Harmine 0.03%

Tetrahydroharmine 0.005%

Harmaline traces




#169 Banisteriopsis caapi VINE (Ecuador - Mono)


Harmine 0.05%

Tetrahydroharmine 0.01%

Harmaline traces




#170 Banisteriopsis muricata VINE (Ecuador)


Harmine 0.24%

Tetrahydroharmine 0.18%

Harmaline traces




#171 - Banisteriopsis muricata LEAF (Ecuador)


Harmine 0.02%

Tetrahydroharmine 0.01%




(older analysis from 2012-2020)
GC-MS

Other minor substances labelled in graphs still unidentified, work will be done in the future. Notice this is NOT quantitative analysis, just approx relative ratio of alkaloids in each plant, The total alkaloid yield has not yet been measured for most of these plants.

Yellow caapi (from k1w1b04ncaya)

Ourinhos caapi (From IC4ROS-DN4)

Red Ayahuasca (Banisteriopsis muricata by k1w1b04ncaya)

Red caapi (from M4Y4)
Methanol soak

Black caapi
NOTE: Some vendors have been selling what we identified as Alicia anisopetala as Black caapi/black ayahuasca. Note that A. anisopetala does NOT have harmala alkaloids as per my tests, pharmacology/toxicity is unknown. Please check this thread for more info.

(Tests of `black caapi` below are from M4Y4) (lets call this Black caapi #1)
Methanol soak

Black caapi #1
A/B extract from same plant material as black #1 above. Yield 0.5% white powder.

Black caapi #2
A/B extract, precipitation with NaOH. Yield 2.5%. From v3g3t4l1st4 botanicals.

White caapi #1
Methanol soak (from MH---UK in nov 2011)
A/B extract, precipitation with NaOH.

White caapi #1
A/B extract, precipitation with NaOH (from MH---UK in nov 2011)

Bali caapi (from M4Y4)
Methanol soak

More caapi analysis to come in the future


As always, im attaching the .MS file which you can open with openchrom to see the mass spectra (feel free to pm me if you want to learn how, its easy). Relative quantification here is approx, and subject to revision, bear with me im just starting with analysis.

Here are the GC-MS details. In the future LC-MS analysis will also be done and info added below

GC-MS analysis was performed in an Agilent 5890 series II gas chromatograph coupled to an 5971A quadrupole mass spectrometer detector (Agilent). The gas chromatograph was fitted with an 6890 auto sampler injector. Samples were injected in split mode into a 12m × 0.2mm i.d., 0.33 µm film thickness 5% phenylmethylsilicone column (ULTRA-2, Agilent Technologies). The oven temperature was programmed at 90ºC during 2min and increased 20ºC/min to 300ºC. Finally was maintained at 300ºC over 4min with a total run time of 14.50min. Insert liners packed with silanized glasswool were used. The injector and the interface were operated at 280 ◦C. Helium was used as carrier gas at a flow rate of 0.48ml/min. The mass spectrometer was operated in electron impact ionization mode at 70 eV

 

[Infundibulum]

whoa! great work!

I'm surprised to find that THH levels are so low, I had always assumed that there are similar levels of THH and harmine! I'm also not surprised that red and and black caapi have similar, if not identical alkaloid profiles. I've always thought that white/yellow/red/black caapi grades represent more of a marketing scheme than qualitatively different varieties.

 

[soulfood]

I'd be interested to see THH levels in white caapi.

It seems less potent by weight but always seems to have a special euphoria. If not placebo, it would be interesting to see if THH levels are responsible.

 

[kyrolima]

Thank you thank thank you, keep up the good work!

 

[3rdI]

This is really good stuff, Endlessness these contributions to the community really are above and beyond.

Nice one.

 

[BecometheOther]

I agree, great to see results from a test like this. I too found it crazy how consistant the two were.

 

[endlessness]

Thanks for the interest

I've edited the first post to include Bali caapi analysis. As you can see, it has much less harmalas (one could also see it clearly in the TLC, picture coming soon), and no sign of THH, not even trace.

Funny enough it was actually being given for free in that vendor's website, 250g (!!) for free, maybe it was end of stock and hadnt been stored well or maybe it was a batch many customers complained (indeed it would make sense if it has so little alkaloids). The main peaks do not seem to be alkaloidal, more like fatty acids or similar, but Ill need some time and help to identify them for sure.

 

[semios]

Endlessness I am not sure how you are supporting the procurement of samples for all your work but it's such incredibly valuable knowledge that you should definitely let us know if there is a way to help with support for the cost of procurement, while allowing you to retain your privacy.

 

[ChaoticMethod]

I'm curious about the difference in vine and leaf contents and potency. Do you have any info on that (or is there a thread on the nexus talking about this?)

 

[endlessness]

Endlessness I am not sure how you are supporting the procurement of samples for all your work but it's such incredibly valuable knowledge that you should definitely let us know if there is a way to help with support for the cost of procurement, while allowing you to retain your privacy.

No need to pay me Just talk to my girlfriend and convince her it's a good use of my time, and I'll be happy

I'm curious about the difference in vine and leaf contents and potency. Do you have any info on that (or is there a thread on the nexus talking about this?)

I haven't tested caapi leaf before and to quantify we gotta make some calibration work with standards and I really dont have the time or possibilities at the moment, maybe in the future. But here's some results about it:

Erowid Online Books : "Ayahuasca: alkaloids, plants, and analogs" by Keeper of the Trout

Ayahuasca: alkaloids, plants & analogs by Keeper of the Trout (full text) title page

www.erowid.org

 

[nen888]

..excellent work endlessness..certainly a great use of time..higher altitude strains of caapi from Equador/Peru may have differences to Brazillian..
you wrote:

No need to pay me Just talk to my girlfriend and convince her it's a good use of my time, and I'll be happy

..sounds like a mission only for the brave..! good luck..
(i've been told i'm 'in love with the nexus' a few times.. )

 

[endlessness]

I have tried both red and black caapi from m4y4 and they are both relatively potent at 50g IME, enough for full MAOI effects (at least the particular batch I tried).




Here's the TLC of the first 3 caapis that were added to the first post:

Both for the TLC and for GC-MS, I soaked 250mg of each shredded caapi in 5ml methanol for about an hour, with some ocasional mixing. For the TLC I added 3 microliters of each of those solutions, but the bali caapi was clearly less potent and barely showed any UV shine so I added another 3 microliters (and even still, one can barely see it).


I cannot yet give absolute quantification because we havent made calibration with a standard, in the next months we might. But I can quantify relatively each plant.

So in terms of alkaloid ratio for bali:red:black
harmine: 1:14:15



So Bali caapi has around 15x less harmine than the other two, and no THH. Black has a bit more harmine than Red but Red has 3x more THH. In the next month I shall analyse some white caapi, maybe some other caapi I can get my hands on. I am also talking to a friend who's in santo daime and also with contacts with indigenous people for him to send me some daime caapi and aya brews, as well as some indigenous caapi.

Nen, interesting about the altitude, its something to consider. I asked the vendor above to tell me characteristics of harvest (date of harvest, age of material, etc) but they were not able to tell me. It says its from iquitos peru. When we have some other material, it will be interesting to compare

 

[polytrip]

I´d like to add that in my opinion, the red vine from this vendor produces a very high-quality experience. There seems to be some truth in claims that THH plays an important role in the unique character of caapi-vine experiences, because i find that this red vine has the most of this unique 'caapi character'.

 

[jamie]

how do you know you have real black caapi endless? True black caapi is not banisteriopsis caapi.."black caapi" is (reported to be) banisteriopsis muricata and is very difficult to get ahold of. I would think what you have as "black caapi" is really just banisteriopsis caapi.

Interesting results nonetheless.. Especially the bali vine. I always heard bali was very potent.

 

[jamie]

I´d like to add that in my opinion, the red vine from this vendor produces a very high-quality experience. There seems to be some truth in claims that THH plays an important role in the unique character of caapi-vine experiences, because i find that this red vine has the most of this unique 'caapi character'.

I also really like red vine. I have a large order of red and what is being called "black caapi" on it's way so it wil be interesting to drink the 2 diff vines seperate and then together to see how they differ. I am skeptical though that I am actaully getting the real black caapi. Red vine had a special energy when I drank it 2 years ago.

 

[endlessness]

how do you know you have real black caapi endless? True black caapi is not banisteriopsis caapi.."black caapi" is (reported to be) banisteriopsis muricata and is very difficult to get ahold of. I would think what you have as "black caapi" is really just banisteriopsis caapi.

Interesting results nonetheless.. Especially the bali vine. I always heard bali was very potent.

What is called Black caapi might or might not have some unequivocal 'original' identification.. You see, thats the hard thing with these names.. Who says black caapi? Is it an indigenous name? From what tribe? And do other tribes of the same ethnic group agree with that identification? What about other ethnic groups, do they also have a classification system that matches it?

Very possibly, it can happen that identifications dont match, between different shamans, different tribes, between vendors and what indigenous people would identify, or between vendors themselves.. So thats why instead of claiming this is generalizable for all black caapi, I will link to the vendor and date bought (if its bought) or I will add as much info on harvest or other details as possible when from other non commercial sources. At the moment there are only 3 tests, which are good but it will be better when more information is pooled in and we see what is the norm nowadays and what are exceptions. For example im looking to get a sample from another european vendor that also sells some "black caapi".. I dont know if their sources are the same, but anyways its interesting to check.

 

[Mitakuye Oyasin]

Thanks for posting, very interesting. Does this mean that there is no Harmaline in any of these tested samples or am I missing something? I always thought Caapi contained Harmine, Harmaline and THH.

 

[jamie]

^yes this is a problem that is hard to address. I just ordered some seeds sold as banisteriopsis muricata(white), sopposed to be "white ayahuasca" I am guessing..but that does not make any sense to me as from what I have always understood the white variety of ayahuasca is a caapi species of the banisteriopsis genus and not muricata..and white caapi I thought was hgih in THH and from what I can gather THH is either absent or much lower in muricata..so who knows what seeds I just ordered in reality.

It would be interesting to find out if some vendors are offering B.muricata as the "black caapi" they are selling, or other speices within the banisteriopsis genus as other vine colors..the natives call it "ayahuasca negra" I think and not black caapi but like you said I dont know what tribe that is in what region etc..

Also banisteriopsis muricata in tests I have seen did contain harmaline which could account for some of the claims of "black ayahuasca" being a more heavy or intoxicating experience etc.

 

[soulfood]

I "know" that a black caapi in ecuador which is also known as "Thunder" is supposed to be significantly more potent than a more common black caapi used in Peru.

From what I've read it's this thunder caapi that's famous for its violent bodily effects.

 

[endlessness]

Thanks for posting, very interesting. Does this mean that there is no Harmaline in any of these tested samples or am I missing something? I always thought Caapi contained Harmine, Harmaline and THH.

Yes, indeed there are no detectable levels of harmaline in any of the tested samples (which would appear as a peak between harmine and THH, but its none of the ones there, neither the very small ones I didnt label, and the GC-MS would detect very small amounts. But if you look at some of the publications like the Callaway one, indeed there seem to be some ayahuasca with no detectable harmaline at all, some with very little, and some with quite significant amount. Lets see if other samples we test show some harmaline

^yes this is a problem that is hard to address. I just ordered some seeds sold as banisteriopsis muricata(white), sopposed to be "white ayahuasca" I am guessing..but that does not make any sense to me as from what I have always understood the white variety of ayahuasca is a caapi species of the banisteriopsis genus and not muricata..and white caapi I thought was hgih in THH and from what I can gather THH is either absent or much lower in muricata..so who knows what seeds I just ordered in reality.

It would be interesting to find out if some vendors are offering B.muricata as the "black caapi" they are selling, or other speices within the banisteriopsis genus as other vine colors..the natives call it "ayahuasca negra" I think and not black caapi but like you said I dont know what tribe that is in what region etc..

Also banisteriopsis muricata in tests I have seen did contain harmaline which could account for some of the claims of "black ayahuasca" being a more heavy or intoxicating experience etc.

Interesting... We should try contacting vendors asking from where they get their identification. As for the white caapi, im probably getting some samples of it soon, maybe from two different vendors.

Im not sure at all on banisteriopsis muricata, Ill research some more on it. If you ever get to come across it for real, be sure to let me know