In keeping with the focus of the forum shifting towards an "Entheogenic University," I thought we might initiate some collaborative efforts to collect information on subjects that aren't thoroughly covered elsewhere. With the large number of active members we now have on the forum, we should be able to accomplish this rapidly if everyone who is interested puts in just a little time.

Considering the work Endlessness is doing with Tetrapterys methystica, it would be nice to collect all the information we can find on that plant into one place. Like Snozz points out (below), there doesn't seem to be any chemical analysis on the plant, but we can still collect ethnobotanical reports and botanical references.

What can you do to help?
Whenever you find good information about the plant, just copy-and-paste it into this thread along with a citation for your source. Legitimate books and journal articles are preferred. Information from unreliable sources should include an explanation of why you feel that source is valuable. Also, if your source includes any references to other works relevant to the plant, please reproduce those citations as well.

Any citation format will do (Chicago, MLA, APA), as long as it includes all the information needed to find the work in question.

A useful approach: Check any reference works and relevant collections you have access to (Botany and Chemistry of the Hallucinogens, Pharmacotheon, Garden of Eden, Ayahuasca Analogues: Pangæan Entheogens, Ethnopharmacologic Search for Psychoactive Drugs, etc.) and follow their citations to the primary literature. Use Google Scholar to search for more recent references. Check specialized botanical resources (Tropicos, the botany collections of the Field Museum of Natural History, etc.) for further information and sources. (Also don't forget typos are common; Tetrapterys is often misspelled as Tetrapteris)

So come on Nexus, let's see what we can accomplish when we work together!

Schultes, R.E. The Plant Kingdom and Hallucinogens Part III. 1970 pp30-31 link



Rodrigues, E.; Mendes, F. R.; Negri, G. Plants indicated by Brazilian Indians to Central Nervous System disturbances: A bibliographical approach 2006 pp. 84 link



This paper has 741 bibliographical references dating back to 1947. I think this is a pretty good indicator that the alkaloids may not be in the literature relating to this plant.

Thanks for getting the ball rolling Snozz!

I believe you're right that it hasn't been chemically analyzed before. Still, I thought we ought to collect all the botanical/ethnographic references (and whatever else we can find about the plant) into one place, so we have some context on the plant's history, use, etc. It also helps with the overall goal of the "Poorly understood family of ayahuasca vines" thread; the more we can learn about these vines, the less they will be poorly understood

Anyway, here's a few more:

Source: Louisiana State Law RS 40:989.1; Acts 2005, No. 159, §1

In the state of Louisiana, it is illegal to "knowingly or intentionally... produce, manufacture, distribute, or possess with intent to produce, manufacture, or distribute a material, compound, mixture, or reparation intended for human consumption which contains... Tetrapterys methystica."

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Source: Ott, J. 1994. Ayahuasca Analogues: Pangæan Entheogens. Natural Products Co., Kennewick, WA.

"Schultes found that the Makú Indians of the Brazilian Río Tikié would prepare a caapi-like entheogenic potion from Tetrapterys methystica... (Schultes 1954A; Schultes 1957; Schultes & Raffauf 1990)"

Sources cited by Ott:
[Schultes, R.E. 1954A. "Plantae Austro-Americanae IX. Plantarum novarum vel notabilium notae diversae" Botanical Museum Leaflets Harvard University 16(8): 179-228]
[Schultes, R.E. 1957. "The identity of the malpighiaceous narcotics of South America" Botanical Museum Leaflets Harvard University 18(1): 1-56.]
[Schultes, R.E. and R.F. Raffauf 1990. The Healing Forest: Medicinal and Toxic Plants of the Northwest Amazonia. Dioscorides Press, Portland, OR.]

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Source: Ott, J. 1994. Ayahuasca Analogues: Pangæan Entheogens. Natural Products Co., Kennewick, WA.

"Gates (1986) regarded Tetrapterys methystica to be synonymous with T. styloptera." {Notice that T. styloptera is synonymous with many other names; we should include information on T. styloptera and its synonyms in our search here as well}

[Gates, B. 1986. La taxonomía de las malpigiáceas utilizadas en el brebaje del ayahuasca. América Indígena 46(1): 49-72.]

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Source: Schultes, R.E. 1954. "Plantae Austro-Americanae IX. Plantarum novarum vel notabilium notae diversae" Botanical Museum Leaflets Harvard University 16(8): 179-228. [This is the original description of the species]

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Source: Schultes, R.E. 1954. "Plantae Austro-Americanae IX. Plantarum novarum vel notabilium notae diversae" Botanical Museum Leaflets Harvard University 16(8): 179-228.

*Presumably referring to his subsequent article: Schultes, R.E. 1957. The identity of the Malpighiaceous narcotics of South America. Botanical Museum Leaflets Harvard University 18(1): 1-56.

Agreed! I did not mean for my comments to discourage anyone...quite the contrary. I think it's really exciting that we are potentially about to identify/study novel alkaloids that do not appear in the literature (in part because the "father of ethnobotany" dropped his sample in a river ) and that seem to be traditionally be extracted via cold water methods.

I think I have some more stuff to post when I get a minute, just wanted to chime in lest people think I was being a downer

ps - if you haven't checked out that bibliographical approach paper, it's a pretty awesome indexing of plants and their alkaloids (with references to the original papers in question).

Thats great stuff here guys. Just for reference, a new thread was started to expand the research to different plants, here:

https://www.dmt-nexus.me...&m=357543#post357543

Greetings!

I recently stumbled on this forum while researching information regarding Tetrapterys spp. I joined the group today to share with you what I have learned recently because it could prevent someone from haphazardly drinking this and perhaps other less studied ‘caapi’ vines before we have 1) confirmed the species’ identity and 2) characterized their chemistry.

I don’t have time to write a full review on this subject, but I will summarize what I have learned which has made me think twice before consuming unknown plants.

To those who may not be aware, there are published reports of toxicity from animals grazing on Tetrapterys spp., Mimosa spp., and Phalaras spp. While some have pointed the finger at tryptamines, I have seen little evidence implicating DMT specifically, though certainly gramine is known to be toxic. Other toxic candidates to be on the lookout for are the monoterpenoid indole alkaloids, aspidofractinine, 15-demethoxypyrifoline and N-formylaspidofractine which has been identified in plants that cause similar toxic symptoms (Araújo et al., 2007, Phytochem Rev (2007) 6:183–188; DOI 10.1007/s11101-006-9044-y).

Below are some excerpts from papers that may be of interest in terms of possible toxicity.

Peace



Abortion in cattle due to Tetrapterys acutifolia poisoning
Pesq. Bras. vol.31 no.9 Sept Rio de Janeiro. 2011
http://dx.doi.org/10.1590/S0100-736X2011000900003

Saul A. Caldas I * , James C. Peixoto I ; Vivian A. Nogueira II ; Ticiana Birth France II , Charles H. Tokarnia III , Paul V. Peixoto III
________________________________________
ABSTRACT
This study aimed to demonstrate experimentally that Tetrapterys acutifolia Cav. (Fam. Malpighiaceae) is capable of causing abortion in cattle and to characterize the clinicopathologic changes in cows and fetuses. These plants are responsible for a significant number of deaths in cattle over one year of age, especially in the states of Rio de Janeiro and Sao Paulo, but until now had not been experimentally proven its abortifacient effect in cattle. The experiments were conducted in the municipality of Barra do Pirai, RJ. Four cull cows receiving fresh shoots and young leaves of T. acutifolia , collected from neighboring properties, at doses of 2.5 g / kg / day, 5.0 g / kg / day (two cows) and 10g/kg/dia, until after the abortion. The clinical findings in cows characterized by cardiac arrhythmia, muscle tremors, anorexia, ascites, jugular engorged, swollen breasts and barb and abortion (23-76 days after the initial intake of the plant), all cows aborted. Only one of four cows (which received 10g/kg/dia) died 36 days after abortion, with symptoms of heart failure. The necropsy of the fetuses / stillbirths revealed hydrothorax, hydropericardium, hydroperitoneum and hepatic congestion, by cutting the myocardium, there were pale areas. Histopathological findings were interstitial edema with incipient fibrosis. In cows that received the highest dose and died, and another intoxicated course, the autopsy findings were similar to those observed in the fetuses, except for the dilatation of the vessels of the heart base and more pronounced pallor of the myocardium. We also observed swelling in the cervical and subcutaneous sternal and engorged jugular veins. The histopathological findings were necrosis and interstitial edema with marked fibrosis in the myocardium, spongiosis of the cerebral white matter and in the liver, congestion and slight fibrosis. Additionally, there was the cow intoxicated spontaneously 17 days after abortion, irregular heartbeat, swollen jugular vein, edema, chest and barb, anorexia with death 43 days after the abortion. This study demonstrates that Tetrapterys acutifolia is capable of inducing abortion and, depending on the dose also cause the death of cows abort.

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Dose and clinical outcome to abortion
All cows receiving the plant (2.5-10g / kg / day) aborted and one died 36 days after aborted (10g/kg/dia). The period of the demonstration of the first symptoms to abortion ranged from 10 to 47 days.

Discussion
“…The poisoning Tetrapterys spp. in cattle and sheep can be compared in many respects to the toxicity caused by various species of rubiáceas ( Pachystigma pygmaeum, P. thamnus, P. latifolium, Pavetta harborii, P. schumannian and Fadogia homblei , also known as F. monticola) that occur in South Africa (Hunter et al. 1972 Kellerman et al. 1988 Fourie et al. 1989) and cause the so called "gousiekte" disease in cattle poisoning plants containing pavetamina (Schultz et al. 2004). In fact, more careful observation shows that the serious nature of cardiac lesions found in regressive-proliferative "gousiekte" (= rapid disease) keep resemblance to those described in poisoning Tetrapterys spp. Moreover, such to produce cardiac damage in animals, these plants also have to be ingested in large quantities for extended periods. However, the unusual influence of exercise as well as the clinical Subacute to chronic toxicity in Tetrapterys spp. differ from the frame determined by African plant, in general, lead to death so hyperacute (acute heart failure and sudden death), especially when the animals are moved and, less frequently, chronic congestive heart failure. In addition, African plants apparently do not cause abortion, or determining the central nervous system lesions ( spongiosus status ) as described in cattle and sheep poisoning Tetrapterys spp. and A. glazioviana (Tokarnia et al. in 1989, Barros 2001 & Gava, Gava et al. in 2001, Stigger et al. 2001) . Another similarity present in clinical cases of poisoning by plants that cause "gousiekte" and T. multiglandulosa has recently been described by Chapman et al. (2006), who observed clinical signs and cardiac lesions in cattle removed two months ago where there was a pasture plant. Experimental studies in sheep poisoning T. multiglandulosa also suggest that there is a latency period between ingestion of the plant and the development of cardiac lesions (Riet-Correa et al. 2005). This latency period (4-8 weeks after ingestion of the plant) is a characteristic of intoxication by African plant (Hunter et al. 1972 Kellerman et al. 1988 Fourie et al. 1989).


A review of poisonous plants that cause reproductive failure and malformations in the ruminants of Brazil
J. Appl. Toxicol. 2012; 32: 245–254

Franklin Riet-Correa,* Rosane M. T. Medeiros and Ana Lucia Schild

ABSTRACT: The objective of this review is to provide a report on toxic plants causing reproductive problems in ruminants in Brazil. Aspidosperma pyrifolium causes abortion or stillbirth in goats, as well as most likely in sheep and cattle, in the semiarid regions of Northeastern Brazil. Intoxications by Ateleia glazioveana, Tetrapterys acutifolia and T. multiglandulosa result in abortion and neonatal mortality in cattle and sheep, and the same signs have been experimentally observed in goats. These three plants can also cause cardiac fibrosis and a nervous disease with spongiosis of the central nervous system. Other plants known to cause abortion include Enterolobium contortisiliquum, E. gummiferum, Stryphnodendron coriaceum, S. obovatum and S. fissuratum. These plants can also cause digestive signs and photosensitization. Abortions have been reported in animals intoxicated by nitrates and nitrites as well. Infertility, abortions and the birth of weak offspring have been reported in animals intoxicated by plants containing swainsonine, including Ipomoea spp., Turbina cordata and Sida carpinifolia. Trifolium subterraneum causes estrogenism in cattle. Mimosa tenuiflora and, most likely, M. ophthalmocentra cause malformations and embryonic mortality in goats, sheep and cattle in the semiarid regions of Northeastern Brazil.

Tetrapterys acutifolia and T. multiglandulosa

“…Tetrapterys acutifolia and T. multiglandulosa are considered shrubs or vines. T. acutifolia is found in the states of Minas Gerais and Espírito Santo, and T. multiglandulosa is located in the states of Rio de Janeiro, São Paulo and Mato Grosso do Sul. The frequency of abortions resulting from these plants is variable. In an outbreak of poisoning by T. multiglandulosa, 230 out of 290 cows (79%) either aborted or delivered weak calves, and seven cows died from cardiac insufficiency (Carvalho et al., 2006). Recently, another species of Tetrapterys, not yet identified, located in the state of Rio de Janeiro was determined to cause abortions (Peixoto et al., 2011).


Mimosa tenuiflora

Mimosa tenuiflora and, most likely, M. ophthalmocentra (Fabaceae-mimosoideae) cause malformations and embryonic death in sheep, goats and cattle.

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The primary toxin in M. tenuiflora remains unknown, but alkaloids that are derived from tryptamine have been isolated from the leaves and seeds of this plant (Gardner et al., 2011). The occurrence of animal malformations in areas of M. tenuiflora or M. ophthalmocentra growth is suggestive of poisoning. Similar congenital defects can be produced by other factors, but the high frequency of defects observed in the semiarid rangelands of northeastern Brazil along with the experimental data on reproduction following M. tenuiflora administration suggest that a large majority of the malformations are caused by this plant.

Ref

Gardner DR, Riet-Correa F, Panter KE. 2011. Alkaloid profiles of Mimosa tenuiflora and associated methods of analysis. In Poisoning By Plants, Mycotoxins, and Related Toxins, Riet-Correa F, Pfister J, Schild AL, Wierenga T (eds). CAB International: London; 600–605.

Awesome contributions, thank you very very much!

Interesting enough, I corresponded with gardner from this last publication and he sent me the mass spectra of his mimosa research. In mimosa leaf with LC-MS he found nearly similar amounts of NMT and DMT, plus some significant amount of tryptophan. In the bark it was mostly dmt, some nmt, a little bit of 2mthbc. With A/B he also found what seemed like the same substance I got in mimosa that we speculated to be 1,2-dimethyl-tetrahydrobetacarboline (and dozuki thought was a yuremamine breakdown product, check jungle analysis thread in my signature). This same substance also appeared in some acacias. I asked him about yuremamine, he mentioned he was not sure about the reported yuremamine alkaloid. He saw a compound that give m/z 476 in the LC/MS of the bark sample, but he thought yuremamine should give a MH+ = 477. He also said there seemed to be related compounds giving base ions at m/z = 461 and 447. He sent me the ESI mass spectra as well as the UV one for these substances, I can try to post at some point.

Funny enough, in his research of mimosa it seems to have hordenine, which I also seem to have detected in trace amounts in mimosa, at the same retention time as phalaris I analysed. In phalaris it had higher amount and the clear mass spectra matched perfectly that of hordenine, though we have no standard of it. Interestingly phalaris also has a mix of tryptamines, beta carbolines and phenolic compounds. It might be its neither of them alone.


It might be with humans this isnt toxic like with sheep, it might be even that its medicinal...Maybe harmalas+DMT would also kill sheeps, did anybody ever give ayahuasca to sheeps?

It's always complicated to extrapolate from animal data. But it might be this combination is not safe for humans either, hard to say with the little amount of actual research with these combinations of alkaloids for humans. Though mimosa does have some decent historical use and doesnt seem to be toxic in any noticeable way so far. It could also depend on amounts of specific alkaloids. And different species have different alkaloids Nevertheless its still not nearly researched as ayahuasca, which seems to lack those phenolic compounds.


I do have the mass spectra of Tetrapterys already I can post sometime, I didnt find really anything I could identify except for maybe oleamide and a couple more substances that seemed like fatty acids. There were others that could be alkaloids but I have no idea what. Maybe this weekend but maybe only later early august when I come back because I travel for 10 days. Tetrapterys seems to have quite some pharmacological use by indigenous, and they dont seem to regard it in any way more dangerous, which is usually a telling sign for the safety of these compouds when consuming some plant for ages. They probably would have noticed some negative effects by now.

Hi sparkgap, welcome to the Nexus

I agree it is appropriate to be as thorough in testing everything as much as possible, but your post strikes me as a tad alarmist.

First I would point out, things that are toxic to one animal, may not be toxic to others. I don't know of any studies of the effects of the aforementioned alkaloids in humans, but if they exist, I think they would hold more meaning with regard to human consumption of these alkaloids.

Second, abortifacient alkaloids are not necessarily toxic to humans. Syrian rue contains at least two abortifacient alkaloids, but afaik, it is not toxic to humans who ingest it.

I also think it's worth noting that none of these studies deal with Tetrapteris methystica. This strikes me as relevant because, as we have seen with pahalaris spp., alkaloidal composition can vary wildly even among plants within the same genus. Additionally, there is decent ethnographic evidence that would suggest that certain indigenous cultures have been drinking T. methystica for quite some time, however the dose used, frequency and potential results of doing so are unknown to me. It would surprise me to find out that there are lasting toxic effects from a plant that has a documented history of long-term human use, but that could be the case.

Ultimately, I think you are right to be cautious in exploring novel ethnobotanical specimens, but I would urge you not to rush to judgement to label these plants as toxic to humans.

I agree with everything you said and it wasn't my intent to sound alarmist. On the other hand, I wanted to make some of this information known primarily because we do not have botanical species confirmation with regards to the Tetrapterys sp being sold as "Tetrapterys methystica" I have no reason to doubt the source (kiwi) and his/her methods of obtainment, but in light of what I found and posted above, I would feel better if we had species confirmation.

BTW, as reported by Schultes, the Maku had a very specific method for this plant, that being a cold water extraction of the vine. I am not a chemist, but I think we can infer that the Maku had a very good reason for doing this (and not because they were too lazy to boil). Perhaps because a hot water extraction may be toxic?

I can confirm that the cold water extraction (15 grams in 8 oz of spring water kept in the refrig for a couple hours) does produce an aquaous extract with a yellow hue just as Schultes reported.

BTW, thanks for the info on the abortifacient alkaloids. I have much to learn

Your point about ID's is well taken, especially in light of earlier confusions. As far as species confirmation, I can think of a few ways, but they're all somewhat involved (from asking for what would essentially be a voucher specimen to trying to get the DNA sequenced). If you've got any ideas, I'd be stoked to hear them

I completely agree with you about the Maku...perhaps if endlessness has (or gets/recieves some) T. methystica, he can run an analysis of both cold water and hot water extractions, we could see what sort of chemical reaction might be taking place. It's awesome to see some confirmation of Schultes' notes on this (and a shame he lost his sample before it could be tested).

Looking forward to engaging with you on this stuff

edit: end said he's got some and will do hot/cold water alkaloid comparison

I would be happy with a high def photo of the vine, leaves, and flowers as a start. It would also be useful to know the time of year it was collected. I did poke around and found that the vendor had some really nice photos of other plants on a facebook page, but I could not find a picture of Tetrapterys methystica (other than a dried root photo).

I will send an email and ask if they have a photo and report back. THX

I've been going through a lot of material about Tetrapterys methystica on this site. Has anyone tried the vine already? (I didn't find anything about the experience part so...)

Mod wrote:

No talk about dry material sourcing/vendors

@samyama

i have a brew of it sitting right now in front of me (its mixed with a few other vines).

if you like and if no one has any info about its effects ill post a tryp report once i work up the nerve to actually go.

Mod wrote:

No talk about dry material sourcing/vendors

also on an unrelated note to all this, are their any pictures of that vine on here? its kind of odd looking and is almost blue in its colour (the stuff looks really old, not like it has been sitting around for a long time but that it comes from some very old growth.)

could upload pictures if anyone is interested.

If you could upload it, please. It seems you're one of few who has the vine, so if you post it, could be handy for comparison.

Relevant paper:

Chemical composition of the bark of Tetrapterys mucronata and identification of acetylcholinesterase inhibitory constituents
Queiroz et al.
J. Nat. Prod. 77 (2014)

Found bufotenine and 5-meo-dmt, amongst others, in this plant. They mention it is sometimes used as ayahuasca and cite plant of the gods and ott´s ayahuasca analogues, but I dont have any of those right now to cross check. Is it possible they have mistaken it for methystica?

Makes me curious now to go back to the mass spectra and see if any of the other mentioned compounds are similar to what we´ve tested.

Looks like those books mention both T. mucronata and T. methystica, practically in the same breath.


From pages 15-16 of Ayahuasca Analogues (1994 English version)



From p. 124 of Plants of the Gods (2001 English translation of Rätsch's 1998 ``updated version'')



That mix of alkaloids -- 5-MeO-DMT, 5-MeO-NMT, 5-OH-DMT, and 2-Me-6-MeO-THβC -- looks quite a lot like Virola, Anadenanthera, and Phalaris. Plenty of reason to expect activity from such a plant. I wonder if the mucronatin A might add some visionary character as well, or if that extra 1-(indole-3-yl)-2,3-propanediol thingy hanging off the 2-position of the bufotenine skeleton makes it too bulky.

Looks like there's an interesting tidbit from the same research group in a 2013 abstract entitled ``Isolation and quantification of alkaloids from Tetrapterys mucronata – a plant used in the ayahuasca preparation'':


That last sentence was what caught my attention. In the 2014 ``Chemical composition...'' paper, I only saw one β-carboline mentioned: 2-Me-6-MeO-THβC. But there was no reference to quantification. Makes me wonder what constitutes a ``relevant amount.''

As far as I can tell, there doesn't seem to be a full article associated with that abstract; it's for a talk given at the 61st International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research.

well well well...

Ok finally installed back the NIST library, willing to go back into the mass spec from Tetrapterys methystica and see if we can finally identify at least some compound.

Would be great if we`d have a list of alkaloids found in T. mucronata and related plants so I can already reduce what I might find (appart from the usual tryptamines dmt etc since I already have those in the database). If we can find mass spectra of each of those or at least chemical structure, that`d be golden

Following up on the quantification of constituents in Tetrapterys mucronata, looks like Queiroz et al. have a new paper out: LC–MS/MS Quantitative Determination of Tetrapterys mucronata Alkaloids, a Plant Occasionally used in Ayahuasca Preparation
http://onlinelibrary.wil....1002/pca.2548/abstract

Haven't read it yet, will comment once I do.

Edit: See also this thread in the Science forum.