Anadenanthera identification & chemical constitution.

[E]

Hello Nexus People !

Some time since I didn't post here. During the time moved from Colombia down too Brazil (SP region).
After exploring a bit the trees of my town I found these guys.

I suspect them strongly to belong to the Anadenanthera genus. I say this from general morphological characters.
From what I have red in Torres & Repke works "Anadenanthera: Visionary Plant of Ancient South America" all 2 species A. colubrina & A. peregrina seem to be present in this region of Brazil. To make things easier and again according Torres & Repke, the 2 less studied of the 4 sub-species seem to be particurlarly present in the South-East region of Brazil : A. peregrina var. falcata and A. colubrina var. colubrina

I would be quite interested in the id. of these local species. Since I am also very much interested getting to know these seeds that fascinate me since a while but wich I have'nt got the occasion to travel with, I'd like to have you opinion on the possible chemical composition. I have red here (anadenanthera falcata) that A. falcata (A. peregrina var. falcata ?) contains WAY much 5-MeO-DMT than Bufotenine. Sadly the original ref. is unpublished (Savio Nunes, D., Narciso da Rocha Filho, G., Elisabetsky, E., & Barata, L. E. S. (1987). Alcaloides triptaminicos de Piptadenia gonoacantha (Mart) MacBr e de Anadenanthera falcata (Benth) Speg. Unpublished manuscript from files of B. Holmstedt.) Frankly I don't know 5-MeO-DMT ... but i don't want to ingest/smoke seeds containing 4.655% dry wt 5-MeO-DMT without knowing :shock:

Ok ... some pics :

A first specimen with a cardboard saying "Angico vermelho"

Another specime quite similar (with no id cardboard thus) produce those seedpods that seem a little bit smoother :

A second specimen with a cardboard saying "Angico branco"
Mainly the pods are different, thinner, smoother.

Another one as got a very caracteristic bark :
This one, called Angico do Campo has fruits smooth and thin like Angico Branco.
It's identified on the web as A. falcata. Strangely in Torres and Repke's work no mention of this particular bark is made for the falcata subspecies.

So a bit of confusion for me here. What are your opinions ?
Happy to receive every info !

Have a nice day.
E.

 

[E]

extracted about 30 whole seed pods (young, no mature seeds found) + a piece (20x40cm) of old dried bark of a specimen similar to Number one (precedent post). Material was not weighed. Extracted with water+EtOH (acidified) for one night. After filtration aqueous phase was defated (DCM) three times. After basification to pH 12-13 extraction by 3x DCM. Organic phase drid with sodium sulfate then under reduced pressure to yield on oily residue.
Definite DMT smell (synthetic-plastic) no idea if this smell is common to tryptamines or restricted to DMT ??
8) will have more info on products inside the oil later on ...

 

[E]

So here goes with the id. of this oily sample.

Edit : After torough drying the sample weighed ca. 450 mg. No idea of the alc. content since I didnt' weigh the fresh material.

Passed in LC/MS/ELSD

The Light Scattering detector seems to indicate a unique compound eluting at ca. 8.9 minutes.

But inscpection of the MS data indicates present of various compounds.
Seems to be mainly Bufotenine (m/z 205) and 5-MeO-DMT (m/z 219).

I also extracted the m/z 189 that should correspond to DMT. It's presence can be noted.

Now what ?
Is there a way to seperate Bufotenine from 5-MeO-DMT ?
(Tried to cristallize the oily mixture in hot EtOAc in a vial then in freezer but no way ...)
I guess these two guys aren't easy to separate.

I'm quite scared at the idea of smoking an extract without knowing the exact amount of 5-MeO-DMT in it.

What would you guys recommend as a first try ? What amount ?
What would be a good way to smoke such an oily product ?

Thanks for the feedback !


E.

 

[jamie]

I would make a 1/1 mix with some innert leaf material and smoke it. Dont worry about dose just smoke a hit every minute or 2 and hold it..bufotenine comes on slow and so you can smoke slowly and judge your dose that way to start.

I guess if there is any 5meoDMT present than you will know right away.

Good luck!

 

[nen888]

..thank you for this interesting work endophytik..only just found thread..

if there is a lot of 5meo, then 5-8mg smoked would produce fast effects, without being too strong at that dosage..
oily extracts can be scraped and 'dripped' into a pipe or similar, though can be fiddly to do this..
.

 

[endlessness]

Excellent thread indeed!

I will take some pictures of suspected Anadenanthera falcata that I also find in the RJ-SP atlantic rainforest area, I've been using it as a snuff lately but haven't had the chance to analyse it yet. I did analyse some falcata that was sold as such for reforesting purposes, and it contained bufotenine as the only detectable alkaloid in significant quantities, but that was a couple of years ago I think. If I get the chance to test this other falcata I will post here.

By the way, bufotenine should be way more water soluble, Im sure it wont be hard to separate it from 5-MeO-DMT based on the xlogp. Maybe a heptane or similar non polar pull will dissolve 5-MeO-DMT and not bufotenine. Or with any A/B step, the bufotenine will probably not migrate as well as the 5-MeO to the non-polar layer unless it's something more broad-range like DCM or so.

Can you post the data files for that LC-MS analysis? Did you do area under curve integration to have a rough idea on relative quantities? Im also curious what other small peaks might be.

 

[nen888]

endophytik wrote:

It's identified on the web as A. falcata. Strangely in Torres and Repke's work no mention of this particular bark is made for the falcata subspecies.

..bark texture is not usually considered a distinguishing factor in systematic botany for defining species/sub-species (usually based on flower and fruit) ..though bark texture is exactly the kind of thing indigenous people factor in when defining a 'kind' of a tree..very interesting looking thanks endophytik..

 

[E]

Hey there !

Thanks guys for the feedback.
Indeed the id. of these subspecies seems to be particularly complicated.

Can you post the data files for that LC-MS analysis? Did you do area under curve integration to have a rough idea on relative quantities? Im also curious what other small peaks might be.

I'll PM this. Didn't do the area under curve integration but globally the Bufo/5-MeO-DMT ratio seems to be 1:1. Nevertheless I don't trust much MS for quantitative analysis on different compounds since they can ionize more or less easily depending on their structural features. The ELSD spectra is more reliable for this concern ... but in this case both compound weren't sufficiently separed.
I'm also quite interested on the other peaks I have detected some interesting masses ... Beta-carboline type alkaloids ? Could be ? :?: I'll try to post this later on.

I will take some pictures of suspected Anadenanthera falcata that I also find in the RJ-SP atlantic rainforest area, I've been using it as a snuff lately but haven't had the chance to analyse it yet. I did analyse some falcata that was sold as such for reforesting purposes, and it contained bufotenine as the only detectable alkaloid in significant quantities, but that was a couple of years ago I think. If I get the chance to test this other falcata I will post here.

Would be great !

I would make a 1/1 mix with some innert leaf material and smoke it. Dont worry about dose just smoke a hit every minute or 2 and hold it..bufotenine comes on slow and so you can smoke slowly and judge your dose that way to start.

I guess if there is any 5meoDMT present than you will know right away.

Ok ... I should bioassay this mix soon.

Thank all for the feedback

 

[iracema]

wow, obrigado amigo!
I remember this angico, for the odd bark structure, but never gave much attention.

 

[jamie]

"Is there a way to seperate Bufotenine from 5-MeO-DMT ?"

That might be be simple. When freebase bufotenine is dissolved in iso(probly acetone too but I have only used iso for this) and and mixture of fasi(fumaric acid saturated iso) is added bufotenine fumarate will precipitate out. Now, this should work assuming that 5meoDMT also wont precipitate out..and that is something I cannot speculate about.

 

[E]

Looking more in detail at the MS spectrum (ESI+), I found some possible m/z peaks of protonated beta-carboline.
See attached file :

I put the m/z 205 (red) of Bufotenine as reference to have an idea of the ions abundance.
I scanned for some possible [M+H]+ ions of carboline and one can see the presence of
m/z 217 in dark green, could be tetrahydroharmine
m/z 203 in yellow, could be pinoline
m/z 215 in black, could be harmaline

I have no idea of the relative tryptamines/beta-carboline ratio in the extract. But I think it's quite interesting to note their co-occurence in the same plant.

I can't remember where but it seems to me that occurence of beta-carbolines had been reported in Anadenanthera sp. Someone got this ?

 

[E]

Last night I had prepared two pyrex tubes containing 1.5 and 4.5 mg of the upper mentioned alcaloid extract.

Smoked both with no distinct psychedelic effects.
The second dosage (4.5 mg) caused "head fullness/fuzziness" about 40 sec after inhalation.
Feeled relaxed (remind me of the effects of a marijuana joint ... wich I haven't smoked for some years now). Pleasant, but light.

I guess I'll try a 10 and 15 mg dosage next time.

 

[MoonMan79]

Endophytik...any news (10 and 15 mg?)?
Bay the way, awsome reasearch!:thumb_up: