Evodia Fruit Extraction Experiment

[Aum_Shanti]

As I mentioned in the thread I linked, I found scarcely any indication how much 5-Meo-DMT there is in Evodia Rutaecarpa.
By then I could only find this indication:
Wu Zhu Yu - Evodia fruit / Euodia / Tetradium ruticarpum - Chinese Herbal Medicine

Where it is said that:

Contains small amount of 5-MeO-DMT (about 0.21% in aerial parts), a powerful psychedelic

And 0.21% would actually be a huge amount of 5-Meo-DMT as a source plant, especially as it is widely and cheaply available from TCM stores.

But I couldn't find any indication, where this value is coming from. So I searched on and on about any papers indicating anything about the 5-Meo-DMT content of this plant. Interestingly there are many many (even recent) papers about the alkaloids of Evodia Rutaecarpa, but strangely none of these even mention 5-MeO-DMT. Their alkaloid analysis just shows the main alkaloids like Evodiamine and Rutaecarpine and other alkaloids which are precursors/byproducts of the internal synthesis of the plants, and also some Beta-Carbolines...

This somewhat didn't make any sense to me: Did they deliberately not mention the 5-MeO-DMT or was the content of it in the plant so rare that it just didn't show up in their analysis?

Finally in Trout's notes ("Some Simple Tryptamines") I found some values:

In unripe fruit. Takagi et al. 1979 recovered 30 mg
from 10 kg unripe fruit. Yu et al. 1997 reported
0.00015% by dry weight in the unripe fruit. [15 mg
from 3 kg.]

Wow that's basically nothing!!!

So one can basically completely drop the idea of getting 5-MeO-DMT from this source...bummer...

 

[Intezam]

This somewhat didn't make any sense to me: Did they deliberately not mention the 5-MeO-DMT or was the content of it in the plant so rare that it just didn't show up in their analysis?

Finally in Trout's notes ("Some Simple Tryptamines") I found some values:

In unripe fruit. Takagi et al. 1979 recovered 30 mg
from 10 kg unripe fruit. Yu et al. 1997 reported
0.00015% by dry weight in the unripe fruit. [15 mg
from 3 kg.]

Wow that's basically nothing!!!

So one can basically completely drop the idea of getting 5-MeO-DMT from this source...bummer...

That all depends whether a target specific 5-MeO extraction route was chosen by the two. 5-Meo can easily be destroyed by both, strong acids and base....(we heard) and also the type of NP used may play a role.....(we think)

It could still be interesting repeating the experryment using milder acid and base and DCM as a NP.....????

 

[Aum_Shanti]

I will try to get the original paper, to see how they did it. I know from 69ron's experiments that he needed some very special technique to successfully extract 5-MeO-DMT (citric acid, sodium carbonate and DCM).
That's why I ordered some Evodia rutaecarpa and wanted to try his method on it. But now it seems that's useless. As their paper was especially about the Tryptamine content, I would suggest they used a proper technique for it...

BTW: The article mentioning the DMT (0.00026%) and 5-MeO-DMT (0.00015%) content in Evodia rutaecarpa is this one:

Yu, L.-L. et al. (1997) Journal of Natural Products 60 (11):
1196-1198. “Two 5-HT1A Receptor-Interactive Tryptamine
Derivatives from the Unripe Fruit of Evodia rutaecarpa.”
(Li-Li Yu, Li-Kang Ho, Jyh-Fei Liao & Chieh-Fu Chen)

Maybe someone has access to it?

BTW: Something with the numbers must be wrong here. As 15 mg
from 3 kg is not 0.00015%. Probably the right number is 0.0005%.

Edit: Also from the other reports the content of the main alkaloids (Evodiamine, rutaecarpine, etc.) seem to be even lower than that indicated primarily (from the mentioned Website) just for 5-MeO-DMT. So it seems that actually the content of 5-MeO-DMT in Evodia rutaecarpa is really extremely small.
So the search continues for a proper accessible source of 5-Meo-DMT...

 

[Aum_Shanti]

So I finally organized that paper.
I have no idea if it would be OK to post the pdf here, anybody knows?
(Probably not, due to copyright I think...)

But IMHO it is actually a pretty bad work, rather hilarious, if not ridiculous.

The idea behind the paper's work:
The evodia rutaecarpa as a medicine has shown some "unpleasant" effects if taken in higher dosages. As the main medicinal alkaloids (evodiamine, rutaecarpine, etc) do not affect 5HT1A, but the total alkaloids show some 5HT1A effect, it was suggested previously that probably the contained tryptamines are responsible for this activation and that probably they are then responsible for the unpleasant effects.

So in this work they showed in the first half of the paper that the contained tryptamines (DMT and 5-MeO-DMT) do bind to the 5HT1A receptors and in the second half that they are present in the plant.

My comments:
It was already well known that DMT and 5-MeO-DMT bind to 5HT1A so half of the work was IMHO completely useless.
With the amounts of these tryptamines in the plant the "unpleasant" effects cannot come from these compounds, that's completely impossible (not even talking about the fact that these compounds are not orally active!). And the needed dosages for even threshold effects are well known. Did they actually even make the slightest research about the properties of DMT and 5-MeO-DMT???
They also knew, that the total alkaloid effects of E. rutaecarpa doesn't have any 5HT2 effects.
If the tryptamines would be in there for any reasonable amount there would certainly be a 5HT2 effect!!! (especially from DMT)

That's at least my conclusion. Maybe I'm wrong...Or were all these things not yet known in 1997?

But back on topic about the measured amounts of DMT and 5-Meo-DMT. As I already suggested, there's an error in Trout's notes: It's 0.0005% not 0.00015% for 5-MeO-DMT.
(maybe somebody could correct this value on the Nexus wiki page: 5-MeO-DMT - DMT-Nexus Wiki)

This is how they extracted the tryptamines from 3kg of the ground dried fruits:

1) Extracted 3 times with 3L ethanol
2) The extract was filtered and concentrated to give 224g.
3) The extract was split up into a water soluble part (81g) and the rest (143g)
4) The water soluble part was basified with concentrated ammonia (no PH indicated) and extracted with chloroform (3x200mL), which yielded 250mg
5) Si gel column chromatography with hexane, hexane-chloroform, chloroform and chloroform-methanol, which gave 19 fractions.
6) fraction 8 (33.8mg) was then run through a Si gel column and HPTLC, which yielded 15mg 5-MeO-DMT and 7.8mg DMT.

The reason why they just processed the water soluble part was, because only this part showed 5HT1A activity in their tests.

Final comment by me:
As the total extract didn't show any 5HT2 activity I am pretty convinced that Evodia rutaecarpa really only has trace amounts of (5-MeO-)DMT and that the problem wasn't an extraction error...
Also it would IMHO additionally be a poor source as there are mainly other (indole-)alkaloids in there and separating them by easy means is basically impossible...
So IMHO this plant has definitely died as a possible source...unfortunately...

Any comments???

 

[wira]

The 0.21% 5-MeO-DMT in aerial parts thing is totally new to me - perhaps unsubstantiated BS? I'll believe so unless I find a good source for that to demonstrate otherwise.

 

[Aum_Shanti]

I also was baffled by this number. That's why I searched everywhere if there's any source for this number. I think someone confounded it with the value for Evodia Leptococca (Meliocope leptococca).
Leptococca itself seems interesting, but it seems it's basically impossible to buy any plant material...