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Help needed extracting TetraHydroHarman from Acacia Baileyana. Options
 
wage.
#1 Posted : 11/30/2012 5:33:41 AM
Hey /nexus/

On the way home from a bush walk today I came across 3 different Acacia Baileyana trees and decided to crop a small amount of Phyllodes from each one. The species supposedly contains TetraHydroHarman



I've had a talk with a few members in chat and one recommended that it might be a good idea to make a thread because of how TetraHydroHarman is different to Harman/Harmaline.

I would really appreciate any advice on this from anyone who has a chemistry background.

"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
nen888
Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling
#2 Posted : 11/30/2012 5:38:47 AM
..it was found to contain tetrahydroharman one time of year, and tryptamine the other..these are the only 2 tests i know of, other than an underground claim of small amounts dmt..

just do a standard A/B of some kind (and IMO try to use a different form of naphtha to the brand shellite, or xylene, or odourless d-limonine)

don't fuss with teks specific to certain alkaloids..no one really knows much about baileyana (which is odd considering how common it is)

..a standard A/B will pull harmalas and/or tryptamines.
 
wage.
#3 Posted : 11/30/2012 5:54:46 AM
Thanks Nen. I'm not so interested in this Acacia for DMT but the THH.

When I get around to the extraction I'll most likely do 3 boils with Water-Vinegar and then Basify with Sodium Hydroxide.
"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
wage.
#4 Posted : 12/18/2012 2:34:49 AM
Last night I filled up a jug with the same dried Acacia Baileyana phyllodes from in my first post.

Instead of trying an Acid Base extraction again which yielded no results, I decided to try using 95% Ethanol.

I shook the mixture every 30 minutes for 3 hours and then filtered the liquid into a Pyrex Dish. The liquid became extremely cloudy by hour 1

I then left it outside to evaporate overnight.

I just checked the evaporation earlier and it's yielded something very interesting. I can't say for certain if it's Tetrahydroharman or not.

Anyway, here's a picture.

"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
AlbertKLloyd
#5 Posted : 12/18/2012 2:46:28 AM
Check it under a black light, is it glowing a strange green color, if so you might have what you are looking for.
 
nen888
Acacia expert | Skills: Acacia, Botany, Tryptamines, CounsellingExtraordinary knowledge | Skills: Acacia, Botany, Tryptamines, CounsellingSenior Member | Skills: Acacia, Botany, Tryptamines, Counselling
#6 Posted : 12/18/2012 3:06:53 AM
^..yes, as he says ß-carbolines glow green to blue under UV, some more than others..

from what i have seen of extracted harmalas that looks quite like it from the pic..

very interesting and significant result WAGE!..thank you!Smile
could be traces of tryptamines in there too..

any idea roughly what %..?
.
 
wage.
#7 Posted : 12/18/2012 9:42:55 AM
I just scraped up the results then and it weighs 300mg.

I never checked the weight of the starting material, so I can't give a percentage. Luckily I do still have 250g+ of Acacia Baileyana phyllodes and will be able to repeat the same process with weight being checked at the beginning.

As for looking at it under a light, I'm not sure if I can get access to the right type at the moment. Also, because of the Tetrahydro group, will it still glow similarly to other Harmalas?

Here's a photo of the yield.



"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
Infundibulum
ModeratorChemical expert
#8 Posted : 12/18/2012 1:55:03 PM
^^
That stuff could be anything, there is nothing in your pics that even *cues* to something interesting. Your best bet is to dissolve some in water or ethanol, then look it under UV.

A/B won't help you one bit as beta carbolines (freebase) are generally notorious for their poor solubility in naphtha, xylene, limonene etc. You'll need DCM or chloroform to do an A/B

Thanks for experimenting however!



Need to calculate between salts and freebases? Click here!
Need to calculate freebase or salt percentage at a given pH? Click here!

 
wage.
#9 Posted : 12/19/2012 10:21:32 AM
What makes you think that it hasn't yielded anything interesting?

"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
Infundibulum
ModeratorChemical expert
#10 Posted : 12/19/2012 10:34:23 AM
Because this looks similar to many crude (ethanol) extractions, be it from a plant with actives or a plant with no actives whatsoever. Plants have so many things that can be pulled off them so it is hard, just by looking the myriad of different molecules in your dried pull, to say if there's anything interesting.

If you'd pulled oak or pine parts you'd had yielded a similar-looking extract.


Need to calculate between salts and freebases? Click here!
Need to calculate freebase or salt percentage at a given pH? Click here!

 
wage.
#11 Posted : 12/19/2012 10:38:55 AM
What could the Ethanol have pulled from the material?
"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
Ambivalent
#12 Posted : 12/19/2012 10:45:18 AM
well, unless we know the correct phytochemical profile of this plant, its just very wild guesses imo. It can be lipids, saponins maybe, polyphenols, depends...its interesting to see its almost free of chlorophylle. it means chlorophylle is not so soluble in strong ethanol, espeacially on cold temps. i have observed this in marij. extractions too.
 
wage.
#13 Posted : 12/19/2012 10:46:24 AM
I'll just wait until I can get hold of a UV light.
"Life moves pretty fast. If you don't stop and look around once in awhile, you could miss it."
 
Ambivalent
#14 Posted : 12/19/2012 10:49:54 AM
thanks for posting your results, i would be interested to see how the uv experiment went after its done.Smile
 
DreaMTripper
#15 Posted : 11/11/2013 5:40:53 AM
What was the end result?
 
DreaMTripper
#16 Posted : 4/28/2014 7:47:14 AM
Curious as to how it appeared under UV, nen what time of year did it contain THH.

While driving near the strathbogie ranges I would notice interesting looking trees in the central reservation then always near them there would be an acacia baileyana tree as if it was acting as a natural marker for the interesting looking tree or vice versa..
 
 
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