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The Acacia Analysis Thread Options
 
endlessness
#1 Posted : 12/7/2011 4:25:34 PM

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For much more Acacia info (geographical areas and identification, sustainable harvest, alkaloid content, etc)

Read the Acacia Info Thread


Results are discussed throughout thread with more details. Ratios and percentages are approximate and subject to revision, im new to all of this so bear with me Smile


Acacia acuminata 1 - phyllodes

broad leaf var. phyllodes were collected June and extracted A/B with water, ethanol, vinegar, NaOH, DCM..20 grams broad-leaf strain phyllodes yeilded a bit over 200mg alkaloid





Acacia acuminata 2 - phyllodes


..the phyllodes of Acacia acuminata Narrow Leaf variety were collected Feb. roadside
using acetic acid/ethanol 50:50, NaOH, xylene..the percentage was 0.9-1.0%. The branch bark (of this specimen) is apparently 1.5% approx.




Acacia confusa - Stem



Acacia confusa - Root





Acacia obtusifolia


(southern NSW) twigs separated from leafs, were collected March. Extracted A/B with water, ethanol, vinegar, NaOH, DCM. Washed of color in solvent (with salty NaOH). Small twigs yielded 0.6-0.7% alkaloids, leaf yielded 0.4-0.5%. Bark 0.5-0.6% yield (Bark initially similar looking to the acuminata leaf extract, was washed with salty NaOH/H20 to become an orange/pale brown wax)







Acacia obtusifolia 2



(southern NSW) twigs separated from leafs, were collected March. Extracted A/B with water, ethanol, vinegar, NaOH, DCM. Washed of color in solvent (with salty NaOH). Yield.0.3-0.4%






Acacia obtusifolia x maidenii


(branch bark & leaf) is from April (autumn/fall) . 3x Boiling in water/ethanol/vinegar careful filtereing several times of particulate matter..basified with NaOH..extracted with DCM. Washed of color in solvent several times (with salty NaOH). 0.6-0.7% yield.




Acacia mucronata var longifolia

the phyllodes (leaf) and twig (grown from seed from northern Victoria, Australia). Young plants 6-8 months old from seed. Extracted with ethanol/methanol/H20 70:5:25, concentrated under acetic acid, basified with NaOH, and extracted with dichloromethane, and left in crude form.yield was around 0.3-0.4%..





Acacia simplex ethanol
ethanol dry tek
(thanks pastanostra for sample and info)

The harvest of the tree was in october 2017 (end of dry season in new caledonia) after 3 month of no rain.

Dry tek STB with sodium carbonate & Ethanol 95%





Acacia simplex ethanol
A/B
(thanks pastanostra for sample and info)

The harvest of the tree was in october 2017 (end of dry season in new caledonia) after 3 month of no rain.

A/B with vinegar, lye and naphtha re-x



 

Ever have a personal encounter with an entity after taking DMT?
 
endlessness
#2 Posted : 12/15/2011 11:40:16 PM

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Now more detailed info from the plants that are already posted in the first post above:

Acacia acuminata



Dark red dry goo/taffy-like. Smells like dmt/indole compounds.


Harvest and extraction methods

nen888 wrote:
(broad leaf var.) phyllodes was collected June and extracted A/B with water, ethanol, vinegar, NaOH, DCM..20 grams broad-leaf strain phyllodes yeilded a bit over 200mg alkaloid



TLC




GC-MS results

(image in first post)

The 3-Methyl-Quinoline is NIST's best guess at 18% chance. The spectra is similar but its certainly not a definite identification. It's some cyclic compound... Im attaching a pic of the spectra of this substance VS what the 3-methyl-quinoline spectra would actually be, for others to check

Plus a few unidentified trace peaks with low signal. Potential identification of unknowns or possible class of compounds:
A- Some plant ketone. NIST gives a 54% chance identification of it being megastigmatrienone, a substance also present in the essential oil of styrax officinalis.
B- Unknown, too weak signal, NIST gives no good guesses. Maybe some fatty acid?.
C- Unknown probable plant acid.
D- Possible tryptamine/indole-based compound. NIST gives 21% chance of it being 4-(1H-Indol-3-yl)-1-butanamine.
E- Another possible indole/tryptamine based compound. NIST gives 73% chance of it being N-Acetyltryptamine. This might also be N,N-formyl,methyl-tryptamine. This peak has also been found in mimosa, check jungle thread in my signature
F- Possibly bitrex. Nen888, was the alcohol you used to dissolve the alkaloids denatured?
G- Some long chain compound, possibly fatty acid


As always, im attaching the agilent .MS file (in the .rar file) for anybody who wants to double-check my work. To open up the file and see peaks, use AMDIS program as linked here. Soon I will also be attaching a zipped file with the images comparing the mass spectra of the unknown/unconfirmed compounds vs some known standard, for those that dont want to download the NIST program.


Comments:

* Very interesting the extremely large amount of beta carbolines. Could significantly alter the experience.
* What about these phenetylamines, can they affect the experience?
* What is the safety of all of these compounds?
* How would different extraction methods and time of year of collection change the results?


Acacia confusa
Stem, and bark (tested separately)

TLC

Results: NMT, DMT + another different spot in stem vs bark


Here's the TLC of both. Left column is DMT standard, middle column is rootbark, right column is stembark. This was done with methanol:ammonium hydroxide 100:2.5, with silica gel F254 from merck (seen under UV 254 nm)



There are the NMT in both, then DMT, and each one has an alkaloid with high Rf

GC-MS

Results: Both Acacia confusa stem and rootbark contain mainly DMT and NMT as the alkaloids, plus other traces of substances.

Full results description:
In the GC-MS system we're using, both NMT and DMT are co-chromatographing, so its hard to give relative quantities because part of the peak curves are overlapping. In any case, with both stem and rootbark, it seems to be around 50/50% of NMT/DMT in both of them (or lets say, due to uncertainties of peak, anywhere between 30/70 to 70/30%). The profile of both stem and rootbark seemed pretty similar, there were only small differences. They both had a few other small peaks (>1%). They both had very small amounts of 2MTHBC (which might be analysis artifacts? This is still an ongoing doubt we are discussing in this thread), plus a few peaks of other substances such as plant sugars and fatty acids, which were a bit different in stem vs bark but both were only trace/very small amounts. What could potentially be different in stem vs bark is the overal quantity of NMT and DMT, but i did not do them in equal dilutions (due to lack of enough plant material) so I cannot really do quantitative comparison between stem vs bark. They both also nearly undetectable trace amounts of Skatole, check this thread for more info


Acacia obtusifolia extracts

Twigs



Harvest and extraction methods

nen888 wrote:
(southern NSW) twigs separated from leafs, were collected March. Extracted A/B with water, ethanol, vinegar, NaOH, DCM. Washed of color in solvent (with salty NaOH). Small twigs yielded 0.6-0.7% alkaloids

Smells DMT-like



TLC

(check post #3 for picture)

DMT


GC-MS

(image in first post)

This 3-methylquinoline is unconfirmed. Someone suggested it might be the cyclicized product of phenetylamines found in some Acacias as we're speculating in this thread?). Below Im posting the mass spectra of this substance) Any small amount of NMT is co-chromatographing with DMT



Leaf



Dark green gooey product, smells DMT-like


Harvest and extraction methods, yield

(same as twigs, 0.4-0.5% yield)

TLC



DMT + NMT + unknown spot or two


GC-MS

(image in first post)

Any small amount of NMT is co-chromatographing with DMT. The 3-Methyl-Quinoline identification is unconfirmed. Its mass spectra is posted below.


Bark



Harvest and extraction methods

(southern NSW) , same as twigs and leaf, initially similar looking to the acuminata leaf extract, was washed with salty NaOH/H20 to become an orange/pale brown wax..0.5-0.6% yield)


TLC

DMT + NMT + possibly another spot
(see picture of Leaf TLC above)

GC-MS

(image in first post)


Any small amount of NMT is co-chromatographing with DMT. The 3-Methyl-Quinoline identification is unconfirmed. Its mass spectra is posted below.


Acacia obtusifolia x maidenii leaf and twigs extract



Smells DMT-like with maybe a hint of something like camphor/menthol

Harvest and extraction methods

nen888 wrote:
(branch bark & leaf) is from April. Extracted A/B with water, ethanol, vinegar, NaOH, DCM. Washed of color in solvent (with salty NaOH)


TLC
(Picture in post #3)

DMT

GC-MS
(image in first post)
 
endlessness
#3 Posted : 12/15/2011 11:40:22 PM

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And here's the TLC of Acacia acuminata, obtusifolia (just twigs) and obtusifolia x maidenii, plus acacia confusa, and few other assorted things.

Methanol:ammonia 100:2.5 eluent system.





In this plate the substances from right to left:

1-Mimosa hostilis

DMT+ two substances on top of DMT, maybe yuremamine and something else? Cant distinguish if NMT is there or not.

2- DMT standard

3- 5-MeO-DMT standard


4- Anadenanthera falcata seeds

5-MeO-DMT presence (same height + green with PDMAB-TS, confirmed with GC-MS as minor component), plus two substances with lower Rf but unknown (one with same height as NMT but turns green instead of yellow/orange). GC-MS showed major alkaloid to be bufotenine, maybe bufotenine is also at same height as 5-MeO-DMT/DMT and turns green with PDMAB-TS? Or is bufotenine one of the other substances below, and why does it seem like there is less?

GC-MS also showed traces of DMT and some fatty acids/other plant impurities.. Full results will be posted soon.

5- Small stems, twigs and leaves that came together with seeds of Anadenanthera falcata (might not even be from same tree)

Two substances with high Rf, no sign of DMT/etc

6- Acacia confusa stem

DMT + NMT, turn yellow/orange with PDMAB-TS (plus other trace components as confirmed by GC-MS, full results come soon). Also check other plate in other post above

7- Acacia confusa stem extraction

Was just a small test with limonene but was too diluted for TLC, can barely see DMT (yellow/orange with PDMAB-TS) + 2 seeming beta carbolines or other UV shining substances with high Rf that do not show up on the pure methanol soak (degradation products from extraction? was done with sodium carbonate, limonene and vinegar) and do not react with PDMAB-TS

8- Acacia confusa root

DMT + NMT, turning yellow/orange with PDMAB-TS (and confirmed with GC-MS plus other minor components)

9- Acacia acuminata
leafs

Seeming DMT + NMT identification (turn yellow/orange with PDMAB-TS, same height), plus other 4 unknown substances.

10- Acacia obtusifolia

Apparently only DMT, turns yellow/orange with PDMAB-TS and at same height as standard.


11- Acacia obtusifolia x maidenii

Apparently only DMT, turns yellow/orange with PDMAB-TS and at same height as standard.

12- Harmine and harmaline
standards in same column
 
nen888
#4 Posted : 12/16/2011 5:52:51 AM
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wonderful endlessness, thank you for the work so far..Very happy
..the acuminata (phyllodes) was collected June and extracted A/B with water, ethanol, vinegar, NaOH, DCM..20 grams broad-leaf strain phyllodes yeilded a bit over 200mg alkaloid..the obtusfolia (small twig) was collected March (i'm surprised there isn't anything else in there, last two times at this site had NMT, but it is a highly seasonally variable species)..and the obtusifolia x maidenii (branch bark & leaf) is from April..it would normally be mainly DMT, unlike the particular obtusifolia specimen provided (based on two past tests) ..the latter two are also A/B, DCM..i want to get obtusifolia from a couple other locations looked at (including the site from which 2000 NMT experimental material was gathered)

(for northern hemispherians, june is mid winter)
.
 
nen888
#5 Posted : 12/16/2011 6:41:13 AM
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..good evidence of the mysterious MHRB 'Jungle alkaloids' too..Wink
 
endlessness
#6 Posted : 12/16/2011 8:36:32 AM

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Thanks for the extra info Nen, and for the samples. Now that you mention it, I think I might see a faint trace of what could be NMT in obtusifolia there. Also the spot form from obtusifolia x maidenii seems somehow strange to me, I think there might be two alkaloids that co-chromatographed, DMT and something else (and not 5-MeO-DMT because it turned yellow/orange with PDMAB-TS). We'll see the results of GC-MS. Also Im keeping a small amount of each sample for the future because we are getting an LC-MS early next year, so will be interesting to cross-check the results.

As for the jungle alkaloids, I dont think they are, though, at least according to what i've been posting from jungle analysis here. It seems, more in tune to what dozuki posted in that thread, that those are yuremamine/maybe something else, that degrade or at least are not extracted when basifying/extracting jungle, because at least one of those higher spots does not seem to appear in jungle spice. anyways Ill keep posting more information on mimosa/jungle research on that thread.
 
nen888
#7 Posted : 12/16/2011 11:12:33 AM
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..what i sent for obtusifolia was actually twig extract..the leaves were pulled off and saved (x maidenii i left the leaves on), i noticed that it crystalized easily and was soluble easily in cold ethanol..previous extracts which contained nmt were gooey/waxy and partially less soluble in cold ethanol with a darker color..Siebert found 2/3 NMT in leaves, the 2000 GCMS was leaf & bark..i think what is going on is that the majority of NMT is in the leaves..the leaves from the same twig material still exist to directly test this theory..Jeremy J. (at EGA 2007 and cited in Voogelbreinder 2009 did one obtusifolia test and found the NMT was mainly in the leaves, along with DMT..
..the good news from all of this, so far, is that the small twigs contained around 0.6-0.7% alkaloid, so one does not have to touch trunk bark (affects tree) for the same yield of tryptamines..

i deliberately sent previously untested material..irony is i kinda like a bit of nmt..Smile

ps. the obtusifolia and obtusifolia x maidenii extracts were washed of color in solvent (with salty NaOH) whereas the acuminata wasn't..it was crude..it is great that it's possible to perform useful extractions on what are quite modest amounts of plant material..

[EDIT: i've long suspected twigs may be where the action for mainly dmt is in this variety of the species..
bark sample extracted from same material was brown/red goo crude..see further on]
 
endlessness
#8 Posted : 12/18/2011 11:01:23 PM

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I've added pictures of extracts crystallization patterns to the first post, and descriptions of smell.

Also here is a picture of acuminata, obtusifolia and obtusifolia x maidenii extracts next to each other:


Nen did you also notice the menthol-like smell in obtusifolia x maidenii?


Tomorrow I'll send them in for GC-MS, hopefully by the end of the week we have some results, otherwise early next year.


 
nen888
#9 Posted : 12/19/2011 5:27:32 AM
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..yeah, it doesn't smell like just dmt..yet it's a clear crystal..it's very interesting, as the tree is subjectively..remember that old polymorphism question? this tree inspired that..
all extracts were A/B same materials..

as for obtusifolia (southern NSW), leaf and trunk bark of the same tree the twig came from were extracted..
the bark extract (about 80-90mg from 15grams trunk bark), initially similar looking to the acuminata leaf extract, was washed with salty NaOH/H20 to become an orange/pale brown wax..
the leaf extract (crude like acuminata) was a golden/amber oil (about 40-50mg from 10grams)
..
ps. the pics above should read: acuminata, obtusifolia and obtusifolia x maidenii (the paler crystal)
 
Gowpen
#10 Posted : 12/24/2011 12:48:11 AM

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Pardon my ignorance, but has any evidence surfaced of extractions from the seed pod casings, if DMT is found then perhaps that would promote sustainable, ethical extractions in australia. I suspect a lot of the official reports that proclaim 'NO DMT content' in many wattles might be false. A way to obtain DMT without destroying a plant would be immencely helpful
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nen888
#11 Posted : 12/24/2011 1:21:11 AM
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..there is some evidence of tryptamines in a few acacia pods, needs more investigation..in cultivation pruning a branch every few years is the least harmful thing to do to a tree..often in the wild storms will cause individual branches to drop..hacking the main trunk or root bark is what destroys them...
 
endlessness
#12 Posted : 12/29/2011 9:53:17 PM

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As always, im attaching the agilent .MS file (in the .rar file) for anybody who wants to double-check my work. To open up the file and see peaks, use AMDIS program as linked here. Soon I will also be attaching a zipped file with the images comparing the mass spectra of the unknown/unconfirmed compounds vs some known standard, for those that dont want to download the NIST program.
 
nen888
#13 Posted : 12/30/2011 1:42:12 AM
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..very interesting, thanks endlessness..
the leaves are said to vary somewhat seasonally in 'character'..the particular sample tested here was known to have been used successfully multiple times, with at least 30 different people (by the person who gave me the leaves) in conjunction with MAOIs with no negative physical reactions..some people may have found the brews 'mentally' strong or challenging..certainly people should be aware that the parameters of this species are still being worked out..

from experience with other ß-carboline containing acacias (mucronata) i would say they would modify the experience, depending on concentrations..
.
 
endlessness
#14 Posted : 12/30/2011 9:50:10 AM

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Cool nen, if you do end up getting it in other seasons we should get it analysed again!

Good to know there were no other negative physical reactions!

Whats your take on pure tryptamine, do you think it will have any effects, on its own or in the mix? What about the small amount of phenetylamines? Was N-Methyl Phenetylamine ever found in acacias? Is there any published analysis on acuminata?
 
nen888
#15 Posted : 12/31/2011 5:48:37 AM
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..it would also be good to get other varieties of A. acuminata tested..at the recent EGA conference 'J.J.' said that the mainly DMT varieties were the narrow leaf and small seed variants..i will collect all the data on this species together in the acacia thread soon..the only formally published [White 1957] result found tryptamine and phenethylamine in leaves (1.5% alkaloid), however White's method does not seem to differentiate between DMT and tryptamine (all species he found tryptamine in have turned out to contain DMT, i.e floribunda, longifolia)

..phenethylamine and N-methyl-phenethylamine have been found in a few Australian and US acacias [Fitzgerald 1964; White 1951,1957; Camp and Moore 1960]..there are a few reports of A. harpophylla (phenethylamine and hordenine) being 'psychocative' or stimulant, but with little detail..there are multiple anecdotal reports of some mainly DMT containing extracts of some acacias having particularly extended and mildly stimulant effects, noticeable up to 2 hours after the dmt-like effects have worn off, and i have pondered in the past whether these are phenethylamines..

..pure tryptamine was apparently described (by Sazra i think) as 'a very fast acting psychedelic' when injected in large amounts..i'm still searching for this reference..

..extracts of A. mucronata which looked and smelled very similar to the A. acuminata extract tested, and which contained a lot of ß-carboline, had a slowed down onset, and slightly extended duration and additional pleasant qualities..a bit like natures's 'changa'..
.
 
endlessness
#16 Posted : 1/7/2012 5:23:31 PM

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nen888
#17 Posted : 1/8/2012 7:05:22 AM
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..great work endlessness!
it will be interesting to see the obtusifolia leaf and bark results..the extracts appear a little different to the twig samples (dmt,2meTHBC) ..
..

a ß-carboline which has turned up in small amounts in a few acacias is leptaflorine - 2,3,4,9-Tetrahydro-1,2-dimethyl-1H-pyrido[3,4-b]indole
[Fitzgerald 1969; K. Trout citing Mulga 2000; suggested tentative trace in obtusifolia S.C. uni. 2000]
have attached the structure below...[EDIT: is actually leptocladine, see post after next..]
nen888 attached the following image(s):
leptoflorine structure.png (4kb) downloaded 4,577 time(s).
 
endlessness
#18 Posted : 1/8/2012 11:08:45 AM

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nen888 wrote:


a ß-carboline which has turned up in small amounts in a few acacias is leptaflorine - 2,3,4,9-Tetrahydro-1,2-dimethyl-1H-pyrido[3,4-b]indole
[Fitzgerald 1969; K. Trout citing Mulga 2000; suggested tentative trace in obtusifolia S.C. uni. 2000]
have attached the structure below...


Hmmmm, nen, very interesting, I think it might very well be there in obtusifolia in trace amounts (And maybe also the mistery substance in Mimosa analysis !). Ill get back to that in a second.

But first about the structure and name, I think you made a mistake there, since Leptaflorine is another name for THH, which would have a methoxy group on the 7 position, and would not have the methyl group on the 2 position where that nitrogen is...

The substance you've drawn has these 2 methyl groups in the position 1 and 2, while 2MTHBC only has it on the position 2, and MTHBC only on position 1.

Now let me show you something about the analysis.. Here's the TIC of Acacia obtusifolia, and then the mass spectrum of that substance (weak signal so not many "certain peaks" appearing), and then the mass spectrum of peak at same retention time but in jungle spice, which had higher concentration.



Now, if I use ChemDraw to draw this substance, it says it will have a molecular weight of 200.13, which agrees with the molecular peak 200 we've been seeing in this mistery substance's GC-MS. ChemDraw also suggests that the possible fragments from a MS collision would have the following masses: 186, 143, 129, 157, amongst others.. So it is a very good match! Im pretty positive this is what we've seen there

Now the question is, can this substance also be artifact from analysis, or did we just find another very common beta carboline that is appearing both in jungle spice as well as in acacia analysis?
 
nen888
#19 Posted : 1/9/2012 9:29:57 AM
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..yeah, got the name mixed up.. 2,3,4,9-Tetrahydro-1,2-dimethyl-1H-pyrido[3,4-b]indole is actually Leptocladine [or Nb-Methyltetrahydroharman]
http://www.lookchemical.com/1H-...yl-_9CI_/27297-47-8.html (i think! ß-carb names get confusing)
 
endlessness
#20 Posted : 1/10/2012 11:23:37 AM

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I've added obtusifolia bark and leaf extract pictures, as well as TLC results on edited post nr 16 further up. I've also edited first post to add the results. This way, the first post will always have the easy-to-check summed up results, and then there will be individual posts throughout the thread with the TLC pictures, GC-MS results full description, as well as the attached GC-MS raw files for those who want to double check my results and look at the files and mass spectra using AMDIS/NIST program which is linked here (pm me whoever is interested in looking at the files so I can help with explaining how program works and how to have a more extended database of standard reference samples spectra, than what comes with the demo program, to help identifying the peaks)

The GC-MS results of obtusifolia bark and leaf will come soon, maybe later this week or next week
 
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