Does this help? GC/MS data for Pinoline (6-methoxy-1,2,3,4-tetrahydro-B-carboline).
Or do you guys need the whole paper?

Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland

http://www.sciencedirect...cle/pii/0006295281902781


The Poupat et al. (1976) Phytochemistry 15: 2019-2020. paper wasn't somehow available to me.

Thanks a lot, it does help! The pinoline spectra above does not seem to match any of the spectra in the Acacia mucronta (notice it's main peaks are 173 and 158, which are not in the mucronata substances) so it seems it's neither of those important peaks.

Glad I could help. I'll try to get the Poupat paper tomorrow. The library system was fragile as %§%&"( and so were my nerves

edit: sorry, couldn't access the paper...

..cool info guys..i don't have the Poupat et al. A. simplex (simplicifolia paper) unfortunately..

..i recall from seeing the paper once that Poupat et al. 1976 were not sure if the N-formyltryptamine was a process artifact or in the plant..it is a very unknown tryptamine..

also, i think the reason Trout's chart had harmine, when it hadn't been confirmed in an acacia at the time, is because the chart's of indoles found in acacias 'and related species'..though what 'related' sp has harmine i don't know..maybe a speculative chart..
one 'Mesquite' (Prosopis sp., also Fabaceae like acacia) contained N-acetyl-tryptamine as well as some uniquely named alkaloids which could always occur in other species [see https://www.dmt-nexus.me/forum/d...m=307216&#post307216]

..one last question, endlessness, any idea why the presumed tryptamine is above the NMT and below the DMT on the TLC plate? i thought having a lower molecular weight than NMT would place it before the NMT..? ..also the DMT peak looks quite broad, like there is NMT co-chromatographing...

Hey Nen, thanks for the words! The bill will come later
J/K of course, I'm very glad to be able to help bringing this cutting edge information, I'm sure if any of you were in my position to do these tests legally you would do the same! And of course, without you and the plant samples and amazing acacia info, this thread wouldnt exist

Regarding possible formyltryptamine peak, I remembered where I had seen the same peak, I saw it in mimosa. It's the T-1 in this concentrated non-dmt alkaloids from mimosa, resulting from a wash of limonene after having separated all the DMT from FASI: https://www.dmt-nexus.me...osts&t=27724&p=3

NIST doesn't have formyltryptamine in the database, can't find it's mass spectra, the closest guess it gives is n-acetyl-tryptamine. So these are the two main possibilities for substance D in mucronata and T-1 in mimosa post-FASI wash.

Regarding it being a possible process artifact, I don't have enough knowledge to agree or disagree.

Lastly, regarding the TLC plate, it's not related to molecular weight but to polarity. The most polar molecules stay below (due to being more attracted to the silica), the less polar molecules go further up.

..50mg which remained of the A. mucronata extract tested was reported bioassayed again recently by vapor..see https://www.dmt-nexus.me/forum/d...m=354868&#post354868
.

Thanks for the link nen! Interesting

So I just added to the first post all the mass spectra, plus information on harvest/extraction/yield. This way its much more organized and easy to read the information

I also added the images for Acacia confusa stem and Acacia confusa rootbark (with some new identified phenolic compounds), and for Acacia obtusifolia x maidenii analysis, which were missing. Notice the confusa NMT/DMT ratio is NOT accurate, its just a very crude approximation, because the peaks overlap so it's impossible to know for sure what area each of these tryptamines would occupy if they were separated.

nen, if you dont mind, can you give more details on harvest/yields of Acacia obtusifolia 2 (maybe you did and I missed it! ) , as well as yield of obtusifolia x maidenii ? Thanks!

..maidenii x obtusifolia (could be that way round ) see this post, obtusifolia#2 was phyllode, method as per leaf sample1, but with salty NaOH+H20 wash..again c.0.3-0.4%...
.
Edit. ps. i notice the Acacia confusa A/B extract didn't seem to have much or any NMT, whereas the methanol soak does..could this be because of certain solvents more selectively pulling DMT instead of NMT ?
with this in mind, a methanol soak of a couple of the other acacias in future could be interesting..
.

Nen, what confusa A/B extract did not have much or any NMT?

And yes it could very well be possible that some solvents pull less NMT.

Methanol is pretty generic, should get all alkaloid salts and other substances present in plant material without degradation like A/B extract would with some of the more unstable alkaloids. But then it's obviously gonna be crude and with other inactive plant material, not a crystalline extract.

..in the post#3 TLC photo labeled 'confusa extract'..or is this still a methanol soak?
am i a-confusa about the confusa..
i have noticed extractions by DoingKermit and others don't seem to be yielding much NMT, only a small amount of yellow oil/goo (the presumed nmt) (see A. Confusa thread post#1 for extraction links)
.from a small number of experiments a while back, NMT didn't have as good a solubility in napatha vs dcm or methanol..

ps. sorry, the answer to obtusifolia x maidenii yield is 2 posts on from the last link i gave you..

Ah, that TLC run of the extract isnt reliable, it's too weak to see.. It was just a really quick and sloppy limonene pull and salt I did after basing a small test amount of acacia, but it's so diluted. I could not say if there was or not NMT in the plate. Maybe in the future a proper extract could be tested

..thanks, that kind of suggests that there is probably a little NMT in the obtusifolia based on the TLC (if we can see a spot)..? be great when you get the LC-MS access..

Ive just updated the first post to include mucronata #1. Also, for those who had already looked at this thread, please reload the first page because mucronata #2 image has been updated with a couple of new identifications. Substance "B" is a probable impurity from one of the solvents used, it's identified as butylated hydroxytoluene, which wikipedia says its an anti-oxidant added to some food and to oils/fuels too, and there's some discussion regarding it's safety.

There's also substance D, which is N-Formyl-NMT, which matches the spectra in poupat et al 1976 which im attaching. Psychoactivity, toxicity, etc is unknown... It was also found in Acacia simplicifolia as the paper says.

Lastly regarding the new analysis, in mucronata 1 there are some very small amounts of tryptophol, which InMotion mentioned is a plant hormone and makes humans go to sleep Maybe it's there in mucronata 2 also but it's diluted sample (too much noise) so its hard to see. I'll see if I can repeat the tests with more concentrated m2.

Nen, confirm to me please if m1 was twigs and m2 is phyllode, or if they are both a mix but from different trees, or what. Also if both yields were the same (0.3-0.4%) or different?

And going back to Acacia confusa, the catechol etc phenolic substances, could very well, after researching a bit and talking to InMotion, be breakdown products of Lignin, naturally present in wood. Notice lignin structure with many catechol-syringol-etc kind of structures built in to it

..that's great you found the paper endlessness and thanks for the latest info.,
..the solvent and process was identical to the other samples (dcm)
..if butane or tolulene had been used i could expect this, but dcm..? are you 100% certain of the identity of this substance B..?
..interesting about the tryptophol..m1 is twigs, yield was about the same..

Nen, im not 100% sure because we dont have a standard for this substance, but mass spectra matches very well, as you can see in attached image of a BHT standard spectra (NIST gives 88% chance of matching).

Ive been searching around and saw that it's also a natural compound, it's been found in potato tubers infected with some kind of fungus: http://onlinelibrary.wil...65-3059.2001.00594.x/pdf

No idea the significance of this, and the relevance regarding smoking it.

I looked at the minor peaks in other acacias that you used the same solvent and I did not seem to find it, so maybe it was naturally present in Acacia, or some fungus was infecting that mucronata (or you used a different solvent batch this time?).

^..i also pondered that the 'lichen-acid' from A. confusa may have indeed come from a lichen growing on the plant..
and to date i can only find known biological sources 3-methyl-quinoline..

Thanks for all the great data endlessness. Few people have the access to equipment and the knowledge to analyze the alkaloids from these acacia species so thanks for taking the time and filling in a lot of blanks.

Very interesting idea, I always wondered what might be extracted from the various organisms growing on the bark.

It would be very interesting to compare a whole bark and a bark cleaned of the outer layer to see if it is in fact something on the outside. Seems possible for untold goodies to be found on raw barks as they are a host to many

The following is purely subjective, the people involved had minimal formal chemisty experience but had done over 20 successful extractions on A. Obtusifolia

From experience(someone else's experience) A. Maidenii has not produced any alkaloids whatsoever doing an A/B and pulling with naptha, samples were obtained from locations several hundred KM apart, all with the same result.
Interestingly, extractions performed at the same time, using the same technique, on A. Obtusifolia yielded higher than the described percentage of alkaloids, up to 0.9% dry weight. Extractions were almost exclusively from the largest trees available. Bark samples were mainly harvested up to about head height.

Ingestion of the alkaloids via inhalation led ??? to believe that it had a significant percentage of 5-meo-DMT present. Unfortunately he had no way of testing the alkaloid concentration at the time so it was impossible to be sure of this.

I'm also unsure of the reason behind the discrepancies, however the results were repeated several times in somewhat controlled environments. All equipment was thoroughly cleaned between each extraction.


Just thought I'd share this.

EDIT: I just realised how bad this sounds. I'd like to add that everyone involved in this project also happened to be native wildlife carers and had a good understanding of the impact of harvesting a living tree. Trees were never ringbarked, and the bare minimum was harvested in order to ensure sustainability. The area's harvested from were generally populated densely enough that it was never considered an option to harvest enough bark to cause lasting damage to the trees.

^^..interesting and thanks, elf..i guess in the old days there wasn't a lot of knowledge about sustainable harvesting, and as you say, small amounts can be taken..but i'd just like to share again with you and all, that
repeated tests by myself and others of A. obtusifolia and A. acuminata show equal percentage in twig bark vs. trunk bark, occasionally slightly higher (this does not include the rarer subtropical obtusifolia tested by Mulga)
..i was quite ecstatic when discovering this, for the sustainability option it introduces to the equation..

the elf wrote: ..very interesting..certainly a sample was sent to Germany in the mid-late 90s of A. obtusifolia and 5meo was detected along with DMT and trace bufotenine..it was sent as bioassay subjects found it overwhelmingly strong and intense at normal dmt dose ranges..this, and the ocurrance of up to five additional alkaloids (see this thread) are partly why i have Not been emphasising A. obtusifolia as a species of first recommendation..that, combined with it's near decimation in certain wild areas by ignorant and/or callous bark strippers..[see photo here in acacia info thread]

..there also seems to be a lot more seasonal variation of alkaloids in obtusifolia than, say, A. acuminata (variety dependent)..although other species are even more variable..

lastly, while i'm not questioning your ID skills elf (and agree there are zero vs yielding forms of maidenii), many have mistaken nsw forms of A. melanoxylon for A. maidenii..see here and that page in general..

good to hear from you elf...