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entheogenic effects of NMT (monomethyl-tryptamine)

Migrated topic.
..i dug up a few keynotes, so i can give a report of another subject in the 2001 NMT experiment (wanted exact wording, plus their permission)

with 60-70mg vaped :

0-2min "I feel trippy but not a lot's happening..very low level, not very active at this dosage.."
2-3min "I'm feeling a wave of something coming on slowly but getting faster, but there's nothing to see visually.."
3min "I've got closed eye visuals..like something descending into me..big entity like..
4min "The visions went away pretty quickly, but i feel really good.. quite high..can you put on some music?" (Music put on)
5-20min "I've sort of got really occasional mild geometrics that change a bit with the music..the music seems more amazing than usual, but it's not warped out or anything.."
20-50min "I've got a building feeling of being more out of it now, somehow..getting rainbows and flashes off the candle & CD player lights ..this is actually a really nice space, now i'm not expecting any kind of dissolvment..good for music and headspace.."
50-70min "It's diminishing but i feel really great, really clear..i feel like going on a walk outside for the last of this.." (Subject leaves test space, returns 25 min later feeling "refreshed".."would try it again, for sure.." )
...................................................................................................................................................................................................................................
..and for the chemists/alchemists..

N-Methyltryptamine was soluble in methanol, warm ethanol, dichloromethane & choloroform. It was soluble to an extent in napatha but not nearly as much as
dimethyltrptamine. It seemed only partially solube in warm acetic acid. It is likely soluble in xylene. It is more polar than it's dimethylated relative...

..i will go into the simplifed paper/column chromatography method that was used to isolate it in the future (the working out of the proceedure was not so simple:)..

..the other month, however, i observed an experiment in which 100g of material known to contain dmt/nmt was extracted with ethanol/methanol/acetic acid>NaOH>dichloromethane..the solvent/alkaloid mix, when almost evaporated was placed unsealed in a freezer (to allow H20 condensation in order to 'skew' the re-x according to polarity)..upon removal the mixture had partitioned into white circular dmt crystals & a clear oil plus H20 condensation on top..the mixture warmed to room temperature turned back into a homogenous clear liquid..left to stand it crystalized as circular white dmt crystals with yellow cemicircular nmt crystals interlinked on top..

..plants with reasonable amounts of NMT include Desmanthus Illinoensis, Acacia confusa (variable), Acacia jurema & Acacia maidenii (there are quite a few more)...
 
..a better description of the crystals..dmt circular white needles, nmt curved-diamond shaped accumulation of yellow crystals, on top of and interlocking the dmt..

ps. i mean dilute acetic acid when refering to acetic acid...
 
..update..the 'crystalized' material, upon being scraped from the dish became a
yellow>orange soft 'putty'..that's the nmt refusing to stay solid..however i suspect that the nmt as an oil is actually 95-98%nmt+something else (maybe betacarboline or 5meo-nmt or a plant oil)..re-purification of this putty/wax should result in a solid re-x of nmt/dmt, but may take away some of the extra 'character'..the crystalized nmt in the 2001 experiment went through two stages of purification/re-x, resulting in white 'swirly circular' needles that turned yellow upon standing..
(NB. because only small amounts are being extracted at a time, large crystals cannot be grown...)...
 
(..thanks Snoozleberry, nice to get some feedback..):)



..OK, so here's how NMT was separated from the other alkaloids in A. obtusifolia in the 2000-2001 experiment..
(i was hoping some chemist would suggest an alternate or tech method, but this hasn't happened yet..)

this is partly from memory as i don't have the lab notes around..
..lab column chromatography with chloroform (due to limited time) was not producing clear enough results, so a few weeks of trial and error experimentation (quite a few attempts) were done to arrive at the clearest separation which was achieved as follows:

Using Simplified Paper/Column Chromatography,

the alkaloid mix (determined by GCMS to be approx. 2/3 NMT, 1/3 DMT &
2% betacarboline, was dissolved in a mixture of 90%dichloromethane, 10%aqueous methanol (9:1)..

in 50-100ml portions the solvent was placed in a flat glass evaporating dish..

into the dish was placed (at a 40 degree angle) a 10x15cm sheet of thin blotting
paper clamped between two sheets of glass..

the solvent over several days 'wicked' up the paper, upon evaporation leaving behind visible bands of alkaloid according to molecular weight..

..seen were a pale orange band (NMT)(from memory,a couple cm), a narrow clear band (approx. 1mm) which became visible under UV (betacarboline), & a very pale yellow band (DMT)(approx. 1/3 the width of the orange band)..
..the bands were distinct & had less than 0.5mm crossover..

..the centre 2/3 of the NMT bands on the paper were cut with scissors (the edges discarded in case of crossover)..the paper was placed in methanol into which the
alkaloid became soluble..

(a few attempts around this point saw the presumed NMT remain only in oil form, but i'll skip this..)

..the NMT/methanol was mixed with 90% salted basic water (NaOH), and extracted with dichloromethane..
..upon drying the material was dissolved again into methanol, mixed with 10%warm ethanol, 80% warm dilute acetic acid, & cleaned with hexane..
..after removing the hexane, the solution was brought to around ph 10-11 in basic H2O, extracted with dichloromethane and left to stand..

..upon drying, white 'circularesque' formations of NMT crystal were seen, which darkened with exposure to air..
..they were, after a while, yellow, turning dark orange, translucent & solid...

(i hope this information helps anyone working with an NMT containing plant...)
 
Awesome work, man! I have been curious about how NMT affects the outcome of an extraction with Acacia's and when i did my small scale extraction on Acacia Confusa, according to your description, there seemed to have been very little to no NMT in the mix.

I had small white snow globes, which didn't melt or turn to goo. I wonder if the bark I have has a higher content of DMT compared to NMT, similar to Mimosa. I NEED to get a bigger Acacia C. extraction on the go, but i have so much Mimosa bark to play with... so I haven't had enough time or materials for both.

I also need to try out the small amount extracted already. Just need to finish my dissertation and all sorts of experimenting will be had :lol:
 
..just to summarize some of the info. to date..

NMT (mono-methyltryptamine or N-Methyltryptamine) is, like DMT a naturally occuring component of human blood/cerebrospinal fluid (a neurotransmitter or hormone)..it is excreted in the urine of both healthy and schizophrenic people..
Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. (link)
therefore, as is said of DMT, it plays an as yet unknown role in ordinary and essential perceptual, cognitive and conscious function.

..while previously described as 'inactive' without reference, in elevated levels it displays psycho-perceptual activity at around 1/3>1/4 the potency of dimethyltrptamine, effects becoming noticeable at around 60-70mg, by vaporization; 90-150mg-estimated orally in conjunction with MAOIs..
No serious toxicity has been found in published animal bio-assays, nor was noted in human bio-assays..

..a handful of higher dose bio-assays were conducted in 2001, leading to more noticeable effects
- 120mg vaped - "..not necessarily of a visual kind, but often 'spatial' in nature and consciousness related.", which will be expanded upon in a future paper/article ["NMT - a Spatial Entheogen" by Nen, or something similar] somewhere..

..it's relative 5methoxy-NMT, has been found in several Virola and Yopo type snuffs/plants, and should be presumed active (activity on 5HT-2 & related receptors demonstrated)..like 5methoxy-Dimethyltryptamine, however, dosage caution would be recommended in it's isolated bio-assay.. (1 report of 1mg intravenously led to 'hair-tingling' and 'very odd burning sensation on sclap' [bluelight.com] - this is the only human bio-assay of 5meoNMT i have heard of, but is questionable in some regards)

..plant NMT has so far not demonstrated any unpleasant side-effects or experiences..
more research needs to be done..

..the possible synergystic interaction between NMT and DMT has not been adequately theoretically explored...

ps. if any writing researchers use some of this info. could they cite it Nen (2001)? thanks
 
..thanks for the input on A. confusa, DoingKermit, from what i've read the NMT may be mainly in the twig bark or phyllodes..looking forward to hearing more results from this plant..

..an afterthought on NMT..
the reason the whole 2001 experiment was conducted was because A. obtusifolia extracts were not behaving excactly as if an inactive extra alkaloid was present,
what really surprises me (& is partly why i've put this info. out) is that, as far as i can tell, this kind of research on NMT has not previously been done..
..why..how..?
 
..i hope my 'cite' comment didn't sound egotistical (information is everyone's), just think it's good to be able to track info down (writers should cite the nexus too):)

..quite surprisingly a bioassay took place recently (by someone else) of what was believed to be at least 90%NMT..

..it came from material once extracted from a known dmt source and said to 'not work'..it was extracted again with ethanol/acetic acid/NaOH/napatha and left behind orange crystal patterns that reverted to an oil/goo..it was said to smell very similar to dmt but a little different

approx. 30mg was vaporized
the subject reported that upon inhalation they could not remember breathing out..
but a few seconds later 'there were no visuals of any kind', instead they were immediately taken to a state they recognized as their usual 'deep meditation space'..
"..there were no visuals, just thoughts."..enhanced hearing & calm clarity..from 30-60 minutes music was particuarly enhanced..

..so, if people in the past had tried say 10-30mg of NMT they may have found it 'inactive'..at 30-40mg it was very mildly active..

..also, the 60-70mg & 120mg NMT (noticeably more active & profound) bioassays described earlier in the thread, may have involved some oxidation (as the material becomes increasingly dark orange over time)
..

...
 
nen888 said:
..i hope my 'cite' comment didn't sound egotistical (information is everyone's), just think it's good to be able to track info down (writers should cite the nexus too):)
Click to expand...
Doesn't sound egotistical at all, I agree completely.

But on that note, is there more complete bibliography info to go with the citation? Was this published in 2001? Or should it just be cited as "Unpublished notes" or "Unpublished manuscript"?
 
the section on NMT in Some Simple Tryptamines might be of interest for those who are looking into the activity of the alkaloid.
In the activity section it notes that Shulgin received a report that 50-100mg caused visuals lasting "maybe 15 seconds"

The occurrence section gives data for several acacias known to contain it
A. confusa
1.43% in root bark
0.04% in dried stem

A. maidenii
0.24% in bark

A. simplicifolia
1.44% in bark
0.29% in twigs

interestingly in one Psychotria viridis specimen NMT was the dominant alkaloid and DMT was absent.

also interesting is the note that NMT does not form N-oxides with peroxide. this is cited to the same author (Fish et all 1955) who notes that DMT readily forms an N oxide when exposed to air during "experimental manipulations'
 
..hey there Entropymancer:) , until i can 'formally' publish, hopefully this year, i meant the date (2001)to indicate when the experiment was done..i exist and can be tracked down on the nexus..this thread is a reference..

thanks for the info. AlbertKLloyd:p , really interesting about the psychotria..

..another thought..when i refer earlier to the possible synergy between NMT and DMT, i give a possible example this..acacia extracts which should contain 10mgDMT and 20mgNMT show more activity than would seem explained by the potencies of each compound in isolation..

i have a couple of theories, still thinking about it...
 
this is really facinating you know from my perspective. I am completely obcessed in every way possible with endogenous neurotransmitters and neurohormones like DMT, melatonin, 5meo, pinoline, 10-meo-harmaline, bufotenine etc..the roles they play in human metabolism and what lifestyle I can live in order to increase them..NMT is something I have just decided to look into as well..there is SO much stuff here that is still not concidered by even the leading researchers I feel. The whole pinoline-5meoDMT-DMT thing is just way way too oversimplified I feel.

NMT is something I need to experiment with and it is cool people here are doing it already.
 
..look forward to hearing what you discover, fractal..:)

ps. re Oxide of NMT, i have just been informed "NMT-N-oxide does not exist. N-Oxides can only be formed from tertiary amines, and NMT is a secondary amine. There may be N-hydroxy-N-methyltryptamine (HMT?), but that is not an N-oxide." (Lycaeum recent)

i'm a psychological researcher, not a chemist,so i'm none the wiser as to the darkening color of the NMT sample...
 
Some Simple Tryptamines has that info...
but it is a bit involved
reddish purple
and was blue gray
depending on some variables
it is hard to distinguish from DMT with erlichs
 
Thanks!

Do you have that book? Would you mind copy-pasting or writting some of the NMT info ? Depending on what variables?

Was there any other test that could differentiate it from dmt? Did it react with marquis or mercke or mandelin or something?
 
i'll try and include some more information that might be of use.

All of the following comes from SST2 Some Simple Tryptamines by KTrout, second edition,
in the Trouts Notes series this is #FS-X7

I'll also note that, while reproduction and distribution are prohibited for this work, the work expressly states:
Trouts Notes strongly encourages the dissemination of any and all factual information contained within these pages so long as proper acknowledgment of the authorships and original sources of data origin are maintained. No one owns facts or factual data.

the Shulgin and Shulgin ref, 1997 pages 573-574, entry #50
is used to cite the following:
vacuume distilled at 135-145*
yielding a while oil that formed crystals that darkened on exposure to air

Manske 1931 (still amazing after all these years!!!)
is used to cite:
Assays for NMT
Heating the base in chloroform with a slight excess of phenylisocyanate, evaporating to a small volume and then adding ether will cause the formation of large elongated hexagonal plates of the phenylcarbamyl derivative of NMT, they melt sharply at 153* when recrystallized from menthol-ether and give an immediate red color with an orange cast with Erlich's reagent.


Now I assume that the easiest way to separate this out would be paper chromotography and recovery of bands

As for the form of the freebase when crystalized:
Manske 1931 reports mp90* stellar aggregates of needles with some individual crystals having a rectangular form

Fitzgerald & Sioumis 1965
mp 86-87* white prisms from light petroleum

I wonder, if you closed the ring via some PS type reaction, what is the betacarboline product?
Could the betacarboline oxidize? Harmine sure can... this would result in a color change as well. Could small amounts of the alkaloid be cycled into carbolines that oxidize resulting in the color change reaction? On this same note what is the betacarboline product of ring closure of DMT? Can it oxidize? lol this is the Pictet–Spengler reaction BTW, an easy test for this kind of thing would be to see if as a product gets darker, if it begins to glow under UV, DMT does not glow in a visible spectrum, despite being very fluorescent.
in plants where some betacarbolines co occur with NMT and DMT, doesn't it make sense that the tryptamines are precursors to the betacarbolines? How would GCMS of the betacarboline product of one of these alkaloids like DMT be different than the parent alkaloid? Did anyone read the ER article stating that 2meTHBC can be easily confused with DMT in some tests?


Sorry about the tangent, but it does relate to manipulations of NMT and potential artifacts.

As for constrasting it with DMT,
Chloranil
en.wikipedia.org

Chloranil - Wikipedia

en.wikipedia.org en.wikipedia.org
NMT is listed as gray (light)-Gray, on silica gel
DMT is listed as not having a color reaction for the same test on the same medium
ref:
Heacock & Forrest 1973 Journal of Chromatography

TNB reagent on silica gel
for NMT goes Yellow--->light yellow
for DMT goes Yellow--->brown
same ref as previous entry

for TACOT reagent on silica gel
NMT goes Orange pink--->Pink
DMT goes Purple (light)
same ref as previous two entries
Also note that the method of preparation of TNB and TACOT is mentioned in the Heacock & Forrest paper.


I am just about done because I really do not want to type out the various RF data in this book though but DMT and NMT do have different RF values, however the RF values of their 5Meo forms, 5Meo-NMT and 5Meo-DMT are incredibly similar to their parent forms.

In addition to the Acacias i mentioned previously, Desmanthus species are also decent sources of this alkaloid.
 
..yeah, you're good with info. AlbertKLloyd, thank you..
that the RFs of 5meoNMT/DMT are very close to the parent forms is very interesting..

endlessness, i will get some new reagent results to you asap..
in 2000-1 a chemist friend did the reagent tests, which i observed..he was using Dragendorfs, Mayers and a silica-tunguskic acid system (will see him soon to clarify this)
..in the latter two (from memory) DMT was orange>pink, NMT pale brown>orange, but they were quite close..multi-trptamine mixtures were pale brown>grey..

there are some things going on with DMT/NMT/betacarboline plants that cannot be explained by the presence of 2%betacarboline (unless the b.c. is super potent in some unanticipated way)..this is what led to the 2001 NMT experiment..

..this trinity of compounds occurs frequently and fluctuates in some plants recorded to mainly contain DMT...
 
.."stellar aggregates" (Manske 1931) is the perfect description, which i lacked, for the NMT crystal shape.. i said 'curved diamonds'..large rectangular prisms can sometimes be seen..
..NMT seemed to take much longer than DMT to solidify..
..when mixed with DMT, the two can crystalize together but their respective shapes are skewed or intermingled
..the less NMT, the more easily a mixture will crystalize..mixtures taking a long time to crystalize can be disturbed or scratched with a pin to speed up the process..
 
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