entheogenic effects of NMT (monomethyl-tryptamine)

[nen888]

Also one kinda mysterious aspect about NMT is the fact it does NOT form oxides, but I think people have mentioned some color change happening with pure NMT too, IIRC? Something worthy of more investigation if so..

Iirc, it's been suggested that oxidation (or some other reaction) causes it to convert to some type of beta-carboline (2-mthbc?)...I would imagine similarly "superficially" as n-oxide oxidation for DMT. I can't for the life of me remember where I came across the hypothesis...(I think it may have come up earlier in the Acacia research?), but if I do, I'll post it.

..yes you're right SnozzleBerry..and bits and pieces of info can get hard to find in these threads..

i mentioned in my summary of 2011 lecture: (that summary has all the key info)

"In the case of NMT, oxidation and cyclization would give 1,2,3,4-tetrahydro-beta-carboline."

also back in post#34 i wrote:

"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."

..that info was from an advanced chemist of the old Lycaeum..

.. i don't know for certain what the observed colour change is, but these seem the most likely explanations..
as for whether it mimics the oxidation of DMT, it may lessen potency, but i've also theorised that it may extend the duration, being a possible betacarboline, not an oxide..as for 'HMT' i have no idea..

..thank you by the way endlessness for your comments and observations ..respect..

and ChimpZ, the effects reported for 90-100mg in the research presented in the thread were from carefully vaporised NMT..if your friend was smoking by some less concentrated method effects may not have been as strong..250mg is a lot..also the NMT was chromatographed to near purity in the test reports..but thank you for that report (and comments) ..it's great to get more NMT reports to expand what is still very limited knowledge (3 test subjects in the 2001 experiments, and 1 report by the late great Sasha Shulgin)

and, as also mentioned earler, like DMT, NMT plays some as yet unknown endogenous role..this alone makes it an important compound to understand..
.

 

[Chimp Z]

Their method was bong with herb on top. Probably got around half of that if it got torched.
So since b-carbs usually show up in pretty low amounts, the oxidization from tryptamine to b-carb is mainly the reason Acacia Confusa and A. Simplicifolia are active on their own?
Higher NMT might prove for better Acacia brews without maoi?
Might be why my Phalaris brews are sometimes active on their own.
What would 5-meo-nmt convert to?
If Phalaris is peaking in b-carbs and NMT and 5-meo-nmt then its potentially a fully active brew.

 

[nen888]

^..the amount of betacarboline generated through oxidation of NMT is i think unlikely to be enough to induce any oral activity..but there are no tests as yet to determine the amount of ß-carbs generated through NMT degradation..i would have to ask an advanced chemist what 5meoNMT converts to..
in the case of A. confusa bark brews i have theorised that it is flavonoids which may be responsible for oral activity, as these are present in reasonable amounts., but ß-carbolines are only trace in this species..
in the case of Phalaris, there are sometimes reasonable amounts of ß-carbolines which could render them active on their own, yes..

 

[downwardsfromzero]

i would have to ask an advanced chemist what 5meoNMT converts to..

6-methoxy-1,2,3,4-tetrahydrobetacarboline, presumably, although Shulgin mentions in TiHKAL:

This base is the botanically and pharmacologically famous 5-MeO-DMT, missing one of its two N-methyl groups. Sort of a nor-5-MeO-DMT. Its human exploration has just been started, but the expected vulnerability of it to metabolic oxidative deamination makes it a good guess that it (as seen with the dimethyl homologue) will only be active parenterally, or when the body's destructive enzymes are held at bay by effective monoamine oxidase inhibition. This base has been found in several Virola species but, as it is always accompanied by 5-MeO-DMT, its contribution to the psychoactivity of the resulting snuff is completely unknown. It has also been found in the skin of the Bufo alvarius at the trivial level of 20-23 micrograms per gram, compared to skin levels of 1.0 to 3.5 mg/g of 5-MeO-DMT.

but also adds:

A fascinating cyclisation product of this "nor-compound" is a cyclic dehydrogenation product where there is a direct coupling of the tryptamine nitrogen to the 4-position of the indole ring. This tricyclic material, O-methyl-nordehydrobufotenine, proved to be of comparable activity to DMT in rat studies, but has not apparently been studied in man.

in the paper edition.

And I've had a little poke around and found this here:

47. Gannon, W.F., Benigni, J.D., Suzuki, J. and Daly, J.W.: The synthesis of dehydrobufotenine. Tetrahedron Lett. 1531-1533, 1967.

and, more importantly,
74. Lee, F.G.H., Daly, J.W. and Manian, A.A.: The synthesis of 0-methyl-nordehydrobufotenine, a new psychoactive indole. J. Med. Chem. 12: 321-322, 1969. (emphasis added)

And a little pic of the molecule:

 

[downwardsfromzero]

i would have to ask an advanced chemist what 5meoNMT converts to..

Also this, here:

If you like those structures, check out that: http://www.ncbi.nlm.nih.gov/sites/en..._uids=11558603
Somei et al. found that serotonin derivatives undergo pictet spengler cyclization rather towards the indolic 4 position, forming sth. like dehydrobufotenine, but with an additional carbon between the sidechain nitrogen and the 4- position, than towards the 2- position, forming a carboline.
And all that cool structures are probably in our brains.

Sorry for straying a bit off-topic!

 

[pitubo]

^^^ fixed url for pubmed:
PubMed

pdf of actual article, freely available at j-stage:
The Chemistry of Indoles. CVII. A Novel Synthesis of 3, 4, 5, 6-Tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles and a New Finding on Pictet-Spengler Reaction

 

[downwardsfromzero]

Great paper, thanks pitubo!

It's given me some thoughts about what might happen when bufotenine is reacted with calcium hydroxide (in the open air as well). These are the conditions that favour the cyclisation at the indole 4-position - high(ish) pH, molecular oxygen available. Maybe better discussed in a bufotenine/5-MeO thread of some kind

 

[Mindlusion]

I want to report my experience so far with NMT.

the NMT was produced synthetically by reduction of the tryptamine formate

The NMT was vaporized in a Mr. bald T cup electronic vaporizer in the same dose and manner that would produce a DMT breakthrough.

45 mg NMT freebase

The dose was vaporized over the course of a minute, the effects first noticed were an apparent increase in heart rate and vasoconstriction in the extremities. Characteristic of these psychedelics.

However there were no remarkable visual or mental effects, baseline was returned in about 15 minutes.

---

Perhaps the dose is too low here, but ive been skeptical that NMT is able to produce DMT like effects. It seems far more likely to me NMT can prolong and potentiate the experience rather than produce the massive psychedelic effects of DMT on its own. Otherwise, you would think we would see a lot more N-alkylated psychedelics.

Also, I'm not sure what sort of NMT the previous reports used, natural or synthetic. At least using synthetic in this case provides the possibility of there being 0 traces of DMT.
I will try still higher dosages to try and produce such an effect.

 

[nen888]

..part of the reason for this thread was to try to get more experiments with NMT, so thanks Mindlusion..

to summarise and clarify a few main points in the thread:

- there were no 'DMT'-like effects of NMT as such, except for the physical sensations, and as described a 'tryptamine headspace', without obvious perceptual effects,except sense of space

- the effects were noticeable at 90-100mg and above vaporised, being not visual, and primarily physical in a way that was described as 'spatial', as well as an altered sense of cognition which suited meditative focus, though some have also described it as 'odd', and others as inwardly reflective

- above 100mg there were in a few cases rapid visuals which lasted for about 15-30 seconds, there is at least one other similar report of this (Shulgin)

- there definitely seemed to be a strong synergistic interaction between NMT and DMT which extended and modified DMT, particularly in physical and spatial ways..the hypothesised synergy between these tryptamines seems to create a very enhanced effect in acacias and other plants in which the two occur simultaneously, when enough NMT is present

- NMT on its own had an action that, while not psychedelic in the usual visual/auditory use of that term, was altering consciousness in ways that may prove useful

- the conclusion was NMT may have some therapeutic or consciousness studying applications

- the NMT was plant derived (Acacia) and separated from DMT and a beta-carboline by planar chromatography..as the beta-carboline (fluorescing) band in between the tryptamines it is unlikely that any DMT was present, the bands were clearly separated.. However, i have been open to the possibility that an NMT byproduct or beta carboline may have been present as the material darkened rapidly with exposure to air..hence my interest above in the thread in NMT breakdown products

thank you pitubo and downwardsfromzero for more on this very question..

NMT is apparently very rapidly metabolised, and this may vary in individuals.. the presence of a beta carboline or MAOI may alter it's level of perceivable effects..

being an endogenous tryptamine it definitely warrants more research, including on a purely medicinal level

 

[moyshekapoyre]

I thought I had smoked NMT/DMT changa many times since I've extracted red goo from acacia for my changa. I guess I was wrong? I've also eaten acacia with harmalas many times but never noticed that much difference from mimosa.

Recently, tho, I extracted the red goo with naphtha. I put that red stuff (with a little bit of DMT) in a DMSO vape cart. Predosed with THH and vaped a small amount (probably got less than 5mg in that low voltage puff but DMSO increases absorption). I guess this red stuff is not NMT, since the NMT was yellow and clearly has very little effects on me. For now I'm naming this red molecule the Metta molcule.

The feeling was... exquisite. Like the room became pink-toned and filled with the spirit of Love hypnotizing me. Not sure what MDMA feels like but I hear it's a love drug. This seemed like some type of ayahuasca MDMA or something. There was absolutely no similarity to DMT or ayahuasca except the hypnotic element at this dose. It had no similarity to ANY drug I've ever tried except maybe an opiate but psychedelicized.

I then took a larger hit (maybe 8mg, higher voltage). Now it was really intense and felt like ego death was about to hit me, but the red "Metta molecule" love spirit was there making it seem Ok, like as if to say "Hey don't worry, you can just drown in the river of love. It's fine." I was not really interested in having a whole ego death at that point so I politely asked the spirit to release me and if it needed anything from me. It doesn't talk in words but it seemed to be 'saying' "Ok, I'll let you go slowly. Please tell people about me. I can help them."

If I were a Christian this would certainly fit right into my religion with the God of Love. I find other psychedelics to be more impersonally transcendent, so this was quite a surprise.

Anyway, I feel that this substance's effect is truly optimal for anyone with drug addiction, PTSD, depression, anxiety, to heal. Assuming they get the effect I got from it. I even made a 15 minute long youtube video on the come-down. I have no desire to do this again because it was a 1hr long experience which almost completely incapacitated me and these days I'd rather just meditate.

 

[dragonrider]

..part of the reason for this thread was to try to get more experiments with NMT, so thanks Mindlusion..

to summarise and clarify a few main points in the thread:

- there were no 'DMT'-like effects of NMT as such, except for the physical sensations, and as described a 'tryptamine headspace', without obvious perceptual effects,except sense of space

- the effects were noticeable at 90-100mg and above vaporised, being not visual, and primarily physical in a way that was described as 'spatial', as well as an altered sense of cognition which suited meditative focus, though some have also described it as 'odd', and others as inwardly reflective

- above 100mg there were in a few cases rapid visuals which lasted for about 15-30 seconds, there is at least one other similar report of this (Shulgin)

- there definitely seemed to be a strong synergistic interaction between NMT and DMT which extended and modified DMT, particularly in physical and spatial ways..the hypothesised synergy between these tryptamines seems to create a very enhanced effect in acacias and other plants in which the two occur simultaneously, when enough NMT is present

- NMT on its own had an action that, while not psychedelic in the usual visual/auditory use of that term, was altering consciousness in ways that may prove useful

- the conclusion was NMT may have some therapeutic or consciousness studying applications

- the NMT was plant derived (Acacia) and separated from DMT and a beta-carboline by planar chromatography..as the beta-carboline (fluorescing) banday in between the tryptamines it is unlikely that any DMT was present, the bands were clearly separated.. However, i have been open to the possibility that an NMT byproduct or beta carboline may have been present as the material darkened rapidly with exposure to air..hence my interest above in the thread in NMT breakdown products

thank you pitubo and downwardsfromzero for more on this very question..

NMT is apparently very rapidly metabolised, and this may vary in individuals.. the presence of a beta carboline or MAOI may alter it's level of perceivable effects..

being an endogenous tryptamine it definitely warrants more research, including on a purely medicinal level

It is possible that NMT modulates receptors that DMT is active on. This could explain synergistic effects. And also why it doesn't seem to be too active on it's own.

The same is true for certain lysergamides and other ergot alkaloids. They can modulate the receptors that are being activated by other psychedelics, and thus amplify and alter the effects of them.

This is a kind of synergy that hasn't been looked into very much yet.

 

[moyshekapoyre]

To clarify, I have tried DMT + NMT. I have a few grams of that stuff here (well, lots more that I haven't dried up). To me it just feels like really weak DMT and after I use it, I may as well quit DMT for a day because it doesn't do much.

The red molecule that is unidentified from Acacia confusa, however, is something completely different. Very hypnotic and very healing for the heart chakra. Easy to go into ego death if using a bit too much of it also.

 

[endlessness]

To clarify, I have tried DMT + NMT. I have a few grams of that stuff here (well, lots more that I haven't dried up). To me it just feels like really weak DMT and after I use it, I may as well quit DMT for a day because it doesn't do much.

The red molecule that is unidentified from Acacia confusa, however, is something completely different. Very hypnotic and very healing for the heart chakra. Easy to go into ego death if using a bit too much of it also.

According to the tests done so far, including my own, there is no "unidentified" molecule from Acacia confusa. It is DMT + NMT in varying ratios.

When you say you have tried DMT+NMT, how was it extracted, from what plant? How did you identify those two molecules, was any analytical test done? What ratios were found?

And when you talk about the Acacia "red molecule" (I suppose you mean red extract), how was the extract done?

 

[dragonrider]

To clarify, I have tried DMT + NMT. I have a few grams of that stuff here (well, lots more that I haven't dried up). To me it just feels like really weak DMT and after I use it, I may as well quit DMT for a day because it doesn't do much.

The red molecule that is unidentified from Acacia confusa, however, is something completely different. Very hypnotic and very healing for the heart chakra. Easy to go into ego death if using a bit too much of it also.

According to the tests done so far, including my own, there is no "unidentified" molecule from Acacia confusa. It is DMT + NMT in varying ratios.

When you say you have tried DMT+NMT, how was it extracted, from what plant? How did you identify those two molecules, was any analytical test done? What ratios were found?

And when you talk about the Acacia "red molecule" (I suppose you mean red extract), how was the extract done?

Theoretically, a different confusa strain could ofcourse contain something that wasn't present in the samples you've tested.

However, it is probably more likely that we're just talking about a mixture with a different DMT/NMT ratio.

In wich case we could say that NMT indeed has the capacity to alter the DMT experience significantly.

If it can do this to DMT, it can probably do this to other classic hallucinogens as well, as they affect more or less the same receptors.

 

[Jagube]

There is something about ACRB that shares qualities with THH. It makes me satisfied in a similar way to how THH does, and sometimes I can't distinguish that aspect of ACRB from THH.

 

[endlessness]

There is something about ACRB that shares qualities with THH. It makes me satisfied in a similar way to how THH does, and sometimes I can't distinguish that aspect of ACRB from THH.

Interesting...

Smoked vs smoked THH? Oral vs oral? Or smoked vs oral?

Are you talking about THH by itself or mixed with other harmalas?

Can you describe a bit more what you mean with the qualities they share?

 

[Jagube]

Smoked vs smoked THH? Oral vs oral? Or smoked vs oral?

Are you talking about THH by itself or mixed with other harmalas?

Can you describe a bit more what you mean with the qualities they share?

* oral harmine, a generous amount of THH and crude DMT-containing tea (other than ACRB)
vs
* oral harmine, little to no THH and crude ACRB tea

It's a pleasant, warm feeling that makes me feel content and leave any worries behind.
Also, both leave me with similar, long-lasting afterglows.

 

[nen888]

..re a bit of the discussion above regarding effects and 'red molecules' etc:

nen888 wrote:

i have been open to the possibility that an NMT byproduct or beta carboline may have been present as the material darkened rapidly with exposure to air..hence my interest above in the thread in NMT breakdown products

..this beta carboline may be more potent than realized..

and also, somewhere here, years back, regarding NMT/DMT psychoactive interaction/modulation, nen888 wrote:

it's about a certain ratio

whatever NMT does, and this may vary in individuals, it isn't 'nothing'