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entheogenic effects of NMT (monomethyl-tryptamine) Options
 
endlessness
#41 Posted : 9/21/2011 1:19:45 PM

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I just added this NMT entry to our psychedelic compounds WIKI

Still gotta add some more information there, as well as the molecular structure but for some reason I cant upload image files to the WIKI.

Thanks Nen for all the info (and feel free to edit the wiki if you want, just gotta register an account)


Also im attaching to this post the publication mentioned before:

Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS.
 

Trippy glass for trippy people.
 
polytrip
#42 Posted : 9/21/2011 5:26:54 PM
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Isn't beaocystin the NMT based-analogue of psilocin? Just like with NMT, the psycho-activity of beaocystin and norbeaocystin are still being debated.

I've experimented some with acacia confusa and find that it's psychedelic effects are slightly different than those of mimosa or psychotria. Where i, if i would have to compare DMT-plants with shrooms, would compare mimosa and even psychotria more with the very 'clean' psilocybe cyanescens, i would compare acacia more with p.azurescens that is slightly more physical and aural in nature and visually less colourfull but more geometric.

I believe that misletoe also contains NMT btw.
 
nen888
#43 Posted : 9/22/2011 3:37:35 AM
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..thanks endlessness,i hope some more people get their hands on NMT to get a proper survey of the effects..

polytrip,interesting observations..i don't know if the extra content of M. hostilis has been chemically determined, but A. confusa has confirmed NMT..

some mistletoes also contain alpha-ethyl-tryptamine (possibly active) i believe...
 
wira
#44 Posted : 9/22/2011 4:45:18 PM

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I haven't heard about NMT being found in any mistletoes, I don't think... any further info on that?
Regarding Mimosa hostilis (tenuiflora), stem bark has seen more published analysis, and besides DMT, tryptamine and serotonin, the only other alkaloid of note is the (relatively) recently discovered yuremamine, which is suspected of being psychoactive and an MAOI. It's likely this will be found in root bark, though I'm not sure if it's identical with the mystery alkaloid (DMT-conjugate?) that J. Ott has been talking about for years.
With Acacia confusa, trunk bark has yielded (besides DMT and NMT) an unidentified tryptamine alkaloid. A more recent paper analysed unspecified parts and obtained low yields of DMT, DMT N-oxide, NMT, and N-chloromethyl-DMT (a new alkaloid which is likely an artefact of the extraction). [Buchanan et al. 2007. "NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa." Magnetic Resonance in Chemistry 45:359-361]
 
jamie
#45 Posted : 9/22/2011 5:27:24 PM

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Ive read about it present in mistletoe as well./

NM it was alpha-ethyl-tryptamine I was thinking of that is present in mistletoe.
 
nen888
#46 Posted : 9/28/2011 1:52:54 AM
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..it should be noted that at certain times, or in individual plants of Acacia obtusifolia & A. floribunda (probably), the major alkaloid content is NMT, on occasion over 90%
..this can explain extracts that only 'semi-work' at normal dosages, though such extracts could contain simple Tryptamine or occasionally extraction artefacts & impurities..
examples of P. virdis & D. illinoensis with mainly NMT have also been found.

..pure NMT in most observations to date darkens fairly rapidly with exposure to air,
Manske and more recent observations showed distinct crystal structures (see earlier)
...

ps. fractal enhancement, i have seen a finding of alpha-ethyl-tryptamine in mistletoes, but can't remember what the paper/book was..it would be interesting to know what the alkaloids of the host tree are...
 
endlessness
#47 Posted : 9/29/2011 4:14:50 PM

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AlbertKLloyd wrote:
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?



Ill try to find the answer to the first question out. What article are you talking about, can you give the year/edition ?
 
nen888
#48 Posted : 10/3/2011 4:19:27 AM
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..i remember an ER article in which an ayahuasca admixture plant (possibly a Calliandra) was several times found by GCMS to contain DMT, but HPLC found the same compound to be 2meTHBC..but i don't have the issue/date..AlbertKLloyd?
................................................................................................................................................................

..a bit more info. on re-agents & the NMT 2001 tests:

the most successful reagent for DMT/NMT and related alkaloids was Silicotungustic Acid Reagent
[see:http://www.sciencelab.com/page/S/PVAR/10426/SLS1552 for constituents/availability]
(with a little chemical knowledge one can prepare one's own solution much more cheaply)

'M'(2002) subjected a number of acacias to reagent testing, following Roveli(1967)'s recommendation for alkaloid field testing..
2-4 grams of fresh plant material was ground in a mortar and pestle with sand..this was mixed with DCM (or hexane), the sand and goo filtered,
and the solution (approx. 10-20ml) put in a test tube..
..to each test tube, the reagent was added (parallel tests were also done with Mayer's reagent, but the results were slightly less clear)..solutions with large amounts of alkaloid would become thickly cloudy, whereas trace amounts would result in very mildly cloudy but still mainly clear solutions.. (the + to ++++ strength scale)..

some of the color changes observed (with Silicotungustic reagent) were:

DMT (P. viridis, A. phlebophylla leaf) - salmon pink>orange
NMT (isolated from A. obtusifolia & A. mucronata) - orange>browny orange
Acacia obtusifolia extract - browny orange>grey + UV fluoresence
Acacia maidenii leaf - browny orange + UV fluoresence
Acacia mucronata leaf - slightly oragne>purple>grey + UV fluoresence
Acacia fimbriata leaf - yellow>grey green (possibly phenethylamine)

under various conditions most tryptamines will show UV fluoresence, particularly 5-meoDMT, but at different wavelengths and not as strongly as betacarbolines..

hope this encourages a few people to try some field tests to add to our collective knowledge...

 
nen888
#49 Posted : 10/7/2011 5:16:11 AM
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..just to slightly clarify the silicotungustic acid color descriptions above, 'browny-orange' was a kind of creamy brown (like cafe ole) with orange tinge..pure dmt should be salmon-pink>pink, but whole plant material with 98%pure (approx) dmt tended towards orange, but without the creamy brown shown by nmt..


ps. i think the plant in the above mentioned (but still not found) E.R. article, was Calliandra pentandra..
checking references shows me that it was found by Shulgin to contain mainly leptacladine (or 2meTHBC) by GCMS, and found by
Callaway (reported to Luna et al) by HPLC to mainly contain DMT..a few other Calliandras have been found to contain betacarbolines...
 
Entropymancer
#50 Posted : 10/7/2011 7:08:29 AM

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The Entheogen Review article you're looking for is in Volume 12, Number 2, on pages 66-67. The portion of the article that you're recalling is actually a quote from TiHKAL entry #54 (tetrahydroharmine):

Shulgin wrote:
I have recently learned of analysis of an Ayahuasca brew that had used the plant Calliandra pentandra as a component, instead of the usual Psychotria viridis. Ott’s magnificent compendium Pharmacotheon makes mention of a Calliandra augustifolia as a component of ayahuasca, but there is no mention of this pentandra species. The preliminary analysis that I have been given of this decoction is that a component that had initially appeared to be DMT by HPLC analysis had proven to be tetrahydroharmine when assayed by GCMS. There was no detectable DMT present. And yet the material appears to have psychopharmacological activity.


The analysis Shulgin refers to was conducted by Jace Callaway, and the article also includes some very interest comments on the activity of THH from Callaway (in response to the Entheogen Review's query).

Ott also mentions Calliandra pentandra in his Shamanic Snuffs or Entheogenic Errhines, as the article alludes to. I could probably dig up the exact quote later if you're interested.
 
nen888
#51 Posted : 10/9/2011 12:11:10 PM
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..thank you Entopymancer, Smile , Calliandras are quite pretty plants..
 
nen888
#52 Posted : 10/17/2011 5:56:35 AM
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..experiments by D. McKenna et al. 1984 (reported in S. Voogelbreinder's Garden of Eden 2009) found, in rat liver, that NMT was a slightly more potent MAO inhibitor than 5-methoxyDMT..
..a single observed human oral experiment of 30-40mg NMT by itself produced no real noticeable effects, but this may need to be looked into more..(5meoDMT was found orally active at 20-40mg by J. Ott, & is known to MAO inhibit when smoked)

..if NMT does also MAO inhibit at some dosage then this would further complicate possible interactions between it and other tryptamines...

ps. NMT is also listed sol. in benzene & ethanol/water in the above reference..

it is also found in reasonable amounts in some Delosperma spp., and Mimosa opthalmocentra (in traces), in addition to previousy mentioned plant sources..

.
 
endlessness
#53 Posted : 10/17/2011 10:16:41 AM

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Just a small note on a comment you made on q21's n-oxide thread, you mentioned NMT was, to your knowledge, not yet found in mimosa hostilis. Indeed searching for different publications of analysis of mimosa hostilis, I couldnt find any mention of NMT (neither it says in trout's notes), but also I noticed several publications were studying stem bark, not rootbark. Burnt found NMT an 2-MTHBC in rootbark, as he posted in the jungle spice analysis: https://www.dmt-nexus.me...spx?g=posts&t=10553

I will see if I can replicate burnt's results sometime in the near future.

In trout's notes, he quotes Johnny Appleseed's TLC analysis of mexican rootbark showing 4 spots, one DMT, one "possibly NMT", and 2 others with high Rf bands.
 
nen888
#54 Posted : 10/18/2011 12:44:01 AM
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..thanks endlessness, i would have thought NMT quite likely to turn up in the species..i also wonder if variation is seasonal or sub-strain based..

with regards to NMT causing MAO inhibition in rat liver:
..i should add, though, that the one common, easy to find, piece of information i had on NMT when i started this thread, was that it had been tried orally (without MAOIs) and found to be inactive this way..the D. McKenna et al (1984) rat-liver result is interesting, but still may not apply to oral ingestion of it (except perhaps at very large doses)
..the 2001 vaporization experiments did not seem to indicate physically noticable MAOI activity, but the number of experiments and subjects was small (most subjects probably had fairly 'clean' diets or empty stomachs for such tests)
further evaluation needs to be done; it is possible smoking may produce MAO inhibition..
.
here's the D. McKenna paper: McKenna D. J. et al. 1984 "Monoamine oxidase inhibitors in South American halluncinogenic plants" Pt.1 J. Ethnopharmacolgy 10:195-223
...

ps. experiments will be conducted in the near future to investigate whether NMT is a mild MAOI...
 
nen888
#55 Posted : 10/19/2011 9:54:12 AM
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..the above linked paper appears to be part 1, so I'm still looking for their NMT/5meoDMT MAOI levels finding..
good paper..can anybody find part 2..?
 
endlessness
#56 Posted : 10/19/2011 11:37:38 AM

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Attaching the other part of the mckenna paper.
 
nen888
#57 Posted : 10/20/2011 6:23:17 AM
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..once again thankyou you are awesome endlessnessSmile , i wanna get to the bottom of this..
pt.2 is about Virola pastes..groovy!
 
nen888
#58 Posted : 10/21/2011 2:47:00 AM
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..apologies for sounding the MAOI alarm bell a bit prematurely..
the NMT reference (Voogelbreinder)to the McKenna paper was perhaps a bit misleading or confusing to read..we should not expect NMT to be any more an inhibitor of MAO than DMT (slightly less in fact)
..from Pt.2 of the McKenna et al. (1984) paper:
p.26
Quote:
Most of the tryptamines assayed (Table 6) were one to two orders of magnitude less effective than
ß-carbolines as inhibitors of MAO...The major exception is N,N-dimethyltryptamine...this compound [is] comparable to tetrahydroharmine and 6-MeO-harmalan...
in other words, tryptamines are not anything like as potent as harmine or harmaline (& other compounds)
NMT was slightly less potent in this way than DMT, 5meo less potent again..
this (very interesting) paper is looking at oral activity of Virola pastes and theorizes this could be due to anti-oxidants working as MAO inhibitors..it also points out that this kind of MAOI test is for once the compound has entered the bloodstream, it does not apply to oral ingestion, so NMT should be (as thought) as orally active as DMT (not very)..But, vaporization puts tryptamines directly into the bloodstream, so we would expect DMT smoked to mildly MAO inhibit at large doses....Johnathan Ott's 5meoDMT oral activity finding requires clarification..
an aside: if McKenna et al.'s findings are correct, then tetrahydroharmine (THH) should be expected to be a lot more active when vaporized than taken orally (as for most tryptamines)

..the paper raises the question of at what level, by i.v. or vapor, do the various tryptamines begin to noticeably MAO inhibit, and why has 5meoDMT in underground reports so far been the one apparently showing MAOI activity? (e.g. J.Ott - oral activity; D. M. Turner - reported vapor MAOI activity)

in the meantime, i wouldn't use up too much NMT (or DMT) in neat oral tests right now..
.
 
wira
#59 Posted : 10/25/2011 3:24:57 PM

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Going back to earlier mention of 1-ethyltryptamine in mistletoe, I've taken this up on an older thread titled "mistletoe??" in the Other Psychoactives forum, so if anyone wants to discuss it or if you have further leads please head over there. Still trying to find a primary reference for that after years of looking, as TIHKAL is the only thing that mentions it, and if the reference s buried in that book's bibliography, it is far from clear! I suspect Sasha may have forgotten to include that one, unfortunately. Maybe it's from a personal communication of unpublished lab work?
 
nen888
#60 Posted : 12/5/2011 2:24:00 PM
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..i've just returned from the great EGA conference in Victoria, Australia..saw lots of lovely people and friends including Snu, Mulga, and Trout, who gave a some great cactus talks..the whole event and vibe was awesome..Smile

presented an hour long lecture "entheogenic effects of NMT from acacia"
..it contains some further research not mentioned yet here, including the use of N-Methyltryptamine in anti-cancer research, and receptor binding findings..a formal summary paper of the findings will be uploaded first to the EGA site, which i will link here, in the next week, and i'll attach it here after..

..thank you to the EGA organizers for an inspiring time..
a few people i didn't get a chance to see..time evaporated...
 
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