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Ayahuasca shelf life

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Well, i have a bottle of MHRB brew that I have been using once or twice a month for about 6 months. It has been kept frozen, thawed & re-heated, then re-frozen many times & does not seem to have lost any potency at all as of 2 weeks ago.

I believe I read someone mention Terrance McKenna having a brew stored in his freezer for years without losing any potency.
 
concombres said:
Well, i have a bottle of MHRB brew that I have been using once or twice a month for about 6 months. It has been kept frozen, thawed & re-heated, then re-frozen many times & does not seem to have lost any potency at all as of 2 weeks ago.

I believe I read someone mention Terrance McKenna having a brew stored in his freezer for years without losing any potency.
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I think the mckenna quote was relating to sediment, but yeah, I believe he said he had a brew in his fridge for years, much sediment had accumulated, mckenna could not remember if he was told to "always shake it up" or to "never shake it up"...Regardless the brew was very active after all that time.

I've had this brew (picture attached) in my fridge for around a year, the last person to taste it claims it was fully active.

I always leave my sediment in. I filter my brews really well immediately after brewing, so this is not poor filtration, and should not be removed...( the brew must be shaken before serving)

I was told that shaking the sediment and letting it resettle too often would decrease potency, I was also told freezing and thawing too frequently was bad for potency, though I'm not sure if there's truth to this.




-eg
 

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entheogenic-gnosis said:
I was also told freezing and thawing too frequently was bad for potency, though I'm not sure if there's truth to this.
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Freezing and thawing something repeatedly doesn't make anything less potent, but it does make things more vulnerable to spoilage.
 
RhythmSpring said:
entheogenic-gnosis said:
I was also told freezing and thawing too frequently was bad for potency, though I'm not sure if there's truth to this.
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Freezing and thawing something repeatedly doesn't make anything less potent, but it does make things more vulnerable to spoilage.
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I was not referring to spoilage, but rather the destruction of the active dimethyltryptamine.

Frequent temperature changes, light, atmosphere, etc...all have the potential to destroy molecules...

I was told that freezing and thawing a brew repeatedly would destroy some of the DMT...

What would it even be broken into?

I know it can oxidize, giving DMT n-oxide...

And when metabolized in vivo it gives indole-3-acetic acid...

But as a result of temperature or time, where is the molecule "breaking" and what is it breaking into?

-eg
 
I don't think the molecules themselves are broken by freezing. Cell walls are, making vegetable matter mushy and stuff. Actually, freezing might make it even *more* potent, because it'd be releasing more chemicals from any sediment that may be containing it.
 
RhythmSpring said:
I don't think molecules are broken by freezing. Cell walls are, making vegetable matter mushy and stuff. Actually, freezing might make it even *more* potent, because it'd be releasing more chemicals from any sediment that may be containing it.
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Not from freezing, from temperature fluctuations, from going from frozen to thaw repeatedly...

LSD is an unusually fragile molecule and some comments are in order as to its stability and storage. As a salt, in water, cold, and free from air and light exposure, it is stable indefinitely. There are two sensitive aspects of its structure. The position of the carboxamide attachment, the 8-position, is affected by basic, or high pH, conditions. Through a process called epimerization, this position can scramble, producing isolysergic acid diethylamide, or iso-LSD. This product is biologically inactive, and represents a loss of a proportionate amount of active product. A second and separate point of instability is the double bond that lies between this 8-position and the aromatic ring. Water or alcohol can add to this site, especially in the presence of light (sunlight with its ultraviolet energy is notoriously bad) to form a product that has been called lumi-LSD, which is totally inactive in man. Oh yes, and often overlooked, there may be only an infinitesimal amount of chlorine in treated tap water, but then there is only an infinitesimal amount of LSD in a typical LSD solution. And since chlorine will destroy LSD on contact, the dissolving of LSD in tap water is not appropriate. -tihkal/shulgin
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See here how shulgin elucidates the weak parts of the molecule and identifies the resulting compound after the molecule is "broken"?

I was simply wanting to know the same regarding DMT, I said I had heard that DMT will degrade over time or by heat , in this case someone told me freezing and thawing (temperature fluctuation) potentially destroyed DMT when in decoction, I said I did not know if this was true.

(If you look up "DMT degradation" pretty much nothing comes up, a few misc. Links without any real info, and a few threads on a few forums, but nothing conclusive...)

Then asked the logical follow up to get my answers...


What would it even be broken into?

I know it can oxidize, giving DMT n-oxide...

And when metabolized in vivo it gives indole-3-acetic acid...

But as a result of temperature or time, where is the molecule "breaking" and what is it breaking into?

I can't find good DMT degradation information in the literature, it's not even in TIHKAL...


-eg
 
Well, while you're on the subject of ayahuasca, it would behoove us to figure out if any of the harmala alkaloids in the ayahuasca vine are subject to alteration by freezing.
 
entheogenic-gnosis said:
LSD is an unusually fragile molecule and some comments are in order as to its stability and storage. As a salt, in water, cold, and free from air and light exposure, it is stable indefinitely. There are two sensitive aspects of its structure. The position of the carboxamide attachment, the 8-position, is affected by basic, or high pH, conditions. Through a process called epimerization, this position can scramble, producing isolysergic acid diethylamide, or iso-LSD. This product is biologically inactive, and represents a loss of a proportionate amount of active product. A second and separate point of instability is the double bond that lies between this 8-position and the aromatic ring. Water or alcohol can add to this site, especially in the presence of light (sunlight with its ultraviolet energy is notoriously bad) to form a product that has been called lumi-LSD, which is totally inactive in man. Oh yes, and often overlooked, there may be only an infinitesimal amount of chlorine in treated tap water, but then there is only an infinitesimal amount of LSD in a typical LSD solution. And since chlorine will destroy LSD on contact, the dissolving of LSD in tap water is not appropriate. -tihkal/shulgin
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This mentions nothing of temperature fluctuations.
 
RhythmSpring said:
Well, while you're on the subject of ayahuasca, it would behoove us to figure out if any of the harmala alkaloids in the ayahuasca vine are subject to alteration by freezing.
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C'mon on now, I have had to say this over and over, not freezing, being exposed to being frozen then and, frozen then hot, frozen then hot...I don't know how else to say it, temperature fluctuation...

It's not unreasonable to think temperature fluctuation may degrade a molecule...

All you ever find is threads like this

(compound37 said) DMT lasts for quite a while if stored properly. Don't know if it would last longer, its fairly easy to put into airtight container to fight oxidation usually.. Imagine changa and dmt would both keep remarkably long time if kept in cool, dark, dry, and airtight location.
Welcome to the DMT-Nexus
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Great, we know DMT is stable in proper conditions, now, what about improper conditions?

Where are the weak spots on the molecule, where would it "break", what would it then become, and what is needed to degrade the compound?

This is all I want to kniw

-----


There was a b. Caapi sample from the 1800s that still contained harmine...it was poorly stored, never frozen and thawed, but poorly stored... when tested the harmine molecules where still there...

FURTHER EXTENSIONS AND COMMENTARY : There is a fascinating unanswered question that I had to ask myself a little while ago. It is a question that, if ever answered accurately, just might throw the entire area of the pharmacology of harmaline into a delightful disarray. I received a small quantity of documented seeds of Syrian rue and I was curious to see, in my hands, what its alkaloid content was. This is, after all, a well known source rapidly increasing in popularity as the inhibitor component of ayahuasca. So I ground a few of them up in a mortar under DMF and carbonate, spun down the extract, dissolved a drop of it in a milliliter of 90:10 toluene/butanol, and shot a microliter into the GCMS. As expected, there were two major peaks, and an intriguing scatter of small things. The spectrum of first was clearly that of harmaline, and of the second, that of harmine. The literature is correct.

Then, to tidy up a bit and make absolutely sure of the relative retention times, I decided to run standards from my reference collection. Reference harmine gave the second peak with identical retention time and MS spectrum. It was when I injected a sample of my reference harmaline that I got my surprise. Here, a sample of E. Merck AG, Darmstadt yellow crystalline material labeled Harmalinhydrochlorid, was very much looking as if it was a mixture of about two parts harmaline and one part harmine. Only 70% pure? Wow.

Three explanations popped into mind. (1) Maybe the harmine was being generated from harmaline, somehow, in my analysis. So I tried another reference sample, one recently purchased, and it gave a single peak. So it was not an artifact arising from some quirk of my analytical process. (2) Maybe the Merck sample, which I had obtained in the early 1960's (and of course I had no way of knowing how old it was when I got it) had come from plant sources, maybe even P. harmala itself. Maybe the analytical tools at the time were inadequate to detect and identify this amount of harmine as an impurity. This is not comfortable, in that these two alkaloids were first isolated, and separated from one-another, from plant sources some 150 years ago. I am sure my sample is not that old. I am not sure that even E. Merck AG is that old. The tools of analysis have been around a long time. Anyway, I wrote to them, and they answered me with the elliptical comment stating that they had never had harmaline in their catalog, only harmine. And thus, they would have no way of knowing what was in the bottle. Of course they could have distributed research samples of many things, of stuff that was never in their catalog, but by replying in this way they are absolved of all guilt. And of all legal responsibility as well, of course. OK.

This leaves (3). Maybe over the years, harmaline spontaneously loses a molecule of hydrogen, and becomes harmine. Not an easy thing to reckon with, chemically, but I am running out of possibilities. I was led to a comment that had been once made by a quiet hero of mine, Bo Holmstedt in Sweden, concerning the analysis of an ancient sample of plant material from Banisteria caapi (now known as Banisteriopsis caapi). The herbarium specimens he was looking at had been collected by the 19th century plant explorer Richard Spruce in the Rio Negro area of South America and had, after a few years of storage in a moist and mildewy hut a few miles down river, been rediscovered and sent on to the Kew Botanical Museum where they had quietly rested for over a hundred years. When Holmstedt worked them up some 30 years ago, he reported that the alkaloid content was 0.4%. This was virtually identical to a newly collected, botanically verified specimen of Banisteriopsis caapi which he analyzed at the same time and found to contain 0.5% alkaloids. The latter material contained, as described by many authors, the main alkaloids harmine, harmaline and tetrahydroharmine. By contrast, the alkaloid content of the Spruce material consisted exclusively of harmine. It is open to question whether the samples collected by Spruce in 1853 originally contained only harmine or, perhaps more likely, that harmaline and tetrahydroharmine have with time been transformed into the chemically more stable aromatic b-carboline harmine.

How can this enigma be answered? Put away a sample of pure harmaline, with its spectral identification, onto the shelf for 50 or 100 years, and then re-analyze it? Who knows, but what might be needed for this conversion is heat, or a bit of iron catalyst, or some unknown species of South American mold. Acid is certainly known to promote this oxidation. It would be very much worth while to answer this question because some, perhaps much, of the results of human pharmacological studies that involve harmaline as a metabolic poison, may be influenced by the independent action of harmine as a harmaline contaminants -shulgin/tihkal
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Here shulgin found his "pure" sample, in fact contained harmine and harmaline, so degradation was consider, and may potentially occur...


There was peyote found in Texas that was thousands of years old, and still contained 2% mescaline...

Some alkaloids are stable over time, some are not, some can tolerate temperature fluctuations, some can not, some can tolerate light, some can not, some molecules can be exposed to air, others can't.

So again, with DMT,where are the weak spots on the molecule?, when it "brakes" what will it brake into?, and what conditions will cause those weak points to "break"?

I can't find this information anywhere else...

-eg
 
I'm still interested in the in storage stability of DMT...

But while digging around found this...

An interesting research paper on DMT metabolism...

www.ncbi.nlm.nih.gov

Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca - PubMed

Ayahuasca is an Amazonian psychotropic plant tea obtained from Banisteriopsis caapi, which contains β-carboline alkaloids, chiefly harmine, harmaline and tetrahydroharmine. The tea usually incorporates the leaves of Psychotria viridis or Diplopterys cabrerana, which are rich in...
www.ncbi.nlm.nih.gov www.ncbi.nlm.nih.gov

Twenty-four-hour urine samples were obtained from 10 healthy male volunteers following administration of an oral dose of encapsulated freeze-dried ayahuasca (1.0 mg DMT/kg body weight). Results showed that less than 1% of the administered DMT dose was excreted unchanged. Around 50% was recovered as indole-3-acetic acid but also as DMT-N-oxide (10%) and other MAO-independent compounds. Recovery of DMT plus metabolites reached 68%. Harmol, harmalol, and tetrahydroharmol conjugates were abundant in urine. However, recoveries of each harmala alkaloid plus its O-demethylated metabolite varied greatly between 9 and 65%. The present results show the existence in humans of alternative metabolic routes for DMT other than biotransformation by MAO. Also that O-demethylation plus conjugation is an important but probably not the only metabolic route for the harmala alkaloids in humans.
www.ncbi.nlm.nih.gov

Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca - PubMed

Ayahuasca is an Amazonian psychotropic plant tea obtained from Banisteriopsis caapi, which contains β-carboline alkaloids, chiefly harmine, harmaline and tetrahydroharmine. The tea usually incorporates the leaves of Psychotria viridis or Diplopterys cabrerana, which are rich in...
www.ncbi.nlm.nih.gov www.ncbi.nlm.nih.gov
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This shows the body has an alternative route of metabolism, other than MAOI for DMT...

Though if it was identified I missed it...

-eg
 
Sorry it should have said MAO not MAOI in my last post...

sekio said:
01-07-2011 23:09
I'd expect oxidisation to N,N-DMT N-oxide and polymerization (to a total mess). Probably some indoleacetic acid, indoleacetaldehyde, dimethylamine, methylamine, ammonia, formaldehyde, CO2, H2O, methanol etc etc.

N,N-DMT degradation?
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I found this old thread from bluelight while digging around...

This is the best answer I've found regarding DMT degradation...

But it's just somebody's speculation...

Research papers are non-existent, or at least not available easily...

-eg
 
Twenty-four-hour urine samples were obtained from 6 DMT users before and after intake of 25 mg DMT doses on two separate sessions. In one session, DMT was taken orally and in another it was smoked. After oral ingestion, no psychotropic effects were experienced and no DMT was recovered in urine. MAO-dependent indole-3-acetic acid (IAA) represented 97% of the recovered compounds, whereas DMT-N-oxide (DMT-NO) accounted for only 3%. When the smoked route was used, the drug was fully psychoactive, unmetabolized DMT and DMT-NO rose to 10% and 28%, respectively, and IAA levels dropped to 63%. An inverse correlation was found between the IAA/DMT-NO ratio and subjective effects scores. These findings show that in the smoked route a shift from the highly efficient MAO-dependent to the less efficient CYP-dependent metabolism takes place. This shift leads to psychoactivity and is analogous to that observed in ayahuasca preparations combining DMT with MAO inhibitors.
Copyright © 2014 John Wiley & Sons, Ltd.

Metabolism and urinary disposition of N,N-dimethyltryptamine after oral and smoked administration: a comparative study - PubMed
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More metabolism (in vivo degradation) research

This involves smoking as the ROA, where as the last paper elucidated oral DMT and harmala alkaloid metabolism.

The first paper claimed that MAO was not the bodies only means of metabolism, generally the result of this metabolization is deamination, N-demethylation, O-demethylation, N-oxygenation and so on, so we have good ideas of how this molecule is being broken down in the body, but it fails to mention by what other means than MAO.

Is there a reason why General degradation research is not available? Has it really not been done?

That seems unlikely, Goncalves had DMT in 1946, Szára in 1956, so this compound has been known to science for like 70 years, you figure it's stability and degradation would have been the first things researched...they still had 14 years before the compound was scheduled to do this research...



-eg
 
entheogenic-gnosis said:
So again, with DMT,where are the weak spots on the molecule?, when it "brakes" what will it brake into?, and what conditions will cause those weak points to "break"?

I can't find this information anywhere else...
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Have you considered that this is because there is no answer to your question--that perhaps the question itself is based on the assumption that there ARE weak spots in the molecule to begin with--weak spots that are vulnerable to mechanical breakdown? You can find all the info you want on chemical vulnerabilities (like to oxidation), but molecules aren't subject to the same newtonian laws that, say, a celery stick is, when it expands and contracts because of temperature fluctuations.

I think we need a real chemist in here...
 
You basically saying that DMT is indestructible? That it has no weak spots and that temperature fluctuation, atmosphere, and time have no effect what so ever on the compound....

sekio said:
01-07-2011 23:09
I'd expect oxidisation to N,N-DMT N-oxide and polymerization (to a total mess). Probably some indoleacetic acid, indoleacetaldehyde, dimethylamine, methylamine, ammonia, formaldehyde, CO2, H2O, methanol etc etc.

I never claimed to be a chemist, I'm an organic chemistry student, second year, I have no problems admitting I'm learning and that I don't know everything...

Molecules degrade, ask any organic chemist, now, every molecule has its own specific properties.

Though somehow I think you know this, you have enough FreeTime to disrupt my research, or I asked a question that you could not answer, so this is the result.


Attitude Page - DMT-Nexus Wiki

wiki.dmt-nexus.me wiki.dmt-nexus.me
Everything in this link above is seen as a joke by everybody here, why even to claim to be a site where people can learn and research when your just going to use it disrupt the people researching this stuff?

-eg
 
Seriously if you have a problem with me you can just say it, but it's obvious this has nothing to do.with research or any questions I asked, passive aggression is how little kids deal with resentment or anger.

Seriously, if you have a problem with me and refuse to a dress it, what can I do?

-eg
 
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