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The issue of Gramine Options
 
dithyramb
#1 Posted : 8/2/2020 10:16:08 AM

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Dear Nexians,

As a pursuer of the Phalaris grass I am feeling the need for more clarity on this alkaloid. There is a general caution about it, which is a good thing when it comes to an unfamiliar alkaloid, however I could not find conclusive evidence that gramine is detrimental to human health in the amounts found in grass.

İt is obvious that cattle eat way more grass than in human psychoactive consumption.

According to the research I have uncovered so far: the proposal that cattle sudden death syndrome is caused by gramine has been disproven. That it is part of the neurological poisoning symptoms in the staggers is possible but not well studied.

https://pubmed.ncbi.nlm.nih.gov/3421887/

https://www.researchgate...etiology_and_toxicology
Quote:
Gramine (a tryptamine) and
hordenine (a tyramine) and 5-MeO-DMT have also been implicated
in cases of phalaris ‘sudden death’, although symptoms of ‘staggers’
could only be produced by experimental administration of 5-MeO-
DMT




On the general safety and properties of gramine, here is what I have found so far:


Safety evaluation of an oat grain alkaloid gramine by genotoxicity assays

Quote:
These results indicate significant antioxidant, non-mutagenic as well as non-genotoxic activity of gramine in vitro and in vivo in the given doses.


Gramine derivatives as neuroprotective Alzheimer medicines

https://www.medchemexpress.com/Gramine.html

Quote:
Gramine (Donaxine) is a natural alkaloid isolated from giant reed[2], acts as an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 µM for AdipoR2 and AdipoR1, respectively[1]. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist[2]. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties[1].


Potential Neuroprotective Effects of Adiponectin in Alzheimer’s Disease

Gramine: A Vasorelaxing Alkaloid Acting on 5-HT2A Receptors
Article in Planta Medica 70(4):373


Quote:
These results suggest that gramine is a vasorelaxing agent acting mainly by antagonism at 5-HT (2A) receptors.



https://www.latoxan.com/...duct.php?id=671&n=4

Quote:
In vitro, it inhibits acetylcholinesterase and butyrilcholinesterase. At 1/5,700 concentration, it lowers the brain and blood serum cholinesterase activity by 61 %.


https://link.springer.co...HAC.0000048140.06266.63

Quote:
Gramine was reported to exhibit radioprotector activity
[333]. Experiments on sea urchins showed the absence of
embryotoxicity [334]. Gramine hydrochloride introduced to
experimental animals induced tremor, moderate lacrimation,
and cyanosis with characteristic coloration of the skin (re-
lated to insufficient oxygen supply developed in cases of car-
diac insufficiency), salivation, clonic convulsions (deliberate
contractility of a muscle or a group of muscles), and loss
within an hour. The LD50 upon peroral administration is
542 mgkg for mice and 575 mgkg for rats. The intravenous
introduction of gramine hydrochloride in a dose of 50 mgkg
led to the loss of experimental rabbits. Gramine belongs to
the group of moderately toxic substances and produces no
skin-resorptive, irritant, cumulative, and allergic effects




Experientially, orally in combination with rue, I have felt significant toxicity from crude extracts of certain wild Phalaris aquatica strains and Phalaris paradoxa. I cannot know if gramine played a role in it. I could classify the toxicity into two kinds. First, the cardiovascular complications, which felt very dangerous and bordering on lethality. I still assume that this is caused by tyramines. Second is the neurological symptoms - tremors, a disconnection, and unconsciousness. This is also highly undesirable. I am not sure which components might be the cause, and gramine might play a role in it.

In my brachystachys experiences so far I have not experienced any of these toxicities, and I don't know if it contains gramine or not as I don't know how to recognize gramine.

I hope that the issue of Gramine gets fully elucidated for the whole community.
 

Have doubts about your samples? Get trusted results by having your samples tested.
 
dithyramb
#2 Posted : 8/2/2020 1:48:47 PM

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That's a lot of properties; gramine has a complex pharmacology in humans.

A lot of it is positive: antioxidant, acetylcholinesterase inhibitor, antiviral, antitumor, anti-inflammatory, neuroprotective.

Some of the rest I don't know how to interpret.

The LD50 seems to be high.

The last source indicates it is "moderately toxic" and has no cumulative toxicity. We don't know the doses used in that study, and the symptoms include tremors and convulsions.

I have two specific questions.

1) Are the neurological toxicity symptoms (tremors, unconsciousness) that I have experienced with P. aquatica due to gramine? The "disconnection/unconsciousness" effects were like an inhibition of the effects of DMT. If not gramine, what else could it be?

2) If so, is the toxicity dose dependent, and is gramine safe or even beneficial in lower doses? I am thinking of beta carboline's, especially harmaline. These molecules are also said to be toxic and bring on serious symptoms with excessive doses and unusual administration methods, but are highly medicinal in appropriate doses.
 
endlessness
#3 Posted : 8/2/2020 2:10:55 PM

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Thanks for the topic and adding sources Smile

Interesting that gramine is 5-HT2A antagonist, I hadn't seen that paper before.. This suggests it can diminish psychedelic effects of tryptamines. So even if it's "safe", it's probably unwanted in combination with psychedelics.

How did you prepare your 'crude' extracts?

Regarding the effects you felt, it's very hard to say because phalaris is a mixed back of alkaloids. People normally worry about gramine itself but there are other gramine analogues as well as other alkaloids of unknown safety profile. According to festi and samorini (1994), these are the alkaloids sometimes found in phalaris:

NMT (n-methyl-tryptamine)
5-MeO-NMT
DMT
5-MeO-DMT
Bufotenine
5-Me-Tryptamine
5-MeO-Tryptamine

2MTHBC
2-Me-6-MeO-THBC
2,9-DMe-6-MeO-THBC

Gramine
7-MeO-Gramine
5,7-DMeO-Gramine

Hordenine

According to Trout, phalaris also occasionaly has 3-methylindole (known to produce Bovine Pulmonary Emphysema in cattle)


IMO considering the variability in genetics and unknown safety profile of many of those compounds, I would not recommend people to consume crude extracts of Phalaris.

I'd advise people to extract and test with TLC or at least colorimetric reagents. And specifically about gramine, it is possible to detect it (and differentiate from just DMT) in an extract even in small amounts with mandelin (as shown here)
 
dithyramb
#4 Posted : 8/2/2020 4:23:22 PM

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Hey Endlessness. Thanks for your reply 🙂

I had been suspecting that gramine might be blocking DMT, also taking into account the 5ht2a antagonism.

To prepare my crude extracts, I simply boil in water with vinegar, multiple washes and combine and reduce.

Wild Phalaris aquatica and arundinacea are often a whole cocktail of alkaloids, and the aquaticas which I have come across have been super potent. Unfortunately I could not find any study revealing the alkaloid content of brachystachys. It supposedly has a cleaner alkaloid profile.
 
dithyramb
#5 Posted : 8/4/2020 10:38:19 AM

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I am very happy to have found a strain of P. brachystachys which (experientially) lacks all the incompatible alkaloids for an ayahuasca analogue - Hordenine, tyramines, 5 MeO DMT. All but gramine. After a time of study I believe I can now recognize gramine and it's undesirability despite it's relative harmlessness. İt is sedative and blocks/buffers the effects of DMT as a 5HT2A antagonist.

Gramine is said to be practically insoluble in water. Could I be feeling it in my crude water extract because of the vinegar I add in the boiling process? Could it be that if I boiled without vinegar, gramine would not be present in the crude water extract?
 
endlessness
#6 Posted : 8/4/2020 11:04:59 AM

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Gramine as a freebase is insoluble in water (merck index). Most salt forms, including the one naturally in the plant material, will likely be soluble in water, so it doesn't matter if you added vinegar.

I personally don't believe us humans are equipped with such sensitivity as to be able to subjectively tell apart different ratios of psychoactive + potentially toxic compounds (specially if you don't have a baseline to compare to, having access to pure amounts of all possible compounds involved and testing the different combinations) . It is not possible to discount self-suggestion and other psychological factors at play, as well as the natural variability of subjective experiences even with the same substance.

I highly suggest you acquire some sort of analytical method, whether its TLC or just reagents (like, say, marquis, mecke, mandelin and ehrlich).

I'm attaching Festi and Samorini's paper. Indeed I couldn't find much info on brachystachys phytochemistry from a quick search.

Good luck either way and keep us informed!

 
dithyramb
#7 Posted : 8/4/2020 11:15:07 PM

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Thank you very much for your help, Endlessness.

Quote:
I personally don't believe us humans are equipped with such sensitivity as to be able to subjectively tell apart different ratios of psychoactive + potentially toxic compounds (specially if you don't have a baseline to compare to, having access to pure amounts of all possible compounds involved and testing the different combinations) .


İ know that the dominant paradigm here is purely scientific and subjective experience is not considered reliable. İt's probably the way it should be. I personally believe we have the capacity to be as sensitive as you describe, even if not tapped most of the time in the modern lifestyle. Traditional ayahuasca practice is based entirely on study through subjective experience, and it requires highly strict dietary conditions including periods of isolation. I have been doing such diets, with this paradigm, to the best that I can in my life circumstances.

My baseline gold standard to compare my Phalaris experiences is chacruna, with which İ have hundreds of experiences. İ am not saying this to claim authority, but simply trying to explain where I am coming from.

All my Phalaris experiences with the exception of P. truncata have involved sleepiness and a "distancing" of the DMT effects. This was extreme with a strain of aquatica, leading to unconsciousness. I have had two strong experiences with a strain of brachystachys and on the second experience İ recognized this effect, less pronounced than in aquatica,

Thanks for the festi and Samorini paper. According to this study P. brachystachys has a single alkaloid - DMT and has no gramine. However I remember reading an analysis on this forum which found gramine in brachystachys. İs it true that there are strains with only DMT (no gramine)? Will I have to find them or is there a way to purify the tea from gramine.. This is one important question for me at the moment. I think finding such a technique would revolutionize our relationship with the grass, opening the door to the possibility of a true local ayahuasca analogue using P. brachystachys.

Thanks for your recommendation for analytical methods. I might catch up with that some day.
 
endlessness
#8 Posted : 8/5/2020 12:43:31 AM

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I don't discount the possibility we can tell some things apart. But which things, in which doses? And how can we know if we're mistaken in some particular case or not? The only way is to test it, right? I'm of the opinion that we should always question our own assumptions, and experiment to prove/disprove impartially (if it's something that is possible to test).

I definitely don't doubt that you have extensive experience with chacruna or phalaris, but the question is whether the perceived difference you have really does relate with a specific alkaloid content. There's always the component of self-suggestion, different dosaging with different batches, and also it can be other alkaloids but not the ones you are supposing. So to eliminate some of these different unknown factors it would be ideal to test if possible.

But yeah take your time in informing yourself about the analytical methods. Here are a couple of links:
https://www.dmt-nexus.me...spx?g=posts&t=91678
https://www.dmt-nexus.me...spx?g=posts&t=25771


As for brachystachys, I had forgotten but as I mention here, benzyme has tested one sample containing 9:1 DMT to gramine. One more data point to consider.

 
dithyramb
#9 Posted : 8/5/2020 11:04:13 AM

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Alongside valuing the traditional approach, I agree with you that testing/analysis is a very important tool for us modern day explorers. Thanks for the helpful links, I will note them down for if I decide to learn this work. İt definitely seems there is a void here, with very little analysis done on the grass. I am surprised to see this. Just one analysis on P. brachystachys throughout the history of this forum?

Are there any others out there who can offer their analysis results for P. brachystachys?

Also, is there anybody out there equipped with the skill to do analyses, willing to receive my seeds for testing?

I also have a special strain of Syrian rue I have been harvesting from the wild for a decade, exceptionally feminine and compassionate which needs to be tested to understand the chemical aspect of it's uniqueness.
 
dithyramb
#10 Posted : 8/5/2020 12:20:32 PM

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Endlessness, here is a post from you from the link you shared:

Quote:
Im not sure if this was noticed for those looking at this thread but hot limonene pulls on that wild arundinacea (sample 123) yielded equal amounts of DMT and Gramine, while the room temperature limonene pulls in the Yugo Red (sample 2661) greatly favored the ratio to DMT and only had small amounts of gramine. This is a good indication that, hot limo is much less selective and will pull more of the potentiall toxic alkaloids, while room temperature limonene will nicely pull DMT but only very little gramine.


It appears you compared results from two different strains of arundinacea, so are you sure this proposal holds?

If so, do you think the same would apply to water, i.e. that a cold water extraction would leave out most of the gramine?

...

Also, I have no idea if this would make any sense, but is there a possibility that juicing the grass could leave out gramine..?
 
Jagube
#11 Posted : 8/5/2020 8:30:52 PM

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dithyramb wrote:
If so, do you think the same would apply to water, i.e. that a cold water extraction would leave out most of the gramine?

I can't answer with certainty, but this case is very different for the following reason:

Water is a polar solvent and (optionally acidified) water extractions aim to pull alkaloid salts. The comment amount limonene pulls, on the other hand, refers to non-polar pulls from an alkaline soup, which aim to pull freebase alkaloids.

There is no general rule that would say that if an alkaloid (such as gramine) in its freebase form is considerably less soluble in cold (vs warm) non-polar solvents, then its salts are considerably less soluble in cold (vs warm) water.

Alkaloid salts are ionic compounds. Dissolution of non-polar compounds (such as alkaloid freebases) in non-polar solvents is a very different concept to the dissolution of ionic compounds in water. The former is driven by entropy, the latter is driven by polarity (opposite electric charges) and happens through dissociation into cations and anions, a.k.a. ionization. The intra- and intermolecular forces at play are very different in these two cases. So I wouldn't expect any correlation between the solubilities of a compound in these two different 'worlds'.

That doesn't mean the answer to your question is no, but if it's yes, the fact in the limonene quote is unrelated to it.
 
dithyramb
#12 Posted : 8/5/2020 10:00:58 PM

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Thank you, Jagube.
 
dithyramb
#13 Posted : 8/6/2020 7:46:28 AM

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I just came upon a quote by Appleseed that drying reduces the "unwanted alkaloids."

Quote:
The last factor to consider is whether to dry the grass
or extract the alkaloids from the fresh material. Drying tends to reduce the alkaloid harvest, but in some cases, especially that of the Turkish variety of P. arundinacea, drying may reduce the presence of unwanted alkaloids. — Johnny Appleseed


I wonder if that means / includes gramine?
If so would drying really destroy more gramine than DMT?
What about oven drying which is said to preserve the DMT content?

Quote:
Pleasantly surprised today from a GC-MS analysis of a methanol extraction of some oven-dried phalaris brachystachys. I heard talk of "up to 3% DMT", but I was sure it was only hype. I don't have a "calibration standard" for DMT but compared to some MHRB crystals, it could very well be 3% (of dried weight). The other good news was that the gramine peak was only about 1/20th or less of the DMT peak.


Does that translate into a 20:1 ratio of DMT to Gramine?
 
 
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