Evenin' all,

I've been doing some research on the extraction of phalaris grass and the toxicity of gramine, an alkaline present in certain strains of phalaris. I haven't had the time to really correlate anything into a useable format and I'm still researching the subject but I thought that I'd post some links to information, studies and other forums that I've come across.

Hopefully it'll be of some use to someone and save you a bit of time scouring the interweb! I'll post more as I find them although I can't vouch for their usefulness I thought they might be of interest.

Erowid Phalaris Vault
N,N-Dimethyltryptamine Production in Phalaris aquatica Seedlings
Trouts Notes On Gramine
Gramine Toxicity Study On Voles
Gramine Details
Toxicity Assesment
Livestock Foraging Behaviour....
The Alkaloids: Chemistry & Pharmacology
Shroomery - Solubility Of Gramine
Botany - CNS Effects
Breeding Non-Toxic Phalaris
Info on Arundinacea

Post your own links, even links back to other postings on here you think are useful, if you find them and we'll see what else we can learn about phalaris extraction and maybe even find out how to remove gramine! Unlikely for the kitchen chemist, I know but it's better that we're educated.

thanks for those links.

getting the phalaris teks nailed down seems quite worthwhile.

No one has ever had much of a reason to explore phalaris in depth, but that will change pretty soon if legal proceedings continue as they are.

We should be exploring alternative sources of DMT as a matter of principle. For the love of all things extractable!

Ident, the links are a great start. Given what I suspect might be a growing interest in alternative sources of N,N and 5-MeO, Phalaris is an excellent alternative, but may not be as predictable in yield. There are literally thousands of acres of Philaris growing in wetlands throughout many countries, so a virtually inexhaustable source. Question: is there is good dialog here on extraction methodologies and yields, including relative solubility data between the two molecules? Extraction/separation of gramine (nasty stuff) from the good molecules? My recommendation is that a discussion section get created that creates the details of the methodologies as elegantly as many of you have done with MHRB STB Teks. Those teks are truly awesome, but we need the same for phalaris.

I totally agree with you! I think it is important to try to work out a tek that not only extract DMT, but also bufotenine and 5-MeO-DMT, if they are present in sufficient amounts. That is, not a full-alkaloid extract, but a tek that will give three end products. If this is successful, we have an easily obtained source for three of our favorite tryptamines.

It is also important to try to get more research on Phalaris done. I feel some of the money our organization (work-name ELF) will earn, should go to this. We need to understand what species make the most tryptamines, what species that has the most stable content, and how we can boost the content.

Anyone has this paper available? "The data suggest that clones that contain gramine are not likely to contain N,N-dimethyltryptamine and/or β-carbolines. Thus, an inverse biosynthetic relationship between gramine and the tryptamine and β-carboline alkaloids seems to exist. However, further work is needed to firmly establish any such relationship between these alkaloids."

Good work on finding that information Ident. I also have been trying to find articles and information on Phalaris species since its a readily available source around my place

@ evening glory
Agreed, more research and projects towards Phalaris species should be done. Can't wait!

EDIT: btw evening glory, I found the article you were looking for. here's the link
Phalaris Paper

Thanks mate, wonderful news! The paper do indeed suggest that clones with gramine DO NOT contain entheogenic tryptamines, and vice versa. Look at their results (+++ indicate 'large' amount, ++ intermediate, + trace):

Edit: I didn't see this quote from the paper: "However, paper chromatographic analysis of extracts from numerous other clones has revealed an occasional clone containing both gramine and tryptamine derivatives." So never mind what I wrote, gramine is still a real problem!

So I've been finding some more articles and papers lately on the Phalaris spp. and will be posting more up once I find where I placed the other articles.

Abstract

I am looking for an article from Culvenor et al. (2005) about Phalaris aquatica. Anyone know where I can get it?

nope, I couldn't find it.

found these though...

a suggestion from my experience growing the grass that might actually be in one of the growing tecks it a way to increase the alkaloid content SUBSTANIALY is to stress the plant a few times before harvest by not wattering it till the leaves wilt a bit and the tips just start to dry up..I usually did this 3 times before harvest. each time the grass got more and more red coloring...combined with leaving it in the shade before harvest a few weeks, and the levels of niitrogen feeding...it's all about timing. I'm pretty sure someone wrote up an article on this technique on erowid or someplace. as stated from the above articles tryp and carbo free phalaris.pdf introduction that "alcaloid levels could be DOUBLED from moisture stressing..even without the leaves wilting"
I grew this grass for many years and was able to produce some suprisingly potent leaves, but producing mostly 5-meo i think..which in my opinion is still a very usable alc..not much else on earth besides death can bring such an overwealmingly intense experience as this!!!

haha, yes 5-meo is definitely an intense experience to say the least. As you've pointed out the key hear really does seem to be stress levels. One of the biggest stress factor's as it seems is the nitrogen levels. Unfortunately though, ALL the alkaloids increase in yield. So we are just stuck with separating the alkaloids. A post a while ago about Arundo Donax had 69ron suggesting distillation as a possible solution but that its was tricky to pull off successfully without vaporizing the spice.

Distillation may be a bit hard for a kitchen extraction. What about using different solvents in order to extract the three different tryptamines? The XLogP3 for these substances are: 1.2 for Bufotenine, 1.5 for 5-MeO-DMT and 2.5 for DMT. Wouldn't these numbers give us a possibility to work out a tek with three different solvents that will extract three different substances, more or less?

Now I don't have an extensive knowledge of chemistry but I believe that should work. DMT in theory would be easiest to pull out but the others might be trickier because, if I'm not mistaken, the XLogP3 of gramine is 1.3 I believe. I can't verify the XLogP3 though since I've lost my source and can't find it.

The XLogP3 for gramine is 1.8. Remember you always have PubChem!

I remember a tek that SWIM was working on (here, https://dmt-nexus.me/for....aspx?g=posts&t=4172) where 69ron suggested using warm Heptane to separate the DMT from the Gramine. The Heptane would pull the DMT but leave the gramine. It would also leave behind the 5-meo-DMT and Bufotenine too though.

Also, in that paper that was posted the grass was extracted with methanol/NH4Oh(1:25) 50ml per 5g of grass. The alkaloids were then picked up with chloroform.
What is NH4OH? Is it Ammonium Hydroxide, the stuff you can buy at supermarkets?

i dunno how much bufo there is in arundinacea at least..i tested a phalris extraction I did last week and I didnt get any of the trademark bufotnenine feelings..I did get a tryptamine buzz, not sure if it was NN or meo becasue I was cautious and only tested a very very small dose..I have enough left to do another higher dose test sometime this week so I will do that..and this is from wild arundinacea so I have unlimited access...

There were def tryptamines in there..I had very very mild visuals at first that were reminescent of DMT..and that typical pineal pressure feeling..but it was all very very mild..and my extract was not pure at all..it was transparent orange resiny stuff that looked like the way jimjam looks when its pulled with limo and evapped.

Gramine is apparently not water soluble..and not soluble in naptha either..so I started with a water boil on the grass after i stuck it in the blender..no acid was used durring the boil.

Ya, it seems to be Ammonium Hydroxide




Yes it would be interesting to see what actually came from the water boiled extract. Was that the entire extraction or did you do any further extracts after that?

@ Evening Glory
Haha, forgot about the PubChem Thanks for the clarification.

Okay, I found an article that seems to give good hints in the direction of what environments the wanted tryptamines will be produced: Alkaloids and Palatability of Phalaris arundinacea L. Grown in Diverse Environments

Can anyone get the full article?