5-MeO-DMT in Phalaris grass species

[Bancopuma]

I thought this could do with its own thread. Viable botanical sources of 5-MeO-DMT are lacking, when compared to N,N-DMT sources. My feeling is that the various Phalaris grass species remain relatively unexplored, and I think they hold perhaps the greatest potential of providing a viable botanical source of 5-MeO-DMT, of all the plants we know so far that contain it.

An interesting passage I've just spied on the DMT Nexus, taken from The Entheogen Review:

Phalaris arundinacea 'Turkey Red' Plant:

From The Entheogen Review Vol. XI 2002:-

My old, "Turkey red," was selected to produce 5-MeO-DMT because this is the alkaloid that I personally prefer for my own work and the work I do with groups around the country. I feel 5-MeO-DMT most closely mimics the natural enlightenment state of a fully functioning pineal-gland. It does not distract one with visuals, but open one's energy field and dissolves the energetic barriers between people. By taking about 75mg of the "Turkey red" extract - equivalent to about 7.5mg of 5-MeO-DMT - potentiated with a RIMA such as Syrian Rue, one can experience much healing, and in the right group, a unification of consciousness within the group. I believe this medicine has a role to play in the next stage of evolution, which must involve some form of group consciousness.

There are about five other alkaloids in Turkey red as well. I do not know what most of them are. I have tried to experiment of separating out just the 5-MeO-DMT and taking that orally with a MAOI, and I do get and effect, comparable to that of chemically produced pharmahuasca from synthesised 5-MeO-DMT. However, It does not have the magical shamanic effect I like to use for my group use. I have about a thousand TLC plates of my tests, each with its own unique and different alkaloid mixture. This could keep graduate students busy for years elucidating the unique healing properties of these mixtures.

https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=16810

...so this particular cultivar of P. arundinacea certainly sounds promising as a potential 5-MeO-DMT source.

Some further information on Phalaris species and 5-MeO-DMT content to be found here:

Phalaris spp.

Phalaris data below is incomplete. Alkaloid concentrations and proportions are highly variable from year to year and show dramatic seasonal fluctuations. Concentrations between plant parts and first growth versus regrowih are also very different. In many populations there may be marked differences in both the amounts present and in actual alkaloid profile from one plant to the next. (i.e. plants in the same population and arising from the same seeds may show completely different chemistry, not simply differing concentrations.) See the amazing Festi & Samorini pieces listed in the Phalaris spp. page about cultivation for a review and overview of what is known so far.

Phalaris aquatica

- A major alkaloid in all samples they examined. (Culvenor et al. 1964)
- 5-MeO-DMT was not present in all clones examined (4 out of 12) Frahn & Illman 1973
- 5-MeO-DMT in leaf. 0.01-0.28% in material from California. (Festi & Samorini 1994a cited Welch 1971 ref Trout's Notes)
- var. AQ-1 (Italy) Weak occurrence reported (HPLC). (Festi & Samorini 1994b ref Trout's Notes)
- as Phalaris tuberosa - Strong in leaf. 2 Nov. and 17 Sept. 1995. Dec 1995. Assay. tlc by J. Appleseed 1995 (ref Trout's Notes)
- var Killer Phalaris (At one point this was synonymous with cv. Uneta, but has been in uncontrolled propagation for long enough this is no longer certain.) 5-MeO-DMT predominated in 25 June, 17 Sept., 2 Nov. 1995 samples. (DMT was predominate alkaloid in Fall 1994 by TLC) (ref Trout's Notes)
- Clone #R5 "large" amount of DMT (5-MeO? possible mistake in Trout's Notes) co-occurring with twice amount of 2-MTHBC (Clone, designated 405-9, originating with U.S. Regional Pasture Research Laboratory, University Park, Pennsylvania)
- Clone #R37 ·'trace" amount of 5-MeO-DMT co-occurring with " intermediate" amounts of hordenine and "large" amounts of 6-methoxy-2,9-dimethyl-1,2,3,4-tetrahydro-beta-carboline. (From highly diverse source population used in plant breeding and genetic studies at the University of Minnesota. Department of Agronomy and Plant Generics".)
- Clone #R51 ·'large" amount of 5-MeO-DMT as sole observed al.kaloid. [Same source as R37)
- Clone #R96 " large" amount of 5-MeO-DMT co-occurring with "trace" amounts of hordenine and "trace" amounts of 6-methoxy-2,9-dimethyl-1,2,3,4-tetrahydro-beta-carboline. (Same source as R37) (Gander et al. 1976. ref Trout's Notes)
- cv. Australian Commercial (CPI 119305) A major alkaloid in 7 day old seedlings. 150 nmol / 100 seedlings. (Mulvena & Slaytor 1983 ref Trout's Notes); In seedlings. (Mack et al. 1988); Mature 0.05% dry wt.(Baxter & Slaytor 1972)
- cv. Sirocco 51 nmol / 100 seedlings. (Mulvena & Slaytor 1983 ref Trout's Notes); Major base. (Frahn & O'Keefe 1971); 5-MeO-DMT in leaf (Ott 1994 cited Culvenor et al 1964; Baxter & Slaytor 1972; frahn & Illman 1973 ; Moore et al 1967; Mulvena & Slaytor 1982; Oram & Williams 1967 ref Trout's Notes)

Phalaris arundinacea

- 5-MeO-DMT in leaf and whole plant Barnes et al 1971; Culvenor et al 1964; Gander et al. 1976; Majak & Bose 1977; Majak et a!. 1978; Marten et al. 1973

Williams et al. 197 1. Many others.

- 0.0002-0.0067% 5-MeO-DMT in material from British Columbia. (Majak & Bose 1977)
- 0-0.02% in material from Minnesota. NRG741 was strongest of those tested & NRG721 the weakest. (Majak eta/. 1978)

Festi & Samorini 1994a

- TLC by Johnny Appleseed
- P.I. 172442 Turkey (cv. Turkey Red)0.0025% to 0.045% total alkaloid by wet weight. 5-MeO is predominate alkaloid. (J.Appleseed (undated manuscript); "Ayahuasca analog plants of the temperate zone." Tlc by Johnny Appleseed: fall 1994, 25 June, 17 Sept, 2 Nov. 1995. (ref Trout's Notes)
- cv Ottawa Synthetic : 5-MeO-DMT present, Amounts not given. Detected by TLC (Woods & Clark 1971 ref Trout's Notes)

Phalaris brachystachys

- PI 202676, PI 231044: 5-MeO-DMT reported, Appleseed tlc evaluation of field trials using USDA seeds. (ref Trout's Notes)

Phalaris canariensis

- PI 167261, and also 284185 (lower levels) 5-MeO-DMT reported, Appleseed tlc evaluation of field trials using USDA seeds. (ref Trout's Notes)
- Traces reported (HPLC). Festi & Samorini 1994b

Phalaris stenoptera (= P tuberosa var. stenoptera)

- Variable amounts. Festi & Samorini 1994b cited Rendig et al 1970 as finding 135-264 J.Lg/ml of expressed juice. (ref Trout's Notes)

https://wiki.dmt-nexus.me/5-MeO-DMT#Phalaris_spp.

Some more relevant information:

Phalaris brachystachys

An extremely strong occurrence of DMT was reported, using HPLC, in material from Portugal. DMT was the sole alkaloid. Festi & Samorini 1994b.

Strongly positive human bioassays have been reported using clones originating from both Algeria and Greece. DeKorne 1997.

30 grams of fresh foliage was reported to be too much by EH, MA (1997 Entheogen Review page 15).

Appleseed's assays detected 5-MeO-DMT in several strains obtained from the USDA GRIN; including P.I. 202676 & P.I. 231044 Greece. (The latter was found to be a spreading form with good biomass production).


Phalaris canariensis may be another species in dire need of more research, apparently being a generous seed producing cultivar of P. brachystachys.


Phalaris canariensis

Individuals containing a uniform distribution of DMT among their offspring have been identified and selected for cultivation [from PI#415822].

A similar undertaking was performed for a high 5-MeO-DMT producing strain [from PI#167261].

Both should become commercially available within the near future. Both tested solidly and appear as good or better than the P. brachystachys strains that were also tested. Both showed a clean profile with only one alkaloid present.

November 1999 update: While this was true of the USDA seed grown material and held true early in the field trials, after being grown out for several successive seed crops, both of the strains in question began to also show the presence of other alkaloids. Further seed production efforts were placed on hold until an understanding of this can be reached.

From:

https://www.erowid.org/library/books_online/ayahuasca_apa/aya_sec3_part2_phalaris_strains.shtml

Further research/gardening is warranted here I think!

[Handshake]

Oh yeah this is very promising indeed!!

Great compilation of info here Bancopuma.

I spoke with Dennis McKenna about this possibility and he also seemed to think Phalaris grass would perhaps be the best option. The next question would be a matter of testing, which it seems ForeverChanging could help with doing a formal assessment of some of these grasses. Also I think it would be worth seeing what other compounds are present in the grass and if any produce negative side effects (gramine for example).

[nottwo]

I did an extraction of Phalaris arundinacea about two years ago with very mixed results. I'd heard a lot of varying advice about best times to harvest it, such as early in the morning, or which part of the grass contains most tryptamines. I found an area covering many acres of public land and picked about 2 kg in the afternoon. I didn't have the chance to do an extraction until 2 weeks later on the material. I ended up with a relatively small amount of brownish goo, despite my best attempts to get crystals. I vaped a quantity, probably 15-20 mg, and thought at first that it had had no or very little effect. However about 15 minutes (not seconds!) later, some sort of tryptamine effect came on with open eye fractals and weird body sense. The main effects faded after about 10 minutes and took about another 40 minutes to completely disappear. My guess would be some sort of tryptamine but not 5-meo or nn-dmt.

[Handshake]

Interesting about your extraction of Phalaris arundinacea! And very interesting effects. I wonder why the effects took so long to come on! Usually when vaped, the onset is much quicker for molecules of this nature.

With a concentration of 0.0025% to 0.045% wet weight, it seems that 2kg would at most yield 90mg. The fact that it was difficult to get crystals speaks to the potential problem we would have of isolating the target compound. That would perhaps be one of the biggest challenges in the plant extraction world of 5-MeO-DMT.

[nottwo]

I boiled the grass with successive quantities of weak citric acid solution but with 2 kg of starting material that means you end up with a large amount of liquid. The main problem was getting rid of any solid in the liquid. I filtered several times then reduced the quantity of liquid over a low heat but this seemed to produce a lot more solid. I used a mixture of letting it settle, pour off the liquid, filter, reduce to half then repeat - several times. After basification, the liquid went from light browny green to darker brown. Lots of the brown came across when adding the NP solvent and attempts to purify it seemed to result in losing everything.

If anyone wanted to try this on a more scientific basis, I'd recommend the use of a buchner filter, which I don't have.

I have no explanation for the delay in the effects. Normally a vaped substance will either cross the blood brain barrier almost immediately or it won't cross at all.

[jamie]

You are not off on the delay. Some strains of phalaris have that effect on myself as well, suggesting novel beta-carbolines/tryptamines present..this is especially true in my experience of Phalaris Arundinacea. The grass also needs a diff extraction tek than what you can get away with when it comes to other more well understood tryptamine sources. I reduce the water extractions all the way down to resin, base and pull with dry ethanol or iso..filter well and evaporate..convert the goo back to a salt and pull with water..filter well and envaporate..back to base..then start np solvent pulls. It's to easy to loose the alkaloids otherwise if you try to go a simple A/B route.

[/size][size=78%]Hi Banco[/size]

I will try to add what I know to the discussion. 


First, anyone who is really considering extracting and ingesting phalaris extracts should become familiar with what we already know at the nexus. No need to repeat the past with something as complicated as phalaris genotypes etc..


https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=48635


https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=16810


https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=29986


https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=407613
^ for anyone who ever doubted the existance of a phalaris crystal
 
..and his pdf..this guy really deserves respect for being one of first I know of..
https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=28869


Volume 3 Issue 1 of Dragibus my article "Phalaris Entheogenesis" I discuss my experience growing/extracting/bioassaying a number of strains. I am not sure if that text is availble online somewhere..I may be able to link it here later.


So..what do we know now that DeKorn etc may not have?..one..gramine is not the toxin once thought..that is totally up in the air afaik, and neither it nor any of the other alkaloids of the phalaris genus are thought to be responsible for the phenomenon of "sheep staggers". The theory now involves infected grass.


okay..hordenine..also perhaps non toxic and consumed as a supplement by many..also present in lophophora etc..but we are not interested in gramine or hordenine. Simple..neither come out of an extraction in relevent levels when naptha is used as a NP solvent, and the alkaloids are precipitated out as tryptamine and beta-carboline salts
to then be converted back to freebase..or whatever..


When talking about chemotypes, most people are going off of DeKorns work, which suggested 3 main pathways for the synthesis of alkaloids in Phalaris Arundinacea. Those unfamiliar should reference his work and become familiar. It is not so simple. For instance, wild grass collected in the PNW, extacted and analyzed via gas chroma showed DMT, NMT, 5-MeO-NMT, 2MTHBC and 6-MeO 2-Me-THBC...the 6MeO2MeTHBC was the main alkaloid, by a large margin. The second highest and main tryptamine present was 5-MeO-NMT. DMT and NMT were present at levels 4x lower than 5-MeO-NMT. No 5-MeO-DMT was found. This throws off the theory..if the tryptamines are going to methylate you would assume to find both 5-MeO-NMT and 5-MeO-DMT..esp with both DMT and NMT present..where is the 5-MeO-DMT? I think this is far more complicated. Phalaris Arundinacea has a very broad chemical phenotype. Extraction processes cannot be ruled out as missing stuff either..nor can analysis..but still the gas chroma is telling enough. I can talk more about arund later..because my experience with it is all over the place.


The strain I currently experiment with is Phalaris Aquatica cv australia. It is an australian cultivar of aquatica thought to have originated in greece and perhaps be synonamous with the AQ1..


k..more on that next post..

[Handshake]

Fascinating information jamie!

I tried going to the Nexus to view those PDFs but unfortunately they were nowhere to be found. People in the thread were talking about the PDF but I didn't see anywhere to download it?

Phalaris grass is indeed a very fascinating direction for plant-based 5-MeO-DMT discovery, right up there with acacias as possible sources...it seems that Virola resin is much too difficult to do a proper extraction on. That being said, Phalaris also seems tricky. Luckily we have pioneers like you who are discovering what can be done with Phalaris!

Please do link to your Dragibus article if/when you do find it.

The gramine fallacy is an intriguing new development! I was always concerned about what when I had read it in the past.

[gurudedicationananda]

OP, thank you for this wonderful information and starting this great thread!
I wanted to ask you something.
If I had the dried clippings of the correct strain (5-meo-dmt containing) of Phalaris grass, which I believe is brachystachys, and chopped them into a fine powder and soaked it in 91% isoproply alcohol with washing soda (base), shaking periodically, and let it soak for 24 hours or more, then filtered the material and evaporated the liquid, would I be left with a resinous or smokeable substance which contained a high amount of 5-meo-dmt?
In other words, could I extract with iso and washing soda, filter, and evaporate, then be left with a smokeable 5-meo-dmt-containing material?
I cannot find the answer to this anywhere.
Thanks!

[jamie]

That is a question with a complex answer. First of all, brachystachys is a species not very well explored for it's entheogenic potential. A number of species( arundinacea, aquatica, canariensis etc) all can express chemotypes that will be 5-MeO-DMT dominant. Any number of alkaloids could be present in unkown ratios with random genetics. Brachystachys is seems to be a more stable producer of DMT/5-MeO-DMT at higer levels than arundinacea.


You will need to either defat or salt the tryptamines out of a non polar solvent to end up with anything you would want to smoke or vaporize. Also, be aware alkaloids such as hordenine are alochol soluble.


The only way to know is to grow it out and test it, however I never suggest anyone go out and ingest plants of questionable chemistry and murky at best historical use. Be safe.
 

[Handshake]

That is a question with a complex answer. First of all, brachystachys is a species not very well explored for it's entheogenic potential. A number of species( arundinacea, aquatica, canariensis etc) all can express chemotypes that will be 5-MeO-DMT dominant. Any number of alkaloids could be present in unkown ratios with random genetics. Brachystachys is seems to be a more stable producer of DMT/5-MeO-DMT at higer levels than arundinacea.


You will need to either defat or salt the tryptamines out of a non polar solvent to end up with anything you would want to smoke or vaporize. Also, be aware alkaloids such as hordenine are alochol soluble.


The only way to know is to grow it out and test it, however I never suggest anyone go out and ingest plants of questionable chemistry and murky at best historical use. Be safe.

Really well put jamie, +1.

Would you be able to speak to some of the questions I posed in response to your previous post?

[jamie]

Hi HumbleVoyager..I have not had time this week to dig up that article online yet..stay tuned


Okay..let's talk about Phalaris aquatica.
 
Phalaris aquatica is a warmer weather perennial grass, which grows with less vigor than Phalaris arundinacea, and spreads much slower from rhizome divisions. The alkaloid profile of this species appears somewhat more stable however than that of P. arundinacea. A number of strains have been selected as high alkaloid producers, useful as potential sources for entheogenic tryptamines.


My own experience has been with conventional seed grown varieties of P.aquatica as well as the strain known as cv. Australian. Phalaris aquatica cv. australian is a strain that was selected for its high alkaloid profile, dominant in DMT, followed by 5-MeO-DMT(Trout (referencing Mulvena and Slayter, 1983( 2007). For over a year I grew out two pots of this strain from seed. Once established the grass can be repotted and will spread via rhizomes. It is slower than P. arundinacea and seems more sensitive to light and water fluctuations.


In the summer of 2014 an unknown but small amount of fresh clippings were collected and frozen for later extraction. There are theories surrounding the freezing and drying process and alkaloid ratios/levels, however this I cannot yet comment on.


The grass was boiled in 3 times in a solution of water and acetic acid. The resulting liquid was well strained and evaporated, yielding a very impure goo/resin. Calcium hydroxide and a small amount of water was added to the resin, mixed, and the mixture was left to dry. This was powdered and extracted three times with hot *sunflower oil. To the oil a mixture of water and acetic acid was added and mixed to allow the alkaloids to migrate to the water as tryptamine and beta carboline acetates.


The solution was filtered through wet cotton to remove any sunflower oil contamination, and evaporated to yield a waxy material. Sodium carbonate was added, then water and mixed into a paste. This paste was powdered and extracted three times with 99% isopropyl alcohol to yield a small ammount of yellow waxy crystal smelling of indole when vaporized.
 
So, the old literature for this strain has a 2/1 ratio DMT/5-MeO-DMT (Trout), and alkaloid content of .15% dry weight in one finding(Trout). Thats .1% DMT and .05% 5-MeO-DMT. This strain is also thought  by some to be the same as the AQ1 strain, both believed to originate in Italy. More work needs to be done to say much about alkaloid levels for this strain, especially if this and AQ1 are synonamous. AQ1 is reported up to 1%(Samorini, 2002).


The extract, weighing 22mg was cautiously vaporized over a short period of time. Visual phenomenon was hardly present, and instead an empathic and euphoric tryptamine energy rushed through my body. The effect built to a peak at around the 2 minute or so mark, and maintained a plateau for 10-15 minutes before tapering off slowly. The state was clearly tryptamine and familiar of very low dose 5-MeO-DMT, likely in ratio with a number of other tryptamines and beta carbolines. The extract had a clean and meditative feel to it. I know only of one other person who has used this strain, as australian acacia researcher who also has similar experience with it. This, along with AQ1 I would suggest folks stick in they're gardens for the future.


I have not gotten around to extracting from this strain again yet. In the future I plan to runing TLC on the extracts.


I have added this grass to brews with peganum harmala and other plants. That is something to discuss later because unextracted phalaris as ayahuasca or "ayahuasca analogue" admixtures brings up a number of issues.


* A number of vegetable oils, including sunflower oil have been shown to be of use as non polar solvents in the extraction of tryptamines. These oils require modified extraction teks to work.


References


-Trout, Keeper. Ayahuasca: alkaloids, plants & analogues. 2007. Retrieved from http://www.erowid.org/library/books_online/ayahuasca_apa/aya_sec3_part2_phalaris_strains.shtml


-Samorini, Festi. "Ayahuasca like" effects obtained with Italian plants. 1994

[jamie]

https://www.dmt-nexus.me/forum/resource.ashx?a=9388
 
Does that link work? It should bring you to the PDF on Phalaris brachystachys by fourthripley.


Also I think an article acacia/tryptamine researcher nen888 and myself on tryptamines in issue 2 of the nexian might be of interest. I have another article in that issue covering some of my exoerience with wild Phalaris arundinacea, from the PNW coastal region of British Columbia.


http://the-nexian.me/the-nexian/the-nexian-issue-2

[Handshake]

Amazing posts! The Phalaris extract that you did sounds fascinating. I am highly curious about this, as a friend of mine has been begging me to look into waxy extracts containing 5-MeO-DMT and the effect you described sounds exactly like what they experienced!

As for the link, here’s a screeenshot of what I got when I clicked your first link...

I’ll check out the other article!

[Handshake]

PS - Could you share the source for the info regarding the sheep staggers?

[Flux]

Thanks Jamie for this incredibly valuable contribution... This method makes Phalaris extraction look relatively straight forward with an achievable result.


HumbleVoyager here is the pdf attached