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Phalaris Canariensis - Extraction Attempt, First Batch Options
 
Vodsel
#1 Posted : 8/24/2012 10:00:40 PM

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Before anything, I was unsure about appending this to endlessness' Phalaris Analysis Thread, since it's still a very basic work and my analytical skills are pretty green. So I'm leaving it to the mods consideration.

One of the hurdles in growing phalaris is the price and availability of seeds for already valuable strains for the community. Phalaris Canariensis, the common bird seed, hasn't been one of them. However, and according to the HPLC analysis by Fabio Calligaris attached of the end of the 1994 Festi and Samorini paper, shared by endlessness in the first post of the mentioned Analysis Thread, the relative alkaloids content of portuguese P.Canariensis is marked as a 2/5.

That bit, along with the fact the P.Canariensis seed is extremely common and affordable in western Europe, made me think it was worth to give it a try in my first attempt with Phalaris.

So, this is my first report - work in progress.

I bought a pound of seeds in my local herbal store for $6, and I germinated a little bunch of them easily indoors under Cool White fluorescents, moving the established sprouts outdoors and giving them a few hours of morning sunlight. The plant grew easily, I fed her every two weeks with a moderate nitrogen solution, and I waited for two months (see photo #1) before harvesting early in the morning a small batch of top leaf cuttings, aproximately 25 grams.

- Leaves were blended in a food processor immediately after harvesting. The texture obtained was not as uniform as what you would get with a wheat juicer, but seemed fair enough to work with.

- The blended leaves were added to a cooking pot with distilled water and a dash of white vinegar, and slowly boiled for an hour, keeping an eye on the water level and refilling when necessary.

- Contents were poured through a cloth filter, and the plant material recovered for a second boil. Both acidic extractions showed a promising color according to the Phalaris teks I know (see photo #2). Liquid was reduced and poured through a coffee filter paper to a mason jar.

- 4 grams of lye were dissolved in hot water and added to the reduction for basifying. That immediately produced a generous amount of precipitate (see photo #3). pH was checked with a litmus paper going virtually off the chart, which should equal 12-13.

- I wanted to use a selective solvent, so I measured 30 ml of hexane and added them to the jar. Analysis so far suggests that undesirable alkaloids such as gramine and hordenine are not particularly soluble in it.

- Proceeded to mix, and let it separate layers for a couple hours. I should have waited longer actually, since after that time I could still see a thin layer of precipitate right between the solvent and the basic mix; that layer has completely disappeared the morning after. I apologize for not providing pictures for this step, I basically forgot.

- The hexane was pulled with a glass dropper and poured in a pyrex evaporation dish. I decided to stay with one pull, reserve the mix and see what I got there.

- The following morning I found in the dish a thin oily layer, with a very slight yellow tint, and an unmistakable smell of tryptamines.

I tested a little amount of the result (rubbing a little improvised blotter in the oil) with reagent Marquis. The initial color reaction was a light-medium brown, slowly darkening after that. The color result agrees with N,N-DMT according to the information provided by endlessness here. You can see the sample color after one minute in photo #4.

I think the results so far are promising. Reports also say that the first re-growth after cutting will deliver the highest alkaloid content in Phalaris strains, so theoretically a second harvest will give better results than the ones obtained so far with just a simple pull.

I have not bioassayed the oil yet. Before that, and even before doing some additional pulls, I wanted to share this and open wide my ears for any comments or suggestions.

Also, I'd like to find a way to ID the precipitates in the solution. I presume TLC is the way to go, so I'll try to learn about that soon and find the required materials.

Thanks for reading Smile
Vodsel attached the following image(s):
plant.JPG (166kb) downloaded 988 time(s).
reduction.JPG (91kb) downloaded 980 time(s).
precipitate.JPG (65kb) downloaded 986 time(s).
marquis.JPG (65kb) downloaded 983 time(s).
 

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acacian
#2 Posted : 8/25/2012 11:02:55 AM

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awesome work mate great to see someone giving the extract a go! .. always see posts by people who are just about to do it and then never hear from them again
will be interested to hearing your bioassay and TLC results..

Smile
 
Ambivalent
#3 Posted : 8/25/2012 3:01:29 PM

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yea, great work Vodsel. really appreciate you posting your results.
 
Vodsel
#4 Posted : 8/28/2012 10:31:50 PM

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Leaving a little update.

Two more pulls and evaporation left more of the same oily residue. Another test with reagent Mandelin gave an orange-ish yellow which again is not bad news.

In order to weigh the little yield, the oil was dissolved in acetone and evaporated in a pinch of previously weighed herbs. The product was roughly 45 mg, which equals a 0,2% yield of that oily product (keep reading) in the first trimming of canariensis leaves.

Bioassay has been made today with a GVG. To be in the safe side due to the possibility of 5-MeO, the equivalent to 10 mg were vaporized first with no noticeable effects. Another 35 mg were loaded and vaped immediately afterwards. The result: pre-threshold sensations. I think there is N,N in the oil (subtle humming, sweat in the brow, familiar aftertaste, and my also familiar tryptaminic clarity in the after-effects) but if I had to make a guess according the subjective effects and my experience, I'd say that only 5-10 of those 45-50 mg of oily residue were N,N or oxide.

Which agrees with the literature. I was hoping to give you guys some cool results, but the outcome is rather meh. However, it does seem possible to extract a smokeable amount of N,N-DMT from phalaris canariensis using good growing technique and a large amount of plant material. But even then, the amount of other plant oils would be too significant. Clearly suboptimal considering the alternatives.

Conclusion: I will make another attempt with the first re-growth of the plant (generally delivering higher alkaloid concentration in other phalaris) and a quite higher amount of material in a couple weeks. If I shamelessly keep from updating, you can assume that the results were negligible.

Love to all.

 
jamie
#5 Posted : 5/1/2013 4:08:24 AM

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any updates? Im going to get some canariensis seeds. I found out it does grow wild where I am but I have never seen it.
Long live the unwoke.
 
nen888
#6 Posted : 5/1/2013 4:34:14 AM
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..good work Vosdel thanks..

i heard it was the seeds of P. cannariensis which had the highest amounts of DMT..
but can't confirm this myself..
 
jamie
#7 Posted : 5/1/2013 6:18:53 AM

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"I wanted to use a selective solvent, so I measured 30 ml of hexane and added them to the jar"

Thats a big mistake I think when working with grasses that many make. I would never use such a selective solvent when working with grasses because a good portion of the content could possibly be oxides..so far that is just a theory though..maybe there are no oxides.

Even so the small ammount you got does not sound bad at all for 25g fresh grass. That sounds pretty good to me. 45g of fresh viridis or alba would prob not give you that much either..the water weight of grass is pretty high in my experience..so that yield dry is not to bad.
Long live the unwoke.
 
Vodsel
#8 Posted : 5/1/2013 1:00:50 PM

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nen888 wrote:
i heard it was the seeds of P. cannariensis which had the highest amounts of DMT..
but can't confirm this myself..


Thing is, P. Canariensis seeds have been widely sold as dietetic supplements... it would be surprising to find significant alkaloid amounts in a material that is regularly consumed in ounces by many people. Regarding the claims by Johnny Appleseed, genetic variability may come into play... But having easy, cheap access to large amounts of seed surely deserves a few tries. Shortly after the leaf extractions I attempted a dry tek mixing ground seeds with lime, hydrating the mix and pulling with hexane. The extract was not active, but the method used takes me to...

jamie wrote:
I would never use such a selective solvent when working with grasses because a good portion of the content could possibly be oxides


The original idea was testing Canariensis specifically for N,N following the reports in literature. Hence the hexane. Considering the results, another extraction with DCM or another less selective solvent might be interesting... I did not have means for accurate analysis when I tried and I did not want to ingest unknown wide spectrum yields.

However, I still have a large amount of seed. Suggestions for further experimentation are welcome.
 
shanedudddy2
#9 Posted : 5/1/2013 2:35:22 PM

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Quote:
i heard it was the seeds of P. cannariensis which had the highest amounts of DMT..
but can't confirm this myself..

Woah, that would be awesome. Source?
 
Vodsel
#10 Posted : 5/1/2013 2:48:01 PM

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shanedudddy2 wrote:
Quote:
i heard it was the seeds of P. cannariensis which had the highest amounts of DMT..
but can't confirm this myself..

Woah, that would be awesome. Source?


The only original reference I know of is a little obscure, and comes from an anonymous letter to The Entheogen Review:

Quote:
MIND-ALTERING BIRDSEED
Maybe we should call this "B.S. DMT" (Birdseed DMT)! So you think maybe this is a joke? A friend of mine recently chromatographed some Canary grass seed and he says some strains checked out quite potent! It's an annual and it must be replanted every time you want to grow some more Ayahuasca, but don't let the birds get to it first! Maybe the U.S. Govt. will outlaw birdseed in Pet Stores! I am sure that some strains are better than others, but anyone wishing to join in on the "Ayahuasca analog research" fun can purchase 3,600 seeds of Phalaris canariensis for only $8.00 from: (...)


We'd need more sources to make the claims reliable. And again, there can be big variations in alkaloid contents between Phalaris strains... I doubt high DMT levels will be found in the commercially available variety found in dietetic stores, but I'd love someone to prove me wrong.
 
jamie
#11 Posted : 5/1/2013 5:24:40 PM

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canariensis is introduced where I am just like arundinacea..and there are wild populations of it listed in some UBC articles abotu 10-15 minutes down the highway from me in wetland..concidering I live in that same wetland sort of on the side of a river delta where it meets the ocean I assume it gorws right where I am also..I just need to go look for it I guess.

I just realized though, that there is a bird sanctuary nature reserve area abotu 15 minutes from me also in that same wetland area..and people must throw birdseed all over that area because I remember them selling it there to feed the birds with..so if the stuff grows here in the wild and people throw the birdseed all over I would assume that I can find that grass growing in that area.

I would not mind a large shopping bag full of canariensis to play with...
Long live the unwoke.
 
shanedudddy2
#12 Posted : 5/2/2013 10:25:25 AM

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Has anyone tested the seeds of Phalaris aquatica or arundinacea?
 
Vodsel
#13 Posted : 5/2/2013 11:12:26 AM

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Not that I have knowledge of, although probably someone has... the problem with other Phalaris strains is precisely the low availability of seed and its price, so using seeds as extraction material (even if the yield was significant) doesn't sound efficient.

Canariensis is an exception because it can be easily found commercially in bulk.
 
skogen
#14 Posted : 6/10/2013 8:29:48 PM
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Very interesting. Any updates?

Just started growing some P. Canariensis seeds from a birdseed mix. They are starting just fine (about 6 cm in five days). Wonder if there are some goodies in this grass...
small-scale phalaris farmer
 
MaNoMaNoM
#15 Posted : 9/22/2013 9:22:42 PM

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GREAT WORK!! This thread fills me with much joy to think that the bird seed growing in everyones grandmothers yard could contain some active alkaloids, and could even be the best source of the future! Hope to get some growing here soon.
*ALL WAYS WITH LOVE
 
Vodsel
#16 Posted : 10/4/2013 9:40:11 PM

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I only want to leave a few notes with some analysis.

The strain I was using is the commercial P. Canariensis seed sold in diet stores in my country, western Europe. Literature suggests that Canariensis may be a domesticated variation of Brachystachys, and that possibility only makes research interesting, but commercial varieties have been selected and manipulated for human consumption.

For instance, take the "glabrous" common variety I've used. Birdseed used to have hairs in the seed shell (like brachys), and since research related those hairs to esophageal cancer, the strain sold for human consumption does not have them anymore. The selection performed might have targeted alkaloid content as well, or resulted in a change in alkaloid content.

Following the results in a paper published in Plant Physiology (N,N-Dimethyltryptamine Production in Phalaris aquatica Seedlings - Mack, Mulvena and Slaytor 1988, leaving paper attached) I sprouted commercial birdseed in two batches, using only water in one and a dilution of nutrients in the other. Seedlings were harvested after a week (the paper detected a peak concentration of N,N in 8 days in the case of aquatica, concentration decreasing in the rest of the seedling stage) and a simple extraction was performed with birdseed and each of the two little batches of sprouts, using acetic acid, sodium carbonate and IPA.

All three samples were tested in TLC using N,N as a fourth control sample. No DMT was detected in the seeds or in the week-old seedlings of this commercial birdseed strain.

There was a couple faint spots in the seedling columns that I haven't been able to identify, but do not correspond to NMT or DMT. I do not have the 5-MeO reference value for the eluent I'm using in TLC, so that cannot be ruled out completely, but as a summary:

There is a low indole yield in the first regrowth of P. Canariensis grass extracted in the late summer, grown from commercial dietetic strain. A significant yield apparently would have required a large amount of grass using this variety, most likely 2x the required amount of aquatica or more.

For anyone wanting to try other commercial strains as potential sources, extraction and analysis of large amounts of sprouts might be interesting, but for several reasons, any wild varieties of P. Canariensis seem more promising than the ones available in dietetic stores.
 
dreamer042
#17 Posted : 10/4/2013 9:50:37 PM

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Good information! Thumbs up

Thanks for this.
Row, row, row your boat, Gently down the stream. Merrily, merrily, merrily, merrily...

Visual diagram for the administration of dimethyltryptamine

Visual diagram for the administration of ayahuasca
 
Intezam
#18 Posted : 8/24/2014 12:45:29 PM

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Sorry for bumping an older thread, but we really wanted to say thank you Thumbs up for this and also for the bold bio essay Shocked . It would be interesting, how the "bird food only" variety of phalaris brachystachys var. canariensis (canary seed from pet shops) would perform (asuming that the trademarked dietary pureza silica fiber freeā„¢ canaryseed variant was used by the thread starter), using careful plant stressing (light & water & nutrient deprivation, secondary growth cuttings, timing, season ....etc) would perform in conjunction with inmediate everclear misting of freshly cut leave blade material, followed by inmediate juicing (manual wheat grass juicer with snail), boiling of juice, when the green clorophyl coagulate splits, straining it off, discarding the clorophyl, leaving that orangey liquid, then, that being acidified (vinegar, citric acid...etc) then based and salted with table salt, then adding hot naphtha, stirring (some pulls), saving the naphtha and then doing a mini defat by adding water in a bottle, bring down the ph again using acid, adding the "enriched naptha saved earlier and shaking the crap out of it, then dicarding that naphtha, then performing a new basifying step, adding fresh warm naphtha, pulling it until done, precipating it, doing recrystallization (if need be) by adding a seed crystal..... ?

(Is it possible, using the mixer/blender causes massive oxidation, enzymic alkaloid degeneration and unwanted plant oil release? How would the same tek perform with p.brachystachys (wild) and comparing the results)? It could be interesting to do a side by side tek of the two. As far as we understood, the canariensis var has been bred foremost to reduce seed loss by selecting varieties of barchystachys that do not prematurely shed their seeds and have a more uniform seed formation, having larger seed, in addition the variety used in dietary stores may have also been bred to get rid of silica, hairs..etc? They have not been bred for low alkaloid content? Basicly, it is still p.brachystachys so more research needs to be done on other srains. Also, since it is a mediterranean grass, it may have certain light & soil requirements, and alkaloid profile could change if grown elsewhere? How much 5-MeO is in there, and is it as consistent as p. brachystachys in regard to it's alkaloid profile? Would it be safe to bio eassay with a MAOI the fresh juice? If in p.brachystachys (wild) a teaspoon full would be a strong dose, even if one were to need a half cup from p.b.canariensis wouldn't it still be a blessing not to be neglected?
We believe we should not let this one go just yet.....it's just a hunch....(...if it looks like a duck...walks like a duck.....)

Trout's notes wrote:
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

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

Nov. 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 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.

Perhaps p.canariensis would (within a couple of plant generations) revert to it's original wild state, if released into a disturbed area and left to struggle....also, we've got a hunch that "alpiste" canary seed (bird only) from Portugal could be a better choice...(?)

nen888 wrote:
I heard it was the seeds of P. cannariensis which had the highest amounts of DMT..
but can't confirm this myself..


If there is any truth in that, we just found out there is a powdered product called leche de alpiste (milk of canary seed) so if there is any spice in the seed, this stuff is already de-hulled and powdered, they do have a medication and pregnancy warning on the label, so they might just be something in there....

We would do all that testing (gladly) but we would need to collect a whole lot of pop cans first and there are other things we need more urgently (like a GVG) but we really do need a wheat grass juicer.

the attached pdf tek & bio essay is from fourthripley, we do not remember in which thread we found this...al credits go to fourthripley.

 
_grass~amine_
#19 Posted : 10/27/2019 3:40:47 AM
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