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~Phalaris = The Way Of The Future~ Options
 
benzyme
#81 Posted : 11/14/2011 1:10:45 PM

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me too.

sublimation is a separation method (purification), but it is really tricky for this application. vacuum distillation has also been discussed, but product tends to accumulate in the condenser rather than the collection flask
"Nothing is true, everything is permitted." ~ hassan i sabbah
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polytrip
#82 Posted : 11/14/2011 3:38:44 PM
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Ginkgo wrote:
I just had an idea. DMT has a melting point of 44-68°C, 5-MeO-DMT of 66-70°C. Gramine doesn't melt before 138-139°C, and other impurities have melting points such as 88°C for NMT and 117-118°C for hordenine. If you were to warm an impure extract to no more than 70°C, the DMT and 5-MeO-DMT should become liquids, while the impurities should stay as crystals. If you were to warm this extract from below in a coffee filter, cheesecloth or similar, the liquid should pass through, while the impurities should stay as crystals. Couldn't that be an efficient way of removing gramine from an extract? That is, if the DMT and 5-MeO-DMT would really pass through.

On the subject of gramine, I've found some more literature, and it points to what nen888 said, that gramine isn't toxic in small doses. Still I think we should be cautious. It is a medium potent 5HT-2A antagonist, which means it will counteract effects of DMT and similar psychedelics, as they do most of their magic on that very receptor type, so gramine should nevertheless be removed from an extract. We also need a way to separate DMT and 5-MeO-DMT. Maybe one of their salt forms have different solubility properties, enabling one to separate them.

Hordenine is a stimulant, by the way, it is well documented as a stimulator of the release of norepinephrine, and is used by body-builders.

I think that gramine could very well be soluble in liquid DMT, given their simmilarity.

Maybe if you would use another liquid that normally doesn´t dissolve DMT or gramine, heat it untill it has the right temperature and then use it to extract the DMT. The DMT would melt, but also maybe immediately be separated from the alk mixture when it flows through the filter with a certain speed (so it doesn´t get the time to dissolve the gramine).
 
endlessness
#83 Posted : 11/14/2011 5:53:41 PM

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I think we're over complicating ourselves with gramine and hordenine.. Once again I'd like to point out that both gramine and hordenine are, according to merck index (as also written in our wiki), NOT soluble in petroleum ether ( = naphtha), so simply pulling with naphtha or doing couple of re-x should get rid of them. In any case I will test this in the next month or so with pure gramine and will let you guys know.

With 5-MeO-DMT and DMT ,though, then yes the column work might be necessary.
 
benzyme
#84 Posted : 11/15/2011 12:13:23 AM

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i've been saying that for the past two years.

I guess people would still rather invest in rootbark than a chromatography column
and some silica.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Dorge
#85 Posted : 11/15/2011 7:14:26 AM

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benzyme wrote:
i've been saying that for the past two years.

I guess people would still rather invest in rootbark than a chromatography column
and some silica.


Well that and the education to simpley use them... But hey...
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benzyme
#86 Posted : 11/15/2011 1:00:09 PM

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wellll.. it's an applied art, just like drawing or painting,
but you don't necessarily need to go to art school to do either

can be self-taught, and practice is essential
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Dorge
#87 Posted : 11/15/2011 11:27:24 PM

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Agreed... But it's slightly out of the range of most of our mhrb mason jar kitchen chemists. Even the simple ease of distilling is a lost art to most.
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smri
#88 Posted : 11/16/2011 2:33:51 PM

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Sorry if this is too old of news, but has anyone seen this?

http://www.erowid.org/pl...ris/phalaris_info1.shtml

Seems to contain some good info. Also, has anyone heard of juicing Phalaris with a wheatgrass type juicer, evaporating the juice, then using the dried substance to vape/smoke and or use for the A/B first used in this thread?

I imagine this would leave too many harmful alkaloids, but I saw that from the same link I got this and thought I would mention. Since I would really like to start using Phalaris for sustainability reasons this really interests me. Great work everyone, this has been a super useful thread.
 
polytrip
#89 Posted : 11/16/2011 2:56:47 PM
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smri wrote:
Sorry if this is too old of news, but has anyone seen this?

http://www.erowid.org/pl...ris/phalaris_info1.shtml

Seems to contain some good info. Also, has anyone heard of juicing Phalaris with a wheatgrass type juicer, evaporating the juice, then using the dried substance to vape/smoke and or use for the A/B first used in this thread?

I imagine this would leave too many harmful alkaloids, but I saw that from the same link I got this and thought I would mention. Since I would really like to start using Phalaris for sustainability reasons this really interests me. Great work everyone, this has been a super useful thread.

There is a dutch ayahuasca site, that mentions using a juicer to make a directly drinkable juice.

Making juice could be a good first step. I don´t know if it would be more efficient than extracting as a first step in the proces of obtaining pure DMT.

You can extract a whole lot of plant material at once.
 
Dozuki
#90 Posted : 11/16/2011 7:40:08 PM

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Back to Toxicity for a moment. While going thru new and old (to me) articles on Phalaris in general I ran into this: Anderton et al 1994 found high levels of N-methlytyramine in the water soluble fractions of P. aquatica extractions. They also found levels of the parent tyramine compound.

These compounds are de-toxified by MAOa and if a MAOI were to be used with an extract of P. aquatica such as just boiling in dilute acid (think ayahuasca) a hypertensive crisis could ensue. It has been hypothesized that these compounds coupled with the inherent beta-carboline compounds (MAOIS) in P. aquatica may be one of the mechanisms in the ruminant Phalaris toxicity.

Phalaris aquatica should not be used in a 'traditional' type of ayahuasca brew, nor extracted juice via wheat grass juicer nor aqueous extraction. The alkaloids need separated from the aqueous portions of any extract.

I did a great deal of looking into P. arundinacea as well and could find no reference to any tyramines other than hordenine. However, this doesn't mean they aren't there, just that there are no reports of them.

The info that I found on hordenine itself is that it is not oxidized by MAOa (the main MAOI in the gut) and has a similar action to a MAObI by being preferential to MAOb.

-D.
 
Ginkgo
#91 Posted : 11/16/2011 7:58:00 PM

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I've not found the Anderton et. al (1994) article, "Identification of a toxin suspected of causing death in livestock grazing Phalaris pastures", online, could you please post it here if you have it? I've never heard of high levels of tyramine-compounds except hordenine in any other studies, only trace amounts, so my suspicion is that they are involved in the biosynthesis of other alkaloids, and the authors of the paper just happened to find a population in a certain stage of the development.
 
endlessness
#92 Posted : 11/16/2011 8:32:00 PM

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Here's what Trout has to say about phalaris stagger/toxicity. Note he starts talking mostly as an answer to those who claimed tryptamines such as DMT and 5-MeO-DMT were responsible, but nevertheless theres some very interesting discussion on other possibilities, as well as his own hypothesis of what is (are) the cause(s):

Trout's Notes wrote:
Intensive breeding efforts to produce low tryptamine strains of Phalaris arundinacea were undertaken, in the US, ostensibly to decrease animal fatalities, in spite of the following demonstrable facts:
1. Highest numbers of animal deaths occur during the times when the tryptamine content was proven to be lowest (by
separate workers in Australia and US),

2. "Low alkaloid' strains of Phalaris aquatica are found to produce higher numbers of dead livestock than "high alkaloid' strains when compared directly,

3. Phalaris arundinacea has NEVER caused any occurrence of staggers in the US: and only two incidences worldwide
(Simpson et al. 1969 & Ulvund 1985] despite it clearly being on record as deliberately cultivated & utilized for forage for over 200 years.

Many workers appeared to operate as if the causative link between 5-MeO-DMT and Phalaris staggers was already
proven (almost as soon as the presence of dimethylated tryptamines was first reported). The known ability of DMT and 5-MeO-DMT to produce a green pigmentation in vitro using enzyme preparations of cells has caused a similar green pigmentation found in animals which died from chronic Phalaris staggers to become both regarded as diagnostic evidence and proof that such methylated tryptamines are the causative agents despite Gallagher's utter and complete failure to observe this pigmentation in any animals afflicted with acute or peracute staggers (This was true whether the
animals recovered or died).

It must be remembered that Gallagher was only able to mimic some of the acute stagger symptoms with the N-dimethylated tryptamines and was entirely unable to reproduce either the chronic effects or degenerative neurological changes like lesions.

I might also mention tha bufotenine was reported by Gallagher to be more active than DMT and produces a brown pigmentation (as does serotonin) under similar in vitro conditions. (Using bufotenine bioxalate. Gessner et al. 1960 reported that deaths of rodents given intraperitoneal administrations of 6 divided doses, of what WOULD have been a lethal dose of given all at once, were delayed by around a week with an apparent return to normalcy after the acute effects wore off.

They could not find anything unusual except for "acute thoracic kyphosis accompanied by a cervical hyperextension ofthe
spine" as well as dehydration and loss of around 1/3 of the totalbody weight. (4 out of 5 rats died this way) The length of time suggests it might be worth looking into some sort of secondary problem resulting from the mechanical aspects of the interperitoneal injection itself in terms of actual site of delivery or infection potential? I have witnessed this performed on rats a good number of times. A quick jab somewhere into the belly is about all the care in target selection that is usually given. It might be added that said rats are not totally compliant in this matter as evidenced by their struggling and screams.

Work by Gallagher is claimed to have established lethality using oral administration of pure compounds, but it must be stressed that at no point in Gallagher's work is it actually stated that any death or deaths were produced by oral administration although he docs claim effects began in 6 minutes via this route. [As opposed to the 6- 12-(72) hours known to be required for onset of symptoms, and up to months before death, after grazing. <Recovery from the effects of administered 5-MeO-DMT is complete within an hour.]

Interestingly, Gallagher also states that bufotenine readily crosses the blood brain barrier. Clearly something needs closer scrutiny.

One idea commonly tossed around is that the presence of B- carbolines orally activate DMT/5-MeO-DMT. While logical, this property is entirely unevaluated for any of the B-carbolines reported from Phalaris. Directly toxic effects are suspected from I or 2 of the quaternary B-carbolines.

The action of the quaternary N-methylated tryptamines that are known to sometimes represent up to 5% of the alkaloids
present in P. aquatica (under poorly defined circumstances must also be considered due to their potential for cyclization. IF the B-carbolines turn out to possess MAOI properties, their interaction with many other compounds present MUST also be considered.

Other alkaloids known to also be (at least sometimes) present in Phalaris: 3-methylindole (known to produce Bovine Pul-
monaty Emphysema in cattle), indoleacetic acid, 5-methoxy-indoleacetic acid, tryptophan, 5-methoxy-tryptophan, (the preceding 4 can be readily converted to 3-methylindole by the gut flora of cattle but not by sheep or goats), gramine, substituted gramine derivatives and hordenine.

Hordenine and gramine are both known to produce toxic effects in livestock and the combination of hordenine with a
MAOI would be more likely to precipitate a hypertensive crisis, than combining tryptamines with MAO inhibitors. (Also
more likely than if combining mescaline with an MAOI].

Another llictor to consider is the known anticholinesterase activity of bufotenine and several of the Phalaris B-carbolines ( see Ghosal et al. 1977.)

The potential presence of lysergic acid type fungal products, from not only grass ergotisms but also fungal endophytes of common pasturage components, would also contribute to toxicity, especially if combined with an MAOI. Combine this gut-full of chemicals with yet other compounds found in the mixed pasturage Phalaris invariably occurs in - Agrostis, Bromus, Carex, Cyperus, Fescue, Scirpus, Sorghum. Tribulus, Ryegrasses etc.. - all of which have been incredibly dismissed as trivial; yet, all are known to produce alkaloids toxic to livestock; most inducing stagger effects on their own], add the potential metabolites produced by gut flora, and there rapidly appears to be many potential sources of toxicity and contributing factors possibly involved with Phalaris; all of which, for the largest part, have been
entirely disregarded in the peculiar quest to blame dimethylated tryptamines.

My best guess is a complex of drug interactions may be involved; hordenine, lysergic acid derivatives, B-carbolines & mixed indoles are hardly a recommended combination.

Incredibly, perhaps due to the politics involved, we still do not fully understand this economically important disorder despite over 3 decades of work and a hell of a lot of money thrown at it attempting to address the tryptamine "problem".
Amazingly, Gallagher went on to further conclude that exposure to DMT/5-MeO-DMT produced a situation where later stimulation by dogs would induce death due to a sensitization to adrenaline somehow caused by prior exposure to the tryptamines.

Another not so insignificant point is that Phalaris staggers are known to be produced by strains that do not contain appreciable amounts of the N-dimethylated tryptamines, containing instead ~-carbolines and gramine and/or hordenine.

Other workers have put considerable effon into linkg decreased palatability with the tryptamines claiming the decrease in palatability was evidence of toxicity; the assumption that sheep would supposedly prefer to eat nontoxic plants.
If sheep were truly this discriminating, it would seem that tPhalaris staggers and a host of other livestock poisonings would be less of a problem. [I must note that, like hordenine and gramine, 5-MeO-DMT is a proven feeding deterrent. Due to their TASTE.]

The majority of the evidence is strongly against the chronic form of Phalaris staggers syndrome being a product of tryptamine ingestion but few seem to care for discovering the truth; politics rule.


See Festi & Samorini and/or Shulgin & Shulgin 1997 for alternate scenarios that are AT LEAST as plausible,if not far better supported.

More recent work strongly suggests that one or more, up to several novel furanobisindoles may be involved in the toxicity. Several have been characterized.

See the recent published accounts by N. Anderton, C.A. Bourke, S.M. Colegate and R. Oram for more
details concerning their research



 
Dozuki
#93 Posted : 11/16/2011 10:45:01 PM

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@Ginko- Nope, unfortunately I've not been able to find the original article, It looks like its from a book out of the UK. I would love to see it however. I was paraphrasing from Edgar 1994 'Toxins in Temperate Grasses - Implications and solutions'. It also references two papers by Bourke and Carrigan from 1988 and 1992 that show that the 'sudden death' syndrome was not due to tryptamines.

I agree that high levels of tyramines could have been due to the sample population, but it is always better safe than sorry. Also, going back over the methodologies; of a lot of the studies on Phalaris focus on alkaloids and not the tyramines. Thus, by extracting alkaloids they are excluding what's in the water soluble portions. This could very well be why the 'sudden death' syndrome is seen even with 'low alkaloid' varieties. Clearly, this needs more study.

Recalling from memory, the tryptamine compounds have now been associated with the recoverable staggers. Other hypotheses for the 'sudden death' syndrome are 1). Nitrogen (ammonia) poisoning and 2) Cyanogenic glycosides. Among possible others. I found more on the Nitrogen poisoning, as I think this is the prevailing hypothesis.

@endlessness - Thanks for posting that. Is it from 'Some Simple Tryptamines'? I've been meaning to pick up a copy of it. Right off the bat, #3 could be disputed via Binder et al 2010: Phalaris arundinacea (reed canarygrass) grass staggers in beef cattle. However, I do think that it's interesting that Trout points out the difference between Australia and the US. The first, and the biggest difference I would conclude is that Australia has focused on P. aquatica as a forage species while North America has focused on P. arundinacea. This, to me, would again point to the fact that the tyramine content of P. aquatica definitely needs more attention. It wouldn't be a bad idea to look into it for any other species of Phalaris, including P. arundinacea.

trout wrote:
Hordenine and gramine are both known to produce toxic effects in livestock and the combination of hordenine with a MAOI would be more likely to precipitate a hypertensive crisis, than combining tryptamines with MAO inhibitors. (Also more likely than if combining mescaline with an MAOI).


This is kind of interesting, despite it being speculative. However, hordenine not being affected by MAOa, would seem to make this point fairly moot.

 
Ginkgo
#94 Posted : 11/16/2011 10:47:46 PM

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What? Tyramines are alkaloids, and hordenine is one of them, a compound that is found in many extractions. A study finding hordenine would have found other tyramines as well, if they were present. When you have only one study showing "high amounts" of tyramine alkaloids, and we can't even find the study to read it, the information is more or less worthless. No offense meant, but this looks like a dead end.
 
benzyme
#95 Posted : 11/17/2011 12:05:30 AM

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I do chromatography all day, HPLC. there's nothing that can't be separated.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Dozuki
#96 Posted : 11/17/2011 12:13:51 AM

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Ginko wrote:
Tyramines are alkaloids, and hordenine is one of them
Sorry about that, I tend to think of things more from a solubility standpoint and thus separate tryptamines and tyramines based off of that. I've seen tyramines noted as Phenols and tryptamines as Alkaloids. The tyramines, being much more polar, were missed in a lot of the early literature due to the methodologies of the time (at least with P. arundinacea).

While I agree that the Anderton et. al (1994)article is a bit of a dead end, I'm not so sure I'm willing to chuck out the possible interactions of P. aquatica tyramines with MAOIs, even with tyramines showing up in trace quantities. (What articles have you read that show them as trace?) There are more articles out there that deal with the tyramines, which shows that the researchers aren't (or weren't) seeing this as a dead end either. In fact Oram and Edlington 1994: Breeding Non-toxic Phalaris proposes the genetics for both the tryptamines and for N-methyltyramine (considered the more dangerous tyramine) in P. aquatica. The paper also shows considerable variablity in the relative amounts of N-methyltryramine. I don't consider this a dead end.
 
Ginkgo
#97 Posted : 11/17/2011 12:32:31 AM

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Ok, I get that. But why are we so concerned with substances that may be toxic to sheep, but will be removed in the extraction if using a non-polar? According to Mulvena et al. (1983) the obscure tryptamines like 5-methyl-tryptamine, 5-methoxy-tryptamine, 7-methoxy-gramine and 4,7-dimethoxy-gramine are normally only found in particular growing stages, suggesting they are part of the biosynthetical pathway of the other substances. I believe the same is the case for the tyramines, except hordenine of course, which seems to be the alkaloid that particular pathway is for.

Anyway, the tyramines will not follow through in an extraction, and if they do, they are not particular toxic to humans, they have a stimulant effect.

(I love ketamine)
 
Dozuki
#98 Posted : 11/17/2011 12:48:16 AM

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Ginko wrote:
Anyway, the tyramines will not follow through in an extraction, and if they do, they are not particular toxic to humans, they have a stimulant effect.


Unless one were doing an 'ayahuasca' like brew as stated in my above post. They would then become a concern when coupled with MAOIs. Full extractions are not the only way P. aquatica has been used.

I should have made that more clear I suppose. I'm also interested in the anecdotal reports of 'toxic' like effects reported here and there with Phalaris.
 
nen888
#99 Posted : 11/17/2011 5:03:16 AM
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..it was in ayahuasca analogue experiments that Samorini et al. found unusually high potency, leading to a perceived mental 'overdose' in one person, not explainable by the total alkaloid content..i will try to dig up this reference..

it should also be noted that Jim deKorne's original 'dmt' crystal that he wrote on in the early '90s, and in his book 'Psychedelic Shamanism", he later confirmed also contained 5methoxy-dmt, but this was not a 'problem' apparently..i believe he was using a variety of Phalaris arundinacea..

..lastly, simple chromatography is, like benzyme says, an art, but not really any more difficult than a high quality extraction..it's just about practicing whatever technique is adopted..if the common tryptamine enthusiast held such relatively simple technology in their hands, they would be considerably more empowered..

an underground researcher i met in the mid '90s extracted some australian p. aquatica, and obtained about 0.3% of a slightly oily yellow 'crystal'..the subjected vaporized effects were judged to be good, so there's a lot of strain finding research (and root division) to do..
.
 
Dozuki
#100 Posted : 11/17/2011 6:23:15 AM

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@nen - I have the Samorini et al article (printed out, not on a drive). I believe that this article was part of the hype around AQ1. It's hard to know from the article what the 'overdose' was exactly. It could well have been a hypetensive crisis from tyramines or an actual 'overdose' of tryptamines, or a highly sensitive person. It's really all speculation.

I also totally agree with the 'strain finding' research. Seems this is what Johnny Appleseed has/had been doing for years, coming up with most of the available strains in North America like 'Turkey Red', 'Yugoslavian Fresh Cut', and 'Big Medicine'. The first two being 5-MeO Genotypes and the last a DMT genotype. These have mostly been available as live plants only so as to keep the strain. I have seeds that are supposedly from the 'Turkey Red' strain and it would be interesting to see what types of plants they produce (I would imagine all 3 of the genotypes).

 
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