I notice the reoccurring theme that MAOIs (in general) will orally activate DMT here, but very few actually do as far as I know.

I therefore strongly question this assumption and think that as long as it is safe, there should be experimentation to confirm or reject this theory.

I regret that while people often post or report their successes they often do not report their failures. I know of multiple failures to get DMT to work with curcumin despite it being an MAOI, Berberine as well...

So I am naturally curious if Kykeon can be explained in terms of MAO-I properties of ingredients in concert with tryptamines...

I will offer the concept that 5Meo can be active without a MAOI and can occur in various Phalaris species... can we rule this out?

AlbertKLloyd wrote:
..very few are actually methodically tested..there are usually a handful (even just one or two) underground experiments..very patchy stuff..without even clear understanding of how efficiently the theoretical compound was extracted etc..e.g. the claim that Harman does not activate DMT is from a single experiment by Ott..recent work seems to have shown otherwise..

Vosdel, on IC50 values..i'm no chemist, but for instance 2.0 nM = 20 μM AFAIK..
a typical harmine/harmaline type figure i'm used to seeing would be for instance:
β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO) T. Herraiz et al. 2009

and on the Kykeon, SKA, the entheogenic Eleusinian drink was highly secret..it was forbidden under pain of death to reveal what was in it exactly and what went on in the ritual..a Mentha is known, the other plants less clear..carvings of grass head at temple..

..ancient historian Plutarch tells us that Alcibiades (a young aristocrat) was sentenced to death (he escaped into exile) for turning the mysteries and the kykeon into a drunken party for a few friends..

http://www.britannica.co...459/Eleusinian-Mysteries
..i doubt one needs to go on a diet for barley and goats cheese, nor that such a profound, secret and sacred potion would have its contents widely known..

Unless there is a particular rule for measuring molarity that I'm not aware of, 1 nM = 10^-9 M, and 1 μM = 10^-6 M, hence 2 nM = 0,002 μM.



This is μg/l though, not μg/ml... 27 μg/l = 0,027 μg/ml, which compared to the approximated 35 μg/ml of the IC50 MAO-A value for M. Piperita extract suggests that the dose required of peppermint extract to attain the same degree of inhibition as rue seed extract would be x 1000 (taking only the IC50 as reference) which does not look very feasible unless the specific active compound/s in peppermint were isolated, and they showed MAO inhibition closer to the order of magnitude of harmine...

..i'm lost in a biology textbook and am meant to be going to work, but for now:
Vosdel wrote:
..the conversions between micrograms/L vs per mL vs nanometre figures becomes confusing..while i work out the conversions i hope a biochemist turns up..

..hopefully a biochemist will turn up..but for now i should mention that due to differing conditions of solution, concentration, pH etc., IC50 values are usually a comparison with a known standard (active) under specific conditions..so the mint is probably mild..but not for certain, condition dependant..

IC50 values have various conversion formulas such as the attached Ki = IC50 divided by 1+[S]/Km
where Ki is the binding affinity of the inhibitor, IC50 is the functional strength of the inhibitor, [S] is fixed substrate concentration and Km is the concentration of substrate at which enzyme activity is at half maximal (but is frequently confused with substrate affinity for the enzyme, which it is not)
different kinds of IC50 values exist..

but, very technical tangent really for this topic..

Actually IC50 is of one kind, and is meant to reflect that effectiveness of an inhibitor. Lower IC50 simply means more effective inhibitor. Vosdel's calculations are correct, and they come to show (when everything is of course viewed under the same denominator) that mint extracts with an IC50 on MAO-A of 58μg/ml is 3 orders of magnitude weaker than p.harmala extract with an iC50 of 0.027mg/ml

It should be noted that the above IC50 values, even when viewed under a common denominator, represent extracts from different studies. "extract" can mean so many things (aqueous extract? alcoholic extract? steam-distilled extract? extract from how many grams of starting material??) indicating that a valid face-to-face comparison is not possible. However, the message is that even if they are not directly comparable, generally syrian rue does a far better job at inhibiting MAO-A.

As said above, there is only one IC50. Ki is similar to IC50, but reflects affinity of the inhibitor for the enzyme it inhibits, given that there are also substrates that have affinity for the same binding site. For this reason it is a more refined and more specific way to express inhibitory power. Also, a Ki value of, say, harmine for MAO-A would be different if we were discussing dmt and different if we were discussing tyramine.

As shown in the formula nen quoted above, Ki takes into account how much substrate ("S" there is around and also the affinity of the enzyme for its substrate ("Km". As you can understand, in real life there are MAOI enzymes + DMT (the "S" floating around that has a certain affinity ("Km" for the MAOI + and then there are also the inhibitors that competes with DMT. When an inhibitor is bound on MAO, MAO cannot process DMT, but when the inhibitor unbinds, then MAO has the chance to process DMT. Ultimately inhibition depends on the balance of whether DMT or the inhibitor latch stronger on the enzyme AND which of the two is more abundant. Just like in a normal battle, the outcome often depends on whether you have a strong or weak army AND whether you outnumber your enemy or not.

Alright. I guess the grated goat cheese came from Greek literature, so I
scraped it off of the list.

So we have 2 theories that both have credibility.
The MAOI from mint and DMT from Phalaris Aquatica-Theory &
the hydrolysis of Ergot-alkaloids into Ergine & Isoergine.

Right now none is significantly more likely than the other,
but my gut sais to put my money on the Ergot-theory.
Since barley was so abundant & significant & ergot infestation so common.

I find it hard to imagine the Ancient Greeks knew of Ayahuasca. I still find
it hard to understand how amazonian shamans found Ayahuasca. It's certainly possible,
as it's possible Moses too did Ayahuasca up on that mountain. But what are the odds?

A mass-grain consuming culture like the ancient Greeks would have been forcibly
introduced with Ergot. People would have gone mad, sick & gangrenous & died.
The ancient Greeks would have learned, even if they didn't know exactly what
Ergot was at the time, at least not to make bread from Barley with "blackened kernels"
to prevent Ergotism outbreaks. Possibly some drug-enthusiastic & mythological-minded
Greeks who survived Ergotism may have recognised it's Psychedelic effects & got the idea
to tinker around with Ergot to transform it into something kinder & even more psychedelic.

You know, like an ancient Eleusian Albert Hofmann...

SKA, I'll try to explain why I wouldn't rule out the mint inhibition hypothesis yet, and since it might be verifiable, I will stick to that atm.

Thank you Infundibulum for the clarifying post.

In fact, the different papers I checked regarding MAO-A inhibition by mint compounds show some conflicting results. For instance:

- In paper 1 (López et al., 2009) Methanolic extract of Mentha aquatica is reported to have an IC50 in MAO-A inhibition of 57,8 μg/ml.
- In paper 2 (Isolation of the MAO-inhibitor naringenin from M. aquatica, Olsen et al., 2007), isolated naringenin is reported to have an IC50 in MAO-A inhibition of 955 μM, which converted results in 260 μg/ml. Would the active compound, or one of the active compounds, be five times less efficient when isolated than the whole plant extract? Are we talking about big differences between yields here?

Not to make the case around naringenin and M.aquatica, because on top of what has been mentioned already, naringenin is difficult to absorb orally... but to remark that IC50 figures in available research appear extremely variable as Infundibulum said.

But even counting with that variability, the difference between rue and mint figures is huge. Even if we took only two orders of magnitude instead of three, having to ingest 100 x the standard harmine dose, which would equal 100mg x 100 = 10+ g of mint extract, seems to make the option difficult for practical reasons, but assuming these amounts of extract, to dose a crowd, could have been obtained by the druids, and proportionally mixed in a drinkable amount of kykeon for greeks to gulp down, would it be safe for us to assay? So I looked further into toxicity, focusing more on peppermint because it's common, documented and also the best score in the paper I left in a previous post.

Potentially toxic compounds in peppermint found in relevant concentrations are menthol, menthone and pulegone. Quoting a safety assessment report of M. piperita:



Still, if we are to be specific, menthol has a LD50 of almost 3 g/Kg when administered orally in rats, and a very low solubility in water (456 mg/l at 25ºC). Menthone has no acute toxicity reports, but it's equally poorly soluble in water (688 mg/l at 25ºC). Pulegone is not water soluble. And the highest oil yields in M. piperita are around 3%.

All this suggests that water extractions of peppermint are extremely safe once oils are filtered out, even if using a lot of plant material. You could brew the plant for hours and not even dissolve a remotely dangerous amount of any of the compounds that have toxicology reports.

Now the thing would be figuring out the amount of plant material required to brew the high dose of extract needed for MAO-A inhibition in the human gut, then decide if the amount is realistic for the hypothesis, and assay whether the concentrated plant tea is actually able to activate oral DMT or not.

So I wouldn't rule it out yet.

Or maybe I just enjoy squeezing my brains around it

Alright. I'll go with the Mint theory for a while.

You mentioned the slightly toxic compounds in peppermint.
But how would you filter them out & exactly what are/is the active
desirable MAOI compound(s) from peppermint one would want to ingest?

If extracting these compounds and ingesting them in a brew together with DMT
would yield an Anahuasca like experience then that could be a Kykeon recipe.
But would it be as mindblowing as the Kykeon was described to be?

Could Peganum Harmala not have been available to the ancient Eleusians?
It's use is ancient in Persia & it grows all through the middle east & appearantly also in
Morocco. If it grows in Morocco, I see no reason why it shouldn't have grown in ancient
Eleusis too. If it didn't grow there it is likely to have been available there from
travelling Mercants. Seems like a much more obvious candidate for a MAOI ingredient of
the Kykeon.

Then there's another 2-fold question:
Did the Hierophants use a Recipe & Preparation that was easy to keep a secret?
Or was it not easy to keep secret, but the Hierophants were just masterfull keepers
of secrets?
Buying/picking massive amounts of Peganum Harmala seeds, or picking THAT much
mint would have caught attention of spies seeking to reveal the recipe of the Kykeon.
Then again boiling the 2 ingredients together would have been fairly easy to keep secret.

Also could the ancient Eleusians have harvested enough DMT-grasses & Harmala seeds or Mint
consistently every year to provide the Kykeon to 1000 participants with consistent potency
& success? I suppose if the DMT-grass & Mint/harmala harvest of 1 year is particulairly
plentyfull, much of it could be dried & saved for following years in which the harvest
might not at all be that plentyfull.


Allthough the Hierophants could have used grasses as their DMT source, I can't help
but think of the most DMT-rich genus of trees in the world: Acacia.

The generic name derives from ἀκακία (akakia), the name given by early Greek botanist-physician Pedanius Dioscorides (ca. 40-90) to the medicinal tree A. nilotica in his book Materia Medica.(Wikipedia)

Would Acacias have grown in/around ancient Eleusis? If so then these too could be a possible source of
DMT for the Kykeon.

Please refer to my previous post. The potentially toxic compounds in peppermint are barely water soluble, and if brewing large amounts of peppermint released them in oil form, they could be separated without much hassle.

MAOIs in peppermint have not been identified and isolated, but considering the reports about naringenin in M. aquatica, the actives in M. Piperita or M. Pulegium might be flavonoids as well. In any case, actives don't have to be known in order to brew successfully. Amazonian shamans have been brewing caapi for centuries without knowing what a betacarboline is...



We might speculate with any psychoactive plant, as it's been done in the past with opium, cannabis or psilocybe mushrooms... if we're considering the mint anahuaskon theory is after nen's suggestion about phalaris, which as far as historical evidence goes, and considering the MAOI properties of mints, might have some basis.



This is what I'm trying to figure out regarding mint dosage, as stated in my previous post.

I'm not suggesting that the phalaris-mint hypothesis is more plausible than the ergot hypothesis so far, I'm simply trying to test it.

What about easily identifiable, non-toxic psilocybian mushrooms? Identifiable due to blueing reaction?

There's a theory out there that when you take the first letter of each ingredient it spells the ancient greek word for mushroom. I do believe the A Greeks were somewhat well acquainted with fungi.

http://www.ebay.com/ctg/...2006-Paperback-/51067838

http://www.google.com/se....ning.com%252Ffiles%252F*F90Jt5furuGJo09BYQiXe8jgCLLM79bYIPOhvGIeJwpCW73VgYREyU1rvS*zhq8BjLdqjV3*5Kc10mzjLhmgGIVaMJfeuK2%252Fmushroom.jpg%3Bhttp%253A%252F%252Fwww.esotericonline.net%252Fprofiles%252Fblogs%252Fthe-eleusinian-mysteries%3B300%3B255

http://www.amazon.com/Mu...zed-Europe/dp/0872864707

^..psilocybin is the other theory..
and thanks Infundubilum for that insight into IC50 values..

SKA wrote:
..ergot poisoning is TERRIBLE..! no one has reported ingesting ANY kind of ergot based brew, i'd say because the risk is too great..
it takes advanced lab techniques like those developed by Albert Hoffmann to get a groovy alkaloid out..

..how could the Ancient Greeks have known about Phalaris?
i think Ayahuasca is a big red herring here..a good example of how would be how Jim de Korne (original Entheogen Review editor) discovered smokable extracts from Phalaris..he simply put in in a wheat-grass juicer and let the grass juice dry..on a whim he smoked some..it propelled him into a strong 5meo/DMT experience..no A/B or NP base etc required..now people have known about smoking things for a very long time..furthermore, many strains of Phalaris contain betacarbolines and gramine (which is actually a mild MAOI) ..even as a child i tasted many plants..i find it unlikely that in a few thousand years of ancient greece NOBODY tried some Phalaris..
and if they noticed something they probably would have experimented..what happens if you add that trippy mint? etc..

..i've discovered 'new' plants simply through dreams..this is how many 'animist' peoples work..intuition..
you intuit what's poisonous or not..and if you were wrong, well the rest of us knew not to take that plant..
once upon a time i would say discovering new plants was more straightforward in some ways than today..
it's not hard to imagine feeling drawn to the ayahuasca vine and deciding to try some..you may well like the effects of Harmalas..then, you add other plants to see what happens..one such plant just happens to be a DMT plant..remember indigenous amazonian tribes often say that they use the Vine to 'study' many other plants (not just chacruna) ..that's why it's called Ayahuasca!

..as for Moses, we now know many Acacias contain betacarbolines (and tryptamines) in the leaves (phyllodes) ..no Rue required..
but, given the advanced Egyptian alchemical knowledge of the time (they trained him) creating a 'natural solvents' basic smokable extract would not have been hard..

Phalaris aquatica is native to Greece..it was everywhere there..still common..
if anyone was going to notice it a long time ago it would be there..

I have read this post whit interest,but are we sure that eleusis mystery need an entheogenic brew ?

No, but since there is no conclusive proof all we have is theories. We can only throw up theories & stick with the most
likely of the proposed theories. Untill, let's say, archeologists find a recipe or a challace or vessel with remains
of the Kykeon that can be chemically analysed. But we really have no solid facts to go on, untill such evidence is found.

We can look at what psychoactives plant & fungi would have been available to the ancient Eleusians. Then we get to narrow
it down to some relatively simple preparation-method that would have been known & executable at that time.

Anahuasca from Phalaris Aquatica & Watermint would fit that bill. Indeed a safe, psychedelic Ergot-derivative
would have been much more far fetched. Then again I often feel we, peoples of present times, heavily under-
estimate the ancient peoples that preceeded us. The ancient Greek, like the ancient egyptians, were quite skilled
& knowledgable when it came to Alchemy.

Exploring the Anahuasca theory would still leave some questions. Wouldn't you need surreal amounts of Phalaris grass
to supply 1000 ceremony-participants with a potent dose of "Kykeonhuasca"? Because what is the average DMT/5MeO content
of P.Aquatica? 0,5% at best? That's why I considered Acacias to have been a possible DMT source instead; Higher yields &
consistent, plentyfull phyllode-harvests.

But that report by Jim DeKorne gives Phalaris credibility again. Smoking finely cut Phalaris Aquatica &
experiencing a DMT-like inebriation would suggest remarkably high DMT/5MeO contents, don't you guys reckon?

SKA wrote:
..actually Phalaris aquatic AQ1 was named for having 1% dry weight DMT..but 0.5% is actually not a 'low' %..
as a weed in australia, for instance, there are an estimated 2.5million hectares of Phalaris..of all the possible plants/fungi it would be the easiest to grow/garvest large amounts needed..also, unlike mushrooms, it can be harvested any time of year, and be more easily cultivated..
1% dry weight, faster growing than any acacia/mimosa, and not much else in there (unlike tannin loaded mimosas/acacias) makes, in my mins, Phalaris the best possible candidate..
basilic wrote:
..from the descriptions of the ceremony/potion it seems highly likely an entheogenic brew was involved..the ancient greeks were well aware of psilocybin mushrooms, and yet the Kykeon was said to mlead to a 'profound' experience..
.

nen, where do we know that greeks have been aware of psilocybin mushrooms? I have seen depictions of mushrooms, but nothing about their entheogenic use. Psilocybin mushrooms also fail to be noticed in scripts written by ancient greek herbalists and doctors.

Similarly, despite the wide use of cannabis in persia, cannabis and its psychoactivity for some reason appears unknown to greeks. And beer was frowned upon, as ancient greeks were snobbish wine drinkers.

Cannabis and it's entheogenic effects unknown to the ancient Greeks? Seems weird as Greece
& Persia have been exchanging culture for a long time. (Zoroaster/Zaratrustra was originally Greek)
Has smoking herbs & spices of any kind ever been a custom in ancient Greece?
Adding psychoactive herbs & spices to wine appearantly was quite common there.

But let's not digress. Cannabis could hardily have accounted for
the glowing experiences of the Kykeon.



Nen... P.Aquatica has an average spice content of 1%? What?! That certainly
would explain DeKorne's journey from smoking the cut up, dried grass clippings.

Would P.Aquatica also be invasive in Northwestern europe? And
is identifying this plant as much of a nightmare as I think it is?
I probably couldn't even distinguish Phalaris species from non-phalaris
species, let alone one specific Phalaris species from another.

I'll try to learn as much about Phalaris-botany & identification as
I can, because I see far too many tall grasses that look suspiciously
Phalaris-like. That 1% got my attention.
Wikipedia sais: "A particular strain of P. aquatica from Italy, labeled 'AQ-1', was reported to contain in excess of 1.0% alkaloid concentration." I'm assuming this content is a mixture
of mostly DMT & 5-MeO-DMT and little else, am I right? And 5MeO is even more potent then NN, right?

How many times has the 1% spice content in P.Aquatica ""AQ1" been confirmed?
I have allways underestimated the spice content of Phalaris species
untill now.


Therefor it indeed is a very likely candidate for the Kykeon.

Ska, I was also weirded by the apparent ignorance (or maybe taboo?) of ancient greeks about the psychoactive effects of cannabis. Anchient herbariums do not even list it!

I haven't been following this thread too closely, but have we excluded other psychoactive plants, such as datura, belladonna, mandrake etc? for some reason I fail to resonate the slightest with the possibility of ancients greeks drinking a dmt-containing decoction, but that's just me.

I know a little some tradition of the mediteranean isle like Corse and sardaigne and an hypothesis :
Adding henbane can be added ,which was what the potion .
I have read somewhere that this plant was mentionned in ancient greek legend.