The ancient Greek world was familiar with a wide variety of drugs... but is it possible that they used DMT and related tryptamines as well? This article looks at the mythology around an obscure Greek grass known as “agrostis” and considers how the ancient Greeks could have utilized Phalaris grass for its psychoactive effects. For the benefit of modern psychonauts, we also look at toxicity concerns surrounding Phalaris.
The genus Phalaris has an interesting niche in the world of visionary plants. For DMT extractors, it is simultaneously a “source of last resort” and the best hope of permanently winning the battle against prohibitionists who would thwart individuals from obtaining DMT. Perfecting the elusive “grass tek” – that is, finding a strain of P. arundinacea, P. aquatica, or P. brachystachys that produces a clean alkaloid profile and developing a simple and efficient method to purify these alkaloids – would effectively make it impossible for governments to stop people from obtaining DMT.
Prior to current efforts in developing a grass tek, the last time that Phalaris saw such a surge in popularity was the early 1990s, during the first few years of the Entheogen Review publication. At that time, people were trying to find viable local plants from which to brew ayahuasca analogues. In the years since, concerns have been raised about the possible toxicity of Phalaris brews (see Toxicity concerns below), and plants with higher concentrations of DMT have become widely available on the Internet.
So Phalaris has largely taken a backseat in the contemporary Entheogenic Revival. Many are aware of its visionary potential, but few actually take the effort to work with the plant. Perhaps sometime in the future it will have its day in the sun.
But all of this begs the question: might earlier cultures have also been familiar with the visionary potential of Phalaris grasses? After all, they are ubiquitous in many regions, and people have not always had the botanical offerings of the entire planet a few keystrokes away as we do now.
A fortuitous footnote
As it happens, there are references in ancient Greece to a grass that possesses divine properties. I was recently rereading The Road to Eleusis, in which R. Gordon Wasson, Albert Hofmann, and Carl A. P. Ruck contend that an entheogenic drug lay at the heart of the Eleusinian Mystery, when I was struck by one particular footnote.
This quotation requires some context. Hofmann had suggested three possible sources of ergot sclerotia which could have been incorporated into the kykeon potion: Claviceps purpurea from either barley (Hordeum vulgare) or darnel (Lolium temulentum), or Claviceps paspali from knotgrass (Paspalum distichum). Hofmann preferred the C. paspali hypothesis because of its cleaner alkaloid profile, but Ruck preferred C. purpurea because its host plants have closer mythological ties to the Mystery. To that end, Ruck argued that we would not find any explicit references in ancient literature to psychoactive effects from the plant which imbues the kykeon with its visionary effects, because any such references would violate the covenant of secrecy surrounding the Mystery.
Ruck tells us that P. distichum is clearly represented as a psychoactive material in ancient sources, where it is referred to as agrostis (Wasson et al. 2008, p. 127), and therefore could not have been the key to the kykeon. We now know that P. distichum is a New World species that did not arrive in Europe until sometime during the last few centuries (Festi & Samorini 1999), so obviously agrostis could not have been P. distichum. Ruck acknowledges that the Greeks do not seem to have distinguished between common species of grass, but neglects to mention how he reconciles this fact with his (incorrect) certainty that the references below involve P. distichum. Leaving aside any speculations about the kykeon of the Eleusinian Mystery, we have the following mythological complex associated with an unidentified species of grass:
The ancient grass agrostis or the ‘hunter plant’ was associated in myth with the sea demon Glaucus and was reputed to have magical properties…. Cronus was said to have sowed agrostis in paradise, the Islands of the Blest, where the horses of the sun god Helius grazed upon it to get the strength needed for their flight through the air. When Glaucus first ate of this grass that the untilled earth bears, he was engulfed in the sea for the archetypal voyage (Alexander Aetolus, p. 465, Rose, quoted in Athenaeus 7.296 ff.). It was an event that involved his love for Hydne, a ‘maiden of the water,’ and when this man from Anthedron, the ‘place of flowers,’ ate the herb, he became immortal (Aeschrion of Samos, quoted in Athenaeus). It must have been a love like that which Hylas experienced when he, like another Narcissus, fell into the embraces of the water maidens in the pool beside which grew this plant (Theocritus 13.42). It was also said that Glaucus found agrostis while hunting in the mountains, where he discovered that the hare he had wounded revived when anointed with the herb; upon tasting of it himself, he was seized by a divine madness and cast himself into the sea (Nicander, frg. 2, Schneider)... It was said that Glaucus could foretell the future (Diodorus Siculus 4.489), an art that he taught to Apollo himself (Nicander, frg. 2, Schneider); the Cumaean sibyl was the daughter of Glaucus (Vergil, Aeneid, 6.36). It was Glaucus, moreover, who built the Argo, the first ship ever made and the one that carried an assemblage of heroes on the primordial voyage to the magical garden on the witch Medea to capture the golden fleece for Jason (Iason, in Greek, the ‘man of the drug’). (Wasson et al. 2008, pp. 127–128)
Much of the information presented in the above quote by Ruck can be found in a work by Athenæus, composed in the early third century C.E., where he appears to draw heavily on older sources:
Alexander the Aetolian also mentions him in his poem entitled the Fisherman, saying that he
First tasted grass,
(and then was immersed in the sea and drowned,)
The herb which in the islands of the blest,
When first the spring doth beam upon the earth,
The untill’d land shows to the genial sun.
And the sun gives it to his weary steeds,
A most refreshing food, raised in the shade.
So that they come in vigour back renew’d
Unto their daily task, and no fatigue
Or pain can stop their course.
But Aeschrion the Samian, in some one of his Iambic poems, says that Glaucus the sea-deity was in love with Hydna, the daughter of Scyllus, the diver of Scione. And he makes particular mention of this herb, namely, that any one who eats of it becomes immortal, saying—
And you found too th’ agrostis of the gods,
The sacred plant which ancient Saturn sow’d.
And Nicander, in the third book of his Europe, says that Glaucus was beloved by Nereus. And the same Nicander, in the first book of his history of the Affairs of Aetolia, says that Apollo learnt the art of divination from Glaucus; and that Glaucus when he was hunting near Orea, (and that is a lofty mountain in Aetolia,) hunted a hare, which was knocked up by the length of the chance, and got under a certain fountain, and when just on the point of dying, rolled itself on the herbage that was growing around; and, as it recovered its strength by means of the herbage, Glaucus too perceived the virtues of this herb, and ate some himself. And becoming a god in consequence, when a storm came, he, in accordance with the will of Jupiter, threw himself into the sea. But Hedylus, whether he was a Samian or an Athenian I know not, says that Glaucus was enamoured of Melicert, and threw himself into the sea after him. But Hedyl, the mother of this poet, and daughter of Moschine of Atica, a poetess who composed Iambics, in her poem which is entitled Scylla, relates that Glaucus being in love with Scylla came to her cave—
Bearing a gift of love, a mazy shell,
Fresh from the Erythrean rock, and with it too
The offspring, yet unfledged, of Alcyon,
To win th’ obdurate maid. He gave in vain.
Even the lone Siren on the neighbouring isle
Pitied the lover’s tears. For as it chanced,
He swam towards the shore which she did haunt,
Nigh to th’ unquiet caves of Aetna.
(Athenæus 1854, Deipnosophistae 7.48)
Agrostis as Phalaris?
The imagery certainly seems to suggest a visionary substance. It gives the gods’ horses the power of flight. When people eat it, they become immortal, or are “seized by a divine madness” or “engulfed in the sea.” One who ate it is associated with the origin of prophecy and with the construction of the Argo (a ship whose quest Ruck insists is fraught with psychoactive symbolism; Ruck et al. 2001). If these references are meant to be purely symbolic or mythological, why choose something so mundane as a simple grass? But if these mythological accounts do point toward an actual psychoactive grass, the pool of potential candidates is quite small, and Phalaris grasses immediately stand out. Notice that we should not make the mistake of equating the Greek agrostis with grasses of the genus Agrostis; while the latter are named for the former, we have no reason to believe they are equivalent.
The following is not an exhaustive treatment of the chemistry and human pharmacology of the genus Phalaris. While that would be an interesting subject, it would require at least a short book to do justice to the material. For good information on that subject, the reader is recommended to consult Trout (2004, chapter 2: section 3), Festi & Samorini (1994), or Voogelbreinder (2009, pp. 272–274), as well as discussions from the DMT-Nexus. For the remainder of the article, we will try to hit the highlights as they pertain to the possible discovery of the grass’s psychoactive potential in ancient Greece.
The very first question we must consider regarding the possible identification of agrostis as Phalaris spp. is that of access: Did Phalaris actually occur in the Mediterranean a few millennia ago? The answer is a resounding yes. It actually appears that the Mediterranean was a center of diversification for the genus (Festi & Samorini 1994), many species are native there and we can safely suppose that they have occurred there for a very long time.
We must also consider whether it is possible that ancient peoples could have discovered the visionary potential of the grass without sophisticated processing techniques. Certainly the potential for visionary activity exists. The alkaloids N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and 5-hydroxy-N,N-dimethyltryptamine (bufotenine or 5-OH-DMT) have all been isolated from some Phalaris specimens (Festi & Samorini 1994), and all three are associated with a rich history of use as visionary agents in South American cultures. Additionally, some specimens contain the monomethyl analogues N-methyltryptamine (NMT or MMT) and 5-methoxy-N-methyltryptamine (5-MeO-NMT or 5-MeO-MMT). The activity of these monomethyl analogues has not been robustly explored, but there are indications that NMT is active orally (Nen 2012) as well as when vaporized, and that it may act synergistically with DMT (Nen 2011).
In modern times, most human experimentation with Phalaris spp. has been in the context of using the plant in an “ayahuasca analogue” type mixture. This means that the focus is on the DMT content. Thus, when taken orally, it is always consumed in conjunction with a monoamine oxidase inhibitor (MAOI) in order to render the DMT orally active (McKenna & Towers 1984; Ott 1994). To suppose that the ancient Greeks would have consumed the grass in conjunction with an MAOI is simply not credible. The South American ayahuasca complex, with DMT-containing admixture plants, appears to have arisen subsequent to a tradition of using the vine alone (Highpine 2013). We have no analogous MAOI plant in ancient Greece which could have made the discovery of this synergy possible. If the discovery of this synergy did occur in ancient Greece, it has been lost to the vagaries of time. One might try to make the case that this is the lost solution to the Eleusinian Mystery, but that is a much bolder claim than I am making here, and would require more extraordinary evidence to support it.
On the other hand, several tryptamine-bearing Phalaris species contain the alkaloids 2-methyl-1,2,3,4-tetrahydro-β-carboline (2-Me-THβC), 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (2-Me-6-MeO-THβC), and 2,9-dimethyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (Festi & Samorini 1994). These alkaloids are very closely related to harmine, harmaline, and tetrahydroharmine – compounds which render DMT orally active by way of their inhibitory effect on monoamine oxidase A (MAO-A), in addition to having significant psychoactive effects in their own right. A quick search turns up no human self-experimentation with these compounds, but a study related to its occurrence in ruminant forage notes that 2-Me-THβC “is one of the most effective MAO-A-inhibitors” (Kemmerling 1996). It is therefore possible that a strain of Phalaris grass with the right alkaloid profile could provide an ayahuasca-like cocktail of tryptamines and β-carbolines, without the need for any admixture plants.
If we discard the possibility of MAOI involvement (and thus any involvement of DMT), we are still left with the significant possibility that 5-MeO-DMT or bufotenine could have provided the visionary power to an ancient Greek who consumed the grass. Conventional wisdom has long held that 5-MeO-DMT, like DMT, requires an MAOI in order to be orally active (Shulgin & Shulgin 1997, p. 535), but experience trumps conventional wisdom, and 5-MeO-DMT has been reported to be orally active without coadministration of an MAOI (Ott 2001b, pp. 103–104; while this claim has often been repeated by others, Ott’s is the only credible report on ingesting 5-MeO-DMT alone that I have read). Bufotenine has been similarly reported to be orally active without the need for an MAOI (Ott 2001a). Neither 5-MeO-DMT or bufotenine are regarded as particularly pleasant when taken orally, but many people are willing to endure unpleasant effects to achieve ecstatic states.
Although we have little direct evidence on the consumption of Phalaris by itself, we can find some interesting parallels in two South American genera: Anadenanthera and Virola. The most common use of these trees among the indigenous people of South America is as a source of visionary snuffs, but there are reports that both Virola (Schultes & Hofmann 1980, pp. 130–134) and Anadenanthera (Torres & Repke 2006, p. 86) are sometimes used orally in traditional settings without the coadministration of an MAOI. Both genera have been shown to produce a range of tryptamines, much the same as have been found in Phalaris, but their primary alkaloids are 5-MeO-DMT (for Virola) and bufotenine (for Anadenanthera). The oral use of these plants seems to justify the notion that Phalaris could have been used orally to produce a potentially desirable visionary state.
A major problem with the ancient use of Phalaris – and its modern use for that matter – is simple inconsistency. The alkaloidal composition and content can vary seasonally, it can vary based on environmental conditions, it can vary among specimens in a given population, and to top it off, the alkaloid profile of offspring will often differ from its parent (Trout 2004). It’s possible that awareness of the grass’ visionary potential was limited by this unpredictability. A drug whose effects could not be relied upon to manifest with a particular dose could not be expected to enter into common usage.
Summary of suggested mechanisms of activity
We have proposed several possible routes of activity:
● DMT rendered orally active by 2-Me-THβC and other β-carbolines in the grass [based on pharmacological considerations]
● NMT orally active, possibly only when coadministered with DMT [based on human self-experimentation with Acacia confusa]
● 5-MeO-DMT orally active [based on human self-experimentation with the pure compound]
● Bufotenine orally active [based on human self-experimentation with the pure compound]
● The mixture of tryptamines work in concert to produce a visionary effect by oral administration [based on ethnographic literature for Anadenanthera spp. and Virola spp., which contain many of the same alkaloids]
With the exception of the β-carboline hypothesis, which is speculative, a patch of Phalaris grass with the proper alkaloid profile could absolutely be expected to produce a visionary experience by any of the abovementioned mechanisms. In other words, it is entirely feasible that people in ancient Greece could have discovered the psychoactive potential of the grass without any sophisticated processing technologies.
Successes from ingesting solely Phalaris?
As mentioned previously, virtually all reported oral ingestions of Phalaris grass involve an MAOI admixture plant, but there are a couple reports which stand out due to the insufficiency of the intended MAOI. These reports appear to represent proof of concept.
Oilman (2012) attempted to use coffee as an MAOI in combination with 10 g Phalaris arundinacea. The result was a relatively mild but pleasant experience. While coffee does weakly inhibit MAO, it does not seem likely to have played a very significant role in the reported effects.
Toltec (2004) attempted to use 3 g Russian olive (Elaeagnus angustifolia) leaves and 1 g St. John’s wort (Hypericum perforatum) flowers as an MAOI in combination with 11 g Phalaris aquatica. The result was a remarkably powerful experience, “one of the most positive” of their life. It is unlikely that either the Russian olive or the St. John’s wort contributed any significant MAOI effect. Elaeagnus spp. contain β-carboline MAOIs, but in such low concentration that a mere 3 g should not have been active (Snozzleberry 2011), and St. John’s wort is currently regarded as having little to no MAOI activity (Greeson et al. 2001).
Because we are entertaining the possibility that Phalaris could have been used as an orally active visionary plant, it is prudent--from a harm reduction standpoint--to also consider the potential negative consequences of consuming the plant. Considering the self-experimentation reported in early issues of the Entheogen Review and around the Internet, it is probably safe to conclude that no serious harm will come of a single ingestion of a reasonable quantity of Phalaris grass. In fact, we have no concrete evidence that Phalaris is toxic to humans, though this could simply be the result of a small data set – few people deliberately eat the grass. Instead, we have hints, suggestions, and possible causes for concern, which will be discussed briefly below. Anyone considering ingesting Phalaris grass would be well-advised to dig a little deeper into these concerns before deciding that the plant is safe to consume regularly or in quantity.
Phalaris staggers is a syndrome which occasionally afflicts sheep or cattle grazing on Phalaris grass. The syndrome is characterized by incoordination and spontaneous collapsing, sometimes accompanied by convulsions or coma. It can prove fatal for the afflicted animals and has consequently received a great deal of study, but the causes are still poorly understood and open to some debate.
Some have blamed the staggers on the tryptamine content of the grass, but this is problematic. While injecting livestock with DMT, 5-MeO-DMT, and bufotenine produced somatic symptoms reminiscent of the staggers, they were not fatal and did not precipitate a chronic condition as is seen in grazing animals (Rendig et al. 1976; Trout 2004). More recent research indicates that fatal cases of phalaris staggers are actually cases of peracute ammonia toxicity (Broad 2006). These cases occur when animals switch from low-nitrogen forage to nitrogen-rich Phalaris grass, which also contains some yet-unidentified inhibitor of nitrogen metabolism (Broad 2006).
All in all, the toxicity represented by phalaris staggers is probably of minimal concern to humans ingesting the grass. It occurs only rarely in ruminants who graze on large quantities of the grass, and appears not to be correlated with alkaloid content desirable to humans. The syndrome has been discussed in greater depth by Festi & Samorini (1994), Shulgin & Shulgin (1997, pp. 259–261), and Trout (2004).
Gramine and hordenine
These compounds are one of the factors that keep Phalaris from attaining the status of a popular modern source of DMT. The average extractor lacks the means to determine whether these compounds have been extracted into their final product, and so they simply err on the side of caution and choose a different plant source. However, it’s possible that these compounds have been unfairly maligned. Both compounds occur in malted barley, and are routinely consumed by people worldwide as a component of beer (Poocharoen 1983).
This is not to say that the compounds lack the potential for toxicity. Gramine has been found to have an LD50 of 44.6 mg/kg, i.v., in mice and 62.9 mg/kg, i.v., in rats (Erspamer 1954), while hordenine is reported to have a minimum lethal dose of roughly 1 g/kg, s.c., in rats (Camus 1906). These figures are well above the range that we would ordinarily expect people to ingest. Gramine and hordenine have been shown to produce some non-lethal adverse effects when fed to chickens, but only with chronic feeding at high doses (500 mg/kg feed for several weeks; Chaniago et al. 2011)
Trout (2004) has suggested that these compounds could be involved in fatal cases of phalaris staggers, remarking that “[a]ny combination of gramines, tryptamines and/or hordenine, coadministered with MAO inhibiting β-carbolines, could produce life threatening cardiac events if ingested in sufficient quantity.” While he suggests that the cause of the staggers is more complex, he also reiterates the possibility that hordenine, in combination with an MAOI, could produce a “serious cardiac risk,” presumably because of its stimulant activity. Gramine has also been found to inhibit norepinephrine reuptake (Slotkin et al. 1979) and thus presents similar potential dangers if taken with an MAOI. Yet Trout (2004) seems to feel these risks are only present if very large quantities are consumed, as when grazing; no mention is made of these risks with regard to human use of Phalaris grasses as an ayahuasca analogue.
Some research has suggested that the presence of gramine is negatively correlated with the presence of tryptamines, but they acknowledge there are exceptions (Gander et al. 1976). It is inadvisable to regard the presence of DMT as evidence for the absence of gramine. The cautious psychonaut would do well to subject their sample to thin-layer chromatography (TLC).
For further references on gramine, see Trout & Friends (2007, pp. 11–12). For further references on hordenine, see Shulgin et al. (2011, pp. 147–152).
MAOI interaction with 5-MeO-DMT
While 5-MeO-DMT can be a trace component of traditional ayahuasca brews, serious concerns have been raised in the past decade over the safety of orally ingesting the drug, particularly in combination with an MAOI (Erowid 2010). The dataset on this issue is not robust, so some measure of speculation is inevitably required.
We know that at least one person has died after consuming a combination of β-carbolines and 5-MeO-DMT (Sklerov et al. 2005), although the dosage and provenance of the drugs is not clear (Callaway et al. 2006). There is another published report where an individual ended up in the hospital experiencing a hypertensive crisis with seizures, fever, and rapid heart rate after ingesting syrian rue (Peganum harmala) extract and smoking a large unspecified dose of 5-MeO-DMT (Brush et al. 2004). Additional reports of varying degrees of unpleasant effects from ingesting 5-MeO-DMT orally can be found online (e.g. Butane 2006; Murple 2000), though these unpleasant effects are not always present, nor are they common among other routes of administration (Ginkgo 2010; Konnexion 2009; Oroc 2009; Ott 2001b).
The mechanism behind these adverse reactions is unclear. Under ordinary circumstances, most 5-MeO-DMT is deaminated into 5-methoxyindole-3-acetic acid, a non-psychoactive compound, by MAO; other metabolic pathways include O-demethylation by CYP2D6 to produce bufotenine and N-oxygenation to produce 5-MeO-DMT-N-oxide (Shen et al. 2010; Yu 2008). When MAO is inhibited, deamination is halted, so more of the drug would be metabolized by CYP2D6 into bufotenine. The efficiency of CYP2D6 varies dramatically based on individual genetic makeup (Droll et al. 1998), so it’s possible that this variation could lead to differences in the incidence of adverse reactions.
But even if this is the case, it’s not clear whether increased toxicity would result from high-efficiency metabolism and the consequent high levels of bufotenine, or from low-efficiency metabolism and the consequent high levels of 5-MeO-DMT and 5-MeO-DMT-N-oxide. In the early literature, bufotenine is associated with some fairly toxic effects, but recent assays and its history of traditional use in South America tends to indicate it as an effective visionary tool (Ott 2001a; Shulgin & Shulgin 1997; Torres & Repke 2006). Until there is better data on the subject, extreme caution is advised when combining 5-MeO-DMT with MAOIs.
Some β-carbolines closely related to the ones that occur in Phalaris grasses have been shown to be neurotoxic, and others have been shown to inhibit mitochondrial respiration. Dr. Shulgin and Keeper Trout have suggested that even if the Phalaris β-carbolines are not toxic in themselves, they could be metabolized into neurotoxic compounds after ingestion. (Voogelbreinder 2009, p. 274)
Do we have enough evidence to identify the agrostis of these myths as a species of Phalaris? Probably not, if we’re being entirely honest. But the idea certainly merits serious consideration, especially in light of the current interest in the plant. Perhaps there is a modern day Prometheus among us who, rather than fire, is stealing grass from the gods to bestow unto mankind.
About the author
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