Businessman’s Ayahuasca

Simple, single plant, short-acting oral DMT without the MAOI (or the vomiting and shitting).

Dennis McKenna likes to say that “Nature is drenched in DMT”, such is its ubiquity in the plant kingdom. DMT is also perhaps the most democratic of psychedelics, since its acquisition depends on little more than the procurement of material from any of the large — and growing — number of plants known to produce significant quantities of DMT in their leaves, bark, or roots. Of course, a little bit of basic kitchen chemistry is also required, but any of the many well-tested online extraction “TEKs” generally produce decent yields within a few hours and with little prior chemistry experience. NOTE: Extracting DMT is illegal in most places.

But, of all DMT-containing plants, one towers above the others as being the go to source of relatively pure DMT, with root bark concentrations reaching close to 2% of the dried material. Internet sellers able to secure a steady supply of high quality Mimosa hostilis (aka Mimosa tenuiflora) root bark can run a brisk trade and, since the bark releases an intense purple-brown dye when steeped in water, its alternative use as a fabric dye provides plausible deniability should anyone question why you’re trying to import several kilos of the stuff from South America.

Shredded Mimosa hostilis root bark.

Although many rich natural sources of DMT have no history of ritual use, Mimosa hostilis most certainly does. Aboriginal cultures in northeastern Brazil used a decoction known as vinho de jurema (wine of jurema), prepared from the roots of the tree, for hundreds of years. Since most of these tribes are now extinct, much of their cultural knowledge has been lost, although some tribes still employ jurema as a ritual drink. However, the psychedelic properties of the brew are hardly in doubt. The word jurema itself means “intoxicating drink” in the Tupi-Guarani language (which actually consists of about 50 languages spoken in parts of Brazil, Paraguay, Peru, and other areas of Amazonia) and Brazilian writer Caminho reported that medicine men, after consuming the drink, experience “fantastic and agreeable dreams”.

In 1942, the Brazilian ethnobotanist and chemist Gonçalves de Lima was invited to observe a traditional ajucá ceremony of the Pancaru indians in the city of Jatobá in northeastern Brazil. Along with the obligatory singing, dancing, and sacred incantations, a pre-prepared batch of wine of jurema was duly consumed. The recipe was simple:

The bark was removed from the tree, steeped in water for 24 hours, strained, and then a little honey stirred in at the end to soften the astringent taste.

Four years later, in 1946, the very same Gonçalves de Lima isolated a prominently expressed alkaloid from the bark of the tree, which he named “nigerine” but which was later shown to be identical to N,N-dimethyltryptamine (DMT).

Structure of DMT.

However, it would be another decade until Hungarian physician Stephen Szara discovered the remarkable reality shattering effects of this ubiquitous plant alkaloid in his attempt to disprove the then prevailing wisdom that bufotenin was responsible for the psychoactive effects of the unrelated cohoba snuffs (derived from the seeds of Anadenanthera peregrina). See my article on Reality Sandwich for the full story HERE.

By initially swallowing the best part of a gram of pure synthetic DMT without effect, Szara also unwittingly demonstrated another unfortunate property of DMT: Its lack of oral activity. It would be another few years, however, before we fully understood exactly why DMT was inactive orally — that it was rapidly degraded by the enzyme monoamine oxidase (MAO) and that the crucial role of the Banisteriopsis caapi vine in the ayahuasca brew was to provide the beta-carbolines (mainly harmine and harmaline) that inhibit this enzyme and thus give oral DMT (from Psychotria viridis and related plants) a chance to reach the brain. This dual plant synergy became known as the “ayahuasca effect”.

So herein lay the problem with wine of jurema: How is it that a decoction of a single DMT-containing plant, sans the presumed indispensable beta-carboline-rich admixture, could have psychedelic properties?

Several explanations have been proposed to resolve this apparent paradox. Least convincing, in my opinion, is the “Lost MAOI Hypothesis”, surmising that, although the original jurema wine did employ a MAO inhibitory admixture plant along with the jurema bark, cultural knowledge of this specific plant — but not the jurema plant itself — was somehow lost to the forest. This seems like a bit of a stretch to me, and the hypothesis was no doubt influenced by jurema’s much more famous multi-plant cousin, ayahuasca, and it was merely assumed that wine of jurema must have employed an analogous pharmacological strategy. However, nobody seems to have any idea what this mysterious lost admixture plant might have been. In fact, although there has been something of a revival of jurema as a ritual drink in recent years, modern Brazilian neo-shamans certainly aren’t claiming to be reconstructing the original decoction. Their neo-jurema is spiked with beta-carboline-rich ground Syrian Rue (Peganum harmala) seeds imported from overseas — it’s not native to Brazil and was certainly never a component of the original jurema recipe. So, why corrupt the original decoction when attempting to resurrect an ancient ritual? The “ayahuasca effect” has achieved almost mythical status and many just can’t accept the possibility that wine of jurema might have no need to exploit it. Ethnobotanist Jonathan Ott has little time for this:

“Why this undue and exaggerated emphasis on the ayahuasca effect in attempting to rationalise the pharmacology of jurema preta? I can assure you that the psychopharmacology of the tryptamines neither begins nor ends with the hallowed ayahuasca effect.”

Another possible explanation is the “Endo-MAOI Hypothesis”: Although the original jurema brew did indeed contain only a single plant, the plant itself, along with DMT, also produces its own pre-packaged MAO inhibitor. For this, there’s actually some evidence, albeit far from conclusive. In 2005, a complex indole alkaloid given the name yuremamine was isolated from the stem bark of Mimosa hostilis (LINK). Based on their proposed structure alone, the authors suggested that yuremamine might bind to MAO but be protected from degradation by a hydrogen bond between a phenyl hydroxyl (OH) and the side chain amine targeted by the enzyme. It would thus act as a competitive inhibitor of MAO, just like the beta-carbolines in the ayahuasca vine. Unfortunately, there’s no biochemical evidence of this MAO inhibitory activity and, in 2015, the originally proposed structure of yuremamine was shown to be incorrect (LINK). The corrected structure also loses that critical hydrogen bond. So, whether yuremamine is a MAOI or not remains pure speculation.

Originally proposed and revised structure of yuremamine. The hydrogen bond in the original structure is indicated at the top of the original structure (left).

Of course, whether you lean towards the Lost MAOI or the Endo-MAOI hypothesis, if jurema is indeed psychoactive when steeped alone in water, then it should be pretty easy to demonstrate. Fortunately for us, legendary ethnobotanist Jonathan Ott has performed this bioassay and his claims are unequivocal:

"It isn't so much that I ‘seem to think that Mimosa hostilis is active without MAOI added,’ but rather that I know this, having felt it in my own body in the only valid scientific analysis I know: the psychonautic bioassay.” (Entheogen Review, 1999, 8, 1)

Ott continues:

"M. tenuiflora (hostilis) is indeed active neat, with no cooking nor additives, simply by hand-squeezing briefly the pounded root-bark in water, 25g twice infused for less than an hour and minimally squeezed in 125 ml cold, neutral water. Each time was quite distinctly visionary and pharmahuasca-DMT-like, albeit with a slightly accelerated pharmacodynamic all-'round.”

Psychedelic author and former editor of the Entheogen Review, David Aardvark, was able to replicate Ott’s findings. His preparation method was similar to Ott’s:

"25 grams of Mimosa tenuiflora (hostilis) root-bark was powdered in a coffee bean grinder…The root-bark powder was placed into a Tupperware container with 125 ml of cold tap water, shaken, and left to sit for an hour. It was then strained through a "French press" coffee filter, and soaked a second time in a fresh 125 ml of water for another hour. This was strained and the two extracts were combined and drunk.”

Side-effects were minimal and easily handled:

"There was some very mild stomach upset at the onset, but no real nausea to speak of at all, and no diarrhea.”

Effects began soon after and closely resembled smoked DMT:

“I was amazed that I started to feel the first effects in about 15 minutes after consumption. These built up over the next 20 minutes or so to a solid "plus 2" on the SHULGIN scale. The effects were indistinguishable from smoked DMT. I felt as though I had smoked about 25-30 mg, the only difference being the more gradual onset, and the longer duration. After hittng the peak, there was a fairly rapid decline to near baseline. This all within one hour.”

Interestingly, Aardvark experienced a total of three distinct waves of effects:

“I was surprised to find myself almost sober for about 5-10 minutes (I could have easily driven a car), and then I started going up again! I peaked a second time, equally as high, but for perhaps a slightly shorter period of time, and came back down. Again 5-10 minutes passed where I felt almost totally sober, and again I started going up for a third time. This third peak was not as high, and did not last as long. The trip was completely over within two hours, and I felt a pleasant afterglow.”

Overall, Aardvark reported an “effective, enjoyable, and brief entheogenic voyage” with almost no body load. So, what are we to make of this?

Ott claims that “preliminary chemical evidence reveals rather the presence of several novel and yet unidentified DMT adducts [yuremamine???] in jurema preta root-bark, apart from free DMT itself.” It isn’t clear what these adducts are but, as Ott suggests, it’s possible that these adducts are themselves psychoactive whilst being resistant to MAO degradation or, alternatively, bind to and thus act as competitive inhibitors of MAO, compromising its ability to degrade DMT. This latter explanation seems more likely to me, but Ott, for reasons he doesn’t make clear, prefers the former.

Obviously more chemical and pharmacological analyses need to be performed on this jurema water extract to work out what’s going on. However, what seems to be clear — at least from these two subjective reports — is that a simple water extraction of Mimosa hostilis root bark provides an unequivocally psychedelic experience that’s both much shorter than an ayahuasca trip and lacks its unpleasant purgative effects. The Businessman’s Ayahuasca, if you like…