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Morris Crowley
#21 Posted : 3/15/2015 7:31:00 PM

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Alright, I gave it a read. Here's what I have:

Methodology seems reasonable. I don't think their voucher specimen is in an online database so I didn't take a look at it; I am presuming accurate identification in the absence of any indications to the contrary.

There is an odd quirk in naming conventions though: They refer to 5-MeO-DMT as as 5-methoxy-bufotenine. Since bufotenine is 5-hydroxy-DMT, that name would suggest a compound with two substituents at the 5-position (a hydroxy- and a methoxy- group), which would not be a stable compound. Normally if you're naming 5-MeO-DMT as a bufotenine derivative, you'd name it O-methylbufotenine. But I digress. The paper makes clear that "5-methoxy-bufotenine" refers to 5-MeO-DMT.

The most significant data are the reported concentrations of bufotenine and 5-MeO-DMT. From an ethanol extraction, they found 0.326% bufotenine and 0.307% 5-MeO-DMT (percentages by dry weight of stem bark). Water extraction (boiling for 24 hours) yielded a bit less: 0.232% bufotenine and 0.153% 5-MeO-DMT. Still, significant concentrations.

Of secondary significance is the concentrations reported for 5-MeO-NMT (0.088% with ethanol, 0.0495% with water)and 2-Me-6-MeO-THβC (0.014% with ethanol, 0.010% with water). The activity of these compounds is something of an open question. The activity of monomethyl tryptamine analogs is, at best, assumed to be weaker or more subtle than di-alkyl tryptamines. And while the latter compound is a β-carboline, it is only present in very small concentrations and is unlikely to significantly inhibit MAO.

Some of the citations in the paper leave me curious about the motivation behind the work. They cite Ott's Ayahuasca Analogues and Schultes & Hofmann's Plants of the Gods when mentioning that the plant was used to prepare ayahuasca. This suggests a casual interest in the plants and their use, rather than a rigorous scientific/ethnobotanical interest. The more reasonable citations would have been Schultes' 1975 article (number 13 in the "De plantis toxicariis..." series) and Schultes' & Raffauf's Healing Forest.

When calculating potential concentrations of the compounds in an ayahuasca brew, they estimate that 4 grams of stem bark is used in a "common ayahuasca dose". I don't see any basis for that estimate in the paper they cite, but admittedly I just skimmed it. And really, for this species in particular, any dosage estimates are purely conjecture.

Curiously, Queiroz et al. cite Ott's Pharmañopo Psychonautics article at one point, but then go on to contradict it by saying "Bufotenine alone, however, has not been reported to be orally active"

The data is scant, but there is reason to believe that bufotenine and 5-MeO-DMT are orally active without MAOI. Much of the testimony from ingesting the purified compounds comes from a single individual (Jonathan Ott), but Nexus member Pharmacognosis has chimed in with his 5-MeO-DMT experience as well. There is also plenty of evidence that Anadenanthera seeds, which generally contain mostly bufotenine or 5-MeO-DMT, are traditionally used orally without MAOI admixture (see Torres & Repke's excellent book on the subject).

In summary, this analysis gives justification to the reported use of T. mucronata as a basis for a psychoactive brew. It does not, however, get us any closer to solving the mystery of T. methystica presented by endlessness's analysis. Based on that analysis, neither bufotenine nor 5-MeO-DMT are present in T. methystica... so how it's active (if it's active?) is an unresolved question.
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#22 Posted : 3/16/2015 12:10:45 AM

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Salvia divinorum expert | Skills: Plant growing, Ayahuasca brewing, Mushroom growingSenior Member | Skills: Plant growing, Ayahuasca brewing, Mushroom growing

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bufotenine is orally active. 5-Me0-DMT..can't comment at this time.

Looks like decent levels of both..bufotenine is not a very useful compound IME, aside from visionary potency..perhaps when combined with 5-MeO-DMT it would be more profound. 5-MeO is qualitatively the superior of the two, in my experience.

Interesting nonetheless.
#23 Posted : 4/8/2019 8:23:14 PM

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Schultes, Richard Evans., and Albert Hofmann. The Botany and Chemistry of Hallucinogens. Thomas, 1980.

Tetrapteris Cavanilles

The genus Tetrapteris comprises some ninety species of vines, rarely treelets, distributed throughout the humid tropics of the New World.
Several writers, notably Spruce and Koch-Gründberg, mentioned more than one ‘kind’ of caapi in the basis of the Vaupés River of Brazil and Columbia (Koch-Gründberg, 1909, 1923; Spruce, 1908 ).
In 1948, Schultes witnessed the preparation and experimented with a narcotic drink amongst nomadic Makú Indians on the Rio Tikié, an affluent of the Uaupés in the northwesternmost Brazil. Specimens taken from a flowering vine, from the bark of which a cold-water infusion was made without the admixture of any other plants, represented an undescribed species of the malpighiaceous genus Tetrapteris, closely allied to Banisteriopsis. The species was described and named T. methystica (Schultes 1954a). The drink prepared from this jungle liana was of a yellowish hue, quite unlike the coffee-brown colour characteristic of all preparations made by the bark of Banisteriopsis caapi in the same region (Schultes 1954a).
Unfortunately, chemical studies have not yet been carried out on Tetrapteris methystica. The closeness of the genus to Banisteriopsis and the similarity of the effects of those induced by B. caapi suggest the probability that β-carboline bases may be responsible for its activity.
It is worth considering that Tetrapteris methystica may represent the second ‘kind’ of caapi mentioned by Spruce and Koch-Gründberg; it might be that the epithet of caapi-pinima (“painted caapi”) reported by both these writers alludes not to the coloured leaves but to the unusual yellowish hue of the drink prepared from it. Recently, Tetrapteris mucronata has been reported as the basis of a kind of caapi amongst the Karapaná Indians of the Río Apaporis basin of Colombia (Schultes, 1975).
Tetrapteris methystica R.E. Schultes in Bot. Mus. Leafl.
Harvard Univ. 16 (1954) 202
Scadent bush; trunk with black bark. Branches ashy-yellowish, with internodes 4-10 cm long. Branchlets terete, lightly canaliculated, grey-sericeous when young, 0.8-3.3 mm in diameter. Leaves chartaceous, ovate, rather long acuminate, basally mostly rounded, marginally entire but slightly revolute, 6-8.5 cm long, 2.5-5 cm wide, strongly discolourous, upper surface bright green, minutely and remotely sericeous, nether surface ashy green, rather densely sericeous and provided with wax. Stipules small. Soon caduceus. Inflorenscences pseudocorymbose, few-flowered (apparently 4-5), much shorter than leaves, 2.5-3 cm long; bracteoles ovate-triangular or suborbicular, 1.5 mm long. Sepals thick, pilose without, ovate-lanceolate, subacute, 3mm long, with 8 black oval-shaped glands 0.5mm long. Petals spreading, membranaceous, mostly yellow but red or brownish in centre, elongate-orbicular or oval, apically rounded, basally obtuse, marginally subcrenulate, 4 mm long, mostly 2.5 mm wide, claw fleshy, 0.5 mm long. Stamens not included, equal; anthers allantois, 1.3 mm long, 0.4 mm in diameter, arcuate, filaments flattened, 1.3 mm long. Styles equal, recurved. Ovary densely albopilose. Samara nut sericeous, glabrescent, complanate-ovoid, 5mm x 6mm x 2mm, ventral areole ovate, about 3 mm tall; wings chartaceous, brownish, lower ones obcuneiform, apically truncate-rotundate, 12 mm x 2.5 mm, upper ones similar but often subovate or semi-orbicular and slightly larger; dorsal wing 2.5-5mm long. Known only from one locality in the Rio Uaupés basin near the border between Brazil and Colombia.
The other species reportedly used follows.
Tetrapteria mucronata Cavanilles, Diss,
9 (1970) 424, t. 262.

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