Aya alkaloid analysis - anything since McKenna et al 1984?

[padawan]

I'm trying to solve the mystery of my pharma fails by re-examining the constituents of aya and making as accurate an analogue as I can.

McKenna, Towers and Abbott's analysis of various samples (Monoamine Oxidase Inhibitors in South American Hallucinogenic Plants: Tryptamine and B-Carboline Constituents of Ayahuasca, Journal of Ethnopharmacology, 1984) gives some great data. For example, a typical 60ml dose of Pucallpa Ayahuasca contains an average 280mg Harmine, 96mg THH, 25mg Harmaline and 36mg DMT.

Does anyone know of more recent constituent analyses of ayahuasca samples?

 

[Kajlian]

In the following 2003 study they analyse an ayahuasca sample:

Human Pharmacology of Ayahuasca: Subjective and Cardiovascular Effects, Monoamine Metabolite Excretion, and Pharmacokinetics. (J. Riba et al.)

"To administer ayahuasca in accurate dosings and masked in a
double-blind, double-dummy design, a 9.6-liter batch of Brazilian
Daime was subjected to a freeze-drying process that yielded 611 g of
powder, which was subsequently homogenized and analyzed. The
DMT content was determined by HPLC, as described by Callaway et
al. (1996), and the beta-carbolines were determined according to a
modified version of the method described therein. One gram of
freeze-dried material contained 8.33 mg of DMT, 14.13 mg of
harmine, 0.96 mg of harmaline, and 11.36 mg of THH, which corresponded
to the following alkaloid concentrations in the original tea:
DMT, 0.53 mg/ml; harmine, 0.90 mg/ml; harmaline, 0.06 mg/ml; and
THH, 0.72 mg/ml" (Riba et al. 2003)

 

[dreamer042]

Good info here as well.

McIlhenny, Ethan Hamilton. "Ayahuasca characterization, metabolism in humans, and relevance to endogenous N, N-dimethyltryptamines." (2012).

 

[padawan]

Thanks guys - that's quite helpful. I'll have to spend some time going through these in detail. Cheers :thumb_up:

I did a 200mg harmine versus 200mg harmaline bio-assay recently - minimal feedback from the harmine but the harmaline put me on my back for several hours with nausea and dizziness. Definitely going to be zinc-reducing most of that stuff.

 

[downwardsfromzero]

padawan - someone here (Jagube, IIRC) complained of having far too much THH on hand after performing a harmaline reduction.

I would suggest you look into converting at least half of your harmaline into harmine as well.

 

[padawan]

Yup, will zinc reduce 3/4 of my harmaline to THH, but I didn't realise that harmaline could also be converted to harmine - thought that was an urban legend that was proven false. Will have to look into it. Thanks.

 

[downwardsfromzero]

Harmaline to harmine conversion is in the scientific literature since a very long time ago.

The paper concerned (one of Fritzsche's harmala alkaloid papers) is somewhere in the existing ayahuasca analysis thread. Something like that, at least.

Eine andere, eine vie1 grossere Ausbeute gebende Methode der Darstellung des Harmins aus dem Harmalin ist folgende: Man übergiesst salpetersaures Harmalin in einem Kolben mit einem Gemische aus gleichen Theilen Salzsäure und Alkohol (oder bringt überhaupt Harmalin mit einem solchen Gemische und einer kleinen Menge Salpetersäure zusammen) und erhitzt nun so lange, bis ein durch Aetherbildung bedingtes Sieden der Flüssigkeit das Eintreten der Einwirkung der Säuren auf den Alkohol anzeigt. Mit dieser beginnt gleichzeitig die Umwandlung des Harmalins in Harmin und ist so bald vollendet, dass man den Kolben sogleich vom Feuer nehmen und in kaltes Wasser zum Abkühlen stellen kann, wobei sich salzsaures Harmin in reichlicher Menge als sehr feine Krystallnadeln abscheidet. Dieses trennt man von der braun-gelben, noch anderweitige Zersetzungsproducte enthaltenden Flüssigkeit durch Filtriren und Auswaschen mit verdünnter Salzsäure, worin es nur sehr wenig löslich ist, löst es dann durch wiederholtes Aufgiessen von kaltem Wasser auf das Filter, wobei auf diesem noch etwas färbende, harzartige Substanz zurückbleibt, und fällt die erhaltene Lösung durch Kali oder Ammoniak.

Translation from German on request! (I was fairly certain I'd read this in English somewhere but haven't found it yet.)

Essentially, harmaline nitrate (or harmaline HCl with a small amount of dilute nitric acid) is oxidised by boiling in 50:50 HCl/ethanol, followed by precipitation from cooling and a dilute HCl wash.

 

[tregar]

Padawan said:

I did a 200mg harmine versus 200mg harmaline bio-assay recently - minimal feedback from the harmine but the harmaline put me on my back for several hours with nausea and dizziness.

I can relate. I once had some caapi so strong in harmaline I could only get to the bathroom by crawling, but I did manage to close my eyes for a period of 10 minutes, and saw scenes from medieval period, beautiful gardens, ships traveling the ocean, all in monochrome green, like looking at the reflection of images on a turned off tv....highly detailed images, like dreaming while awake, but these were not things I ever saw in nightime dreams, they were caapi visions, completely unrelated to night dreams.

Approaching a couple hundred mg of tetrahydroharmine can result in fantastic visions in dreams, similar to brew amounts below.

2005: Brew below is 100ml or 3.3oz, simply multiply each figure x 100 to get the mg amount, examples:

entry #1 from UDV is 183mg tetrahydroharmine, 9mg harmaline, 172mg harmine.
entry #22 from Santo Daime is 168mg tetrahydroharmine, 0mg harmaline, 198mg harmine.
entry #29 from Shuar Indian is 163mg tetrahydroharmine, 0mg harmaline, 180mg harmine.

Psychedelia page 61

A traditional saying among Ayahuasqueros is that the jungle vine brings powerful realistic visions, but that the chacruna brings light to these visions. According to the view of Western research, this is not the case; essentially the entire psycho-activity resides with the chacruna leaves DMT content.

Ayahuasca researcher Luis Eduardo Luna recently observed that when surveying tribal lore praising the jungle vine, he could find no traces of similar mythology around the two most common plant admixtures; psychotria viridis or diplpterys cabrerana, even though these DMT plants to a Westerner would appear much more important than the harmala alkaloids of the B. caapi liana.

Bottom painting: what a typical traditional Ayahuasca vision looks like when you combine large amounts of the teaching Caapi with psychotria to light up and color the visions. I have seen the beautiful naked women before like in the painting, they were spinning in front of slowly rotating marble pillars, breathtaking visions similar to what Amaringo painted.

The Ayahuasca artist Pablo Amaringo, "The Shaman -- the Visions"

 

[Aum_Shanti]

Translation from German on request!

Did it anyways...

Another method, with much higher yields of converting Harmaline to Harmine is the following:
In a flask you pour a mix (50:50, hydrochloric acid:Ethanol )over the harmaline nitrate (or put harmaline in such a flask with this mix and "a little" nitric acid). Now you heat until the solution boils (due to ether creation), which indicates the reaction of the acids on the ethanol. With this, at the same time the conversion of harmaline to harmine starts and is quickly finished, so that you then quickly have to take the flask off the fire and put in cold water to cool, whereas a lot harmine HCl precipitates in fine crystal needles.

Now you separate it from the brown-yellow liquid (also containing other decomposition products), by filtration and washing with dilute HCl, in which it is only barely soluble.
Then you dissolve it by repeated pouring of cold water on the filter, on which some colored resin like stuff remains. Now you precipitate this liquid with KOH or Ammonia.

 

[Jees]

...2005: Brew below is 100ml or 3.3oz, simply multiply each figure x 100 to get the mg amount, examples:
entry #1 from UDV is 183mg tetrahydroharmine, 9mg harmaline, 172mg harmine.
entry #22 from Santo Daime is 168mg tetrahydroharmine, 0mg harmaline, 198mg harmine.
entry #29 from Shuar Indian is 163mg tetrahydroharmine, 0mg harmaline, 180mg harmine....

Ehh, sample #22 at 100ml drink would contain 1415 mg of dmt?
Even a small near invisible 10 ml drink would contain already 141 mg of dmt?
And they're standing up chanting and dancing all the time in their ceremony?
Something is off I guess if compared to the others, sample 21 alike.

 

[endlessness]

Extra concentrated samples are a thing in the ayahuasca churches, usually reserved for special "works", they boil down to a syrup and often call it honey (mel) due to the consistency (and sweet taste that accompanies the bitterness and astringency). I'd imagine that's what's up with those very potent samples..

Here are some unpublished ayahuasca results from the last couple of years from the NGO I collab with:

Sample 1- DMT 0.1mg/ml, THH 0.074mg/ml, Harmaline 0.00001mg/ml, Harmine 0.168mg/ml
Sample 2- DMT 0.11mg/ml, THH 0.04mg/ml, Harmaline 0.43mg/ml, Harmine 0.48mg/ml
Sample 3- DMT 1.07mg/ml, THH 0.01mg/ml, Harmaline 0.04mg/ml, Harmine 3.2mg/ml
Sample 4- DMT 0.49mg/ml, THH 0.02mg/ml, Harmaline 0.08mg/ml, Harmine 1.4mg/ml
Sample 5- DMT 0.62mg/ml, THH 1.03mg/ml, Harmaline 0.08mg/ml, Harmine 1.5mg/ml,
Sample 6- DMT 0.25mg/ml, THH 0.29mg/ml, Harmaline 0.036mg/ml, Harmine 1.68mg/ml
Sample 7- DMT 0.48mg/ml, THH 1mg/ml, Harmaline 5.62mg/ml Harmine 0.05mg/ml
Sample 8- DMT 0.67mg/ml, THH 0.33mg/ml, Harmine 0.059mg/ml
Sample 9- DMT 0.4mg/ml, Harmine 1.2mg/ml
Sample 10- Nicotine (unquantified), Unidentified compound

 

[tregar]

Jees, yes...those 2 entries appear to have errors

Thanks for that unpublished data endlessness.

Second to last page:

The average ratio of tetrahydroharmine to harmine in the vegetals was consistently near 1:1 from all sources (table 2) while this ratio was closer to 1:5 in a large survey of source plant material. It is presently unclear whether harmaline is being chemically reduced to thh during the acidic process of decoction.

 

[tregar]

TIHKAL harmine entry:

In measured experiments, the use of harmine in the 140 to 190 milligram range, administered with 35 to 40 milligrams DMT, produced unmistakable effects lasting from one to three hours. Trials with smaller amounts, with 120 to 140 milligrams of harmine and 30 milligrams of DMT produced no signs of central activity at all.

 

[Jagube]

Another method, with much higher yields of converting Harmaline to Harmine is the following:
In a flask you pour a mix (50:50, hydrochloric acid:Ethanol )over the harmaline nitrate (or put harmaline in such a flask with this mix and "a little" nitric acid).

Nitric acid is hard to obtain or synthesize in a low-tech environment. Any idea how difficult it would be to create harmaline nitrate from harmaline?

 

[Elrik]

So I've been systematically toying with harmala dose and timing to try and get 100mg DMT admixture to have an effect beyond a gentle psychedelic feel. My last trial went up to 450mg harmine•HCl, 150mg THH•HCl, and 50mg harmaline•HCl. Based on much older research I thought this was high dosing the harmalas.
I've been reading the paper tregar posted, happy to see that actual brew dosage is reported in addition to alkaloid concentrations. A few things stand out. My THH dose has been way low, when I started using THH 150mg had a big effect on 250mg DMT and I havent yet explored higher doses, the brews in those papers have triple or quadruple that THH dose.
Its also known that people often take repeated doses of the brews. In pharma circles we talk so much about RIMAs being used to 'activate' DMT that I suspect we may be vastly underdosing [a tendency reinforced by most people not removing harmaline from rue alkaloids], the people drinking those brews in that paper are taking Gram Quantities of harmalas. Some times several grams in one night! :shock: My last dose with 450mg harmine was a low harmine dose, and only the first dose, according to the data in that paper.
I think my next 100mg DMT test in a few days will be to make the THH catch up to the harmine, like 525mg harmine•HCl, 500mg THH•HCl, 25mg harmaline•HCl. I want to have a new archetype to try with a serious session on winter solstice.
Has anyone actually been using home made THH in half gram to gram quantities?

Thanks for nudging me over to the right thread endlessness, and thanks for posting that paper tregar!

 

[GordoTEK]

Regarding the Callaway paper, when I originally read it, I felt like he didn't quite finish the work, meaning a mg/ml value is not helpful as anyone can simply boil their brew down more and have a more concentrated result, so measuring actual dosage amounts is required, and while you are right that he did provide "loose guidance" for 3 out of the 4 religious groups (one is completely unknown but looks similar to his "Santo Daime" numbers), even that is not really sufficient - you need dosing for each and every individual brew, it is also quite apparent that these did not come from a single shaman from each group, but from multiple locations and multiple brewers. I still think this paper was poorly done, but I appreciate having something vs. nothing. Here is my attempt at improving the table plus adding averages, I can attach the excel if anyone wants to play around with it (but keep in mind, these numbers are still unreliable for the reasons I've mentioned, and these values are around 2-3 times higher than what other researchers have reported. I'm thinking one explanation could be that his samples dried out somewhat either in storage or in transit before he even got his hands on them):

Other sources:
Phytomedicine. 1998 Apr;5(2):87-96. doi: 10.1016/S0944-7113(9Cool80003-2.
Effects of Ayahuasca on the human EEG.
Don NS1, McDonough BE, Moura G, Warren CA, Kawanishi K, Tomita H, Tachibana Y, Böhlke M, Farnsworth NR.

Endlessness' data:

 

[tregar]

Awesome, good work GordoTEK.

 

[padawan]

This is pretty cool stuff, guys. Appreciate all the efforts :thumb_up: