I'm actually having a bit of trouble visualizing this setup. The only thing I can picture that is consistent with that description is the iron standing up, washer mounted and the mason jar put on top of it upside down. But I can't see how the vacuum wouldn't be lost entirely as a mason jar is placed atop the soldering iron.

That's quite correct, Nigredo. Since I stopped researching for a while, I put all these things some far place away (in the hands of like-minded people that is ), so I can't simply take a picture. The setup is made by pouring concrete in a +/- 15cm wide PVC pipe; the soldering iron held in place as well as a piece of gardenhose that exits from the side and top (to connect the vacuumpump afterwards, see also my vacuum-filtering setup earlier in this thread). Afterwards, the mason jar's cover is epoxy-glued upside-down onto the concrete, having holes for the soldering iron and the hose. Then, some freebase THH is put upon the washer, the jar is pulled vacuum (until it 'clicks', somewhere around 0,3 bar) and heat is applied. It's better to use low heat and patience than high heat and ending up with burnt THH. It's a question of 30 min- 1 hour to get the THH to sublime. On the washer, only a small amount of black/brown residue remains, given the 91% purity of my THH. I don't think it's worth the trouble though, just do a Manske, which is at least as beautiful (check out the pictures and vid of my THH-manske earlier in this thread)

Good luck Nigredo!

Ah, I see. That fills in a lot more of the picture. To what would you attribute your lost mass?

I have yet to actually do a conversion to THH, so I'm in no hurry to purify with sublimation. It just seems interesting to explore. I'm imagining if out of all the content in syrian rue none of the alkaloids save for the harmalas would sublimate at some pressure+temperature. Then it seems to me that one can boil the seeds, do only the coarsest filtrations (seeds+overnight settling) and then add the base and sublimate the harmalas out. It's wishful thinking, but *if* it worked that way, it would cut out most of the work in extracting harmalas. So before considering it further, I was interested to find out how DIY sublimation set ups have fared.

I'm not sure to which picture you refer, but I was delighted by the microscope images you posted of recrystallized harmalas of varying compositions. Upon reading the paper, I also wondered if one may be able to get a fine gauge on the purity through microscopy alone.

Thank you for the good wishes, and for all that you've contributed to this topic.

This is the kind of sublimation apparatus I would use, although I wouldn't heat the glass with a direct flame like that. Maybe a heating mantle, a hot air gun, or an oil or water bath, depending on the temperature required.

I've been doing research on the best method to do the THH conversion and read over this monster thread. From a purely safety perspective, I'm concerned about cadmium and lead contamination from the zinc, but this was only briefly discussed here. I was hoping to get more feedback on this. In looking at spec sheets for zinc powders I see both contaminants mentioned, for example:

(this is from a listing on ebay with hundreds of sales and comments from people saying they use it for reductions in both Organic and Inorganic chemistry). Does anyone have any more feedback on the level of risk here? Would some lab testing for toxic metals on the output be a good idea? (not really sure where that could be done or how much it would cost, but it seems like it could be a nice data point to have). I was also wondering if there might be some advantage to using higher purity "granules" vs. "dust" (for example ebay "High Purity 99.99% Zinc Zn grain Granular Meta Lumps particle" ). Also wondering if there are alternative ways to do this without zinc besides what is described here which doesn't seem very accessible ("low tech" )?

This thread had a lot of great discussion but it didn't seem to culminate into a TEK as far as I can tell. Is the conclusion that the VDS methods for THH conversion are fine as written with no need for modification? I am under the impression that using ammonia (vs. sodium carbonate) may have some safety advantages in terms of the purity of the final result, looking for confirmation on this.

My final thoughts - there is almost nothing in pubmed on THH, it only has 39 total mentions and mostly only in passing as a constituent of ayahuasca. Only Callaway/McKenna seem to even speculate on its role in ayahuasca as weakly inhibiting serotonin reuptake.(1) We know its not important for MAOI. Is it possible the "THH mystique" is mostly hype and unreliable anecdotes? If you get 100 people harmine only, 100 people harmine/harmaline mix, and 100 people THH+harmine+harmaline in a 2:1:1 ratio, all done blind, do you think anyone would be able to tell from experience reports who got what? Keep in mind, that just to obtain the THH you not only have to do a bunch of extra work, but you end up losing potentially valuable DHH in the process which we know is good for MAOI and not only that but now you also have to use more total harmalas every time due to the lack of MAOI from the THH so its like a "triple whammy" (in other words, it better be worth it, but the evidence that it is seems pretty weak).

Refs:
(1) Callaway, James C.; McKenna, Dennis; Grob, Charles S. ; et al. (June 1999). "Pharmacokinetics of hoasca alkaloids in healthy humans". Journal of Ethnopharmacology. 65 (3) : 243–56. doi:10.1016/S0378-8741(98 )00168-8. ISSN 0279-1072. PMID 10404423

Cadmium will always be in zinc, the only thing that can be controlled is quantity.
Even the pharmaceutical grade zinc supplements and IV drip bags in hospitals have cadmium contamination, they just try to get the cadmium load down low enough that intake stays within the established maximum tolerable daily intake of 25µg.
For good 'ultra-pure' zinc the specification is a maximum of 0.0005% cadmium with a typical content of 0.0001%. With material like this a minimum of one half of a gram of zinc dust would be required to fill up that days maximum tolerable intake.
Of course, there are other sources in the diet.
I doubt we'll get a double blind active-placebo controlled trial of THH/DMT synergistic effects any time soon.
There has been talk and speculation about routes to further reduce cadmium contamination of home made THH. Tests and assays along those lines might be something members here could conceivably arrange some day.
At the very least, do not use cheap zinc dust intended for fireworks. Get ultra-pure grade from a reputable source. At least that way your up to pharmaceutical grade.

Oh, and people could easily tell harmine from harmine+harmaline

Hello Gordo,

I must say I have a lot of respect for anyone going through this monster-thread and unfortunately...



...the information herein was never compiled into a single 'TEK'. However, it got clear that the VDS-paper is indeed quite correct as well as detailed and this sort of got the motivation out of creating a quasi-identical TEK.

It is regrettable however that the WIKI on harmala extraction and separation on the Nexus never got corrected. It does talk about the separation using sodium carbonate/bicarbonate, which is indeed a correct way to do it (confirmed in this thread by microscopy and outlined in the VDS-paper). However, it still mentions the "pH 8.5-way" of separation which is clearly incorrect given all the information in this thread and the detailed analysis in the VDS-paper. This way, the precipitate will contain A LOT of harmaline as well. I don't know how to edit a WIKI, perhaps Endlessness can help?



While 'reviewing' the THH-conversion we discovered an error in the type of base that can be used to precipitate the alkaloids. ONE CAN NOT USE SODIUM CARBONATE BUT SHOULD ALWAYS USE AMMONIA IN THIS STEP. Otherwise, the zinc-salts that are in solution will precipitate. Ammonia manages to keep them into solution (complexed?). Referring to the paper, this means that protocols 3 and 4 are incorrect and should only mention ammonia as the base. For precipitation in the least, but I would certainly advise to use it for the washings as well, giving the presence of heavy metals in any zinc-residues.
GC-MS by EC confirmed my THH-base to be 91% pure. I wonder if I had converted it to a salt-form it would have remained more stable and pure in transport. Might still do this sometime...

Good luck, Gordo!

Thanks for the responses guys. In my research I also noticed that the ammonia should keep the cadmium dissolved in solution which is encouraging, however apparently that is NOT the case for lead. From what I've read, the lead may remain dissolved in solution of excess NaOH however. Perhaps doing two precipitations would increase the purity? But then I wonder about NaOH contamination

Also in the vein of "low tech", what would you consider acceptable filter material to ensure as much zinc as possible is removed? Is a simple coffee filter adequate? Double coffee filters? Or should something more "lab worthy" be recommended?

[quote=GordoTEK]

I forget who it is, but someone on here uses diamanteous earth. I checked it out and ended up getting a hold of a bag of the stuff but haven't tried it out yet.

Not sure actually. I used lab-grade filters that fitted my Büchner-funnel. I suggest you give a double-layered coffee-filter a chance and check the filtrate for clouding. You still have the ammonia washes to rinse further.

You can also perform a 'Manske' afterwards. That way, you both further purify and convert it to the more stable HCl-salt.

And I guess that should be diatomaceous earth: https://en.wikipedia.org/wiki/Diatomaceous_earth.

Since after a good bit of searching, I could not find anyone having previously sent their post-zinc reduction THH off to a lab for heavy metals testing, I am planning to do this as my small contribution to the body of knowledge around harmala extraction. I tracked down four reputable labs that do this testing routinely for regulatory/consumer safety purposes. Only 2 of the labs responded to my inquiries and gave me the forms to submit along with a sample. Unfortunately both of these labs require a 5g minimum sample, so it looks like I will be sending them my entire extract (don't want to think of all the hours behind that). Now I'm probably only going to do this one time since the loss is so painful

My original thinking was that I'd send the sample resulting from the post-zinc reduction, ammonia freebase precipitation. If the testing results in unacceptable levels of heavy metals, then I guess it would be worth doing the Manske on this post-zinc reduction, ammonia freebase precipitate and test again to see if there is significant improvement and/or to use a higher purity zinc for the reduction (99.99% purity zinc is expensive, I'm not sure that too many people would be using it unless they thought it was required for safety).

But now I'm wondering if I should do the Manske and send that instead, IF indeed this step would be recommended anyway for storage purposes of the THH? This question lead me to of course search on what knowledge is out there about long term THH storage/stability and I'm having a hard time finding anything credible/definitive. I do see several references to the possibility that THH is not very stable (especially in freebase form) but has anyone really put this to the test? I know some of you guys have been at this for years, do you have any 2 or 3 year (or older) THH freebase that you can simply put under a microscope? I'm also wondering what impact, if any, storing in a freezer might have? Do we have any general guidelines like "THH freebase will remain stable at room temp for X months/years? and stable in a freezer for Y months/years?" and similarly, "THH salts will remain stable at room temp for X months/years? and stable in a freezer for Y months/years?" If we don't have good science around that, I think it would be yet another phenomenal contribution to the community if someone would do this (I'll do it myself, but I don't have any old THH laying around, so its going to be years before I have any results).

So the pressing question anyway just to summarize is this - if you were only going to do heavy metals testing once, would you do it on the post-Manske salt form since its likely to be cleaner and you'd likely be storing it in that form anyway? Or do it on the earlier stage post-zinc reduction ammonia freebase form because most people are probably going to use it in that form (to avoid losses as well as salt contamination) and it would be nice to know what if any real world health risks there may at this stage? Or is the whole idea of heavy metals testing just a waste of time & money since if it comes back clean it won't really prove anything (maybe the zinc I used was just very pure but the next guy won't be as lucky)? And if it comes back as contaminated - I will have no idea if using a more pure zinc or doing other cleaning procedures would bring the levels down to acceptable? Most likely if it comes back as contaminated I will just not make THH from zinc again period and not recommend the method (especially since I'm not convinced yet that THH is worth taking even when pure).

Gordo,

From my own experimentation in the course of this thread, it has become clear to me that THH-solutions are readily oxidised again to DHH. As soon as you remove the Zn, it doesn't take long for the solution to lose its pale-blue fluorescence and return to yellow-green. Didn't Callaway write something about the alkaloids in aya-brews when left standing?

Concerning the Cd-exposure. If you take the above percentages, 1g of Zn will contain 30 mcg of Cd, right? Say you used this to reduce a gram of DHH. Then a dose of 100mg THH will contain only 3mcg of Cd, if the atom were to be incorporated in the molecule itself, which is not the case. It will merely be something that wasn't completely washed away from the molecule. According to Wikipedia, normal DAILY intake of Cd is somewhere between 10 and 120mcg. If all this is correct, and please correct me if I'm wrong here, how can this ever become a problem? So no, I would not send 5000mg of THH away if it could be used for research that demystifies the molecule. Just like you, Gordo, I would like to know if THH can live up to its reputation. Please let us know here at the Nexus.

Thanks for your cogent response, I think you just saved me from losing 5g of harmalas, haha. I was actually more concerned about Pb than Cd, but when you do the same math you just did, it's apparent that it should not be a serious concern. The FDA considers 75 mcg of Pb per day for a normal adult to be "safe and tolerable" and with careful filtering and washing far less than that, if any at all, should end up in the final product.

As for stability - I think you are referring to:
J Psychoactive Drugs. 2005 Jun;37(2):151-5.
Various alkaloid profiles in decoctions of Banisteriopsis caapi.
Callaway JC1.


This implies that the THH may actually be more stable than you think? I'm not convinced a color change of post zinc-reduction solution indicates the conversion of THH back to DHH (also note that the color change can't even be observed to begin with if you haven't separated and excluded the harmine).

I was thinking more about the possibility of trying to organize a "citizen science" experiment, recruiting volunteers to do a blind study of THH effects, but I feel like the exercise would be futile. Just too many variables to control (even with exactly the same ingredients the same person can have wildly different experiences from one trip to the next, also a "first trip" is often subjectively better than subsequent trips, etc). Callaway sort of investigated this as well but as far as I know, never published his findings (?).

From Entheogen Review 1995



His language was not very precise, but when he says "a strong correlation was found with teas that contained high amounts of THH and not DMT!" I'm assuming he means strong correlation between higher THH and better subjective experience. It does not surprise me at all that higher DMT amounts would not be correlated with better subjective experience (as excessive DMT is overwhelming to most people and changes the field of vision too quickly to be appreciated like watching TV while someone else changes the channel every half second).

I will try to follow up with him about this.

Good luck, Gordo! It sure looks like you've done your homework

Nice post GordoTEK. What the researchers in GordoTEK's post above failed to realize (but they were on to something) is that serotonin blocking is a main effect of all the natural oral entheogens like the semi-synthetic LSD, mescaline, Ayahuasca, mushrooms, 5-meo-dmt & bufotenine (found in snuffs). Snuffs give effects which last for 3 hours. We now know this thanks to Ray's 2011 receptorome study...see chart below. This is where THH comes in, as it is a mild serotonin reuptake inhibitor as well.

Some more info you won't easily find is below (as this was discovered when reviewing the 2011 Thomas S Ray Receptorome study, and putting all the values into chart form). Even most academic and scholars don't seem to be aware of the recently published receptorome data for DMT from Thomas S. Ray's study, and it's comparison with the other natural psychedelics.

DMT lacks anti-serotonin properties. (Ref 1 & Ref 4)

Tetrahydroharmine appears to play an important role in blocking serotonin which happens when 5-ht1a is agonized, as dmt does not do this by itself, but requires either caapi or components of Amazonian snuff to do this, ie teamwork. THH also agonizes all 3 adrenal receptors (a2a, a2b, and a2c) with good strength.

2011 Thomas S. Ray study: Breadth of Receptor Binding, 4.00=max, 0.00=min
(these serotonin filters/gates/barriers/doors make up >80% of brain 5-ht & are broken down when 5-ht1a is agonized)

Real life examples that occur when serotonin filters are broken down at 5-ht1a AND the psychedelic molecule works in the place of serotonin at the other 20% of brain 5-ht (everything that is not 5-ht1a): music sounds better, infinite beauty is easily perceived, feelings of universal eternal Love, spiritual things and qualities take on a significance that is utterly stupefying, etc.

Dmt by itself has been found in the Receptorome study to not block serotonin...while the following traditional team players have been found to strongly block serotonin: 5-ho-dmt in Amazonian snuffs, 5-meo-dmt in Amazonian snuffs and the 2nd largest alkaloid in caapi (thh or tetrahydroharmine). All 3 are thus anti-serotonin, and surprise: traditional.

Ibogaine inhibits both serotonin and dopamine reuptake transporters (it is an SDRI or serotonin & dopamine reuptake inhibitor). (Ref 6)

New discovery: the recently discovered adrenoglomerulotropine (a hormone of the pineal gland, otherwise known as 6-Methoxytetrahydroharman) (Ref 2) is an isomer of tetrahydroharmine, found in caapi. Caapi was said by the Indians to have Telepathine qualities as Ayahuasca was said to facilitate telepathic communication among tribal members.

DMT is super potent at the other 20% of brain 5-ht receptor sites, way exceeding even psilocin (see chart below), but in doing so, it must give up 5-ht1a binding, (serotonin blocking) which makes up over 80% of brain 5-ht, so when you combine admixture with components of caapi you get a "team action".

LSD scientist & founder of Heffter Institute Dr. Nichols:

Dr. Nichols

Thomas S. Ray, Psychedelics and the Human Receptorome (2010):
https://journals.plos.or...371/journal.pone.0009019
hxxp://journals.plos.org/plosone/article?id=10.1371/journal.pone.0009019
Breadth of Receptor Binding, 4.00=max, 0.00=min

As we go thru day to day life, the brain serotonin filters (or gates) are in place so that we will not be overwhelmed by the perception of the way things would appear to an un-filtered mind, or "Mind at Large" as Aldous Huxley describes it in "Doors of Perception" as "infinite or eternal". (Ref 5) He also referred to the visions as coming from "the other world" in his book "Moksha". I prefer to think of it in similar terms as well "the spirit world" or "the other world". 5-ht1a inhibition while the psychedelic molecule works in the place of serotonin at the other 20% of brain 5-ht theoretically causes this filter system to be lifted, and the infinite mind to manifest in combination with dmt for example.

Technical analysis with help from Ray's study: these molecules can only "do so much" on their own, as the docking size of the molecule to the receptor is like a key fits a hole. Example: LSD is super potent at almost all the brain 5-ht receptors thanks to it's large molecular size, but it must give up binding strength at adrenal sites a2b and a2c so that it can still hit 80% of brain 5-ht at 5-h1a with great strength.

Mescaline is the world's strongest adrenal a2c agonist (off the charts strong with 4.00 at a2c). This helps to explain how mescaline is more aesthetic and primal compared to the more analytical LSD, which lacks a bit aesthetically. Unlike what Wikipedia states, mescaline has no activity at 5-ht2a.

5-meo-dmt is off the charts strong with 4.00 at 5-ht1a, and can easily obliterate or shatter the ego into a million pieces even at the tiniest of doses due to it's extreme strength at over 80% of brain 5-ht (5-ht1a).

Additional 1988 study which backs up the 2011 Thomas S. Ray receptorome study:

Pharmacology of 5-hydroxytryptamine-1A receptors which inhibit cAMP production in hippocampal and cortical neurons in primary culture. https://www.ncbi.nlm.nih.gov/pubmed/2828913


N-Methyltryptamine (NMT) found in barks: https://en.wikipedia.org/wiki/N-Methyltryptamine

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References:

(1) Ray, Thomas S. "Psychedelics and the Human Receptorome", Feb 2 2010, PLOS one research article.

(2) Naranjo, Claudio. "Psychotropic Properties of the Harmala Alkaloids", Ethnopharmacologic search for psychoactive drugs, Jan 28-30, 1967.

(3) Nichols, Charles D. "Serotonin Receptor Signaling and Hallucinogenic Drug Action", The Heffter Review of Psychedelic Research, Volume 2, 2001.

(4) Dumuis, Sebben, Bocaert. "Pharmacology of 5-hydroxytryptamine-1A receptors which inhibit cAMP production in hippocampal and cortical neurons in primary culture", Molecular Pharmacology, Feb 1988; 33(2):178-86.

(5) Goodman Ph.D, Neil. "The Serotonergic System and Mysticism", 2002.

(6) Bulling, Schicker, Zhang, Steinkellner, Stockner, Gruber, Boehm, Freissmuth, Rudnick, Sitte, Sandtner, "The Mechanistic Basis for Noncompetitive Ibogaine Inhibition of Serotonin and Dopamine Transporters", J Biol Chem. 2012 May 25; 287(22): 18524-18534.

(7) Nichols Ph.D, David. "LSD and it's Lysergamide Cousins", The Heffter Review of Psychedelic Research. 2001;2:80-87.

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Question asked:

Ibogaine binds directly to the serotonin transporter (SERT), so it does not have to target the 5-ht1a substrate pathway. This could be likely what happens with tetrahydroharmine, as THH and ibogaine have similar basic beta-carboline structures.

Thomas S. Ray's study shows a value of 3.57 at SERT for Ibogaine (4.00 is max). Ibogaine has been shown to inhibit serotonin transporter (SERT) noncompetitively, in contrast to all other known inhibitors, which are competitive with substrate.

Thomas S. Ray Receptorome study, 4.00=max, 0.00=min.

top = ibogaine (inhibits both serotonin and dopamine reuptake transporters, it is an SDRI or serotonin & dopamine reuptake inhibitor)
bottom = tetrahydroharmine (serotonin reuptake inhibitor, it is an SRI)

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Bonus references from a few authors who describe personally perceived subjective differences:

Graham Hancock, "Supernatural", pg 428:
Daniel Pinchbeck, "Breaking Open the Head":
Gayle Highpine, "Unraveling the Mystery of the Origin of Ayahuasca":
professor8 (11/1/2010):
Patrick Lundborg, "Psychedelia", page 61:
Graham st. John, "Mystery School in Hyperspace: A Cultural History of DMT", see his interview at Reality Sandwich:
69ron:
James Oroc:

Most interesting, tregar! Didn't know that M doesn't work on 5HT-2 by the way. It does give quite a different headspace and this might be the underlying explanation? Any info on other PEA's?

And do you have any first-hand experience with THH as well?

And how fascinating this all may be, perhaps people will not find the way to this thread to partake in the discussion. Can it be relocated to a more specific subforum?

Thanks An1cca! enjoy reading all your posts by the way...just wanted to add some comments to what GordoTek listed above. Back to your regularly scheduled topic. I just like to talk theory.

I still think DMT has 1A agonism, multiple sources state that it does, whereas the one source says it doesn't. Also keep in mind THH is not necessary, it's said that 1A can be activated even from SSRI's, MAO-A inhibition in general, Tryptophan and 5-HTP supplementation, as well as Limonene.

Also it should be noted that for me personally, i haven't gotten nearly as much from mushrooms, 4-ACO-DMT, or LSD, as i have from DMT, idc what DMT does, it's the top of the crop for me personally, gives me everything i need.

Yes, very interesting ShamensStamen. Found this quote from tapatalk:


p.s. above 2011 paper by Ray is backed up by 1988 paper on last paragraph of post, same findings of lack of anti-serotonin properites for dmt. MAOI's, harmmine and harmaline have been found to have zero activity in blocking serotonin.

I encountered the same thing, but seems like it might not be the case:
THH > DHH