I think this is a fascinating area and I would be very interested in experiencing a darkroom retreat. I think the theory stated behind the build up of these different endogenous tryptamines is interesting. I know of a Prof at a past uni whose focus is sustainability and wildlife law, but he's open minded and a nice guy, and ran the odd shamanic drumming session. He is friends with a guy who runs these darkness retreats, and he has experienced one himself and seemed pretty moved by the experience. I heard via one of my best friends who was in the year below that he encountered a unicorn while in darkness!

The neurochemistry is really interesting. I, along with a fair bunch of other people, have experienced some of these key compounds supposedly involved in the darkness retreat experiences...melatonin, DMT and 5-MeO-DMT. But I have never experienced and know of no one else who has experienced pure pinoline, our endogenous MAOI. I spoke to Dr David Nichols about it and he said "I could easily make some and have its receptor properties examined. Probably 40 years ago I read something that said it was a "pure" psychedelic." This is one of the top psychedelic chemists in the world and even he doesn't know that much! I feel this could be a very interesting and largely unexplored piece in this whole darkness/pineal/endogenous puzzle. 'Endohuasca' sounds pretty tantalizing to me...if one we able to experience that in a dark room it would make for a very interesting comparison with the experience of a darkroom retreat.

Its worth pondering the proposed interconversions and ask what would be involved enzymatically for them to be possible. For instance DMT being in any cycle involving serotonin and melatonin and a similarly ring-substituted betacarboline.
There are some good reasons that biochemists and pharmacognocists are not involved in promoting the suggested biochemistry as sound.
When we discussed the problems I saw with his proposed notions (not long after his book came out), Rick Strassman actually agreed with me that the chemistry as he described it was implausible.
Chia does not appear to have asked Strassman for more details but he certainly ran with what Strassman had written as if it was based in scientific research rather than being conjecture (which is what Strassman has always considered it to be since no actual work was done to elucidate endogenous formation of those alkaloids).

The darkroom techniques can clearly produce potent results, just as sensory deprivation or a number of other mind altering techniques can produce potent results. (I've had incredible real psychedelic results with sensory deprivation, with aroma-assisted meditation in a warm bath and with prolonged whirling/spinning.)
I'm not dismissing the techniques but suggest more accountability based on facts and less smoke is needed for an actual explaination about what is actually occurring.
Its being presented by Chia as if the explaination is based on science but the science it is based on is purely speculative at best and this area needs to be approached with eyes wide open. Any time that a mistaken explaination is widely accepted as true, it becomes less probable that an investigation enabling a real understanding will occur.
I believe that there are some fascinating areas of mind science and an underlying pharmacology that is waiting to be revealed in this area.

"Pindoline" is fairly easy to synthesize in two steps using melatonin as a starting material.
It is a bit perplexing that it has appeared in the literature for more than half a century yet there seems to be only one single human evaluation of it in print or mentioned. That alone suggests some things considering how many people have interest in this subject and how many competent and *active* chemists are among them who are very willing to bioassay new things. Maybe it was so incredibly amazing that no one wanted anyone else to know about it or perhaps it was simply not worth reporting? For whatever reason a "Journal of Negative Results" does not seem to exist yet. I for one find knowing what did not work or where alkaloids were not found can be almost as valuable as the details about what did work or what was there but maybe I'm just weird?
It was said to be more spiritual and contemplative than psychedelic if I am correctly recalling what Naranjo commented back in 1967? Its been fairly a long time since I've read that particular book though. Callaway seems to largely talk about things he either did not experience or does not admit to experiencing. Either way that omission (at least for me) limits that value of what he has to say.
Betacarbolines should leave metabolic evidence of their formation? Surely a blood or urine analysis could help support or refute its formation?

If someone learns more in these areas please let me know!

I hear you on the negative results front, these tend to get under reported in science to some degree as they are deemed not as interesting, although they are just as important. No significant pattern in your result is still a result. If science is conducted well, whatever you find should be of use or interest, be the result significant or not.

Dr's David Nichols, Dennis McKenna and Steven Barker all seemed interested in the possibility of synthesizing or conducting research on pinoline/pindoline when I was in email contact with them, but they weren't able to say much about it despite their expertise, it being so little known. I think this would be a really interesting frontier to explore.

On the "fairly easy" to synthesize from melatonin front, just how fairly easy are we talking?? Like possible at home with the necessary knowledge, apparatus and chemicals easy or a full organic lab type set up easy? This is something I would love to know more about.

Some input from Steven Barker (co author on the Strassman study detecting DMT in the pineal gland of live rats) and Dennis McKenna that may be of interest. I think Steven and his team may be planning to use blood tests to look for endogenous compound residues in meditators, and suggested they do the same for darkroom participants.

From Steven:

We are pursuing a number of avenues, including meditation, for the detection and quantitation of a number of these compounds. It may well be that up-regulation/down regulation of these pathways occurring only in response to specific physiological cues. We have to figure that out and actually demonstrate the cause and effect cycle. The article being published on DMT in pineal included an examination for pinoline; none was found. However, as with DMT, we will need to look at more samples and at physiological changes that may lead to its increased synthesis. The method we applied actually looked for 23 compounds, including several beta carbolines, indoleethylamines and metabolites. I do have an interest in 6-MeO-THBC-[pinoline]-I reported its presence in adrenal glands of rats in 1981-and we will continue to monitor for it. If Dennis is interested, please give him my e-mail.

From Dennis:

And you're right pinoline is very interesting too. You are familiar with our work on hoasca, the biomedical study with the UDV. One of our findings was that it caused a long-term elevation in the serotonin transporters compared to controls. This was a persistent effect, not a transient effect that faded with the experience. Turns out that it was THH, 7-methoxy-tetrahydroharmine, that was responsible for this effect. I'd be surprised if pinoline didn't do exactly this; and it may be that is what it does, is regulate the up and down regulation of the 5HT transporters. I agree it should be looked into. But that said, one needs funding, time, resources for that kind of research, none of which I have. Time to write a grant I think. Franz Vollenweider could look into this and has expressed interest.

Very intersting Bancopuma! Thanks for posting those replies.

Inmo has synthed pinoline and did a few experiments with what I think were lower doses, but I could be wrong. He found it very sedating and somewhat similar to other harmalas from what i recall, but also quite different. I can't remember the exact details so maybe he can chime in here.

Very welcome contributions guys.

The pinoline speculations are always fascinating, and it would be great if we could get InMo to chime in.

KT, you may wanna watch giving out your email on this forum... you seem like an astute enough cat to understand why without me elaborating.



I should point out that Chia goes beyond the basic pineal meme by suggesting that the "endohuasca" is a product of the pineal, the pituitary, the thalamus and the hypothalamus in concert.

I know that chemists are very particular about the exact pathways and locations of the production of the compounds in question--and I am also rather interested in this--but the larger, overarching fact is that these chemicals are made in the human body... somewhere. Wherever that may be, they certainly do make their way to the 5HT receptors. So, the "what we have to do" aspect of the how these compounds are made question seems more practical than the former line of thought. In this case, the yogic techniques and darkrooming do seem to provide results in the form of repeatably induced altered states.

I, for one, have used a number of yogic practices that have provided me with tryptamine-like experiences, so I can safely (albeit subjectively) say that there is gold in this vein. I am happy that my more chemistry minded colleagues here can fill in the blanks... but achieving the requisite yogic skill to achieve endohuasca is not secondary to this IMHO.

Keep it coming... loving this.
HF

If I remember correctly, both Harman and 10-methoxy-harmalan are endogenous as well.

Thanks for the suggestion. I've been 'outed' and placed in public viewing so extensively in recent years I often don't care enough about that.


If a person is in possession of phosphorous pentoxide only minimal glassware suitable for refluxing is required.


10-methoxy-harmalan is another way of saying the same molecule. 6 and 10 refer to the same carbon in different numbering systems.
I'd love to learn more if there turns out to be more.

Hey Bancopuma,
Thanks for bringing that Barker article to my awareness. It was a really refreshing thing to see.
Well done for your role in that!

Hey no worries. I just sent him an email, asking about pinoline and his research and got a really friendly reply back. I got the feeling from him, Rick Strassman and Ede Frecska that there is some interesting research on this horizon. Had a good exchange with Dennis McKenna too, he's a great guy. In fact only one guy didn't get back to me. Good to connect with interesting people doing interesting things.