Lysergamides LSI, Ancient LSD, Secret of the Eleusis Kykeon and Vedic SOMA

[Dr. Trismegistus]

so you're performing a schiff base which is not physiologically stable if swallowed. LSH is even more unstable. This is why no one cares to "confirm this at a lab".

I HAVE SEEN THIS STUFF ITS A BROWN LIQUID A NASTY ONE AT THATT SO UNLIKE LSD IT HAS A FOUL BITTER TASTE. IF YOU HAD BROWN LS-WJATEVER ITS A THING HIPPIES DO THAT WISH THEY COULD SYNTHESIZE LSD ITS THE CLOSEST THEY COME SO IT MAKES THEM FEEL LIKE THEHY ACTUALLY HAVE A KEY OR HOLD A KEY ANS THEY DO NOT

 

[Dr. Trismegistus]

absolulty you have the knowlege so you are now your own boss is they way I look at it.

 

[Quantamide]

I HAVE SEEN THIS STUFF ITS A BROWN LIQUID A NASTY ONE AT THATT SO UNLIKE LSD IT HAS A FOUL BITTER TASTE. IF YOU HAD BROWN LS-WJATEVER ITS A THING HIPPIES DO THAT WISH THEY COULD SYNTHESIZE LSD ITS THE CLOSEST THEY COME SO IT MAKES THEM FEEL LIKE THEHY ACTUALLY HAVE A KEY OR HOLD A KEY ANS THEY DO NOT

Isn't it supposed to be a green color...that is a problem. Finding quality seeds in the first place , then finding barley grass that has been fermented properly. That is the biggest factor. There are so many methods it's a science onto itself. There is even one company that uses mushroom's in their fermenting process. All these different methods all produce different chemical profiles . I'm going to have to say, in this setting it's a toss-up. Aged goat cheese has a more uniform and consistent profile and the same ingredients as the properly fermented barley grass.

 

[Dr. Trismegistus]

Green/brown same thing when we talking about this . Check it... your gonna like this. Take about 4 - 5 grams of those seeds and mix it into yogurt for your gut and eat it. If my science is right it will give you the effects you are looking for....

 

[Quantamide]

Green/brown same thing when we talking about this . Check it... your gonna like this. Take about 4 - 5 grams of those seeds and mix it into yogurt for your gut and eat it. If my science is right it will give you the effects you are looking for....

I can buy that..yogurt has proline , lactic acid , and some amines..making for a neat transamidation. Greek yogurt has approximately 0.546g of alanine in a 156 g serving. Alanine is responsible for ethylamine formation.Definate potential for lysergic acid ethylamide LAE or D-LAE or LAE-32 formation, and a whole pile of adducts.

Edited to correct acronyms for lysergic acid ethylamide

​

 

[Allylbenzene]

Also I am very curious WHERE these adducts form as in which Nitrogen does the aldehyde bond to. My understanding it is NOT the amide nitrogen?

Likely at the amide N. The indole N is a separate yet equally interesting phenomenon with it's own potential applications (eg LSD + acetaldehyde already discussed in another BL thread and on dmt-nexus).

Here's some almost century-old papers on amide–aldehyde adducts:

Aldehyde—Amide Condensation. I. Reactions between Aldehydes and Acetamide
doi: 10.1021/ja01335a085

The best known aldehyde-amide condensations are those that take place between urea and formaldehyde to give polymeric compounds. However, amides have been condensed with aldehydes to form bimolecular compounds. This is illustrated by the reactions of acetamide with formaldehyde, acetaldehyde, propylaldehyde and benzaldehyde. These reactions have been found to be general for alkyl and aryl aldehydes, as the accompanying table will show. In each case, a small amount of acetic acid catalyzes the condensations, which take place according to the following equation:

The condensation of aldehydes with amides
Part VII. The condensation of piperonal
doi: 10.1007/BF03049118

Piperonal condenses best when heated without any other condensing reagent, with seven of the common amides, giving characteristic piperonyl bisamides. It does not condense with formamide

The condensation of aldehydes with amides
Part II. The condensation of cinnamaldehyde
doi: 10.1007/BF03045405

As far as we are aware, there has been only one such condensation reported, and that is by Gupta, of cinnamaldehyde with phenylacetamide, brought about without any condensing or catalytic agent, by merely heating the two together, and resulting in the production of cinnamylidene-bisphenylacetamide.

The adduct theory which is the namesake of this thread does not really hold up in my opinion, and I’ve failed to find any evidence of adduct formation with ergine or isoergine when mixed with this young barley powder in the conditions described

It is equally possible that adduct formation occurs in-vivo which clearly complicates things. In-vivo conditions are distinctly unpredictable and no two people are alike.

Barley aside, this LSA/aldehyde adduct formation has been performed by various people, including a mod from dmt-nexus. Others were members of a forum I once participated in. I've shared the reports from one of these members (flickedbic) in previous posts.

 

[xdrc]

You know, there is software to draw molecules. It would be helpful to ensure we are all talking about the same thing. But it's all rather futile imo because anyone with a decent understanding of chemistry would be very skeptical of any of these proposed adducts being more than mere fiction (at least in concentrations that would be of any pharmacologic relevance).

It always takes 10x more effort to debunk nonsense than to write it in the first place. Unfortunately with the advent of LLMs the effort to write nonsense has become zero, while debunking it can not rely on them.

Worse yet tregar seldomly responds to remarks, criticism or additional questions or if so only ever partially, and uses a lot of the same textblocks over and over.

Also suspiciously many fresh accounts start talking in this and related threads, making the whole debate even more tiring.

For myself I have decided to not engage further, but with every new post here I can't help but click and cringe at what's written.

 

[donotdothis]

schiff bases have been around since the 60s, this is all ready well documented. nothing about the op is false but it's basically like you buying a "slime making kit" to just throw it away afterwards. Even if you did drink the slime, it's going to be no different than any other acidic ethanol extraction+whatever flavor you added (cinnamon/peppermint/vanilla, etc.) You will have nausea, vasoconstriction, everything associated with regular ingestion of the acidic favored epimers (LAA/LAP).

 

[xdrc]

I said I didn't want to post here anymore but it's been bugging me. Sorry for the long text, I may be under the influence of an amine that causes me to write long texts

schiff bases have been around since the 60s, this is all ready well documented. nothing about the op is false but it's basically like you buying a "slime making kit" to just throw it away afterwards. Even if you did drink the slime, it's going to be no different than any other acidic ethanol extraction+whatever flavor you added (cinnamon/peppermint/vanilla, etc.) You will have nausea, vasoconstriction, everything associated with regular ingestion of the acidic favored epimers (LAA/LAP).

Nothing about the OP is false? Well, that's one statement to make.

The namesake of the Schiff base, Hugo Schiff, died 1915, so safe to say they have been known for a longer time. Well, to be fair you are correct about the 60s, just that it is 1864: https://zenodo.org/records/1427225

Schiff bases/imines occur under (preferably) anhydrous conditions by stirring aldehydes or ketones with primary or secondary amines, some form nicely, some do not, a tiny bit of catalytic acid can help, as well as heat and sequestering the water that is formed during the condensation. They are also typically only in an equilibrium (depending on their stability and the exact conditions) with the carbonyl/amine and may quickly hydrolyse back with any water present. LSA is a tertiary amine.

So what would it react with? The amide group. This is a reaction that is not really taught in the standard ochem curriculum because for the most part it is not really relevant. Why? Because the nitrogen electron lone pair in amides is conjugated with the amide carbonyl and thus not available for nucleophilic attack on the aldehyde or ketone carbonyl, making this reaction extremely unlikely. Why does it work anyways in that one publication tregar and Allylbenzene like to cite? (https://pubs.acs.org/doi/10.1021/ja01335a085) Because it really only works if you push things enough, by using anhydrous conditions, heat and long reaction times which limits the scope in such a way to (in my opinion) to exclude LSA from the possible substrates to make these N-acyl hemiaminals/N-acyl imines (which every chemist aside from tregar will tell you). Besides that it doesn't even make the N-acyl hemiaminals, but N,N-diacyl aminals, which are a little more stable than those pesky hemiaminals. In any case, just tossing some questionable aldehyde source with some acid and stirring in non-anhydrous conditions will lead to zero conversion (well, never say never, but if it is more than 0.05 % conversion under the conditions tregar describes, I'll burn my degree). And besides even if you were able to form these N-acyl hemiaminals (like LSH is one), I'd be surprised of them being pharmacologically relevant as anything but a prodrug as they'd very rapidly degrade in the aqueous soup that is your body.

Now you may ask if LSH does not form from acetaldehyde and LSA, how is LSH in the seeds then?, and this is an excellent question - there is a trick. Lysergic acid reacts with a protein bound alanine, the alanine carbonyl is oxidised to a monothiocarbonate, then NADPH reduced the monothiocarbonate facilitating bond cleavage to form an LSH formate ester which is hydrolysed to LSH. All LSA arises from the eventual hydrolytic degradation of LSH (spontaneously, without enzyme catalysis): https://pmc.ncbi.nlm.nih.gov/articles/PMC10034635/ So in a way LSH is a very good precursor for LSA, but LSA is not a particularly good one for LSH (there are ways to prepare these N-acylhemiaminals in the literature, and the sane ones would start from the acid, not the amide, just like in nature, but much different reactions).

There is of course also the other theory tregar came up with that an adduct may form on the indole nitrogen between LSA/aldehyde/ethanol, but if that arises, it would unlikely to be psychedelically active (just like the N-acyl hemiaminal is unlikely to fit into 5-HT2AR but eh I've had better conversations with my wall than trying to talk to tregar) and would at most exist as a pro-drug. Now while pro-drugs can change the properties of a drug, they don't typically change the whole character of an experience.

It's all quite complicated too in that one would need to have a standard of either the amide adduct or the indole adduct to really verify that whatever analytical method one is using does not hydrolyse the compound during the analysis. But then one could work with an internal standard and just compare if the peak size changes meaningfully. And of course here too tregar has not yet confirmed for us the structure of his LSI, or rather it changed from being proposed first as an amide adduct, then the indole adduct. I must confess I have not read about the concentration of the aldehydes in the plant extract because I see the chemistry side a bit futile.

I'm glad tregar has nice trips with whatever he is doing but I think this is a good example how a mixture of overconfidence (if tregar is a chemist, then not a competent) paired with sycophantic LLM hallucinations (tbf, tregar had these tendencies pre-LLM) can lead to delusional thinking.

I don't really have the same confidence in the method working beyond (delusion-induced) placebo but if anyone is up for some blind experiments (tregar did not seem to care) and does find a significant difference (make sure to not use the absurd dosages tregar suggests), that would be quite interesting and worth a closer look. But the adduct hypothesis is just way too flimsy to be considerable.

@bluelightbird I think a prep-TLC extract of isolated LSA may be of interest to confirm (by bioassay) whether it is responsible for the main psychedelic action or not.

 

[donotdothis]

I asked flash and it said this:

"Summary: LSA is a complex alkaloid that contains both amine (secondary and tertiary) and amide functional groups."

 

[xdrc]

...furthering the LLM psychosis in this thread.

 

[red22]

...furthering the LLM psychosis in this thread.

I posted most of the AI info. Was any of that info bad?

 

[donotdothis]

I HAVE SEEN THIS STUFF ITS A BROWN LIQUID A NASTY ONE AT THATT SO UNLIKE LSD IT HAS A FOUL BITTER TASTE. IF YOU HAD BROWN LS-WJATEVER ITS A THING HIPPIES DO THAT WISH THEY COULD SYNTHESIZE LSD ITS THE CLOSEST THEY COME SO IT MAKES THEM FEEL LIKE THEHY ACTUALLY HAVE A KEY OR HOLD A KEY ANS THEY DO NOT

I've had brown liquid that was perfectly fine. If it's gone black, that's usually a sign of degradation. It's hard to tell them apart if you haven't had both separately. The taste is gnarly though. Try not to get it on your tastebuds. I usually spit it out after 10-15 minutes.

 

[xdrc]

I posted most of the AI info. Was any of that info bad?

I have not read all of this thread in detail, but from what I remember things were reasonably sound.

 

[xdrc]

Just to be clear, LSA has three nitrogens within its structure. The amide (not an amine), the tertiary one with the methyl group at R6, and then of course the indole nitrogen (which can be seen as a secondary heterocyclic aromatic amine). So yes the statement is not wrong, but the reactivity when compared to an aliphatic amine is much different.

 

[bluelightbird]

I thought the three questions I posed to tregar we’re fairly reasonable and straightforward, but until he provides an adequate response, I don’t plan on spending further time on this specific technique. I simply could not reproduce his results given the information provided. If some other experimenter cares to confirm my results, then perhaps we can put this to rest.

1. In the last step, when adding the scraped up residue to the water (with additional DL-tartaric), do you also find this residue floating and remaining insoluble? If so, do you skim or remove this somehow before ingestion? In your procedure, there was no mention of this, so I assumed you drank everything. I do suspect in my case that this remaining ethanol soluble fraction is quite emetic.

2. Back in January, you mentioned running TLC and observing a shifted spot. Can you provide more details on what was observed, and how that plate was run, so I can try replication?
'" new home made TLC performed (1.24.26) even shows LSI (new indole product) forming externally with stirring in water acidified to ph=4 for at least 10 minutes. I compared before and after home made TLC of LSA extract (before) with LSI + LSV + LSCr extract combo (after stirring)."

3. In your experiments, you've already identified several aspects of the procedure that are critical, e.g. it only works with tartaric acid, and it only works with the Aojiru barley powder. Have you tested the robustness of the procedure to seed quality and source? I'd be very curious if you succeed (or fail) to get the same results with seeds that are older, or from a different supplier. I suspect this will be a key variable when others like myself attempt to reproduce this.

I’ve tried to avoid the theoretical hypotheses that tregar and others have proposed, simply because I think experimental reproduction should come first. But since that day may never come, I will add my opinion that the adduct theory (specifically, the N-acylhemiaminal formed by an aldehyde and the amide of ergine) is highly unlikely. Many others have said this already, but under the conditions of this technique, this product should not be expected. I’m not saying formation of something like LSH from ergine and an aldehyde is impossible, but look into the literature and the specific conditions needed to form such a product. For example, here's a paper that provides a synthesis pathway from amide to N-acylheminaminal (unstable as we know) to the N-acyl-N,O-acetal (relatively stable): https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201500655. Note that the first step requires a Grignard reagent under anhydrous conditions to activate the amide before the aldehyde is added.

I still find these fungi and their host plants fascinating, and believe there is more to their story. I’ve read of nocturnal rituals using Rivea corymbosa and Ipomoea tricolor seeds with strong effects, while there are accounts of the same seeds shipped to curious chemists who could not reproduce the effects. Other than individual or racial differences, I’m left suspecting that the freshness of the seeds matters a great deal. Others seem to share this suspicion, for example in another bluelight thread, JackARoe commented:

Here is a fact we can address the Morning Glory and HBWS. There is a reason why Morning Glory has a history of use like a lot of other psychedelics. Fresh seeds can be as potent as LSD. In fact even when I had a good supply of LSD years ago I would always squeeze in a Morning Glory trip. I almost had one freakout once when I plucked to seeds off the vine fall and ate a handful. Hit very quickly, then I remember sitting in the dark on my bed and watching jungle like visuals over whelm me. Another time a friend that grew his own HBWS sent me 6 pods with 3 seeds each. I took 3 seeds from one pod. Thank God I only took 3. It hit so hard it really drove home how fresh seeds are different than older ones. After 6 months I would not even bother taking any. Most people that try these have never grown their own so it gets written off. But there is a valid history with these seeds for a reason that us up and coming psychonauts miss. Fresh seeds need more experiments to analyze content. I know we have the whole LSH, LSI and LSA in discussion but would like to see more facts. Then once we have facts we can scrutinize those too till we get a better picture.

@bluelightbird I think a prep-TLC extract of isolated LSA may be of interest to confirm (by bioassay) whether it is responsible for the main psychedelic action or not.

I agree, someone should do this Maybe it will be me if I get bored enough.

@xdrc similar to you, I’ve taken to growing my own plants this year, and have planted HBWR, Rivea corymbosa, and two species of Ipomoea tricolor (heavenly blue and pearly gates). The morning glories are already 9+ feet, while the HBWR and RC are still only starting (germination was much, much more difficult with these two). Over the next few years, I hope to study the fresh seeds from these plants, both analytically and subjectively, to understand more about these plants and what they can do. Until then though, I'll still lurk around here to discuss with other like-minded people.

 

[red22]

Dr. Mckenna

His twitter profile was deleted…

https://x.com/DennisMcKenna4

 

[donotdothis]

Yes Machine_Elf23, as matter of fact Red22 has done extensive research on how the Greeks could have used wood ash to eliminate the toxic alkaloids in purpurea but be left with non-toxic LSA (then convert to LSI brew). Other than that, there is the non-toxic claviceps paspali which infects barley grass and paspalum grass.

If you look into teotlaqualli, it was very similar.

 

[donotdothis]

Yes Machine_Elf23, as matter of fact Red22 has done extensive research on how the Greeks could have used wood ash to eliminate the toxic alkaloids in purpurea but be left with non-toxic LSA (then convert to LSI brew). Other than that, there is the non-toxic claviceps paspali which infects barley grass and paspalum grass.

If you look into teotlaqualli, it was very similar.

 

[Allylbenzene]

So what would it [aldehyde] react with? The amide group.
...
Why does it work anyways in that one publication tregar and Allylbenzene like to cite? (https://pubs.acs.org/doi/10.1021/ja01335a085) Because it really only works if you push things enough, by using anhydrous conditions, heat and long reaction times which limits the scope in such a way to (in my opinion)

Allow me to expand the scope on aldehyde–amide rxns, at least some additional literature context, perhaps someone with the appropriate equipment & skillset will investigate the LSA scenario. Originally posted on thevespiary:

Spoiler: amide/aldehyde condensations

The condensation of aldehydes with amides: Part I. The condensation of salicylaldehyde
Proc. Indian Acad. Sci. (Math. Sci.) 7, 361–368 (1938).
doi: 10.1007/BF03045403

The condensations of aldehydes with acid amides have been studied by a very large number of workers and the literature is extensive. Often the condensation is brought about by merely heating the aldehyde with the amide alone, in other cases condensing agents of several kinds have been used, such as, hydrogen chloride, potassium hydroxide, potassium carbonate, diethylamine, triethylamine, sulphuric acid dilute, anhydrous sodium acetate with, or without, acetic anhydride. Frequently, the condensation has been carried out without a solvent.

The condensation of aldehydes with amides: Part II. The condensation of cinnamaldehyde
Proc. Indian Acad. Sci. (Math. Sci.) 7, 376–380 (1938).
doi: 10.1007/BF03045405

As lar as we are aware, there has been only one such condensation reported, and that is by Gupta, of cinnamaldehyde with phenylacetamide, brought about without any condensing or catalytic agent, by merely heating the two together, and resulting in the production of cinnamylidene-bisphenylacetamide. In the present paper, the condensations of this aldehyde are studied with four amides, namely, phenylacetamide, acetamide, propionamide and benzamide, under several different conditions of temperature, molecular proportions and catalytic influences. The condensations in all cases take place and produce the cinnamylidene-bisamides. The yields are fair and at times good, but are not generally as good as were noted with salicylaldehyde in Part 1.

The condensation of aldehydes with amides. Part V. Of p-hydroxybenzaldehyde
Proc. Indian Acad. Sci. (Math. Sci.) 10, 282 (1939).
doi: 10.1007/BF03170451

p-hydroxybenzaldehyde condenses readily with formamide, acetamide, propionamide, benzamide and phenylacetamide, and the products are the corresponding p-hydroxybenzylidene-amides, as in the cases of the o- and m-hydroxybenzaldehydes. The condensations are brought about by heating the aldehyde with the amide for 4-5 hours at 130C, in the presence of absence of a trace of organic bases like pyridine and piperidine. The presence of the base improved the yield only slightly (contrast salicylaldehyde) and compare m-hydroxybenzaldehyde). The yields, however, were uniformly very good, never being less than 60% of the theoretical, and reaching up to 92% as the highest...

The condensation of aldehydes with amides: Part VII. The condensation of piperonal
Proc. Indian Acad. Sci. (Math. Sci.) 14, 18–24 (1941).
doi: 10.1007/BF03049118

Piperonal condenses best when heated without any other condensing reagent, with seven of the common amides, giving characteristic piperonyl bisamides. It does not condense with formamide

Condensation of aldehydes with amides: Part XII. Condensation of benzaldehyde and o-chlorobenzaldehyde
Proc. Indian Acad. Sci. (Math. Sci.) 24, 487 (1946).
doi: 10.1007/BF03176919

The condensation of benzaldehyde and o-chlorobenzaldehyde with several amides has been studied, in the presence as well as in the absence of pyridine. The base slightly increased the yield in many cases. The rise of temperature as well as the prolongation of heating raised the yield more effectively. All the products were the corresponding bisamides. The presence of chlorine on the aromatic ring of the aldehyde, had the expected tendency to increase the yield, particularly in the condensations with benzamide, propionamide and n-heptamide. Condensations with formamide, as has been the general experience, did not give good yields; in all other cases, the yields were good, starting from 30% and reaching up to 86% in some cases.

Condensation of aldehydes with amides: Part XIV. Condensation of n-heptaldehyde
Proc. Indian Acad. Sci. 27, 196 (1948).
doi: 10.1007/BF03174832

In the papers so far published in this series, the condensation and the conditions of condensation of eighteen aldehydes with more or less common amides have been studied. Almost all the aldehydes have been aromatic: cinnamaldehyde and dihydrocinnamaldehyde being the only exceptions, in the sense that, though each contains a benzene ring, the aldehyde group is not situated on the ring but is on the side chain...

Condensation of aldehydes with amides: Part XVII. Of 5-chloro- and 3,5-dichlorosalicylaldehydes
Proc. Indian Acad. Sci. (Math. Sci.) 29, 56 (1949).
doi: 10.1007/BF03172438

Usually the highest yields were obtained at 100–110° and in the absence of any condensing agent.

This is a reaction that is not really taught in the standard ochem curriculum because for the most part it is not really relevant. Why? Because the nitrogen electron lone pair in amides is conjugated with the amide carbonyl and thus not available for nucleophilic attack on the aldehyde or ketone carbonyl, making this reaction extremely unlikely.

Clearly someone at the Indian National Science Academy(?) was set on exploring the amide/aldehyde condensation back in the 1930s & 1940s.

Proceedings of the Indian National Science Academy is a peer-reviewed journal, publishing original research and reviews across various scientific disciplines. The journal has a rich history, dating back to its inception in 1935.