Sorry nothing to contribute but just wanted to say that this is a nice thread

Thank you.
It's nice to hear, that some rare individuals actually are interested in my often longer monologues here...

Back on topic:

As I mentioned earlier, the remark from Albert Hofmann relating to the decomposition of LSH just didn't make sense. In "The Ergot Alkaloids" (from Manske's, "The Alkaloids", 1965, Volume 8, p747) he wrote:


And as described before, that just couldn't be IMHO correct, as others had LSH for hours in an acidic solution, but still most LSH remained intact.
I could only come up with the explanation, that maybe the translator made an error here. Although confounding "acid" with "alkaline" in such a text is highly unlikely.

So I went to the library today and got the original work from Hofmann in german ("Die Mutterkornalkaloide", 1964). And I literally freezed and was just thunderstruck...
How could the translator make such a big mistake???
Translated by me from the original, the same passage as above sounds like this (p34):


That's quite a difference!!!
So as it seems water is the culprit! That would actually match this strange "conversion TLC" result, where the conversion didn't work if there was plenty of water (50%).
Although I still cannot believe that this conversion really builds LSH.
OTOH it really makes one question the common preparation method by CWE. There could be some explanations: E.g. the CWE should only be done for a short time, or that the salt form, as it is in the plant isn't as easily decomposed in water.
Question to the chemists: Would it being a salt make a difference here? Where would the salt part attach?


I also read again Wasson's report ("Notes on the present Status of OLOLIUHQUI and the other Hallucinogens of Mexico", 1963) and found a few things interesting:

They gave the women Turbina Corymbosa seeds, and the men Ipomoea Tricolor seeds.
Wasson and Hofmann speculated that maybe this is because the I.Tricolor has more alkaloids in it, and is therefore stronger, so for the men.
I thought this isn't really a good explanation. (Women could just take less...)
But then I remembered the stuff I already read. And if you look at the alkaloid profile differences of T.Corymbosa and I.Tricolor, there is to note the following:
T.Corymbosa has only a small amount of Ergonovine (Ergometrine) but Lysergol. I. Tricolor OTOH has no Lysergol, but a substantial amount of Ergonovine.
Now Ergonovine is known to have a strong effect on the uterus. So a high dose Ergonovine could be problematic for a girl especially if she is pregnant.
Maybe back then the indigenous people also got aware of this difference, and that's why they gave the women the seeds with neglectable amounts of Ergonovine, whereas they gave the men the seeds with a substantial amount of Ergonovine.
It is to note that Ergonovine has also psychedelic effects.

So that would be my Hypothesis.

IMHO also interesting to note that from the described preparation method (the patient itself had to cut off a twig with the seeds), one could conclude that the seeds used were quite fresh.
To note is also that the CWE is only for a very brief time! No long soaks!

Also interesting that sometimes they consumed them in water and sometimes in alcohol.
One could get to the idea, that maybe they used different preparations for different usages? (e.g. for the shamanistic usage they used alcohol, and otherwise water?)
(E.g. for the reason as mentioned above by Hofmann this could make sense. Although, as I understood, Hofmann meant this for the FB. I have no idea how the salt form would perform in water.)


Edit:
It could be an interesting research for someone having access to the proper materials (e.g. HPLC), to look if there is any change in the LSH:LSA ratio in relation to the known extraction methods:
E.g. do a pure methanol soak. Compare with CWE of different durations.
is there a change?

Edit2:
BTW: In the work from Heim et al ("Die psychische Wirkung der mexikanischen Droge 'Ololiuqui' am Menschen", 1968 ) there is something interesting to note, regarding LSH decomposition.
Namely that Hofmann told them personally that (p47) (translation by me):


That again would match all the descriptions from the other papers, where it seems the worst you can do is exposing LSH to an alkaline environment.

Also in the same work they did conclude that LSA has basically no psychedelic effect, but that iso-LSA showed some very slight psychedelic effects.
LSA was dysphoric, while iso-LSA showed some slight euphoric action.
That is IMHO quite astonishing, as usually the iso-version is the totally inactive one.
So there could be something about the theory that the strange known LSA conversion actually just changes the epimer ratios.
They also concluded that Lysergol showed no psychedelic effects, but also no strong unpleasant effects (unlike (iso-)LSA, which showed strongly unpleasant effects).

It is IMHO also interesting to note, that at the end of this paper they say, that in a current research they test the effects of LSH in a chemically stable form.
But I have no idea if they ever published their outcomes, and what they meant with "chemically stable form" (just the tartrate or maleate?).
Anyone knows if there's a publication about this? I couldn't find anything.
BTW: Where would one best search for such unknown articles from that time? E.g. tried Worldcat, Pubmed, Springer, Google Scholar to no avail.

Sorry if this gets exhaustive, but I'm just collecting data, on how LSH behaves under different conditions, as I just couldn't find any data.

In the well known C.Paspali work from Arcamone et al ("Production of a new lysergic acid derivative in submerged culture by a strain of Claviceps paspali", 1961), they tried the following IMHO interesting conversions (abbreviated by me):



It seems an acidic environment pushes the isomerization of both LSA and LSH, when heated.
LSH decomposes either when heated, or in an alkaline environment even at normal temps.

So it gets clear, that if you ever want to get LSH FB, the alkaline step must be of a very short duration and with a PH as little as possible.
I also read that especially Hydroxy-Bases are the killer for it. So e.g. Ammonia or carbonates should be used.

Had a look at the work from Cerny et al ("Epimerization of the simpler amides of D-lysergic, D-isolysergic and 1-methyl-D-lysergic acids", 1969).
They looked at how the environment changes the isomerization reaction, and concluded:



Temp also plays a big role here. While if you boil it, it changes quite quickly, the reaction can sometimes take hours at room temp under the same conditions.

But in all their tries they didn't shift the final equilibrium ratio of the isomers significantly.

As I have said above, if you look at the work from Heim et al, one could conclude that their description of effects of iso-LSA quite well matches the effects description of people having done the alleged LSA->LSH conversion. (more euphoric, more psychedelic)
So one could well think that all this conversion does, is just an isomerization.

But unfortunately the conversion TLC isn't compatible with this theory, as there it seems, something gets almost completely converted to something else.
If it would just push the isomerization, you would end up with the equilibrium isomer-ratio.
Although I didn't find the ratio for (iso-)LSA, I would estimate it to be similar to most of the other known Ergoline ratios, namely almost 50:50. It seems only LSD and the dimethylamide have quite different ratios.

One could only come up to keep this theory by guessing the acetaldehyde somehow binds one isomer, but not the other and prevents it so from reverting...

So I'm still not 100% off to think that maybe the "famous conversion" is just an isomerization reaction.
It is IMHO just too stunning that the reported difference in effects due to conversion readily match the tests on iso-LSA:
* Euphoric, instead of Disphoric
* faster acting
* acting psychedelic (e.g. synesthesia and altered time experience)

Also interesting: In smaller dosages from seeds, the experience is mainly in the direction of iso-LSA, whereas with bigger dosages, the experience is mainly like LSA.
IMHO that could be, because as mentioned earlier (from subjective reports) LSA seems to have the tendency to block the psychedelic effects of other substances. So maybe the more LSA you get the more the iso-LSA effect gets suppressed.

But unfortunately this isomer-theory isn't compatible at all with the fact that fresh seeds seem to have a more psychedelic effect: Because AFAIK in fresh seeds, most is in the non-iso-form.

Really a pity: Would have been such a nice theory...

BTW: In relation to fresh Seeds:
It seems if you wanna get the most out of your seeds, you have to harvest them at about 40 days after the flower (I. Tricolor). Then they do have the highest content. Afterwards it's getting smaller again.
And the drop afterwards is quite significant, being from 30-50% less, when they are ripe. That roughly means, such unripe seeds have up to double the potency of ripe ones.

See the work of Genest ("Changes in ergoline alkaloids in seeds during ontogeny of ipomoea violacea", 1966) if you are interested about the details.

OTOH if their ratios of LSA vs iso-LSA is correct, then this could again push the theory of isomerization, because there the ratio of iso-LSA:LSA is higher in unripe seeds.
But as the isomer ratio changes that easily with extraction methods, I can hardly take this as a serious point in my argumentation.

Keep up the good work, Aum_Shanti. I am following every post!

I've tried to figure the mysteries of the morning glories for years, and I grasped at less than you have here.

If I come across anything you haven't I'll be sure to post. Perhaps it would be a good idea to collate all known scientific articles on the lysergamides and even other compounds found in the psychedelic morning glories

What kerelsk said


Having high hopes for my heavenly blues, this fall, and the added info posted here. Thank you Aum_Shanti!

Thanks for the replies.

But honestly I think I'm stuck in a dead end right now.

There's just too many unknowns and possibilities.
After reading tons of material (research papers and forums), there's basically IMHO just one thing that is pretty sure: LSA is not psychedelic and you actually want to avoid it as much as you can.

Now what else does make it psychedelic is another story. If it is iso-LSA, LSH, iso-LSH, or some of the other ergolines or a mix of them, or...

Further research would need IMHO someone with access to the proper materials. Ideally a HPLC with the proper solvents. A MS isn't actually really needed, but certainly would help.
TLC would also be a good possibility, but there I have the problem, that I cannot get the needed solvents. The solvent in the sold TLC-Kit is very likely not usable for this as it would very likely alter the alkaloid profile itself during the process.
And the solvents that have been proven to work good are impossible to get as a non chemist nowadays.
Where I live, you cannot get even things like MeOH anymore...

If only we would know, what substances relate to the streaks of the known conversion TLC...
This would help a lot.
E.g. is the fattest streak before conversion LSH or LSA or ...???
(e.g. one possibility would also be that this TLC shows how LSH and iso-LSH got converted to LSA and iso-LSA, so just the opposite of what people think)

So far it seems every chemist commenting on this clearly stated, that it would be totally unexpected (if not impossible) that the reaction LSA->LSH would take place like that. If at all the acetaldehyde would react on another nitrogen (most likely the 1 position).
So it seems LSA+Acetaldehyde <-> LSH is not an equilibrium reaction, as many laymen think, but only goes into the direction of LSA. Only through much more complex chemical reactions one could make LSH again.
I'm no chemist, but I tend to believe them.

Then there's this other theory that mainly it's the alcohol you drink while ingesting MGs that makes the difference. E.g it could be a similar effect like cocaine and alcohol, which results in cocaethylene.
An enzymatic reaction taking place in the liver, when both substances are there at the same time.

(Edit:
If the ratio of iso-LSA:LSA makes the difference, then the trip should change over time.
In Paulke's work ("Analysis of lysergic acid amide in human serum and urine after ingestion of Argyreia nervosa seeds", 2012) they observed that the inital ratio from the seeds they used (16% iso-LSA) changed in blood plasma in favor of iso-LSA over time, often reaching >40% after about an hour.
So there's obviously an epimerization happening in vivo quite readily.
In this respect it would seem odd to me, that initial ratios influence the trip that much, when after an hour you almost attained an equilibrium in vivo.

OTOH we have the research from Heim et al, which clearly showed effect differences between people taking LSA and people taking iso-LSA.
I really cannot explain this.
If anyone has an idea which could explain this, please come forward!
The only thing I could remotely think could be happening, is what Dr Nichols once said, that maybe iso-LSA passes the BBB faster.
But IMHO that wouldn't explain the effect differences, just a difference in comeup.
Except if maybe the difference on the BBB is really extreme, meaning, that LSA has extreme problems crossing and iso-LSA easily does it.
Like that you would in the beginning have quickly a lot of iso-LSA in the brain, if you would already take pure iso-LSA, and the converted LSA over time would need long to counter the effects of the iso-LSA (first it has to be converted to LSA and then it has to reach the brain).
But I also wouldn't know, why the epimerization shouldn't take hold in the brain also, with the iso-LSA already there...
Is there any difference in environment between normal blood and brain (more acidic, more basic, ...)???

Overall although iso-LSA could be the main psychedelic effective component, IMHO as said before it doesn't fit the observations that fresh seeds are more psychedelic. As fresh seeds do have a ratio in favor of LSA.
So I personally still think that LSH or maybe even iso-LSH could be the main effective component.

It's really difficult, if nobody does some serious testing in vivo on this, with the pure substances.
)




Lol, my current collection of research papers on this topic is at 700MB...and it is still growing...

This is one of the most interesting threads on nexus. I look forward to new data

As said, I'm mostly at a dead end right now.
So don't expect any newer findings.

But for those interested:
IMHO the best paper summing everything up is from Heacock ("Psychotomimetics of the Convolvulaceae", 1975).
It seems nothing much changed in relation to knowledge since then, except for the fungus stuff.

Looking back I have to say that the study by Heim et al about LSA and Iso-LSA needn't be very conclusive as the sample size was very small, so it's hard to generalize the results.

I personally do not think that any significant epimerization takes place in the blood. I think this happens mostly in the stomach. But that's surely just a personal guess.

Currently I only try to figure out some details:
E.g. when and where did Hofmann say that LSH probably decomposes in vivo. To get the context, how and why he concluded this.
(
Edit:
It proved that this is not that easy. E.g. in Ott's Pharmacoteon he says that Hofmann said this, and gives a reference. But in this reference Hofmann nowhere says this!
So still looking further...
)

I try also to find who was the first to discover LSH in the seeds.
(
Edit:
OK, as I discovered, it was really Gröger who first discovered LSH in the seeds, published in his 1963 paper "Über das Vorkommen von Ergolinderivaten in Ipomoea-Arten".
It seems later also Hofmann then extracted it from the seeds. It probably was in 1967,as Heim wrote in his work from August 1967 that Hofmann said he recently extracted it from the seeds (personal communication, as they knew each other very well).
And there was not yet a publication by Hofmann mentioning LSH. The first seems to be "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico" from 1971.
)

BTW as a sidenote:
Some people e.g. a user Tregar on BL thought some clavines are maybe mainly responsible for the effects
Link.
Unfortunately the amount of the clavines he puts forward to be maybe responsible for the effects is minimal in the seeds.
He relates to a certain paper ("Extraction and Identification of Clavine and Lysergic Acid Alkaloids from Morning Glories", 1975), but he confounded the rf values of the TLC of the different substances as weight values. So he got the completely wrong impression of how much of these clavines are in the seeds.

Edit:
After going through several papers it seems I have to correct my prior statement, as the amount of clavines varies a lot in the seeds and can also be in the same amount as LSA/LSH.
But only 2 clavines really are in the seeds in relevant amounts: Elymoclavine and Chanoclavine.
Usually there is only a quite small amount of Elymoclavine. Most is usually Chanoclavine.
I read many times in papers that Chanoclavine isn't active, but there was never a reference to a source which shows any human tests. So I'm not sure if this is really true.
Human tests on Elymoclavine by Isbell showed only a sedative effect.
Also the tests done from Isbell with the total alkaloid mixture (including Elymoclavine and Chanoclavine) didn't prove as psychedelic.
So unless LSA masks their effect totally in these tests, these clavines do not seem to be psychedelic, or at least not in the amounts as in the seeds.
(see accordingly also the bookpage I added at the 1st page of this thread)

I was just again thinking about what would be a good way of extraction, as easy as possible, to keep the LSH.

As already said, Gröger used the following:
* Ground the seeds to a fine powder
* Washed (defat) 5 times with Naphtha (Petroleum-ether)
* About 0.5g of the powder in 10ml (2g tartaric acid in 30ml water + 70ml acetone) shaken for 1 hour (repeated an additional 2 times, for 3 runs in total)
* Heated in water bath until acetone evaporated
* Washed several times with ether
* Made alkaline with ammonia PH 8-9
* extracted 3 times with DCM

But some steps seem a bit strange to me. Maybe someone could shed some light, on why they make sense. For example:
* Why wash again after the acetone/water extraction. It has already been washed before (defat step)? What could now be extracted by it, that wouldn't have been extracted before?

* Why using the acetone at all? We know CWEs work. So why adding this acetone step, with the tedious following boiling off step?

Another question would be if the DCM step could be simplified somehow. As DCM is hard to get. Benyzme said once(Link)

But these solvents are all hard to get...

Hmm, I think as a basic solution, one could just stop after the initial extraction (a CWE also stops there).

Does it make any difference to already add the water with the tartaric acid, and then do a defat?
Ok then it would probably be difficult for the naphtha to get to the seed mush, as the naphtha will always float on top. Is this the problem?

Edit:
Just discovered that some glycosides responsible for purgative action are glycolipids and therefore amphiphilic. ("Resin Glycosides from the Morning Glory Family", 2010)
So there has to be a non polar wash before adding any water, if you wanna get rid of it.

Found the book "Solanaceae and Convolvulaceae: Secondary Metabolites" online. (unfortunately don't have the link anymore).

Quite interesting if you wanna know what else is in these plants. Although it is clearly over the top for my chemical knowledge...

But it is baffling to see these huge complex molecules which are in these plants. Nature is Amazing! (e.g. see attached a pic of Tricolorin)

But from having a short look through it, IMHO a few interesting things emerged:

E.g. that it seems that it is rather a myth that these seeds contain cyanogenic glycosides.
They do contain Anthocyanins, which are basically responsible for the colors of the flowers.
Maybe someone once confounded these, as they sound similar?
But Anthocyanins are not toxic at all, on the contrary they count as very healthy.

They do not contain any saponins. No Convolvulaceae does.

Actually quite a lot of plants have been identified positive for ergolines.

I. Tricolor is used by traditional farmers to get rid of unwanted weeds. First they let it grow, then they plough it into the soil, then they seed/plant their stuff. Upon decomposition, the tricolorin gets released and it works kinda like a herbicide. (Other) weed grows much worse due to this. It seems like a kind of trick the plant developed to get an advantage over other weed.

But back to my boring ramblings:

I had again a thought about the work from Heim et Al about the different effects of iso-LSA vs LSA.
I thought again about Paulke's work, where he showed how it rather quickly isomerizes in vivo.
Again from all I read so far, IMHO it seems quite unlikely that there's any significant isomerization in the blood (it's very slightly alkaline). OTOH I would expect quite an isomerization in the stomach (PH 0). (I could surely be totally wrong here!)
The iso version is seen as (almost) inactive for all well researched ergolines.
Now what if the same is true for iso-LSA?
That would mean, that first the body absorbed mainly iso-LSA into the blood, which is inactive, then more and more isomerized and you get more and more LSA into the blood.
In total that would mean, you got less LSA than if taken as LSA.
So the effect of taking iso-LSA orally should be as if one has taken a smaller dosage of LSA.
Then I had a look at the dosages they used, and they were IMHO quite big. They never tested "small" dosages of LSA.
So the difference they observed could simply be a dosage difference of LSA.

Then I read again their summary, and there they say that the effects of the total alkaloids is in small dosages like they tested the iso-LSA, and in bigger dosages like they tested the LSA.
IMHO that observation would perfectly match my theory, that the effect difference they observed was mainly because of LSA dosage and not because of the difference of effects iso-LSA has compared to LSA.

I also again wondered what happened about their research with LSH. At the end of the paper they mention that they already started research on LSH.
But in the meantime I'm almost convinced that this work never got published, as I couldn't find anything about it in any database I found.
Just upfront I could only come up with 2 theories why it got dumped:
1)
As LSD got more and more politically incorrect, probably research on this topic got more and more problematic. Maybe the university ordered them to stop any further research on such topics?
2) (more of a conspiracy theory)
Heim and Heimann were friends of Hoffmann. They knew each other very well (all living in Switzerland). Maybe they discovered that LSH is quite psychedelic. But, other substances which got known to be psychedelic got banned, so maybe Hofmann wanted to prevent this for LSH and therefore told them not to publish their results?

I have to admit IMHO the first one is much more likely.

Edit:
I have to indicate, that it seems Merremia/Ipomoea Tuberosa (Hawaiian Woodrose) is also active. Although there doesn't seem to be a paper with a clear analysis, several accounts of people trying these seem positive. It seems they are about as potent per seed as Argyreia Nervosa (Hawaiian strain), just the seeds are much bigger. It also already gets mentioned in Gottlieb's 1973 book "Legal Highs", so this knowledge seems quite old, but still somehow has hardly made it onto modern forums. E.g. where I live Merremia Seeds are even cheaper to get than Argyreia, so it's interesting they don't get used more. I'm wondering why.

Edit2:
So far it seems noone found ergolines in the Argyreia Nervosa plant matter itself. This is quite different to the other species, where the ergolines are also in the plant matter itself, if they have not been fungicide treated. But the work from Gross ("Untersuchungen zum Vorkommen von Ergolinen in Höheren Pflanzen der Familie der Convolvulaceae und in endophytischen Pilzen", 2004) showed that at least the flowers of Argyreia Nervosa do contain ergolines.
I read once, that some people like to steep the flowers and consume it. It seems that could be active, although you would probably need a lot of flowers to really get a decent experience.

This year I produced a tincture from the flowers of Ipomoea cv. "Grandpa Ott" which seems to be a purpurea given its hairy stems and the pointed (rather than rounded) notch in the leaves where the petiole attaches.

Whatever, some 40 drops of the tincture produced a noticeable euphoric effect. More than noticeable - quite strong. This was not accompanied by any significant visionary effect, except the associated mental state was, for want of a better term, somewhat psychedelic. Further testing is necessary although there was a possible hint of cardiotoxicity to watch out for.

Is there a possibility that this liquid preparation could be analysed? It should be possible to seal a small amount into a melting-point tube, for example.

Some additional things are worth noting:

About 200 fresh flowers added over the course of two months to roughly 25mL of 90% ethanol in order to produce this tincture.

The I. purpurea was planted alongside I. violacea (Heavenly Blue) specimens which flowered but did not set seed.

Some species of Ipomoea produce, among other things, ipalbidin which is a fairly powerful, "non-addictive", opioid analgesic.

Ora, lege, lege, lege, relege et labora

Alkaloid salt calculator

Here are The Rules

[1]

Nutmeg reference post

“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli

Yep, "Grandpa Ott" is I. purpurea. IMHO the easiest way to distinguish them is really the hairs. I. Tricolor has an absolutely smooth surface, whereas I. purpurea is hairy as hell. But also from the colors: If it's a dark color (e.g. violet) it's certainly not I. tricolor.



Really interesting. Although the general consensus seems to be that I. purpurea doesn't contain the psychedelic ergolines. But as you said, there is also a ton of other stuff in there...



Strange. But you can always just make a plant extraction. As analysis has shown, the plant matter itself is also quite potent. But there I would surely do a proper extraction, to get rid of a lot of stuff.

I don't know about MGs, but I've had a wide range of experiences with HBWR seeds, from mindblowingly psychedelic, visual and euphoric, to dysphoric, to sedative and indifference-inducing, depending on the batch.

That's what I would expect, as you never know the freshness of the seeds and under which conditions they haven been stored.

That's why I recommend anyone, get some heavenly blue seeds and plant them.

Strange indeed. I concluded that the seed manufacturer had either hybridised the plant or in some other way made it sterile.

This might be interesting to test. I'd likely go for a CWE approach - but what is the ball park figure for the likely potency? Although I'm also thinking that if the seed merchants (N. Europe) bothered to make the plants sterile they might also have treated them with fungicide.

Next year, indeed, I shall be trying with some proper Heavenly Blue seeds. (The Grandpa Otts are lovely plants, I always grow them )

This is indicated earlier in this thread, in the Gröger extraction post:

Just a short update/summary, if anyone is interested:

One knows basically that the fungi only grow on the upper sides of the leaves. But one still has no idea how the fungi get there, or how the plant distributes them on itself (e.g. also how they do get onto the flowers), as no traces of fungi have ever been found within the plant. The fungi seem to be asexual, so do not make any spores. I find this especially interesting, for as it seems Argyreia Nervosa (HBWR) only has the fungi at the flowers/seed pods. So how do they get there, if the fungi are nowhere else?

The viability of the seedling exceeds the viability of the fungi, so that it is possible if very old seeds get planted, to get plants devoid of the fungi, and therefore also devoid of any ergolines. Logically also all further offspring of these plants is inactive. I only hope this information doesn't make it to the broad mass, as otherwise, in a trice deliberately inactive plants get grown, and seeds become inactive. I could even imagine that active seeds would become illegal, due to the easy possibility to grow inactive plants. And as research has shown, it is basically impossible to again make such an inactive plant active.

What I personally wonder: Nowak et al showed in their work that even from active plants, some single seeds were basically devoid of any ergolines. The interesting question IMHO now is: Do these seeds contain any fungi or not? As this could mean such seeds would deliver inactive plants (although they are from an active plant). I personally can only imagine, to get seeds devoid of any ergolines, that due to some circumstances a certain flower/seed pod did not get any fungi on them, and this again would implicate to me, that also no fungi would make it into the seeds of this pod.
If this is the case, I can only imagine that due to the advantages the fungi deliver, the active plants dominate usually naturally.

Again some summarization of LSH and the other actives in the seeds:

LSH decomposes in neutral water solutions, and quickly in alkaline solutions, but it is quite stable in acidic environments. Traditionally (e.g. as reported from Wasson) they only soaked the mushed seeds briefly in water, then strained and immediately drank. IMHO is the decomposition of LSH in water one reason for this short soaking time of the traditional tek (another reason being that the glycosides are amphiphilic, see chapter below).

According to Hofmann's (later) opinion the effects stem mainly from LSA, LSH and ergometrine. And e.g. in fresher seeds there's mainly LSH (in relation to LSA). Only in old seeds, the LSA is dominant. This is because the fungi on the plant can only biosynthesize LSH (not LSA), and LSA is then a decomposition product of LSH over time. Ergometrine is the precursor/intermediate in the biosynthesis of LSH and is so always also present. But the amount of ergometrine can strongly vary (depending on its production rate and how quickly it gets further converted to LSH). But it is often not in amounts in the seeds to be considered a strong contributor of effects, especially as it is not as potent.

The fungi on the vines biosynthesize:
From Tryptophan -> Chanoclavine -> Agroclavine -> Elymoclavine -> Lysergic Acid -> Ergometrine -> LSH, which then decomposes over time into LSA.

Regarding the effects the different contributors have on their own as pure substances (as derived from studies/experiments):

* LSA: Is mainly a sedativum and rather dysphoric (although stimulating and euphoric in very low doses), non visual (even in high doses), putting you in a dreamy, mentally kinda disconnected, self-reflective state. Severe bodily sideeffects on higher dosages (salivation, vomiting, giddiness, diarrhea).

* Ergometrine: Is visual in higher dosages, where also severe bodily side effects occur. Also headspace is typical "psychedelic" in these high dosages. Has been widely used in medicine in low doses due to its uterotonic effects (nowadays a chemical derivation of it gets used).

* LSH: Has never been officially tested by humans. Animal tests showed behavioral effects very similar to LSD. As the molecule is very similar to LAE-32, one might assume it is also visual and "psychedelic", but with a slight narcotic component (not as strong as LSA), as it is a weak adrenergic blocker.

Attached a pic from Solms' study about the differences of LSA, LAE, and LSA (translation by me). As mentioned is LAE structurally very close to LSH, so I could well imagine the findings for LSH would probably be about equal.



For anyone interested, here some short advices from my side, to circumvent the typical pitfalls in the usage of these seeds:

* The seeds have to be the right ones: If HBWR seeds, then it has to be the "Hawaiian" or "Madagascar" variety (e.g. "Indian" or "African" don't work). If the common smaller vine seeds, then they should be Ipomoea Tricolor ("Heavenly Blue" ). But as it seems quite some vendors/distributors in the US sell instead I. Hederacea as "Heavenly Blue". And generally (also in Europe) vendors/distributors often confound I. tricolor with I. purpurea, and so mislabel their seeds. The "Heavenly Blue" (I. tricolor) seeds should be asymmetrical pointy at one end and are always black. If they instead have a "C"-shape, don't use them, as they are not Ipomoea tricolor. You can also use Turbina Corymbosa seeds. Here a pic of the typical shaped "Heavenly Blue" seeds:

(Image doesn't get displayed, link here: https://www.weberseeds.de/gallery/ipomoea-tricolor-seeds.jpg)

* If not in the EU, your seeds may be treated and this being not indicated on the package. If this is the case, ask the manufacturer. E.g. tell you have an organic garden, and don't wanna plant any treated seeds, and so you wanna know if they are treated.

* The fresher the seeds, the better, as only then they contain mostly LSH (in relation to LSA). Actually unripe ones are even better! Ideal time is when the seed pod just lost its green, as then they have the best LSH/LSA ratio and being overall the most potent. They lose up to half their potency until they're ripe, as a study showed. Getting fresh seeds is often a big problem when using HBWR seeds, as for most people they do not grow locally. That's why I personally recommend these people to grow the proper Ipomoeas (no "C" shaped seeds) in their yard and then use the seeds freshly.

* If you do a CWE, pestle first into a fine mush (a conventional mortar doesn't work, take e.g. 2 concrete plates or a concrete floor and a plate, stand on it and wiggle/rotate), or grind/chop into a fine powder (e.g. with a coffee grinder or a high speed mixer in intervals, as not to heat them up too much), then only soak briefly, no long soaks. Then strain and immediately drink. No exposure to daylight during the whole preparation! No usage of chlorinated tap water (halogens like chlorine kill ergolines)!

* If you do a total alkaloid extraction (e.g. Kash's tek), then make sure your basifying step is as short in duration as possible and that you never go beyond PH 9 during this time.

* Take some L-Citrulline (2-5g) together with it, or 30Min in advance, as it is a good vasodilator. If you still experience too much vasoconstriction, then add some L-Arginine (needs around 20Mins to take effect).

* Don't use these seeds if you could be pregnant!!! (LSH as well as ergometrine have quite a strong uterotonic action, which could lead to abortion/miscarriage)

Interestingly the traditional (Zapotec) usage, as reported by Wasson or Hofmann, fulfills these preparation aspects. IMHO no coincidence.

But some people rather like the effect of LSA itself, and it's mainly sedative non visual dreamy aspect, and don't want the typical psychedelic ride. They should basically make sure they get rather old seeds, or to let the water stand for quite some time (best to even add some slight base), to make sure all LSH has converted into LSA.

Also to mention is, that LSH seems to show a more pronounced bronchoconstriction effect than LSA.

Cyanogenic glucosides in the seeds?

This is rather one of many myths about these seeds, where probably someone once came up with this idea, and after several incarnations of rewriting on the net it has become a "fact".

The plants do contain cyanidin glycosides, but these are so called anthocyanins and have nothing to do with cyanogenic glucosides, albeit they sound very similar.

The occurrence of cyanogenic glucosides is pretty rare among the Convolvulaceas in general, and if they occur (in relevant amounts), you usually immediately be aware of it, due to the typical (marzipan) smell. But among the Convolvulacea family, one has found in some few Merremia and Ipomoea species as well as one Stictocardia species, that they do indeed contain cyanogenic glycosides.

But the ones, which usually get used for their psychoactive effects (Ipomoea Tricolor, Argyreia Nervosa or Turbina Corymbosa) contain only non-cyanogenic glucosides. One can be pretty sure about that, as any works using very sensitive "modern" means of detection (like e.g. HPLC/MS), didn't find any. There's only ONE paper (*) finding any in Argyreia Nervosa, and this is an IMHO a bit questionable work from a Nigerian university, done with non-modern means. But even if the findings in this paper are correct, the amount would be irrelevant small, even if you would take huge dosages of these seeds.

But still the non-cyanogenic glucosides can have quite some sideeffects (and have traditionally been used for these, e.g. for purging).

These glycosides which are likely responsible for much of the bad effects are amphiphilic, so also soluble in water, but not as good as the ergolines, which are very soluble.
This is IMHO a reason why the reported CWE soak times in traditional Zapotec usage are only brief: As ergolines are very soluble in water, and these amphiphilic substances not so much, you get a better ergoline/bad stuff ratio with short soaking times. But you will lose a bit of potency.

(*):
Link to Paper

E.g. their citing of an amazingnature online article as one major part of the paper is IMHO already quite unusual and unprofessional.

It seems very strange to me, that in various other works of them they get sometimes very unusual high cyanogenic glucoside values (especially if none were found previously by others or only in very low amounts), also for other completely different plants. Maybe they miscalculated the error size of this tek? E.g. a similar Pakistani work, using the same tek concludes that the measured values are still within the error window, and therefore it could be nothing, but could also be a very little...

downwardsfromzero said:
Wow! thanks so much downwardsfromzero! Reading book all ready.

Also this Paper contains invaluable comments from downwardsfromzero, Triglav, dragonrider, Hermes, Nogal & others, with 5 extremely visual trip reports from all these contributors on page 2 & 20 photos further down:

"Potent LSH & penniclavine fresh from morning glory vine & relation to ancient Greece"

https://www.dmt-nexus.me...aspx?g=posts&t=94737