Which are the active components of MGs?

[Aum_Shanti]

As I had to learn, it seems LSA isn't really the substance doing the job (Link).

Hofmann describes it mainly as a kind of sedativum, to get into a dreamy state.
His notes from a LA-111 (LSA) self trial experiment on the 30.10.1947 ("The active Principles of the Seeds of Rivea Corymbosa and Ipomoea Violacea", 1963))

10.00 h: Intramuscular injection of 0.5 mi of 1 per mille solution of LA 111 (=0.5 mg d-lysergic acid amide)
11.00 h: Tiredness in the neck, slight nausea.
11:05 h: Tired, dreamy, incapable of clear thoughts. Very sensitive to noises which give an unpleasant sensation.
11.10 h: Desire to lie down and sleep. Genuine physical and mental tiredness, which is not experienced as an unpleasant. Slept for 3 hours.
15.00 h: Return of normal condition with full capacity for performing work.

Later he summarized the effects like that (e.g. excerpt from "LSD, my Problem Child" ):

This effect was characterized by a sensation of mental emptiness and the unreality and meaninglessness of the outer world, by enhanced sensitivity of hearing, and by a not unpleasant physical lassitude, which ultimately led to sleep.

Solms confirmed this and stated it is... ("Chemische Struktur und Psychose bei Lysergsäure-Derivaten", 1956):

[...] charakterisiert durch Antriebsschwäche, Indifferenz, Schlafbedürfnis, bis schliesslich die zunehmende Bewusstseinstrübung etwa nach 0.5-1h in einen erweckbaren Schlaf übergeht.
[...]
Auch bei Dosensteigerung trat nie sichere "Halluzination", wohl aber sehr unangenehme vegetative Symptome (Speichelfluss, Erbrechen, Schwindelgefühl, Durchfal]) auf [...]

(translation by me)

[...] characterized by a decrease in psychomotor activity, indifference, a desire to sleep, until finally an increased clouding of consciousness does produce an arousable sleep after about 0.5-1h.
[...]
Also with increased dosages, there was never a certain "hallucinating", but very uncomfortable vegetative symptoms (salivation, vomiting, giddiness, diarrhea) [...]

IMHO interesting, that it gets explicitly mentioned, that no visual effects from LSA were observed, even in high doses.

Heim also didn't observe any typical "psychedelic" aspects from LSA ("Die psychische Wirkung der mexikanischen Droge 'Ololiuqui' am Menschen", 1968 ):

[...] there was little evidence of typical alteration in consciousness and hallucinations as typically seen with psychotomimetic drugs like LSD 25 and Psilocybin.

So IMHO one can conclude, if the seeds have any visual property (which they have, at least when fresh), then this isn't caused by LSA (alone?).

Reading the related work, Shulgin came even to the conclusion, that LSA doesn't contribute an effect at all (LSD entry from TIHKAL):

Both compounds [LSA and iso-LSA] are probably correctly dismissed as not being a contributor to the action of these seeds.

By reading further ("LSD, my problem child" and "TIHKAL" ),it seems the following substances seem the best guess to could be involved:
* LSH (D-Lysergic acid α-hydroxyethylamide or D-lysergic acid methyl carbinolamide)
* Ergometrine (D-lysergic acid beta-propanolamide, also called Ergonovine, Ergobasine)
* Lysergol
* Elymoclavine
* Penniclavine
* Chanoclavine

Well we do actually know, that as it seems the psychedelic effects in the seeds degrade quite quickly over time. So the responsible active ingredient(s) also must be prone to easy decomposition.

Now my question would be to the chemists among you: Which one of the above molecules is quite unstable?

As I heard LSH is very unstable, so it could be a good guess, for being the main culprit.
Also from a layman's perspective LSH is nearest to LSD, with just having one ethyl group instead of two and an additional Hydroxy-group.
And we do know that the very closely related LSE (LAE, lysergic acid ethylamide) is psychedelic, acting similar to LSD, but with ten times less potency, a shorter duration, and "characterized by a narcotic component" (LSD, my Problem Child).
OTOH Hofmann said, that LSH very likely quickly gets metabolized into LSA in vivo.
(Edit: I'm not so sure anymore about that. Couldn't find yet a work from Hofmann, where he said that. It seems this statement is from Ott)

But what about the other substances?

Edit:
BTW, does anybody know, if Dr Nichols ever said anything about LSH?
Edit2:
Albert Hofmann himself thought the following about the active components (from "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico", 1971 ):

According to the results of experiments performed thus far with pure alkaloids, it appears that d-lysergic acid amide, d-lysergic acid N-(1-hydroxyethyl) amide, elymoclavine, and lysergol, and possibly also d-isolysergic acid amide are mainly responsible for the psychic effect of ololiuqui.

Edit2:
In the same source Hofmann trashes Ergometrine as a relevant component:

Psychotomimetic effects are unknown for ergometrine, which is used to a large extent in obstetrics as a uterotonic and hemostatic agent. In small dosages, which are administered for this purpose, the alkaloid apparently has no action on the psychic functions. Its occurrence in the alkaloid mixture of ololiuqui can thus have no significant effects on its mental action.

But according to another paper (Entheogenic Effects of Ergonovine, 1979) Hofmann himself stated that 2mg Ergometrine were psychoactive for him. Maybe he changed his mind later???
Ott verified in that paper that Ergometrine (Ergonovine) is psychoactive. He stated the activity as being simliar to LSD but with a potency of about 1/200th (10mg about equivalent to 50ug LSD).
But the somatic effects at 10mg were already that strong, that one wouldn't want to try higher doses.
So did Hofmann just mean, that there is not enough Ergometrine in the seeds to be active?

 

[Aum_Shanti]

OK, found in this thread (History of morning glory seeds (and other psychoactive bindweeds) - LSD, LSA, LSH - Welcome to the DMT-Nexus)
that Hofmann discovered the psychoactivity of Ergometrine 1976. So at the time of writing the article in 1971, it seems he wrongly discarded it as a possible contributor of effects.

Also in this history thread is one very interesting paper mentioned:

1965 - Isbell and Gorodetzky found that mixtures of synthetic lysergic acid derivatives mimicked the effect of the whole alkaloid extract of T. corymbosa, both of them differing substantially from LSD in that there was a strong sedative component to the effects (Isbell & Gorodetzky 1966)

I couldn't find the article for download. But I could find a book ("Ergot Alkaloids and Related Compounds", 1978, p594), relating to this article.
(see attached pic)

And IMHO it is very very interesting. First they did not use LSH in it.
With the seeds they used, they didn't get the proper effects. So they very likely were not fresh.
With the chemical mix they made to mimic the MGs, they got the same inproper effects.

So from this IMHO it gets quite clear that LSH is really a very good candidate for the actual psychedelic effects taking place.
For at least with the mix of LSA, ISO-LSA, Ergometrine, Lysergol, Elymoclavine and Chanoclavine, they didn't get the psychedelic effect.

So the only missing substances from the ones listed above are LSH and Penniclavine (and there's only very little Penniclavine in it).
So IMHO the only thing speaking against LSH being really the main psychoactive component, is that it very likely decomposes in vivo [edit: Later correction, as above, it seems Hofmann never said this]. But this was just a guess by Hofmann. I think noone ever tested that. Or is anyone aware of that, or of any human tests with LSH?
What would be needed to convert LSH to LSA? Heat? Basic or acidic environment, ...?

Also is anyone aware if anyone ever tested the LSA:LSH ratio depending on the freshness of the seeds?

IMHO also interesting to note, that by the time most of these papers were made, it wasn't yet known that LSH is in the seeds.
In the first analysis of Hofmann he didn't find any LSH. IMHO this was either because the seeds were old, or because the extraction method used did convert it to LSA.

Edit: Found the paper in the meantime and attached it.

 

[dragonrider]

I'm pretty sure that the psychedelic effect of fresh seeds can for a huge part be attributed to the synergy between some of these compounds.

I've personally experienced that a small amount of fresh seeds hugely amlify the effects of 1P-LSD, while old seeds diminish the substance's psychedelic effects.
So these different compounds definately affect eachother, both positively as well as negatively, depending on the specific mixture.

Because of my experience with old as well as fresh seeds in combination with 1P-LSD, i think it isn't a very bold guess to say that LSA most likely counteracts the psychedelic effects of LSD and other LSD-like substances.

 

[Aum_Shanti]

I'm pretty sure that the psychedelic effect of fresh seeds can for a huge part be attributed to the synergy between some of these compounds.

That was also my first guess. But the whole mix that they tested (but without LSH) seemed to have no psychedelic effect. So I'm not so sure about that anymore.
Or it is a synergy together with LSH.

I've personally experienced that a small amount of fresh seeds hugely amlify the effects of 1P-LSD, while old seeds diminish the substance's psychedelic effects.

That's very interesting, and I actually heard something similar already quite some times before (e.g. here Recipes for Organic LSD (LSH) - LSD, LSA, LSH - Welcome to the DMT-Nexus). IMHO it could well be that LSA itself is actually diminishing the actual psychedelic effect. Did anybody ever test this with pure LSA?

I would be really very very interested how pure LSH would perform.
OTOH maybe in the mix above, the LSA stopped the action of the other actives. So the question would have been how it would have worked with the same mix, but without the LSA.

Relating to the same idea:
Could it be that the famous peppermint oil conversion actually doesn't convert LSA to LSH (which is anyways unlikely), but convert LSA to something else (or isomerization?), so that it doesn't block anymore the action of the other actives?


Edit:
The only work about testing the activity of LSH I know of is the one from Glässer in 1961 ("Some Pharmacological Actions of D-lysergic acid methyl carbinolamide" [other wording for LSH] ):
He tested it on animals. But at the end he comes to an interesting conclusion:

Some of my results suggest that it could have a lysergic acid diethylamide-like activity, but this hypothesis must be checked by experiments on humans.

Edit2:
Found the paper in the meantime and attached it.

 

[Aum_Shanti]

Just a short update, as I don't have much time:

When reading Gröger's "Über das Vorkommen von Ergolinderivaten in Ipomoea-Arten", I really get the impression as they did, that there's a high probability that LSA isn't actually built by the plant, but instead the biosyntheses produces LSH, which then degrades into LSA.
E.g. on one example TLC plate of them LSH seems to be the predominant alkaloid in I. tricolor.

Anyone knows any newer research on this?

And again a question to the chemists. What PH (high or low) is needed to convert LSH into LSA?
Strangely I read in some papers acidic, and in others alkaline.

That would really interest me, as the stomach is obviously quite acidic.

One thing is for sure. Temperature is a real LSH killer. E.g. Gröger converted the LSH into LSA at PH 8, 30 Mins at 70°C.

Edit:
Added TLC of I. violacea (tricolor) from Gröger Paper with added substance info.

 

[Aum_Shanti]

Short addition:
In the paper from Klinke, 2008 ("Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose" ) there is one very interesting thing mentioned:

Namely that they found LSH in the blood and urine of people having ingested HBWR seeds.

IMHO this strongly indicates that LSH is NOT so quickly metabolized to LSA as Hofmann suggested, so it could IMHO really be the main active molecule!

But I'm still puzzled how this can go together with Hofmann's findings (The Alkaloids, Vol. 8, p747):

easily decomposes in a weak acid solution to form ergine [LSA] and acetaldehyde

IMHO also interesting what Owsley Stanley stated in an interview (http://archive.li/RAUXH#selection-759.0-759.14):

O: No, that’s not true. Ergot contains many natural, highly psychedelic alkaloids. Iso-ergine is one of them, hydroxy-methyl-lysergamide is another one, and in fact, is considered nearly identical to LSD in effect. Albert Hofmann told me so himself. They believe that it was this derivative contained in extracts of c.paspalum that was used in the Eleusian Mysteries.

The name "hydroxy-methyl-lysergamide" is seemingly wrong. But maybe he meant LSH?
But then it's usually hard to get anything precise out of Bear's statements...

 

[Aum_Shanti]

As it seems Gröger could extract the alkaloids from the seeds in a way to preserve most of the LSH, it may be interesting to note how he did this alkaloid extraction:

* 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

IMHO interesting that he had the stuff for quite a time (hours) in an acidic environment and then even heated it! But this didn't seem to kill the LSH, contrary to what Hofmann stated.
This honestly really baffles me. How could he be so wrong???
Anyone an explanation for that?
OTOH Gröger easily converted it to LSA in a slightly alkaline environment and a bit heat.
Maybe that was a typo in the Hofmann paper, and he actually meant alkaline???
[EDIT: Hofmann didn't state this. This has been a terrible translation error, see later in this thread]

Edit:
OTOH when Gröger did a plant material (leaves and stems) extraction he used the following tek:

* Ground the plant material
* wetted it with 3% ammonia
* 6 hours in the soxhlet with DCM
* Reduced in vaccuum
* extracted 4 times with 2% tartaric acid
* washed 3 times with ether
* Made alkaline with ammonia PH 8-9
* extracted 3 times with DCM

Now he first makes an alkaline environment and then 6h in the soxhlet. Why then did not there the LSH degrade???
Or is the environment not that alkaline if you just wet it and then do the DCM Soxhlet???

As a sidenote: It seems the plant material contains basically the same alkaloid profile, but only in a 1/4 of the density of the seeds.
Also another work from Gröger ("zur Biogenese von Ergolin-Derivaten in Ipomoea rubro-caerulea Hook" )seems to indicate that the alkaloids are actually produced in the stems and then transported into the seeds.

 

[Aum_Shanti]

Anyone having a drugs-forum account and could download me the following?

https://drugs-forum.com/studies/bio...ecated-to-dr-a-hofmann-on-his-90th-bday.6625/

I tried many times to get an account there and it always failed (waiting on the admin confirm, it seems the admin always just deleted the account without any reply of why).

 

[downwardsfromzero]

The name "hydroxy-methyl-lysergamide" is seemingly wrong. But maybe he meant LSH?

Hydroxy-methyl-lysergamide is not impossible. It's like the formaldehyde adduct as opposed to the acetaldehyde adduct. I'd have to trawl through the literature to find if it is in fact present. Possibly Shulgin mentions it in passing, in a list?

Now he first makes an alkaline environment and then 6h in the soxhlet. Why then did not there the LSH degrade???
Or is the environment not that alkaline if you just wet it and then do the DCM Soxhlet???

Considering the BP of DCM is only 42°C, it's not that hot (less than the 70°C described, for example.)

Great topic, BTW! Fitting that I found the 1P-EthLAD :twisted: Oh, and that paper as well

 

[Aum_Shanti]

Thank you very much for the doc.
As it is basically a summary of the topic which is rather new (1998 ), I had high hopes for new information. But it seems not much research has been done in the meantime...

Really a pity.

Hydroxy-methyl-lysergamide

As they were talking about a natural substance I strongly doubt he meant this substance, as although I read a lot of papers in the meantime, I'm not aware that this has ever been found in nature. Maybe he mixed up the "methyl-carbinolamide" and the "hydroxy-ethyl" naming? Or it was just a transcription error from the interview? ...

Considering the BP of DCM is only 42°C, it's not that hot

Surely not that hot, but I would still expect serious changes. I just cannot believe that only this slight temp difference makes the conversion difference.
OTOH we don't have solid data about how much LSH was in it.
He basically just said they all had similar alkaloid profiles. Really a pity they didn't show all the TLC results for comparison.

Edit:
BTW: Does anybody have some pure LSA of the chemists here, or at least quite purified seeds extract?
For IMHO it would be very interesting to let it react in Rum and then do a side by side TLC: LSA, LSA reacted (24h in refrigerator) in Rum (high in acetaldehydes) , and Rum alone.
If anything changes, it should be visible.

There are so many reports on the net of how strongly this "conversion" changes the effect that IMHO it is very unlikely being pure placebo. They all report a much more stimulating effect from it, in contrast to the sedative effect of pure LSA.
If it changes to LSH is another story.
Someone on Bluelight suggested it gets added not to the amide chain nitrogen, but to the indole nitrogen. (The Big & Dandy HBWR/MGS/LSA Thread - Second Iteration)
But IMHO that would just yield something like 1A-LSA. And we already know from 1P-LSD and 1A-LSD that these molecules by themselves are inactive and only get active in vivo when this sidechain again gets removed.

Edit2:
Found this interesting post:
Recipes for Organic LSD (LSH) - LSD, LSA, LSH - Welcome to the DMT-Nexus

According to the TLC there really seems to be a molecular change going on with MeOH+acetaldehyde. But what exactly happens would be interesting!!!
Unfortunately the origin source of this test hasn't been mentioned.
And the descriptions in the post seem contradictory.
But as it seems adding water prevents the reaction to take place.
It would be a blast if someone with a *C/MS could replicate this test.

 

[downwardsfromzero]

Or it was just a transcription error from the interview?

Easily done, especially if it's not in the normal vocabulary of the journalist.

Found this interesting post:
Recipes for Organic LSD (LSH) - LSD, LSA, LSH - Welcome to the DMT-Nexus

Looks like a rum and peppermint tea combination and comparison should also be worth investigating. The Kykeon is fairly reliably thought to have been ergot with added Glechon, which has been translated as Pennyroyal (Mentha pulegium) - although there is also the plant Glechoma hederacaea, in English, ground ivy or in German, kleiner Gundermann. While the Latin binomial is to a certain extent a linguistic and cultural artefact (the plant has also been placed in genus Nepeta, etc.), I still feel this one may also be worth a look.

 

[Aum_Shanti]

Yeah I also read before about this Kykeon ingredient, which could have been more than just for taste. But IMHO it could also be very likely that the base was C. Paspali.

Anyways...I undistorted the TLCs in the link and scaled them for comparison.
It is very obvious that two streaks (C, E) change to two other streaks (B, D).
So IMHO it seems like possibly LSA and iso-LSA get converted to two other substances.
Maybe really LSH and iso-LSH?
Interestingly it seems on the right TLC not everything has been converted completely, whereas on the left one this seems to be the case.

He used chloroform-methanol (4:1) on silica.

Gröger used Ethylacetate-Acetone-Dimethylformamide (5:5:1) on silica for a good separation.
(to give a picture like the one I posted above)

On Gröger's TLC LSH and iso-LSH are further away from the startline than LSA and iso-LSA, whereas the new substances on this TLC are nearer to the startline.
Could this be because of the different solvents? What would one expect in comparison?
Any chemical guy here?
I only know that LSH is more lipophilic than LSA and that the iso-versions also are more lipophilic.
If the different solvents should yield about the same pattern then one could exclude that the products are LSH and iso-LSH.
But if due to the different solvents one would expect a pattern inversion, then IMHO it would be quite likely that LSH and iso-LSH are built.

The only question I would then still have is: Where is Ergometrine on this TLC?
On Gröger's TLC it's in between LSA and LSH.
Or are the two substances that get changed maybe even LSA and Ergometrine?
This would then IMHO point out that the change doesn't happen at the amide part.

Edit:
Just realized that Gröger made the FBs for the TLC, whereas on this TLC this hasn't been made. So this could be the reason for a pattern inversion (salt vs FB)???

Edit2:
But I really find that extremely interesting. I wonder why this post back then didn't get more resonance. It basically proves that really some chemical reaction is taking place modifying the substances, and that it isn't just some synergistic effect (e.g. with peppermint oil). The most important remaining question is certainly: In what substances get they converted? Really (iso-)LSH???

Also that water seems to block the conversion could be an explanation why the conversion failed for many.

 

[Aum_Shanti]

Unfortunately I'm a complete layman regarding chemical reactions.
I tried to find out why the alcohol seems to be an important factor and the water seems to be disadvantageous.

The only thing I found that could be related is that aldehydes together with alcohols build hemi-acetals (and then acetals, if in an acidic environment).
For this the concentration of the alcohol is absolutely important: The less water and the more alcohol the more (hemi-)acetals and vice versa.
At least that could be an explanation why adding water is bad for the conversion.

Could the (hemi-)acetal react easier with the LSA molecule? And then decompose again and split the alcohol off?

Would really be very very interested what someone with knowledge in chemical reactions would think. Could shortly anyone chime in and give his view, what could happen in this conversion, where LSA, MeOH (seemingly also EtOH), and Acetaldehyde are involved.

Edit:
It seems some people speculated that putting LSA in alcohol will force an epimerization, leading to mainly the d-epimer.

To me this all is a real mystery.
As it seems alcohol+acetaldehyde really change the molecules somehow. But to what? Epimers or new compounds?

 

[downwardsfromzero]

Well, a comparison could be to dump the LSA into neat acetaldehyde except for the inconveniently low boiling point (21°C) of MeCHO. Use pressurised apparatus? At least removal of the solvent would be easy!

some people speculated that putting LSA in alcohol will force an epimerization

This seems very unlikely, especially with ethanol or methanol. Epimerisation is an equilibrium reaction anyhow.

Reacting the amide with acetaldehyde might promote epimerisation slightly more. Epimerisation essential proceeds through an enol transition state.

There should be some way of following this (putative) reaction spectroscopically.

 

[Aum_Shanti]

The problem is that as a private person you don't really have access to acetaldehyde.
I wouldn't even know how you can transport/store that properly with such a low BP.

Anyways I stumbled upon a dissertation from germany which is IMHO extremely interesting (attached to this post, but unfortunately in german).

They actually really discovered, that the T. Corymbosa plants themselves do not produce the alkaloids!!!
At first I just couldn't believe it. But after reading, it really seems a solid work.

It's a surface fungus on the plant which produces the alkaloids. If you heavily treat them with fungicide, you will get plants producing no ergoline alkaloids anymore!!!
Even if you "infect" them again with a non treated plant (get into contact) they will not again produce ergoline alkaloids!
So don't use any fungicide on your plants!

They named the fungus on T.Corymbosa "Tcor-F01". And as it seems the fungus is within the seeds. So an external fungicide treatment of the seeds will not kill the fungus

Unfortunately they couldn't manage to grow the fungus by itself. They tried many different growing media, but they all didn't work. So it seems it's metabolism is very closely connected to the one from the plant.

Also interesting that the best alkaloid production was when the plants were starved a bit of nutrients and in the shadow. Also the plants did grow the best in these conditions.

IMHO additionally interesting is that it seems the alkaloids vanish quite quickly in the plants. E.g. when they used the fungicide, the plant alkaloid content dropped very quickly over time.

Edit:
Also added HPLC of the leaves. Green is LSA (11min) and iso-LSA (16.5min). Red is LSH (13min), iso-LSH (14.5min) and other LSH Epimers (17.5 and 18.5min).
It really seems that in fresh material the (iso-)LSH content is quite bigger than the (iso-)LSA.
IMHO very astonishingly is that also the other LSH epimers are very prominent!
BTW: They extracted the alkaloids very similar to above (Gröger):
Put in 1% tartaric acid, basified with ammonia PH8-9 and extracted 3x with ethylacetate.
(they didn't defat as they also wanted to analyze the fats)

Edit2:
Another work discovered that I. Violacea also has a fungus (which is genetically very close to the one from T.Corymbosa). So it seems not too far to guess the same is true for Argyreia Nervosa.

Edit3:
Just saw, that this was already a topic some years ago:
morning glory leaves - LSD, LSA, LSH - Welcome to the DMT-Nexus
The last paper in this thread is really interesting. It shows which genes are responsible for what and also how the biosynthesis really works.
It seems it goes from lysergic acid to Ergonovine and then to LSH.
That's probably the explanation why you will always find also Ergonovine in a LSH plant.
LSA is as it seems never synthesized by the plant but only a degradation product.

 

[downwardsfromzero]

They actually really discovered, that the T. Corymbosa plants themselves do not produce the alkaloids!!!

Ah, I thought this was common knowledge for quite a few years already! The name for this type of organism is 'endophytic fungus', which just means 'within the plant'.

There is at least one other ergoline-producing endophytic fungus, I believe. Stipa robusta, commonly known as Sleepy grass, springs to mind. We're then but a short step away from ergot itself, in terms of it being a grass species 'infected' with the fungus.

Further alkaloids produced by endophytic fungi would include the lolines :lol: but they're nothing like ergolines.

 

[Sandgrease]

After growing both MG and HBWR for fresh seeds and thorough experimentation with them Im pretty sure the effects of these seeds are a synergy of the various alkaloids present. The fresher the more enjoyable and clear headed the experiences are.

HBWR has more of a sedative effect compared to MG.

 

[Aum_Shanti]

Thats very interesting.

Im pretty sure the effects of these seeds are a synergy of the various alkaloids present.

How did you get to this conclusion? Did you once separate the alkaloids for comparison?

As said, IMHO the experiment by Isbell and Gorodetzky, where they did human tests with the exact copy of the alkaloid profile of the plants but without LSH, and showed no psychedelic effect, clearly points IMHO into the direction that the main psychedelic effect is from LSH.

As said above, I could only think that maybe LSA stops the psychedelic effect of the other ingredients. And from this POV more LSH means less LSA and therefore more effects of the other alkaloids as well.

The fresher the more enjoyable and clear headed the experiences are.

IMHO exactly this statement just shouts out loud "LSH". For as all my reads in the meantime showed, LSH is basically the only alkaloid which changes significantly over time in the seeds.

HBWR has more of a sedative effect compared to MG.

IMHO this is because usually HBWR has more LSH decomposed into LSA. I'm not quite sure why.
Do the HBWR need longer until the seeds are ripe from the flowers?
Do you grow them at the same place, same amount of sun?
E.g. MGs are not very demanding regarding environmental conditions, whereas Argyreia Nervosa surely is much more delicate (cannot stand colder temps).
E.g. Argyreia Nervosa likes direct sun and heat, therefore I could well think under these conditions, already a lot of the LSH decomposes into LSA.
Whereas e.g. Turbina Corymbosa is a jungle plant and therefore doesn't like very hot climate and also likes shadow.
But if you keep your MGs and HBWRs in the same conditions, I could only think the time window "flower -> ripe seeds" could be an explanation.

Did you ever test the unripe seeds?
As I read also on the Nexus (Link), the effect is stronger in them and the side effects much less.
This would make sense, as in the unripe seeds LSH:LSA certainly would be much more on the LSH side, and as most of the bad stuff is in the hull, it also makes sense, that unripe seeds are better in this relation.

@downwardsfromzero:
Lol, as I wrote, I got aware that you people here discussed this some years ago. But IMHO this knowledge is still spread very rarely. If you read all the popular sites about them (E.g. Erowid or Wikipedia) you won't read anything about this.
IMHO it is clearly a very good explanation why some of the tested plants seem to have the alkaloids in all parts of the plant, whereas others don't (there the fungus was killed).

It also seems to have sparked quite some interest in research, as it seems such a strange way of fungus/plant interaction was unexpected. (an endophyte fungus, but which then grows on the surface not penetrating the walls from the host plant at all, but still with quite a metabolic interchange).
E.g. the latest work I found is from 2016.

It's really a pity that noone managed to grow the fungus on its own. Even using host plant material as nutrient didn't work. So it really seems it needs the connection to the living plant metabolism.

 

[Aum_Shanti]

In the work from Chao ("Ergoline Alkaloidal Constituents of Hawaiian Baby Wood Rose, Argyreia nervosa", 1973) I found the Rf values for the chloroform-methanol (4:1) mix that has been used for the above TLC.

I couldn't yet match exactly the values as the original pics are bad and distorted, so you cannot read directly the Rf values from the pic.
But one thing is IMHO already sure now: LSA was not converted to LSH on this TLC!!!
Also does this solvent system not seem to be very good for analyzing these specific ergolines, for iso-LSA, LSH and iso-LSH all have about the same value. Only LSA is clearly different.

Attached a 2D-TLC from this above work (Solvent system 1 is the same as the one of the conversion TLC)

Edit:
Honestly, I even think that on the test TLC a lot of LSH was converted to something else...
But not yet sure...

Edit2:
Ahhh darnnn!!! Made again the mistake of comparing these results. But they didn't use FBs for the conversion TLC, so they probably cannot be compared at all...(really a pity it wasn't basified)
I wouldn't even know in which salt form they are in the plant.

 

[Aum_Shanti]

I found some interesting points in the paper from Nowak et al. ("Identification and determination of ergot alkaloids in Morning Glory cultivars", 2016):

They got some LSA with the wrong retention times (LC-MS), namely the same retention times as LSH.
They tried changing different things (e.g. exchanging the LC column), but the picture remained. So they concluded that it seems that some LSH gets converted to LSA in the ion source of the MS.
This BTW also explains the unknown LSA peaks in the work from Hellwig (the picture I posted a few posts above). All these unknown LSA peaks have the same retention times as the LSH peaks. So one can conclude that actually this was all LSH at the end of the column, before entering the MS.
So in total there's even more LSH in it...

Another interesting point is, that they discovered that with one of their extraction methods, they did convert quite some LSH into LSA (see attached pic). And this extraction tek worked with EM-Waves.
The LSA peaks under the LSH peaks actually were also LSH (explained above). So the total amount of LSH actually clearly was much larger in this tested seed. Unfortunately they didn't correct their numbers in this work accordingly...

They also observed, that the freshest seeds had the highest LSH:LSA ratio.

IMHO also interesting:
Tests of single MG seeds showed that their alkaloid content varied widely. Some seeds had basically nothing in them, while others had about double the mean amount.
IMHO this could be interesting to discover how and where the fungus creates the alkaloids for the seeds, so that it can happen that some seeds basically get no alkaloids...
It's a pity they didn't try to analyze single seeds from the same seed pots. E.g. if they also can vary widely, or if basically all seeds in a seed pot have the same alkaloid concentration.