LS/Aldehydes ?

[lysurgeon]

We're working on various experiments seeking to explore the world of variously substituted lysergamides, and some analytical work performed on a freshly prepared LSA/aldehyde extract would help us immensely.

Mostly what i wonder is whether or not structure can be elucidated through any available means, and if anyone here would be interested enough to make it happen. A comparative analysis of Morning Glory CWE, Peppermint Oil, and the combination of the two would make a big difference. Similarly, the analysis of morning glory cwe, cinnamon oil, and the combination would give great results to compare and contrast.

 

[benzyme]

there is no evidence nor feasible reaction scheme to suggest that peppermint oil combined with LSA will yield anything other than minty LSA solution. The amide would need to be reduced before an adduct reacts with the parent compound, and that's just not happening with peppermint oil, cinnamon oil, or any essential oil.

 

[polytrip]

This peppermint oil/LSA mixture sometimes gives LSD-like experiences and sometimes it doesn´t...Simmilerly....Unprocessed LSA-seeds also, sometimes give LSD-like experiences and sometimes don´t.

 

[benzyme]

coca-cola from a soda fountain sometimes tastes like a pepsi, and sometimes it doesn't.

 

[Kash]

I like your experimental attitude lysurgeon. Whether LSA combines with aldehydes or not, it would be very beneficial for psychonauts everywhere for there to be a solid thread with solid clear experiemental trials of LSA not cluttered with experience reports, using differnt combinations and dosages.

Provided of course, relatively pure lsa extract or cyrstals are being used, it would be good to perform trials of:
-only lsa itself
-lsa dissolved in cold water
-lsa dissolved in alcohol
-lsa dissolved in alcohol and test subject already having alcohol in their system
-lsa/alcohol/various aldehydes
-lsa/alcohol/various aldehydes and test subject already having alcohol in their system

Multiple trial runs posted on these parameters I would find very useful. Maybe alcohol could even act as a stabilizing medium in the bloodstream allowing more lsa to reach the brain or absorb faster through the stomache?

 

[benzyme]

pure LSA is unstable, and alcohol will not stabilize it. instead, lsa is complexed with a diprotic acid, such as maleic or tartaric, which can also function as proton acceptors (they are antioxidative). having worked with some ergine derivatives, I can tell you what does and doesn't work. just give up on the idea of converting LSA to LSH, the latter is even more unstable, and readily converts back to LSA with exposure to room temp, light, and air.

 

[lysurgeon]

I posted this in this subforum exactly to try and find out the truth, not to speculate based on any kind of bias, either in favor or against. Just want to know.

 

[endlessness]

pure LSA is unstable, and alcohol will not stabilize it. instead, lsa is complexed with a diprotic acid, such as maleic or tartaric, which can also function as proton acceptors (they are antioxidative). having worked with some ergine derivatives, I can tell you what does and doesn't work. just give up on the idea of converting LSA to LSH, the latter is even more unstable, and readily converts back to LSA with exposure to room temp, light, and air.

Pure LSA is unstable, but in it's natural form in the seeds, its reasonably stable, no? Thats why it reaches the end consumer which can make a brew and trip from LSA-seeds, correct?

So then you say to give up the idea of converting LSA to LSH, and you claim LSH is even more unstable... But even if it is unstable, the question is, does the reaction happen at all in the first place? I mean, even if its unstable but the reaction happens, maybe there is a window of time between preparation and consumption, where one can effectively trip from LSH, or do you think the reaction never takes place?

The problem with analysing this is that between preparing and having the sample actually inserted in analytical instrument, it takes days for me, so I couldnt get this analysed.. Im wondering if TLC, though, could show something...

 

[Pup Tentacle]

I've gone mad on LSA... I've gone mad and had better smelling breath on LSA mixed with peppermint oil. That is the result I have found on a number of occasions. The feeling wasn't any different for me from LSA with no Peppermint Oil, but I didn't expect it to be. Everything I have read about this supposed LSH conversion has been based on 2nd grade logic and 1st grade chemistry.

 

[polytrip]

In terms of effectiveness, peppermint oil doesn´t seem to change the effectivity of LSA. As i said before: sometimes the seeds are very psychedelic and sometimes they aren´t, regardless of whether peppermint oil is added or not.

When seeds are not very active on their own, people will say that the quality of the seeds is low, while when an LSA-peppermint mixture is inactive, people will say that the reaction failed.

The most common complaint about LSA-seeds is that they cause stomach-aches. Especially HBWR seeds. Maybe peppermint oil diminishes those effects somewhat.

If you want to have LSD-like experiences with these seeds, you should try to find fresh seeds. In my experience, ololiuqui seeds give the most consistent results.

The fact that they rapidly loose their effectiveness indicates that benz is right about the stability of LSH. But i wouldn´t want to discourage anybody to experiment with these seeds....they absolutely cán give experiences that are virtually indistinguishable from high quality LSD.

 

[Pup Tentacle]

In my experience, LSA has never been like LSD. Similar, absolutely, but NEVER any visuals on LSA and it's definitely a gentler ride overall although it seems it can be just as lengthy at bigger doses.

On a side note, I've been thinking that it might make for an excellent launching platform for some Spiceflight.

If I may also add... this family of compounds (ergolines I believe) are vasoconstrictors. While seed material may not be all that nice on the tummy either - even pure LSA is going to cause some discomfort. This also explains other muscles cramping up some as has been reported... the way around? vasodilators! Try some ginko biloaba and/or niacin before your ride and it should alleviate some of the vasoconstriction.

 

[polytrip]

In my experience, LSA has never been like LSD. Similar, absolutely, but NEVER any visuals on LSA and it's definitely a gentler ride overall although it seems it can be just as lengthy at bigger doses.

On a side note, I've been thinking that it might make for an excellent launching platform for some Spiceflight.

Yes, most of the times, seeds will produce little to no effects or just some sort of sedation. But sometimes they´ll produce a true LSD-experience. And when they do, it´s often an experience like you´d have with very pure, high-quality acid. Very energetic, visionary warm and euphoric and with that typical 'electricity'.

 

[Pup Tentacle]

I'm just saying that in my experience LSA, even at mind-spinning doses, doesn't compare to LSD. Just my 2-cents, but I think it's unfair to imply that you can get to LSD-land using LSA. I mean no disrespect in disagreeing.

Blessings

 

[AlbertKLloyd]

a lot of people, including chemists, who have looked at the use of morning-glory seeds have observed that despite being the predominant alkaloid lysergic acid is not likely to be responsible for the psychedelic effects.

There are other alkaloids in the seeds that are worth investigating.

According to Shulgin ergometrine is a far more likely candidate... this makes a lot of sense.

The aldehyde speculations are interesting, i'd love to see some formal analysis.

 

[lysurgeon]

There are a lot of possibilities that somehow I am an idiot because you haven't considered. I am doing something quite respectable right now, contributing what I consider to be valuable information to the psychedelic community, on my dollar and between other things I have to do, and for this? so that my awesome discoveries can be, without testing or analysis, dismissed and not considered due to what I consider a prejudiced hypothesis. Those who call "bunk" on the light reveal themselves in the light as bunk individuals.

I am not limited by the adduct paradigm. How many different places does (natural lysergic alk X) interact with the world during its existence?
1. grows in the plant
2. accumulates in seed
3. exposed to air in grinding
4. exposed to water unless absolutely anhydrous conditions and solvents (this could even be human saliva)
5. subject to salivary enzymes
6. exposed to hydrochloric acid in the stomach
7. exposed to enzymes in the stomach
8. absorbed into bloodstream, subject to possible accumulation in bodily organs and their enzymes, otherwise possible blood enzymes
9. finally makes it to CNS, possibly more metabolisis before binding to serotonin receptors.
10. activity in CNS
11. metabolised into inactive substances
12. back to blood to kidneys and excreted

I know I'm missing steps here due to poor understanding of human physiology, but my point is that there are many places this alkaloid goes where chemical changes are in fact likely to occur, and the presence of an additional reactive compound could alter these chemical changes, whether its during exposure to water (like forming an aldehyde-amide adduct in cold water extract), or exposure to hydrochloric acid (change takes place in stomach, change is altered by aldehyde) or stomach enzymes (maybe the lsa is protected or the enzymatic function is altered by the aldehyde).

The idea of analysing a cwe with an aldehyde is to be able to possibly rule out spontaneous or ratio-driven reaction ex vivo prior to consumption. and thanks for all your supportive attitudes.

 

[benzyme]

while I commend your efforts in experimenting with seeds, without any means of verifying alkaloidal profile, all that remains is speculation and anecdotes; which is all fun and good.
I've worked with a strain of fungus that naturally produces the hydroxyethylamide variant, but LC/MS analysis only revealed the parent compound LSA. This suggests, indeed, that any LSH present likely decomposed into the parent compound. The reaction equilibrium tends to favor LSA, so any synthetic mechanism and/or metabolism of it, will eventually convert it to LSA anyway.

 

[endlessness]

Yeah benz but the question is, cant the reaction be done and the product consumed before it is converted back to LSA (considering the reaction happens in the first place)?

Also, your work was with a particular strain of fungus, not with the particular seeds with which the supposed LSH conversion is done, so can you really generalize it?

If LSH is there in the first place, will it show distinct to LSA in TLC with the right mobile phase?

lysurgeon, why dont you look into TLC ? You could do tests at home....

 

[benzyme]

Yeah benz but the question is, cant the reaction be done and the product consumed before it is converted back to LSA (considering the reaction happens in the first place)?

it can, but once it is consumed, you can safely assume it will spontaneously convert to LSA.

Also, your work was with a particular strain of fungus, not with the particular seeds with which the supposed LSH conversion is done, so can you really generalize it?

yes.
regardless of the source, the LSA <--> LSH equilibrium is constant.

If LSH is there in the first place, will it show distinct to LSA in TLC with the right mobile phase?

possibly, given conducive conditions i.e. chamber purged with inert gas, working under low light conditions with no blue light present

 

[endlessness]

So lets say I have some pure LSH and I consume it.. Your theory is that I will not have any effects from LSH, but actually from LSA? Like a psilocybin -> psilocin kind of thing?

 

[benzyme]

absolutely.

know why?
H+ in the stomach protonates the amine, and acetaldehyde dissociates as a gas.