HBWS & LSA Adducts(any advice??)

[BigJungleBuds]

So I have done alot of reading about the adducts of lsa from hbwr seeds that can be converted from aldehydes e.g. lsh and lsc but heard there are alot of adducts in hbws that can be converted from lea with aldehydes so does Anyone know a list of the adducts of lsa in hbwr seeds that can be converted from lsa with aldehydes and a list of what aldehydes will covert the lsa to the lsa adducts from hbwr seeds only not just a list of lsa adducts or is it that because lsa is an amine group then any aldehydes will convert the lsa in hbwr seeds to the lsa adducts and can I covert lsa from hbwr seeds with a range of different aldehydes that will covert lsa into lsa adducts with a range of different aldehydes (that will convert lsa from hbwr seeds into lsa adducts) and end up with not only one lea adducts from hbwrs but a range of different aldehydes or will echo batch all convert to just 1 adduct at a time for each batch e.g if I add cinnamon oil and peppermint oil to lea will I get both lsh and lsc or just one or the other depending on what it chooses to covert to if I were to add both aldehydes?? Please shed any light into this thread that you can that may help me understand thanks

 

[Aum_Shanti]

These "adduct" reactions (e.g. allegedly creating LSH or LSC, or ...) are highly doubtful to happen as imagined.

You have to remember that not even in nature e.g. LSH gets made like that from LSA. There's no known biosynthetic pathway for LSA, so LSA in nature is always a decomposition product (e.g. from LSH). The fungi on the vine plants synth only LSH, and this then decomposes over time into LSA.

The suggested "adduct" reaction is a Micheal addition. The only way this could happen at ambient conditions is if it was catalyzed (e.g. by an unknown enzyme). But as pointed out, LSH in nature is a product of a completely different pathway (with ergometrine as intermediate), so it's highly unlikely there's a corresponding enzyme.

But adding these essential oils really seems to substantially change effects, if certain parameters seem to fit (e.g. in an alcohol like MeOH or EtOH, with not much water). But if this is due to a chemical reaction, or just because of the actual synergy of effects of the essential oils themselves, nobody knows, or has ever tested. E.g some report also a difference using these oils with LSD...

But what someone once tested by TLC is, that pure acetaldehyde added really changed the molecules in MeOH, if not much water was present. This could clearly be seen by a change of the stripes on the TLC. But noone knows what reaction was exactly taking place. As mentioned above, it's highly unlikely that LSH gets created, but I could well think it's some kind of (semi-) acetal reaction.

Without anyone putting the result through a MS, we will probably never know.

 

[BigJungleBuds]

So your saying that the reaction that changed the effects of the lsa trip from lsa containing seeds was with the extraction solvent residue or a reaction takes place with the lsa in meoh because these are the links please check them out and try and answer what I was asking if you can?? Also what is the many thing in the hbwr seed that react with aldehydes or is the other way many aldehydes that react with lsa ??

https://www.reddit.com/r/LSA/comments/332jpv/lsa_lsh_and_lsc

https://www.reddit.com/r/Drugs/comments/8250z7/lsc_notlsalsdlsh_experience

LSC?....skeptical - LSD, LSA, LSH - Welcome to the DMT-Nexus

Nature's Herb Forum-LSA + Cinnamaldehyde (cinnamon essential oil)

1/2 - 1/3 of the regular dose! o.O Is that being compared to LSH dosage or LSA? Cause LSH itself was more potent than LSA in SWIM's opinion. Either wa

www.tapatalk.com

And my main question even speaking theoretically is if I add 2 or more different aldehydes containing oils that are known to convert it or can I use any with aldehydes do all aldehydes do something different each time or is there a list and is it just the lea in the seeds or are there alot of something else what would this be that reacts with the aldehydes ??

Any one answer this best they can??

 

[Aum_Shanti]

First, I'm sorry, I have a very hard time understanding what exactly you mean. Do you use google translate? If yes, what is your mother tongue, maybe directly would work better (e.g. I speak german and french)?

So your saying that the reaction that changed the effects of the lsa trip from lsa containing seeds was with the extraction solvent residue or a reaction takes place with the lsa in meoh because these are the links please check them out and try and answer what I was asking if you can??

I really do not quite get what you mean. What I said is, that the alleged theorized chemical reaction e.g. from LSA into LSH is very very unlikely to happen as imagined, from a chemical POV. But as it seems something does really change in an alcohol together with pure acetaldehyde. But nobody knows what exactly happens. My best guess is still, that it's a (semi-)acetal reaction.

But noone tested yet if this chemical change also really takes place with these essential oils, or if natural effects of these oils just synergize with the ergolines, leading to different effects. But I personally assume, due to specificity of needing an additional alcohol, that indeed a chemical change likely is happening. Or maybe a chemical change is then only occuring in-vivo, similar e.g. to cocaethylene.

From personal experience I can say, also effect wise, the "peppermint oil"-transformation does not create LSH, as its effects are IMHO quite different from fresh seeds (which really do contain mainly LSH).

Also what is the many thing in the hbwr seed that react with aldehydes or is the other way many aldehydes that react with lsa ??

Again, I'm sorry, I don' get what you mean here.

https://www.reddit.com/r/LSA/comments/332jpv/lsa_lsh_and_lsc

https://www.reddit.com/r/Drugs/comments/8250z7/lsc_notlsalsdlsh_experience

LSC?....skeptical - LSD, LSA, LSH - Welcome to the DMT-Nexus

Nature's Herb Forum-LSA + Cinnamaldehyde (cinnamon essential oil)

1/2 - 1/3 of the regular dose! o.O Is that being compared to LSH dosage or LSA? Cause LSH itself was more potent than LSA in SWIM's opinion. Either wa

www.tapatalk.com

In these threads it's usually Mumbo-Jumbo chemical explanations, with no real tie to chemical reality. But e.g. if you look at the Nexus thread, you can see that people are very critical in this relation.

And my main question even speaking theoretically is if I add 2 or more different aldehydes containing oils that are known to convert it or can I use any with aldehydes do all aldehydes do something different each time or is there a list and is it just the lea in the seeds or are there alot of something else what would this be that reacts with the aldehydes ??

As these reactions are purely theoretical, noone knowing what exactly is taking place, further speculation about other reactions are even more purely speculative. So IMHO it doesn't really make sense to go that far in speculation, unless at least the foundation is settled. Sure some people on the net speculated about all kind of fancy reactions, but again IMHO this is just fantasy...

 

[BigJungleBuds]

Mother tougue ??? I never said this lol

And sorry I'm a bit misunderstood on parts of this subject so I suppose it just lessens the nausea and like an hbwr seed trip the lsa reacts with the essential oils and creates a synergy that works with the trip with positive effects but not proven to actually convert but are you saying there is actually a reaction that happens with the alcohol together with the acetaldehyde are they in the essential oils and the same as aldehydes or are they in the hbws and what react with the alchahol so is the reaction with the Leeds and the alchahol or the alchahol and the especial oils with the seeds or just the alchahol and the essential oils if a reaction were to be happening then adding 2 or more oils would you get 2 different reactions or more or would it all go 1 way and convert to the majority instead of lsa hbwrs and 2 oils lsa to lsh and lsc and would all the lsa convert or would some stay as lsa or the same with 2 oils but just get either lsc or lsh theoretically or a likely reaction if a reaction were to be happening as is can't be dangerous if its wrong

 

[Aum_Shanti]

Mother tougue ??? I never said this lol

That's why I asked in what language you naturally speak (your mother tongue), as if it would happen to be german or french, we could talk directly in such a language for better understanding.


I think you basically got it what I meant. If you add these essential oils in alcohol to these seeds, then indeed the overall effects seem to change. But nobody exactly knows why.

It could be a molecular change, but the proposed chemical reaction is very unlikely. But maybe some other chemical reaction is taking place. But as long as nobody does some proper research on this, and does some MS runs on the results, one cannot say what exactly is happening, and so any further speculation (e.g. what happens with other oils, or a mix of oils) remains purely speculative.

So in this respect, no one can really answer you question, as it's simply not known.

 

[downwardsfromzero]

The other thing to bear in mind here is the LSA, and whatever else you combine it with, is not passing directly to the magic receptor button in the brain. There are innumerable possible interactions in the digestive tract, in the liver and in the bloodstream before these substances even approach the blood-brain barrier.

Even if candidate aldehyde adducts were successfully isolated in meaningful quantities, this would still be no guarantee that they are responsible for any psychoactivity when ingested. There's just as much of a likelihood that hypothetical aldehyde adducts would act as a prodrug in a manner akin to that suspected in the case of ALD-52 and similar compounds, or indeed some other yet-to-be-anticipated effects.

Lysergic acid amide has three nitrogen atoms and the amide nitrogen atom would not appear to be more likely to react with aldehydes than either the indolic nitrogen or the remaining, aliphatically-substituted nitrogen atom. Working this out on a molecular level would be a serious scientific endeavour as Aum_Shanti rightly points out.


If it's simplicity that you're more interested in - my most effective experience with HBWR was after a night of rather too much brandy. The acetaldehyde was generated in vivo and any reaction with the HBWR seed material will also have occurred within the vessel of my body while I slept. On waking there followed a productive morning's instruction from what wholly authentically felt like an ancient plant teacher, stern but kind. Initially the nausea was awful - perhaps unsurprising given the prior alcohol consumption - but deliberately induced vomiting cleared this up completely.

Maybe it's possible to have smoother and cleaner experiences using CWE methods and essential oils although my own experiments in this area were inconclusive and not very thorough or systematic

 

[Aum_Shanti]

The other thing to bear in mind here is the LSA, and whatever else you combine it with, is not passing directly to the magic receptor button in the brain. There are innumerable possible interactions in the digestive tract, in the liver and in the bloodstream before these substances even approach the blood-brain barrier.

Exactly, as I also pointed out above, it could be a reaction e.g. similar to cocaethylene, only happening in the liver itself. There are so many possibilities.

E.g. what I find strange, that some people reported different effects, just drinking alcohol alongside with it. If this is placebo, or just the alcohol effect itself, or if there's really something happening chemically, I don't know.

E.g. we do know that traditionally they also did sometimes use alcohol. Maybe they only used alcohol when the shamans themselves used it, to alter the effect? So many unknowns...
And the original usage of these seeds from ancient times, is not really known, as although the Spanish conquistadors even tortured the indigenous people to get more information about these seeds, they didn't comply, as it was too divine for them. We only have very strange reports about their ancient usage, which do not seem very believable and are lacking any detail.

The only more or less conclusive point we have is that LSA really seems to undergo a chemical reaction, when in an alcohol (with only a minimal amount water), and pure acetaldehyde. This was seen by a change in stripes on a TLC. But it isn't known, in what they converted and if these are stable products at all, or if they will immediately again decompose when not anymore under these conditions.

As said, I personally could think it's some kind of semi-(acetal) reaction. But this surely is a far shot.


BTW:It seems some people speculated that putting LSA in alcohol will force an epimerization, leading to mainly the d-epimer. E.g. this is from the famous Hive forum.

I find this very unlikely, as I read quite some works on how to push the balance of ergolines in the direction of a certain epimer, and these works with all kind of equipment, get a bit better ratios, but nothing wild. So I think it would be very strange if just alcohol would tilt the epimer balance, as then this would have been known by chemists and used.

But as you are a chemist, what do you think about this change in epimer balance by an alcohol?

 

[downwardsfromzero]

Exactly, as I also pointed out above, it could be a reaction e.g. similar to cocaethylene, only happening in the liver itself. There are so many possibilities.

Ugggh, yes you did - my brain is so unwieldy at times!

But as you are a chemist, what do you think about this change in epimer balance by an alcohol?

The epimerisation is dependent on the lability of the proton on the carbon adjacent to the carboxyl/carboxamide group. Because the ergoline 8-position in question is adjacent to a double bond which itself is conjugated with the benzene ring of the indole moiety in the molecule, this epimerisation will occur more readily than it would were the 9,10 bond of the system to be saturated instead.

The epimerisation (from what I gather, in the instance of LSD-25) is typically forced using ethanolic or methanolic KOH, as this greatly speeds up the rate at which the proton will be removed. The epimerisation can and presumably does occur without the base catalysis, albeit at a much slower rate. The question is also what the equilibrium ratio of the two epimers is under the particular conditions. It could be the case that the epimerisation in alcohol sans base favours one epimer more so than when KOH is used - both epimers can lose a proton and this relative rate of proton loss is important for establishing where the equilibrium lies.

I haven't read the information at the Hive so I'll forego further speculation until I've seen it


A small point on nomenclature - if nitrogen is involved in this putative reaction with acetaldehyde we'd be looking at a hemiaminal rather than a hemiacetal.