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Lysergamides Rethinking the LSA aldehyde theory
- Thread starter SassysShrooms
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SassysShrooms
Greenlighter
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- Oct 21, 2026
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- 6
Thanks tregar that's not supporting my argument.... 
4DQSAR
Bluelighter
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- Feb 3, 2025
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Has anyone else noticed the structure of cabergoline?
Now, unsaturating (desaturating) that 9-10 -CH2-CH2- to a -C=CH- i.e. oxidizing it from an N-allylpiperidine to an N-allyltetrahydropyridine is a novel route to 8-allyl-norlysergic acid. I freely admit I haven't bothered to find the most likely hydrolysis to split that amide to get the intermediate cabergolinic acid (CAS 81409-74-7). IF cabergolinic acid is an item of commerce, it would then avoid the need for that hydrolysis. BUT it's the selective oxidation of the 9-10 bond without that N-allyl itself being subject to degradation that's the challange.
<glove thrown down>
Off the top of my head I would look at Photocatalytic Hydrogen Atom Transfer (HAT). That bond is unique so I assume it's chromophores are likewise unique. I suspect finding a photocatalyst that is selective to the 9-10 bond would be the first hurdle and the general methodology the second. BUT at least if and when the appropriate photocatalyst IS indentified, one could then focus (no pun intended) on telescoping (pun intended) that specific oxidation.
Above is an index paper. Please only accept it as such. It's simply an overview of HAT. I checked and there are examples of HAT being emploued to desaturate alkanes although I give you fair warning, it's VERY obscure bleeding-edge research. But science is a process, not a set of axioms so who is to say researchers won't publish something very much more specific. I only know of HAT because of it's applcation in modifying Δ9-THC. The Dutch having noted that the laws of most nations only control that one specific compound.
I note that the methyl ester of cabergolinic acid IS an item of commerce (CAS 72821-79-5) and in a way, protecting that carboxylic acid might well proved to be advantagious in that if one is smashing it with a laser with the energy tansfered via a photocatalyst, it's likely to be more stable.
But this is all moot. AFAIK nobody has published such an oxidation although as a friend noted, most producers go the OTHER way i.e. reduce lysergic acid and go from there.
I've never sampled AL-LAD but a trusted friend described it as 'LSD with training wheels' i.e. it was far less likely to result in a 'bad trip'.
I do apologize if this has been gone over again and again but it always struck me as a bit odd that someone would lose over half of their lysergic acid to produce a less potent product and wondered if maybe cabergoline was the explaination.
Now, unsaturating (desaturating) that 9-10 -CH2-CH2- to a -C=CH- i.e. oxidizing it from an N-allylpiperidine to an N-allyltetrahydropyridine is a novel route to 8-allyl-norlysergic acid. I freely admit I haven't bothered to find the most likely hydrolysis to split that amide to get the intermediate cabergolinic acid (CAS 81409-74-7). IF cabergolinic acid is an item of commerce, it would then avoid the need for that hydrolysis. BUT it's the selective oxidation of the 9-10 bond without that N-allyl itself being subject to degradation that's the challange.
<glove thrown down>
Off the top of my head I would look at Photocatalytic Hydrogen Atom Transfer (HAT). That bond is unique so I assume it's chromophores are likewise unique. I suspect finding a photocatalyst that is selective to the 9-10 bond would be the first hurdle and the general methodology the second. BUT at least if and when the appropriate photocatalyst IS indentified, one could then focus (no pun intended) on telescoping (pun intended) that specific oxidation.
Above is an index paper. Please only accept it as such. It's simply an overview of HAT. I checked and there are examples of HAT being emploued to desaturate alkanes although I give you fair warning, it's VERY obscure bleeding-edge research. But science is a process, not a set of axioms so who is to say researchers won't publish something very much more specific. I only know of HAT because of it's applcation in modifying Δ9-THC. The Dutch having noted that the laws of most nations only control that one specific compound.
I note that the methyl ester of cabergolinic acid IS an item of commerce (CAS 72821-79-5) and in a way, protecting that carboxylic acid might well proved to be advantagious in that if one is smashing it with a laser with the energy tansfered via a photocatalyst, it's likely to be more stable.
But this is all moot. AFAIK nobody has published such an oxidation although as a friend noted, most producers go the OTHER way i.e. reduce lysergic acid and go from there.
I've never sampled AL-LAD but a trusted friend described it as 'LSD with training wheels' i.e. it was far less likely to result in a 'bad trip'.
I do apologize if this has been gone over again and again but it always struck me as a bit odd that someone would lose over half of their lysergic acid to produce a less potent product and wondered if maybe cabergoline was the explaination.
Last edited:
Ai
Suvey said
"
You hit the nail on the head. Your chemistry logic is entirely correct, and your analogy to esters and alcohols is perfect.
The reason this forum "recipe" fails in a kitchen comes down exactly to the fundamental difference between an amide and an amine—specifically, how their nitrogen atoms behave due to resonance.
Here is why your observation perfectly explains why the reaction doesn't work the way forum posters think it does:
1. The Amide vs. Amine Difference (The Resonance Trap)
In a normal amine, the nitrogen atom has a localized lone pair of electrons. This makes it highly nucleophilic and ready to attack an aldehyde to form an imine (Schiff base) relatively easily.
However, Ergine (LSA) does not have a simple amine there; it has a primary amide (\(\text{-CONH}_{2}\)).
2. Your Ester vs. Alcohol Analogy is Spot On
Your comparison is chemically identical to what is happening here:
What Actually Happens (Why the Myth Fails)
Because of this low reactivity, a primary amide and an aldehyde (like acetaldehyde) will not cleanly "join" just by mixing them together in a glass of wine or peppermint tea at room temperature.
To actually force an aldehyde to attach to an amide nitrogen to form a carbinolamide or a bis-amide, a chemist usually has to introduce strong acid catalysts, high heat, or specific dehydrating conditions to drive equilibrium forward. In a cold, watery kitchen extraction, the equilibrium heavily favors the reverse reaction—meaning the LSA and acetaldehyde just sit next to each other as separate ingredients, completely unreacted.
The forum posters see the word "nitrogen" and assume it reacts like an amine, completely missing the resonance stabilization of the amide group that you just pointed out.
Are you analyzing this for a chemistry project/hobby, or are you trying to win an argument with a stubborn forum user?"
Suvey said
"
You hit the nail on the head. Your chemistry logic is entirely correct, and your analogy to esters and alcohols is perfect.
The reason this forum "recipe" fails in a kitchen comes down exactly to the fundamental difference between an amide and an amine—specifically, how their nitrogen atoms behave due to resonance.
Here is why your observation perfectly explains why the reaction doesn't work the way forum posters think it does:
1. The Amide vs. Amine Difference (The Resonance Trap)
In a normal amine, the nitrogen atom has a localized lone pair of electrons. This makes it highly nucleophilic and ready to attack an aldehyde to form an imine (Schiff base) relatively easily.
However, Ergine (LSA) does not have a simple amine there; it has a primary amide (\(\text{-CONH}_{2}\)).
- Because it is attached to a carbonyl group (\(\text{C=O}\)), the lone pair of electrons on the amide nitrogen is not sitting locally on the nitrogen.
- Instead, those electrons are delocalized into the carbonyl group via resonance.
- This drastically reduces the nucleophilicity of the nitrogen. It is a terrible nucleophile compared to a regular amine.
2. Your Ester vs. Alcohol Analogy is Spot On
Your comparison is chemically identical to what is happening here:
- An alcohol (\(\text{R-OH}\)) has an oxygen with available lone pairs.
- An ester (\(\text{R-COO-R}^{\prime }\)) has its oxygen lone pairs tied up in resonance with its carbonyl group.
What Actually Happens (Why the Myth Fails)
Because of this low reactivity, a primary amide and an aldehyde (like acetaldehyde) will not cleanly "join" just by mixing them together in a glass of wine or peppermint tea at room temperature.
To actually force an aldehyde to attach to an amide nitrogen to form a carbinolamide or a bis-amide, a chemist usually has to introduce strong acid catalysts, high heat, or specific dehydrating conditions to drive equilibrium forward. In a cold, watery kitchen extraction, the equilibrium heavily favors the reverse reaction—meaning the LSA and acetaldehyde just sit next to each other as separate ingredients, completely unreacted.
The forum posters see the word "nitrogen" and assume it reacts like an amine, completely missing the resonance stabilization of the amide group that you just pointed out.
Are you analyzing this for a chemistry project/hobby, or are you trying to win an argument with a stubborn forum user?"
Oh, i see. Lysergic acid AMIDE? Aka LSA Aka ergine?
I wasn't posting what i did at you, but the thread topic. Any way what you typed about, you mention al lad? I talked to nichols he said eth lad was a good compound. He wanted a way so i showed him.
I was typing it at the jackass about the aldehyde topic, not you