OK, real chemist dropping some truth bombs here. Tired of some of these age old rumours with zero proof.
If you think that imine formation is going to occur in aqueous environments, maybe Journal of Organic Chemistry would like to hear your methodology
It's an equilibrium reaction, amine + aldehyde <-> imine + water. If there is an abundance of reactants on one side, it will want to equalize both sides. So if a lot of water is around, any imine that forms will most likely bump into water and revert to amine+aldehyde again.
But wait a second, I missed something.
LSA is an amide and not an amine. Amides are
way less basic than amines and have totally different reactivity. That is why alpha-hydroxyethyl LSA doesn't just fall apart like an imide would-
it's not an imide.
Part of the problem here is that while, yes, technically speaking LSH is an adduct of LSA and acetaldehyde,
studies only ever show the adduct being decomposed to LSA and acetaldehyde, and never created.
I can say that THC-COOH is an adduct of CO
2 and THC, and indeed, if you heat/acidify it, it decomposes to CO
2 and THC. But no matter how much CO
2 you add to THC you will
never reform THC-COOH (in fact supercritical CO
2 is used to extract THC...)
I cannot find any references to alpha-hydroxyalkyl amides forming spontaneously in solution (or even at all). Putting things on amides is a lot tougher than putting things on amines. (Wonder why we don't go from LSA to LSD directly? That's why) There
is an
OrgSyn paper making a
2,2,2-trifluoro-1-hydroxyethylamide from an amide and
2,2,2-trifluoro-1-methoxyethanol. but the analogous reagent to make a plain 1-hydroxyethylamide (1-methoxyethanol)... is not a bench stable compound, as a hemiacetal of acetaldehyde. (Also the reaction
does not proceed with the aldehyde, it needs the hemiacetal.)
You would figure that if the reaction between LSA and acetaldehyde was as quick and easy as it is claimed, that I would be able to find
plenty of other references and papers of similar reactions occuring, between an aldehyde and an amide in aqueous solution. But I can't find anything aside from this repeated playground rumour of LSA forming adducts.
There has never been a proven literature synthesis of LSH from LSA. I am willing to be proven wrong with any journal article that clearly demonstrates a plausible reaction pathway and can demonstrate formation of LSH with at least chromatographic evidence (either isolation of the pure material, or just a mass spec from a mixture on LC or GC). This means no trip reports, no hypothetical wishy washy shit. I want to see hard proof.
I might even send a trinket or postcard to anyone who does so as a prize for scientific achievement in drug sciences. (I will give a consolation prize to anyone showing a proven synthesis of an alpha-hydroxyalkyl amide (
any synthesis at all) or anyone who can, in a
double blind study with preferably more than 10 peopls, prove that LSA and LSA+aldehyde is actually any different than LSA.)
I also have serious doubts that anyone with a head full of acid would be able to effectively judge the effects of, well, any added drugs. Especially if they verge on placebo.
LSD makes people more suggestible so it's hard to take any claims based exclusively on how you feel when you're, y'know,
high on acid.
The one semi reliable reference from those papers that references a reaction between an amide and an aldehyde is
an Indian Academy of Sciences from 1938 that apparently nobody (including you) actually read fully. They make some freak compound of
two amides and one aldehyde
instead of an imide or hydroxyethylamide though. And their synthesis was not at room temperature, at millimolar dilution, in aqueous solution.
They heat a neat mixture of pure amide, pure aldehyde, and fucking pyridine at temperatures between 100C and 160C for several hours to a day and get yields of
between 6.2-50%. Also none of their amides used were even close to lysergamide in terms of complexity. LSA/ergine
melts and decomposes at 135C. Also you will note that the catalyst used (pyridine) is
basic not acidic, and not the kind of thing you want to eat. (Smells like rotting fish taint)
The other papers you linked are either mislabeled or total shit and do not form a body of evidence to support your claims at all.
"Has the Mystery of the Eleusinian Mysteries been solved .pdf" No. Next.
"DunningRobertL1956 (2).pdf" is someone's dissertation and presumably "evidence" of 3-methylbutanal in peppermint oil. If you spend 5 minutes to actually
read the paper, it's pretty poor evidence. They are still using paper chromatography, and most importantly, seemingly cannot effectively seperate isovaleraldehyde from the menthol (oops). Also, they don't do any quantitative measurements (they don't determine how much isovaleraldehyde is present).
Another problem is that peppermint, like many plants, can exist in many differing
chemotypes that have different compositions of essential oil. So, some peppermint oil may contain some, but other oils may not (and in my experience I have never seen isovaleraldehyde in peppermint oil, and I ran a GC doing terpene chemistry for ~5 years).
"3-methylbutanal or isovaleraldehyde safety sheet, low in general toxicity after oral exposure.pdf"' - Yeah, it's probably not super toxic, but it's a skin and eye irritant, and also smells strongly of toejam. It is not pleasant. (I would regularly use large volumes of isovaleraldehyde as a precursor to
cryptone and
2-menthen-1-ol. Always used it in a fume hood. Would not consider eating it.) It is, however, rated as food grade for flavor and fragrance use from some suppliers.
"Chapter5_Excerpt_Peppermint.pdf" - Cool stuff about peppermint oil and its potential for allergies, but
isovaleraldehyde does not appear in the list of typical components of ISO standard peppermint oil. It only indicates that one study found that there was isovaleraldehyde present in some samples, and didn't specify an amount. (Not quantitative.) Not very strong evidence.
"The LSA component of claviceps paspali forms LSH when dunked into fermented liquor (wine).pdf ", actual title
"Production of a new lysergic acid derivative in submerged culture by a strain of Claviceps paspali", apparently never read the paper either (noticing a pattern here), because the "fermented liquor" is not wine, it's the
fermentation liquid being used to grow the C. paspali! The paper talks about how they isolated a strain of ergot that naturally produces lysergic acid hydroxyethylamide exclusively, and says
nothing about synthetic methods for making LSA into LSH.
"2016 Polish morning glory study shows LSH and penniclavine two highest alkaloids in MG (3).pdf" I don't have an issue with, I think it's established LSH is present in (at least fresh) morning glories/HBWR. (Penniclavine doesn't look active to me.) No claims for making LSH from LSA.
"5 Ergot alkaloids in morning glory just as stimulating as LSD in animal experiments, Yui and Yuji Takeo, 1958.pdf " again, no issue. We know that LSA is about 1/10 the potency of LSD in man, and LSH is presumably between LSD and LSA. Except I have to point out the obvious, animals are really,
really bad at writing trip reports or describing body load. Does not describe LSH synthesis.
"Adduct formation of d-Lysergic Acid Amide or (LSA) and aldehydes.pdf" has the
actual title of
"The Theoretical Synthesis and in silico Modelling of Lysergic Acid Biscinnamylidene Amide from the Adduct Formation of d-Lysergic Acid Amide and Cinnamaldehyde" (translation:
We never did any actual chemistry, We made some wild guesses, drew a structure, and plugged it into a web tool to predict activity)
It is the
worst paper of the lot. There is nothing actually proven or discovered. Totally masturbation worthy of this very forum. It has such laugh-inducing content as:
This adduct formation is supported by anecdotal evidence of co-administering LSA with fresh peppermint leaves on forums [...] Fresh peppermint leaves are high in acetaldehyde*; thus, it is probable that individuals are forming LSH through the adduct formation of LSA and acetaldehyde**
* (They give no reference for this. Peppermint leaves have almost no acetaldehyde, in fact peppermint oil is
mostly menthol and menthone. Acetaldehyde is toxic, volatile, reactive, and has a very objectionable smell, from having worked with it.)
** (They also give no reference to the mechanism that would form a hydroxyethylamide from LSA,)
The whole paper is basically them making hypothetical claims with zero actual evidence backing up the synthesis being possible.
"Tryptophan analogues form adducts by cooperative reaction with aldehydes and alcohols or with aldehydes alone, 1992 Austin.pdf" indeed shows compounds like indole acetic acid (which, wait a second, where's the amide to link up with there?) forming adducts with aldehydes.(imines).
on the aromatic secondary nitrogen of the indole. Whoops. (No reaction at any amide groups shown.)
Convert ml to drops: https://www.unitconv...ter-to-drop.htm
'Drops' are not a standard unit of any sort, and depends on the size of the dropper aperture, atmospheric temperature/pressure, the surface tension of the liquid, the specific dropper bulb, skill of the person using it, etc. Getting a 1mL syringe to do measurements is not going to break the bank.
There's two ways you can respond to this. Consider all the evidence here and make a change, or continue believing rumours and whispers.
I'm sure taking LSD and morning glory together is lots of fun, but as a chemist with years of experience and a thing for dispelling drug legends, continuing to make claims that have never been verified in a reputable way (no isolation of LSH from LSA+whatever mixtures, not even a TLC plate which would take 15 mins and show a new compound forming quite clearly, costs minimal, can be done by average Jose). It's always bioassays and trip reports. Well, people are fallible. (even moreso with a head full of acid.) Consider Shulgin's famous anecdote:
While at sea, he suffered a serious thumb infection that required surgery. Handed a glass of juice by a nurse, he spotted some undissolved solids at the bottom of the glass, assumed it was a sedative and fell unconscious. It was actually sugar; the placebo effect had knocked him clean out.
If Sasha Shulgin can be fooled, so can
you. So "trust, but verify".
This is like claiming the blotter art signifies different 'types' of LSD that produce different 'flavours' of trips. Or
Cannabis sativa and
Cannabis indica having differing effects (nowadays both are usually high THC low CBD cultivars). Or terpenes having major effects at all beyond smells. IME, all of these are old rumours that need to go away.
Otherwise I could mix my piss in your MG wine and claim that it makes a superactive hallucinogen from, I dunno, glucuronic acid or something, based upon solely my claim that "Well, I drank a 50/50 piss and MG wine mixture and had an intense and highly sexually charged trip that lasted 4 days." I could come up with a bunch of misread "evidence" papers too! But I don't because I'm trying to practice actual science and critical thinking.