You are all familiar with the whole LSH discussion? The theory states that acetaldehyde, as found in peppermint oil, will bond with lysergic acid amide (LSA) to yield lysergic acid hydroxy-ethylamide (LSH). All it takes is mixing the two together, maybe so or maybe not in the presence of ethanol, bubbles will form upon mixing (indicating a reaction)....and the effects of this LSH, according to my friend, are like a stimulating, "hilarious" and poetic version of something in between being like LSA and LSD. The seeds from which this particular experiment took place were themselves tested by bioassay and found to be typical morning glory seeds - sedating, vasoconstricting, tendon constricting, and visionary. A change definitely took place.

So why stop at peppermint, I began to ask myself. There are other aldehydes out there in the world. For example: Cinnamon contains cinnamaldehyde, which could theoretically yield lysergic acid phenylpropylamide, which could then also possibly be metabolized into phenylpropylamine, which I imagine would also have stimulant effects. Almonds contain benzaldehyde, which could theoretically yield lysergic acid phenylmethylamide, possibly being metabolized into phenylmethylamine.

awesome work.
hope someone helps ya out...
maybe a more synth friendly board is out there?

very interesting and inspiring work! i applaud this post but cannot offer any retort

Hello lysurgeon

First about the placebo effect: How can you say it is definitely not placebo, unless you made a blind test? The whole point of placebo is that belief can affect the outcome and effects of a substance or practice, and we have seen often enough how people can be absolutely sure of something not being placebo while it is. A good example here in the forum is the FlowingVision's supposed THH controversy, that is apparently harmine and not THH (while soooo many people described the effects as completely different than harmine and never even questioned it). So, if you can do a blind test (masking somehow the taste of the additive mixed with LSA), that would be an interesting experiment. Im not saying the effects you had are placebo, they might be, or they might not be, thats why more tests in this sense would be beneficial.

Regarding synthesis, as DG said, many times we dont allow synthesis talk here, but thats not a blind absolute rule. For example we allow talks about the reduction of dmt n-oxide to dmt using zinc, or the supposed LSA-LSH conversion. Our criteria for not allowing synthesis is: if it involves watched or dangerous chemicals or proceedures. So if its a simple 'mix the essential oil of such plant with such legal seeds', I see no problem in talking about it. Im not sure though on sassafras's legal status in different places, so others who know better can give us the information. Im also unsure on the health risks associated with using it.

As for the chemistry plausibility, you'll have to wait for one of our chem experts to chime in.

Regardless if it works or not, I like your experimenting-explorer attitude. I just hope what you're doing is safe for your health.

I really like all these possibilities and your spirit - and I'm all ears!

Of course just be careful with synthesis discussion that involve dangerous chemicals, watched chemicals as well as procedures above those that can be performed by an average chemist. And in whatever you plan to do please please please know that you cannot add too many appropriate disclaimers about potential health risks and whatnot! Some of these can possibly kill in microgram quantities! 69ron was advocating strychnine as a 4 star stimulant experience some time ago and despite his addition of disclaimers and possible health hazards one person died by taking strychnine at a party because it was said it makes you high at low doses (WTF is a "low dose" but whatever).

This is very cool. There is a real chance that you'll find something that could completely replace LSD. There are many lysergic's that are said to be more powerfull than LSD-25, but most of them are just another form of LSD, like ALD-52.

I think what you are doing is awesome. I can picture early man finding plants which brought so much more than calories, and then seeing for themselves what the plants had to offer, how to prepeare them, and how mixing certain plants together would change the experience. Take Ayahuasca for example. How long did it take amazonian tribes to figure out the mixtures that would take you into the spirit world, and if they never had, how differant so many peoples lives would be, including i would bet many members here. Now of course you are using more complicated procedures, but some of the goals are the same. To learn what is really out there, or in there ( depending what side of that debate you're on), I wish you the best of luck. and wish that this type of experimentation was being conducted by our government, as I believe entheogens are not the answer to the problems we face, but at the same time they are catalyst that could help to bring along a new chance to finish what the 60's started and yet in the end failed at. We just need to be more respectful towards these sacred substances, and not treat them as just something fun to do on a saturday. good luck again. and if you find the breakthrough you're looking for Ill be coming over.

Sassafras has its own psychoactive effects and Safrole is afaik carcinogenic.
Cinnamon isnt a known psychoactive , right?

Quote:

The primary constituents of the essential oil are 65% to 80% cinnamaldehyde and lesser percentages of other phenols and terpenes, including eugenol, trans-cinnamic acid, hydroxycinnamaldehyde, o-methoxycinnamaldehyde, cinnamyl alcohol and its acetate, limonene, alpha-terpineol, tannins, mucilage, oligomeric procyanidins, and trace amounts of coumarin. 3 , 4

C. verum differs in composition from C. cassia in eugenol and coumarin content. Coumarin is only found in cassia (0.45%). 5 Varying sources of material and extraction techniques alter the chemical composition of the extracts, and may impact the intended medicinal and experimental effects. 6 , 9

A friends friend might give this experiment a try, as I am awaiting Seeds and have the pure Essential Oil of Cinnamon on hand.

So you hypothesize Cinnamaldehyde and LSA extract will possibly form an adduct under specific conditions
Adding a drop of the Oil to a bit of wine and then dissolving LSA extract in this Solution(ph4) and giving it 24h time will likely be the approach.

Had he more quickly realized just who they were,he would have shown them more respect.Had he tried harder to fathom their brilliant minds,he would have taken more of their teachings to heart.Had he more clearly understood the purpose of their being,
he would have more vigorously tried to assist them.They were truly honorable; he was sadly prejudiced.
They were exceedingly well informed; he was grossly ignorant.They were totally indefatigable; he so often, and so quickly,gave up. Still, for many years there was a strong inter-species alliance between the Eleven-Eleven of the Half-way Realm, their Seraphic Associates,and their flesh-and-blood friend, a common mortal. Much was accomplished, many profited, and, there’s only one regret...They could have achieved so much more...
All Hypnotizing Hypnotizes Hypnotizing

Thanks, i thought so.

Thank you all for your barrage of positive responses! Sorry, Mods, didn't mean to break any rules here. I do actually believe that cinnamon oil, some form of alcohol not likely to contain other aldehydes, and a cold water extract of morning glories would be quite likely to lead to something good. I don't know why but I haven't tried seeking out any plants that contain aldehydes, they have just stumbled upon my path as if to say, "give me a shot and tell your experimentor friend about me". The unfortunate, or at least variable-inducing thing about sassafras as an aldehyde source for morning glory alkaloid altering experimentation is that it contains two different ones with similar structures - and while similar structures could mean similar activities, it could also mean wildly different activities, potencies, and such. Not that I really think this is happening, but it could even be that the piperonylacrolein and the coniferaldehyde form adducts which have opposite effects. That's pretty much not likely at all, but possible. Anyhow...I have higher hopes for cinnamaldehyde than benzaldehyde, just based on the idea that there is an existing phenylpropylamine with psychoactive effects and I've never heard of a phenylmethylamine with psychoactive effects. And I think someone said something either here or at the shroomery theorizing that a longer chain might lead to higher potency. It could be...

this looks like some promising stuff lysurgeon! keep up the great work. be sure to report back of all the conducted experiments regarding this, despite of whether its a success or failure. best of wishes on your project

Lysurgeon I'm so glad you are experimenting with ergolines and aldehydes because I'm there too!
This is really exciting for my, and I'll tell you why:
Last year SWIM started experimenting with HBWR, his first experience was with only one seed, chewed, holded in mouth for 20 minutes and swallowed. SWIM get lysergamides effects: head change, stomach ache and that horrible vasoconstriction. SWIM continued trying to get out more "juice" out of them, mixing with lots of other herbs for potentiation and side-effects counteraction, ginkgo biloba, chamomile, yerba mate, yohimbine, organic cacao, datura, catuaba, among others.
Then SWIM come across with the LSH controversy, make 3 trials with wine, 2 where success and 1 didn't do much. I attributed that to acetaldehyde instability and low BP.
So I made the same conclusion that you did and decide to try with another aldehydes. Your first choice was sassafras oil and I can see why, my first choice was Cinnamon, I love that stuff. In my head it all make sense, cinnamaldehyde have a BP of 248ºC, so it wouldn't boil out of the solution, fixing the first problem, in my understanding at least, of acetaldehyde. If its a reversible reaction at least this way it would do the reaction over and over again, instead of bounding, breaking down followed by acetaldehyde evaporation. In the other hand, cinnamaldehyde is a vasodilator, stimulant and enhances visuals. So for me it make perfect sense.
I am not going to argue about if the conversion is about LSA being molecular changed, just because I don't know if is really LSA the compound being modified, but I have no doubt that at least some aldehydes react with some ergolines changing their effects, as a whole, very drastically.

This is great stuff! A friend of a friend will be trying your combination out soon and let me know how it goes. I'll report back his experience :-)

Okay! Well, it's been well over a year and a half since I first thought of the idea to extend the "LSH" theory to include other aldehydes besides acetyl, and the first thing I hear from it lately is a friend of mine tells me people have been trying it and liking it. Then I do a google search to find that good ol' 69Ron, the same person who coincidentally was researching sassafras alkaloids at the same time as me without us being in contact with each other, read this post and gave cinnamaldehyde a shot. There's a long thread on maxforums about it. I actually didn't get around to trying any of these, but here's what's happening:

I have 100 HBWR seeds, which allows for 5 experiments (which include 3 people each). All the experiments will be done with at least 7 days in between to allow tolerance to settle. All the experiments will be performed using the exact same amount of seed material (20 seeds finely ground, extracted with cold distilled water mixed with a small amount of citric acid, for 1 hour in the water, followed by 1-2 hours aldehyde-adduct-formation time in the fridge). The first, to be conducted later today, will be using cinnamaldehyde, obtained from commercial cinnamon extract (mcCormick brand). The second, to be conducted at least 7 days from now, will employ benzaldehyde, obtained from commercial Imitation Almond Extract (mccormick does it again), and the third will employ vanillin, obtained from commercial extract of vanilla (maybe not mccormick on this one).

The other aldehydes which interest me are:
-Cuminaldehyde (4-isopropyl-benzaldehyde) due to its being 4-substituted with alkyl group, and would represent a third control to determine the difference between differently substituted benzaldehydes (the others being benzaldehyde and vanillin).
-a-Hexyl-Cinnamaldehyde, obtainable from the essential oil of chamomile.
-Piperonal (3,4-methylenedioxy-benzaldehyde) due to being another substituted benzaldehyde
-Perillaldehyde (similar to cuminaldehyde, interesting to see how it affects things)

If a 3,5-diethyl-benzaldehyde or 3,5-diethyl-cinnamaldehyde exists, that might be the ticket to microgram potency.

I'm extremely excited about this, especially after receiving the rave reviews of this combo. I did have an experience involving being accidentally fingertip dosed during the preparation of heavenly blue cwe/sassafras root tincture (contains 2 different substituted cinnamaldehydes, 3-meo-4-oh and 3,4-MD). It was definitely not a "placebo". Blindsided by the realization that I'm tripping, but...I didn't eat anything. Indicates intense potency potential given just the right conditions and plant matter.

I will definitely be checking up on this thread to see how your experiments go. I've always been interested in LSA but can't get past the horrible pains in my legs from the vasoconstriction.

I have a big bag full of MG seeds, so if this turns out to work great, that would be awesome.

I hadnt heard of using anything other than peppermint oil. This is a great post. It makes sense you could substitute in other aldehydes.

I have been doing experiments similar to this trying to standardize a way of making a simple relatively pure LSA/LSH concentrate that is visually active 100% of the time. I unfortunately havent had the time to run enough experiments to post conclusive results yet. Real life obligations ugg.

But ya any info you post is much appreciated, hope to see your results soon.

okay, the seeds didnt come through as planned, and i couldnt find any cinnamon extract until about 5pm anyway. but all in the spirit of these experiments i decided to play with different conditions trying to observe bubbling upon addition of cassia essential oil (thats cinnamomum aromaticum aka cassia aka cinnamon, high percentage cinnamaldehyde oil anyway) to a/b/np/citric harmala alks.

first was direct addition (dry) and was uneventful. harmala slightly dyed the cassia oil.

second was addition of cassia oil to water solution of harmaloids. oil formed a bubble at the bottom which rapidly recondensed after shaking. small gas bubbles were seen to form on the outer surface of the oil bubble.

addition of cassia oil to ethanolwater (everclear 151 thnx ca) solution of harmala alks also uneventful. oil and alks evenly dissolved. no bubbling.

addition of cassia oil to water-diluted everclear solution of harmala alks was comparable to water solution, except the oil bubble took about 3x as long to reform after shaking, and smaller more evenly distributed oil bubbles seemed to kick out more of the gas bubbles.

assumption is that due to indolic nature of harmalas they would also serve as a substrate for aldehyde adduct forming. and that bubbling indicates the aldehyde adduct reaction. based on assumptions and observations alcohol and water is the optimal solvent for aldehyde lsa adducts

I'm sorry I can't add to the chemistry discussion on this thread. I just wanted to point out however that my acid trips kind of match the profile of your description except for around 16 hours. For me, it's 10 hours of "harder" tripping followed by a 4-6 hour comedown. It doesn't seem to have so much to do with the compound itself to the extent that even when I take the same dose from the same batch as my friends, it always lasts significantly longer for me. If I drop at 11 am, I'll most likely be tripping till I pass out, but I've gotten used to falling asleep with visuals abound.

Nichols says something along these lines (link).

A friend of mine and I did blind experiments three times with LSA and "LSH."

I could tell no difference between the experiences. My friend claimed his second experience was different, and believed it was offered by LSH. He reported that his first experience was completely of the LSA realm, and the second was more beautiful and introspective, which he attributed to taking LSH. He received "LSH" his first time, and a week later ingested beautiful LSA crystals we had extracted. I can not say for certain if the LSA to LSH conversions work via common techniques described. I really don't think any of us can unless we perform IR/NMR/GC-MS work with our material.

In regards to synthesizing LSH with peppermint, or in my opinion, having LSA extracts that contain peppermint or menthol, the resulting material could offer a different experience due to menthol's subtle kappa opioid agonism.