Reflections on chocolate

[tregar]

The 1992 National Academy of Science adducts paper above which achieved a new indole-acetaldehyde adducted product (attached) at the NH group on the indole using only 0.1% acetaldehyde in ph=4 water solution found to happen "with or without the addition of ethanol" is similar to how the proposed dream recipe in this thread is transforming the LSH & LSA ergoline molecules from the morning glory seeds at the bottom NH group of the indole...forming a new compound which resembles ALD-52 at least at the bottom indole part of the ergoline ring.

The table from Sandoz suggested that ALD might actually have advantages over LSD, reducing any side effects but achieving a stronger trip. Measurements of brain waves while people were taking the two drugs showed that while LSD produced brain waves associated with intense concentration and anxiety, ALD produced brain waves showing a more relaxed mental state. It is possible (though I doubt it) ALD-52 was the active chemical in the "Orange Sunshine" LSD that was widely available in California through 1968 and 1969.

As stated earlier, ALD-52 also has double the "antiserotonin" properties of LSD, meaning it has even more activity at inhibiting 5-ht1a receptors (blocking serotonin, see green in chart below), which make up over 80% of brain 5-ht according to Dr. Nichols, retired LSD scientist at Purdue University. Blocking serotonin is a very important activity of LSD, mescaline, ibogaine, psilocybin, Ayahuasca with caapi, 5-meo-dmt & bufotenine.

The more anti-serotonin a molecule is, the more stimulating it tends to be as well, which would help to explain why the proposed recipe results in stimulation/energizing trip rather than sedation. Indeed, experienced no sedation but rather both entire dream trips were energizing & entheogenic/psychedelic with high levels of euphoria, just as Kash and 69ron have experienced and discussed as well in their dream reports.

 

[Tony6Strings]

Nick Sand said the whole ALD-52 as Orange Sunshine was BS, it was a defense tatctic from his atttourney I think?

If I recall the article correctly they were just very strong (ie large) doses of LSD.

 

[tregar]

Yes, I agree with you Tony6Strings.

If you can...let the dream solution (after you have extracted out the seed mush) sit in the fridge an hour or more so all the ingredients can react just like in the study (and around once an hour or more give it a swirl). I used to let it sit 3 hours, 69ron would let his sit in fridge overnight, but he only added 2 tablespoons leaf worth of chilled peppermint tea to his solution.

It reacts faster with all the ingredients I give above. I also acidified my water to ph=4 which is what the study calls for. The study showed 60% yield after 1 hour, but decreasing the concentration of acetaldehyde to only 0.1% of the solution (very similar to our proposed recipe) actually INCREASED the reaction rate and percent yield of product! This would explain my 100% conversion in such a short span of time.

69ron also reported 100% conversion several times. I think he could have avoided the failures by acidifying his solution. He said he either had 100% complete success or 100% failure other times. Acetaldehyde is naturally already at ph=4, just as the researchers in the study noted, so this may explain why the 2 tablespoons of peppermint leaf tea 69ron used was at least able to acidify his solution to some small degree, but I still recommend dropping the ph down to 4 (just like in the study) right away with an acidifier to guarantee success, don't count on the mint tea to do it for you, if it does it won't drop it that much.

The table from Sandoz suggested that ALD might actually have advantages over LSD, reducing any side effects but achieving a stronger trip. Measurements of brain waves while people were taking the two drugs showed that while LSD produced brain waves associated with intense concentration and anxiety, ALD produced brain waves showing a more relaxed mental state.

ALD-52 has been shown to block serotonin even stronger than LSD. Entheogens which inhibit 5-ht1a (shown in green below in chart) block serotonin or 5-ht and are thus "anti-serotonin". Our hypothetical LSH and LSA "indole NH group enhanced molecules" not only reduce any side effects but achieve a stronger trip just like ALD-52 has been shown to do (Hoffer & Osmond, 1967). In addition, it's more stimulating...as the higher stimulation follows higher anti-serotonin.

Thomas S. Ray study: Breadth of Receptor Binding, 4.00=max (off the charts), 0.00=min

LSD: 5ht1a = 3.73, DMT: = 0.00, psilocin = 2.88, mescaline = 3.61, 5-meo-DMT: = 4.00 (make up >80% of brain 5-ht)
LSD: 5ht1b = 4.00, DMT: = 0.00, psilocin = 2.19, mescaline = 0.00, 5-meo-DMT: = 2.41
LSD: 5ht1d = 3.70, DMT: = 3.91, psilocin = 3.40, mescaline = 0.00, 5-meo-DMT: = 3.48
LSD: 5ht1e = 2.62, DMT: = 3.28, psilocin = 3.03, mescaline = 3.16, 5-meo-DMT: = 1.72
LSD: 5ht2a = 3.54, DMT: = 2.58, psilocin = 2.14, mescaline = 0.00, 5-meo-DMT: = 0.98
LSD: 5ht2b = 3.11, DMT: = 3.91, psilocin = 4.00, mescaline = 3.97, 5-meo-DMT: = 0.69 (sensual & entactogenic)
LSD: 5ht2c = 3.11, DMT: = 3.42, psilocin = 2.52, mescaline = 0.00, 5-meo-DMT: = 1.55
LSD: 5ht5a = 3.64, DMT: = 3.16, psilocin = 2.83, mescaline = 0.00, 5-meo-DMT: = 1.84
LSD: -5ht6 = 3.75, DMT: = 3.35, psilocin = 2.82, mescaline = 0.00, 5-meo-DMT: = 2.73
LSD: -5ht7 = 3.77, DMT: = 4.00, psilocin = 2.82, mescaline = 0.00, 5-meo-DMT: = 3.69
LSD: ---D1 = 2.34, DMT: = 3.51, psilocin = 3.37, mescaline = 0.00, 5-meo-DMT: = 2.38
LSD: -A-2A = 2.93, DMT: = 2.75, psilocin = 1.36, mescaline = 2.92, 5-meo-DMT: = 0.00 (aesthetic/beauty adrenal a2a)
LSD: -A-2B = 0.00, DMT: = 3.53, psilocin = 1.57, mescaline = 0.00, 5-meo-DMT: = 0.86 (aesthetic/beauty adrenal a2b)
LSD: -A-2C = 0.00, DMT: = 3.53, psilocin = 1.03, mescaline = 4.00, 5-meo-DMT: = 1.57 (aesthetic/beauty adrenal a2c)

Dr. Nichols (Heffter.org LSD paper):

LSD has very strong potency in blocking the action of serotonin. LSD is strongly "anti-serotonin". The morpholide lysergamide cousin had only about 1/10th the potency in blocking serotonin. Of the 5 diferent dialkylamides we studied LSD was the most potent and specific serotonin antagonist. 5-ht1a makes up >80% of brain 5-ht receptors.

As we go thru day to day life, the 5-ht1a brain serotonin filters (gates, or day to day survival filters as I like to call them) which make up over 80% of brain 5-ht are in place so that we will not be overwhelmed by the perception of the way things would appear to an un-filtered mind, or "Mind at Large" as Aldous Huxley describes it in "Doors of Perception" as "infinite or eternal". He also referred to the visions as coming from "the other world" in his book "Moksha". I prefer to think of it in similar terms as well "the spirit world" or "the other world".

5-ht1a inhibition by entheogens (in green above) theoretically cause this filter system to be lifted, and the infinite mind to manifest in combination with oral dmt from traditional psychotria for example with the caapi and/or harmalas providing the 5-ht1a inhibition, just as bufotenine in snuff's provide the 5-ht1a inhibition combined with the dmt in the snuff's, resulting in a 3 hour experience ie both examples of Teamwork on how these entheogens are used traditionally in the Amazon.

Thomas S. Ray's study shows a value of 3.57 at SERT for Ibogaine (4.00 is max). Ibogaine has been shown to inhibit serotonin transporter (SERT) noncompetitively, in contrast to all other known inhibitors, which are competitive with substrate. Ibogaine inhibits both serotonin and dopamine reuptake transporters, it is an SDRI or serotonin & dopamine reuptake inhibitor. Tetrahydroharmine is a serotonin reuptake inhibitor, it is an SRI found in caapi. In other words, both are strong serotonin reuptake inhibitors which inhibit over 80% of brain 5-ht at 5-ht1a.

In contrast, as an example, Cocaethylene (coca leaf tea bags soaked in wine, the orally active & potent ingredient formed in the liver from cocaine + ethanol in the 1860's "Vin Mariani" wine popular with both Popes, Thomas Edison and scores of other famous people) increases the levels of serotonergic, noradrenergic, and dopaminergic neurotransmission in the brain by inhibiting the action of the serotonin transporter, norepinephrine transporter, and dopamine transporter. These pharmacological properties make cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor [SNDRI; also known as a "triple reuptake inhibitor"].

Cocaethylene has a higher affinity for the dopamine transporter than does cocaine, but has a lower affinity for the serotonin and norepinephrine transporters. In McCance-Katz et alia's 1993 study cocaethylene "produced greater subjective ratings of 'High' in comparison with administration of cocaine or alcohol alone."

Teamwork, just like the high levels of penniclavine + LSH (both CNS stimulants) in the MG seeds...all working together for the experience.

 

[tregar]

In conclusion, I was messaged this:

Jeez. Why diddle with all this? Just take some LSD, would ya?

Have dreamed Ayahuasca 65 times (Antipodes of the Mind is the best book on Ayahuasca imho) & cactus/Hofmann's potion hundreds of times in the distant past yet fresh MG right off the vine around a handful of times, but 3 of those were using this exact same recipe given here, and they were powerful experiences, unlike anything I had ever experienced with fresh MG before.

This dream recipe transforms LSH and LSA into "indole NH group enhanced molecules" in dreams. The new hypothetical molecules not only reduce any side effects but achieve a stronger trip just like ALD-52 has been shown to do (Hoffer & Osmond, 1967). In addition, the trip is stimulating (not sedating like LSA)...as the higher stimulation naturally results from the new molecule's higher anti-serotonin qualities.

Long ago, used to stretch cactus dreams out (dosed w/tea amount in dreams corresponding to perhaps 300 to 400mg) by dreaming it with Hofmann's potion. Never preferred Hofmann's potion much on it's own, but in combo with cactus, extraordinary and the visions with closed eyes unbelievable, even many hours later before falling to sleep, still CE visions going on and on.

In answer to the message: MG might possibly add new dimensions and headspace in combination with other entheogens, as we know the semi-synthetic LSD has good activity at A2A but zero activity at A2B & A2C. I have examined the receptorome for natural LSA related alkaloids in the past (I only wish I could locate the paper again, sadly I cannot) and remember viewing significant activity at A2A, A2B and A2C (adrenal receptor sites in the brain believed to be associated with love, beauty & euphoric feelings).

Penniclavine (found in high amounts in the seeds, found to be CNS stimulating, Yui & Takeo) is a metabolite of agroclavine, and is active at the following brain receptor sites: Dopamine D1A, Dopamine D1B, 5-ht2a, Adrenal A2A, Adrenal A2B & Adrenal A2D, in comparison LSD (as far as adrenal sites are concerned) only has activity at A2A, but zero activity at A2B, A2C, and A2D.

The teamwork between the newly created "LSH & LSA indole NH group enhanced molecules" by the recipe and Penniclavine in the seeds is what imho results in the potent & very euphoric experience.

Ayahuasca, cactus & shrooms have great activity at A2A, A2B & A2C as well. LSD imho seems to be more analytical and has less of an aesthetic component compared to the natural entheogens, which is why LSH and other alkaloids in MG seeds may just add new dimensions & headspace to the experience, possibly even expanding upon the visuals & visions. Many have mentioned increased feelings of closeness with nature and high levels of euphoria.

 

[tregar]

Heavy duty ten hit 15 year old decomposed acid trip report...

and it has to do with how I got into growing morning glory...this is a true story below, and you may find it hard to believe, but this is how it all got started...

About 22 years ago, a dear friend of mine had given me a bunch of acid that he had kept stored in between the pages of a book (not even put into a baggie!)...and this acid he gave me was over 15 years old!

Took the 20 hits or so of 15 year old acid home and placed it in front of a blacklight, and noticed that it had decomposed quite a bit, instead of seeing uniform bright blue glow of LSD, it was splotted on the blotters, with each blotter still containing maybe 60% of what it used to have originally.

So I gave 10 hits of this decomposed acid to my girlfriend (who was at the time talking to her sister on the phone) and I took 10 hits of it myself in dreams, to our amazement, it began to work...it sort of had a strong sick feeling in the stomach to begin with as much of it was decomposed, but after 2 hours, it kicked in to super high strength for both of us, and the sickness had dissipated. I think it took 2 hours to work cause the chemically left good acid was in such bad shape.

Now to the good part...

There was a fake tree in the living room in the corner that had Christmas tree lights on it and gave off a pattern of shadows on the wall behind it...we both began to stare at the shadows on the wall, as it seemed to be beckoning us...as we could see images forming out of the shadows...then we both began to see the exact same thing on the wall!

We both saw an ancient powerful Shaman from South America who was wearing a huge beautiful head dress made of feathers. He seemed to be of great spiritual prominence...and he sat on a Living throne chair like something you might see out of Game of Thrones..but this chair he sat on was no normal chair...it had animals like Jaguars, Lions, and birds living in it, and they constantly morphed into different animals the whole time he sat there. Spirit animals that lived with him.

The image of the Shaman sitting on the Living Spirit "Game of Thrones like Chair", was incredible, it was beyond 4k, and highly detailed, we were both in shock and awe...and like I said...we both saw the exact same vision which is even more striking.

In the background behind the Shaman, we both also saw what looked like the Great Pyramid in the Aztec capital of Tenochtitlan. My girlfriend (now my wife) and I both saw hybrid creatures to the left and right of the Shaman. Upper-half human, lower half animal.

We saw centaurs, creatures from Greek mythology with the upper body of a human and the lower body and legs of a horse. Behind the centaurs I saw snakevines growing out of the ground which appeared to look like Ololiuqui climber plants...this vision went on for a good 20 minutes straight...we did not move an inch while we watched the "Amazonian tv-like movie visions" on the wall. The whole time the TV in the room was playing, but we ignored it.

The rest of the time the Shaman showed me visions of the rise and fall of civilizations throughout time, he would disappear for a few minutes, and be replaced with the historical visions, then he would reappear to show me another historical period in time. I was shown different periods of human history. I remember seeing the rise and fall of the Roman empire, the ancient Maya, over-exploitation of natural resources. Telepathically, he seemed to be telling me that if humankind was to survive, the only hope was a spiritual solution, a radical shift in consciousness.

Towards the end, the Shaman with his piercing and highly detailed eyes, looked us both straight in the eye, we were in shock, he stared intently, then he gazed with his eyes to the right motioning me to look to the right of the living room, ouside the window, to the patio area where I had a large plot of garden with nothing in it. That's when I instinctly knew that he was trying to tell me to plant entheogenic plants in the garden plot.

And that's exactly what I did, that summer I bought the best morning glory seeds I could find on-line and planted them in a bed of miracle grow (w/dried cow manure compost mixed in from garden store) in the garden plot, with a trellis I put into place with 2 cement supports to hold it upright.

Fed them 1 gallon of watering can with spout containing 1 tablespoon of miracle grow mixed just once a month, and at the beginning of planting. This I read would keep the lysergic acid amide levels high in the plant which eventually all transferred into the seed embryo's found in the pods when picked at the end of the fall season. Feeding only occasionally like this kept the foliage down, and the flowers large, they were monstrous. When I opened up the dried pods in the fall and picked the ever so slightly un-ripe black seeds, I could detect the faint smell of acetaldehyde given off the seeds when they were ground.

Dreamed the seeds right off the vine (vacuum packed all the extra black heavenly blue MG fresh seeds in food saver bags and froze them to keep their original freshly picked high potency) at least 5 times, 3 of those using the dream recipe in this thread, and those 3 dream experiences were extraordinary...I had found the adducts paper doing hours of research one afternoon, and that's when I knew that I had stumbled upon something extraordinary...and used the details from the study to hypothetically transform the high levels of LSH and LSA ergolines/indole structures in the seeds into something possibly intensified or amplified.

Reading the book "Sacred Mushrooms of the goddess, by prof Carl AP Ruck" and "Road to Eleusis" by Hofmann, Wasson & Ruck gave me the additional idea of adding mint/peppermint in the recipe along with the shot of high acetaldehyde Sherry (my idea from the adducts paper). Later in 2005 Krystle Cole (a former goth stripper from Kansas, who fell in love with LSD chemist Todd Skinner in 2000) describes her dream experiences in the book "Lysergic" with "ergot wine". Supposedly Todd had prepared 6 jugs of the ergot wine many years beforehand, and stored them all in the abandoned underground missile silo they lived in. She reports seeing constantly floating hieroglyphic symbols floating in a circle around Todd's head.

The end, now you know the story of how this all came about. When I experienced the three incredible dreams (after comparing them to my other normal fresh MG experiences) I knew I had accidentally stumbled upon something personally fascinating imho, and posted the dream on the now defunct Lycaeum forum long ago.

The vision of the Shaman with the huge beautiful headdress made of feathers sitting on the living thrown made of Spirit Animals, with the Great Pyramid in the Aztec capital of Tenochtitlan in the background & snakevines in the distance...sort of looked like the attached pictures with the centaurs to the left and right. I must admit, these attached pics still don't do the vision justice, the visions were way beyond 4k, extremely detailed, as if newly created, of an artistic rendering unimaginable.

 

[tregar]

Breakdown of this entire paper:

In conclusion, this is how close the mystery molecule hypothetically formed (1992 adducts study confirms it can happen, see post 41) with proposed recipe in this thread from over 20 years ago (LSH & LSA ergoline NH group indole adducts with acetaldehyde) is to looking like ALD-52 at the bottom indole NH group:

1) acetyl added to LSD at the bottom indole NH group to form ALD-52, acetyl = C2 H3 O, molar mass = 43 g/mol

2) acetaldehyde adducted to bottom indole NH group on LSH & LSA, acetaldehyde = C2 H4 O, molar mass = 44 g/mol

I also verified by reading a page on ALD-52 from the book "Ergot alkaloids & related compounds" by Berde that indeed ALD-52 has 2.1 times the "anti-serotonin" properties of LSD, and higher stimulation follows higher anti-serotonin, which may help to explain why our newly formed mystery molecules result in a stimulating/energizing trip instead of a sedating trip like with solutions heavy in LSA. Indeed, myself, 69ron and Kash have all confirmed the resulting trips are energizing/stimulating and not sedating.

69ron:

Fact: This conversion, when it works, produces an effect that is very different from LSA. Far more like LSD, and stimulating instead of sedating. When it works, the difference is HUGE, not a tiny difference, the experience is TOTALLY DIFFERENT. I know the effects of LSA and LSD very well. He has used them many times. He guarantees that when the reaction works, there is NO NOTICEABLE LSA left at all in the experience. It becomes almost identical to an LSD experience at low doses. Totally different from LSA.

Kash:

Just took a 40 seed portion of LSA extract that was mixed for 15 minutes with peppermint oil yesterday and tripped his face off with a friend. Was very clean feeling and relaxed. Rainbows and vibrant fractal energy danced all over the skies and throughout his surroundings and music sounded great. The head-space was very acid like but different. Was a bit intense but he was able to keep it together lol. Whole trip was about 8 hrs long.

Swim has tried a 20 seed extract without peppermint oil and it seemed uncomfortable and sedating with no visuals, while every time he has added peppermint oil he has gotten visuals.

Recall in the 2014 forensics paper attached from Paulke that no LSH was found in HBWR seeds, but only found LSA & iso-LSA (83-84%) & ergometrine (10-17%) & rest: lysergol, elymoclavine & chanoclavine. We know that MG has centuries of Shamanic use, while HBWR has no history of Shamanic use.

All the experiments performed by 69ron and Kash were with extracts of HBWR seeds, they were transforming ONLY the high amounts of LSA and ergometrine in the seeds to the 1-acetaldehyde versions...so just imagine what kind of incredible experience they COULD have had if they had only dreamed with traditional Shamanic used morning glory seeds (like I did) which contain high amounts of not only LSH but also penniclavine. I have yet to read of anyone using this same recipe with morning glory seeds on the net...something to ponder. See my potent dream recipe experiments/experiences in this thread on post #41.

Penniclavine (found in high amounts in the seeds) has excitory effects on the central nervous system [Yui & Takeo, 1958] as well as lysergic acid hydroxyethylamide (LSH) which also excites the central nervous system in animals & caused dilation of pupils (Glasser, 1961). LSH is very similar to LAE-32 which is described in human experiments in TIHKAL, to be LSD like and stimulating at 1.5mg (1500ug). Albert Hofmann later discovered LSH in MG seeds around 1967 and put colored drawings of it in his book "LSD, my problem child." and apparently told Owsley that it was very "LSD-like".

Penniclavine (CNS stimulating, Yui & Takeo) is a metabolite of agroclavine, and is active at the following brain receptor sites: Dopamine D1A, Dopamine D1B, 5-ht2a, Adrenal A2A, Adrenal A2B & Adrenal A2D, in comparison LSD (as far as adrenal sites are concerned) only has activity at A2A, but zero activity at A2B, A2C, and A2D.

The teamwork between the newly created "LSH & LSA indole NH group enhanced molecules" by the recipe and Penniclavine in the seeds is what imho results in the potent & very euphoric experience.
----------------------------------------------------------------------------------
ALD-52 is named 1-acetyl-LSD, therefore...

the names of the two molecules (both found in abundance in the MG seeds) transformed with this recipe are then named:

1) 1-acetaldehyde Lysergic acid hydroxyethylamide (1-acetaldehyde LSH)

2) 1-acetaldehyde Lysergic acid amide (1-acetaldehyde LSA)

The table from Sandoz suggested that ALD might actually have advantages over LSD, reducing any side effects but achieving a stronger trip. Measurements of brain waves while people were taking the two drugs showed that while LSD produced waves associated with intense concentration and anxiety, ALD produced brain waves showing a more relaxed mental state.

In The Hallucinogens by Hoffer and Osmond (1967), ALD-52 is listed as having a lower [approximately 1/5] intravenous toxicity (in rabbits), a lower [approximately 1/8] pyretogenic effect, an equal psychological effect in humans, and double the "antiserotonin" effect as compared with LSD.

Erowid ALD-52 experiences: ALD-52 (also 1-Acetyl-N,N-diethyllysergamide) : Erowid Exp: Main Index

Off to the water park to take a much needed vacation from writing (my favorite summer Nature get-a-way year after year...many Covid measures in place). This is the end of this thread, I promise, this last page breaks it all down so it's easy to understand.

 

[tregar]

If you are limited on space, you can plant heavenly blue morning glory seeds in a bed of miracle grow garden soil (w/ added dried cow manure compost & some perlite mixed in from garden store) in a large wide clay pot, with a trellis put into the pot to support the fast climbing snakevines. I actually did it this way when I moved again into a new house, and kept all the clay pots sitting atop 1 foot x 1 foot square bricks to the side of the outdoor patio, so that they only got morning sun, very beautiful. You can find the very tall trelliss that fit inside the clay pots at your local garden stores.

Fed them 1 gallon of watering can with spout containing 1 tablespoon of miracle grow mixed just once a month, and at the beginning of planting. This I read would keep the lysergic acid amide levels high in the plant which eventually all transferred into the seed embryo's found in the pods when picked at the end of the fall season. Feeding only occasionally like this kept the foliage down, and the flowers large, they were monstrous. When I opened up the dried pods in the fall and picked the ever so slightly un-ripe black seeds, I could detect the faint smell of acetaldehyde given off the seeds when they were ground. The seeds are extremely potent when picked fresh.

Dreamed the seeds right off the vine (vacuum packed all the extra black heavenly blue MG fresh seeds in food saver bags and froze them to keep their original freshly picked high potency) at least 5 times, 3 of those using the dream recipe in this thread, and those 3 dream experiences were extraordinary...I had found the 1992 adducts paper doing hours of research one afternoon, and that's when I knew that I had stumbled upon something remarkable...and used the details from the study to transform the high levels of LSH and LSA ergolines/indole structures in the seeds into molecules which were intensified or amplified in their psychedelic effects & euphoria....trips were also energizing, not sedating.

Reading the book "Sacred Mushrooms of the goddess, by prof Carl AP Ruck" and "Road to Eleusis" by Hofmann, Wasson & Ruck gave me the additional idea of adding mint/peppermint in the recipe (just like the priest at Eleusis were know to add in to their sacred potion) along with the shot of high acetaldehyde Sherry wine (my idea from the adducts paper). Later in 2005 Krystle Cole (a former goth stripper from Kansas, who fell in love with LSD chemist Todd Skinner in 2000) describes her dream experiences in the book "Lysergic" with "ergot wine". Supposedly Todd had prepared 6 jugs of the ergot wine many years beforehand, and stored them all in the abandoned underground missile silo they lived in. She reports seeing constantly floating hieroglyphic symbols floating in a circle around Todd's head.

Now you know the story of how this all came about. When I experienced the three incredible dreams (after comparing them to my other normal fresh MG experiences) I knew I had accidentally stumbled upon something personally fascinating imho, and posted the dream on the now defunct Lycaeum forum long ago.

The recipe is given above along with how long the solution needs to sit in the fridge (a few hours to guarantee 100% conversion just like the study) for the acetadehyde adducts to form on the bottom NH group of the indole on ergoline/indole LSH and LSA structures to form the new 1-acetaldehyde LSH and 1-acetaldehyde LSA, forming new molecules which look very similar to what ALD-52 looks like at the bottom of the NH group indole as well.

ALD-52 is a cousin of LSD shown by Sandoz to have less side effects while achieving a stronger more relaxed trip, with twice the anti-serotonin properties of LSD, and the more anti-serotonin, the more stimulating, which may help to explain why the trips resulting from the recipe's transformed ergoline molecules result in very visual & euphoric psychedelic trips which are energizing and not sedating. You can view ALD-52 sample trips at Erowid's vault. However, our transformed mystery molecules have one more hydrogen on the group as compared to the 43 g/mol of ALD-52's acetyl vs 44 g/mol of our molecule's acetaldehyde adduct, which may help even more with the resulting energizing trip vs sedating trip as with typical normal LSA saturated solutions.

However, the recipe calls for use of morning glory seeds in dreams which contain high levels of LSH, we know from the 2014 Paulke study that HBWR contains no LSH, but rather high levels of LSA/iso-LSA (83%) and around 17% ergometrine, which will transform to the 1-acetaldehyde versions of themselves as well, but ergometrine is not as strong as LSH and results in some cramping and side effects, ergometrine levels are extremely low in MG seeds in comparison.

I actually had the chance in dreams to try ALD-52 around 10 years ago twice, and the blotter had diagrams of the ALD-52 molecule on the back of the blotter, and both times I found the high dosage trips I experienced to be PROFOUNDLY VISUAL, I remember looking at my wife's face and seeing it covered & overlayed with colored hieroglyphic symbols. The trip was very strong visually and yet I found it relaxed and potently humorous, I laughed for at least an hour watching episodes of "Funny or die" at the time.

I also remember seeing a group of Indian Shaman's sitting in a circle floating in mid-air when I walked into the bedroom, the trips blew me away with their potency and visuals...I miss ALD-52, but the recipe above will transform the morning glory seed's LSH and LSA into similar molecules at least at the bottom indole NH group, which helps significantly in achieving a much visually stronger trip, and sounds are amplified and music sounds absolutely heavenly, strong audio heightening qualities, the trips are very euphoric as well, also stimulating yet relaxed.

 

[tregar]

I have re-named this thread "Alchemy conversion of LSH & LSA in morning glory to 1-acetaldehyde LSH & LSA" which starts on page 3, post #41, supported by 1992 adducts paper and 2016 Polish morning glory paper. p.s. Have had 2 years of University Chemistry & many years of chem studies beyond that.

500ml ph=4 acidified spring water (prevents LSH from re-arranging to LSA in neutral water) containing filtered morning glory seed mush + one shot (30ml) of high acetaldehyde sherry (contains 10mg natural acetaldehyde) and 2 tablespoons fresh Bigelow leaf mint/peppermint fresh from foil chilled spring water made tea (contains avg 3mg natural acetaldehyde & it's corresponding acid) w/or without 5 drops peppermint extract (contains avg 2mg water soluble acetaldehyde & it's corresponding acid) and allowed to sit for 3 hours in fridge w/swirling once per hour for new 1-acetaldehyde LSH & 1-acetaldehyde LSA to form with 100% conversion according to adducts paper.

Note: this converts the high levels of LSH and LSA in MG seeds to 1-acetaldehyde LSH & LSA, by adduction of acetaldehyde to NH group indole on bottom of ergoline LSH/LSA ring indole.

Note how close the mystery molecule hypothetically formed is to looking like ALD-52 at the bottom indole NH group:

1) acetyl added to LSD at the bottom indole NH group to form ALD-52, acetyl = C2 H3 O, molar mass = 43 g/mol

2) acetaldehyde adducted to bottom indole NH group on LSH & LSA, acetaldehyde = C2 H4 O, molar mass = 44 g/mol

However, our transformed mystery molecules have one more hydrogen on the group as compared to the 43 g/mol of ALD-52's acetyl vs 44 g/mol of our molecule's acetaldehyde adduct, which may help even more with the resulting energizing trip vs sedating trip as with typical normal LSA saturated solutions.

Note: the recipe calls for use of morning glory seeds in dreams which contain high levels of LSH, we know from the 2014 Paulke forensics study that HBWR contains no LSH, but rather high levels of LSA/iso-LSA (83%) and around 17% ergometrine, which will transform to the 1-acetaldehyde versions of themselves as well, but ergometrine is not as strong as LSH. LSH is similar to LAE-32 active at 1.5mg in human experiments in TIHKAL, shown to be very "LSD like". Ergometrine in HBWR results in some cramping & vasoconstriction and side effects, ergometrine levels are extremely low in MG seeds in comparison.

All based on the studies above and mint which we know was added to the sacred entheogenic potion the priest administered. Read more about mint addition in the books "Road to Eleusis" by Hofmann, Wasson & prof Ruck and "Sacred mushrooms of the goddess, secrets of Eleusis" by prof Ruck...who describe the rites held at Eleusis for initiates in ancient Greece for over 2,000 years believed to be propelled by the effects of a powerful psychoactive potion into revelatory mind states with profound spiritual and intellectual ramifications. Plato, Socrates and a host of other philosophers drank the sacred entheogenic brew kept secret by the priest at Eleusis. Men, women and even slaves were allowed initiation.

 

[downwardsfromzero]

2) acetaldehyde adducted to bottom indole NH group on LSH & LSA, acetaldehyde = C2 H4 O, molar mass = 44 g/mol

The acetaldehyde adduct would be C2H5O, as CH3COH attached at the indolic nitrogen - another 1-hydroxyethyl group, just like in LSH. From what you describe, this seems like an argument for soaking one's N¹-unsubstituted lysergamides in cold peppermint sherry for a while before consumption. Would this also include tryptamines such as DMT-containing potions for oral consumption, one might wonder? And what about psiloc(yb)in?

As I've mentioned, my most successful plant-derived lysergamide experience - in dreams, of course - albeit with HBWR, coincided with intake of a fairly large quantity of brandy which, in all likelihood, produced a significant level of acetaldehyde within my body, exposing the plant lysergamides to the correct conditions (as reported in the Austin & Fraenkel-Conrat PNAS paper) within my stomach for the putative 1-(1-hydroxyethyl) or, rather, it seems, the 1-(1-ethoxyethyl) derivative to be formed. In this case, the effects were clearly stimulating, unlike the sedative effects usually reported for HBWR. I see that brandy weighs in fairly well on the acetaldehyde content scale as well, btw (post #17)

Looking at the PNAS paper, and the molecular structure "indole after p8441", what we appear to get is a 1-(1-ethoxyethyl)indole, with an ethyl group on the oxygen atom. This would be more lipophilic than the 1-(1-hydroxyethyl) derivative, as would, incidentally, the cinnamaldehyde adduct proposed by 69ron. It is only with the combination of both ethanol and acetaldehyde (EDIT: rather. an alcohol and an aldehyde; see below) that we get a stable product. It would seem likely that under mildly acidic conditions ethanol and cinnamaldehyde (or, we might also surmise, any other sufficiently stable, sterically unhindered aldehyde) would also form a stable adduct. The systematic naming starts to get a bit horrible, but here goes: 1-(3-phenyl-1-ethyoxyprop-2-en-1-yl)indole derivatives. Now have a cookie.

And isovaleraldehyde would lead to the production of a 1-(1-ethoxy-3-methyl-1-butyl)indole derivative under this scheme. That'll have to do for now as I need to sleep. [EDIT: also of interest, we see the following: "Reaction mixtures were also prepared using 1-, 3-, and 4-carbon-chain aldehydes and alcohols. After 24 hr of reaction at ambient temperature, these alternative mixtures were analyzed on the same HPLC system. Reaction products (data not shown) were detected in all cases, except when the aldehyde was formaldehyde, and product retention time increased along with the length of the reagents' carbon chains. The yields decreased with increasing alcohol and aldehyde chain length (methanol/acetaldehyde - butanol/butyraldehyde)."]

 

[tregar]

Thanks so much for your expert opinions downwardsfromzero! I agree completely with everything you have said, again much appreciated. Interesting that you also found it stimulating in dreams and not sedating.

This on-line report by "u" echoes my own opinion of my own 2 dream experiences over a decade ago with ALD-52 as well "HIGHLY underestimated ALD 52". This is shown in order to relay a better understanding of similar qualities inherent to the hypothetical 1-acetaldehyde LSH. Again, LSH is found in high amounts in morning glory seeds (3x higher in seeds direct from grower vs retail) along with penniclavine (both CNS stimulants), but LSH is not found in HBWR, only LSA/iso-lsa (83%) and ergometrine (17%). LSA appears to be a breakdown product of LSH in the Shamanic mg seeds.

https://www.reddit.com/r/LSD/comments/4yn8ou/highly_underestimated_ald52

hxxps://www.reddit.com/r/LSD/comments/4yn8ou/highly_underestimated_ald52/

Highly visual & aesthetic, relaxed yet stimulating...actually had the chance in dreams to try ALD-52 around 10 years ago twice, and the blotter had diagrams of the ALD-52 molecule on the back of the blotter, and both times found the 200ug trips experienced in dreams to be PROFOUNDLY VISUAL, remember looking at a living woman's face and seeing it covered & overlayed with colored hieroglyphic symbols. The trip was very strong visually and yet found it relaxed and potently humorous, laughed for at least an hour watching episodes of "Funny or die" at the time.

Also remember seeing a group of Indian Shaman's sitting in a circle floating in mid-air when I walked into the bedroom, potent visuals...miss ALD-52, but the recipe above will transform the morning glory seed's LSH and LSA into similar molecules at least at the bottom indole NH group, which helps significantly in achieving a visually strong trip, sounds are amplified and music heavenly, strong audio heightening qualities, euphoric & stimulating yet relaxed journeys.

Anything longer than around the length of an acetaldehyde molecule (C2 H4 O) attached at the NH indole of the ergoline LSD molecule (especially 1-p-LSD, propionyl = C3 H5 O) may not fit properly into the very specific receptor binding site (as ALD-52 fits, acetyl = C2 H3 O), so cinnamaledehyde (C9 H8 O) and similar very long structures may not have a chance of docking into the receptor site properly.

David E. Nichols reportedly commented on the potential 1P-LSD serotonin receptor binding dynamics:

I am sure that the 1-propionyl would also hydrolyze off of an indole, but I don't know whether in vivo conditions would work. In a chemistry lab, you can get off an N-benzoyl, so an N-propionyl will probably come off too. But in the body? I don't know the answer to that. The compound would not be active as the N-propionyl however. The way that LSD docks into the 5-HT2A receptor, the indole NH hydrogen bonds to serine 5.46. With the propionyl, it won't fit into the receptor.

-----------------------------------------------------------------------------------------------------------
From sedation to --> stimulation & increased visuals, hypothesis:

Harmaline (C13 H14 N2 O) is an example of a betacarboline (class of indole alkaloid compounds) that when it gains 2 hydrogen molecules on it's indole --> transforms into tetrahydroharmine (C13 H16 N2 O), transforming from "sedating dreamy visual harmaline" to "stimulating & visually bright & colorful tetrahydroharmine". Harmaline does a complete 180 degree transformation with the addition of 2 hydrogen molecules on it's indole --> turning from tranquilizing to energizing.

According to a 2012 paper "Various alkaloid profiles in decoctions of Banisteriopsis caapi" by Dr. JC Callaway found in Ref (1) at bottom in wikipedia under the entry for "tetrahydroharmine" large amounts of the energizing & euphoric THH were found in the Ayahuasca brews prepared by the Vegetal groups UDV and Santo Daime.

Dr. Shulgin has said in the "Entheogen Review Journal" that vitamin C acts as a "hydrogen doner":shock: and when the Santo Daime brew their Ayahuasca with vitamin C for long periods of time, the vitamin C contributes two hydrogens to the harmaline in the brew, converting all the leftover harmaline to tetrahydroharmine. How is that for Alchemy?

In fact, in the above paper, no harmaline was found leftover in the brews prepared by the Santo Daime, their Alchemy brewing process had converted all the leftover harmaline to THH. Page 2 of above paper shows zero mg of harmaline was left in each & every one of the brews. In another study mentioned in the same paper, the "likeness" of the brews transformed into ones with high levels of THH were rated by the members at an all time high, and preferred over brews with harmaline. There was so much THH in their brews according to page 4 of the study, that it was found in a 1:1 ratio with harmine.

This may translate over to LSA as well ie "the sedating qualities" :? of LSA into "stimulating qualities" like 1-acetaldehyde LSA and an "even more stimulating & visual" version of LSH --> into 1-acetaldehyde LSH.

LSA (C16 H17 N3 O) + acetaldehyde (C2 H4 O) at bottom indole NH group = 1-acetaldehyde LSA
LSH (C18 H21 N3 O) + acetaldehyde (C2 H4 O) at bottom indole NH group = 1-acetaldehyde LSH
LSD (C20 H25 N3 O) + acetal (C2 H3 O) at bottom indole NH group = 1-acetal LSD (C22 H27 N3 O2) or ALD-52

LSA could be transforming from a "sedating" version of itself into a "stimulating" version of itself, and LSH becoming even more stimulating/visual as they both gain double the anti-serotonin properties (just as ALD-52 is 2.1 times the anti-serotonin strength of LSD), just as we know that tetrahydroharmine in caapi is a strong SRI (serotonin reuptake inhibitor, strongly anti-serotonin) and thus stimulating like coffee vs sleepy harmaline.

Does THH also become a more visual form of harmaline? many believe so, but in a different way. Psychonaut wiki reports that at doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations/bodily felt high vibrational frequency and an extensive array of psychedelic effects. The literature from Dr. Naranjo (1967) reports visionary qualities at 300mg, defining them as "oneirophrenic" or fantasy & dream-inducing visions. Quote "Other recurrent visual phenomena were a rapid lateral vibration in the field of vision and double or multiple contours in objects, especially when these were in motion or when the subject's eyes turned away from them. Some described lightning-like flashes. With closed eyes, imagery was abundant and most often vivid and bright colored, with a predominance of red-green or blue-orange contrasts. Long dream-like sequences were common with certain themes."

Professor Benny Shanon who took Ayahuasca over 125 times said the visions are completely un-like sleeping dreams and involve instead visions of ancient civilizations, Royalty & people of great Spiritual prominence, mythical & heavenly scenes, animals (especially birds), artwork, grand architecture and palaces, gardens like those seen at Versailles in France, floral scenes, ET's and spaceships, etc.

Researchers believe it is most likely a combination of the small amounts of harmaline (10 to 40mg) in Caapi along with the modest amounts of THH in Caapi (2nd highest ingredient) that are responsible for the Ayahuasca visions, formed even without addition of admixture leaf, which is said by the Shaman's to add brightness and color to the visions formed by the Caapi, which is considered "Ayahuasca" by the Shamans whether without or with the admixture leaf added.

Will LSA & LSH become more visual forms of themselves as the 1-acetadehyde versions? definitely believe so! based on dream experiences comparing recipe enhanced versions vs. non transformed extracts from the past.

How else are we to explain the highly visual and stimulating properties of these 1-acetaldehyde versions vs the normal sedating qualilties of LSA? Remember how Kash said he always got visuals & stimulation with the 15 minute peppermint soaked LSA vs the non-peppermint soaked LSA which was sedating, uncomfortable & no visuals? Also see trip reports from myself, 69ron & Kash at beginning of thread & downwardsfromzero also recognized the stimulating properties of the new acetaldehyde adducted extract vs normal extract which he writes about in a dream above. Kash is known for his extensive LSA extraction dreams stickied at top. Krystle Cole writes for several pages about her powerful "ergot wine" experiences in the book "Lysergic".

The 1992 adducts paper specifically adducts acetaldehyde to indole at the NH group in one experiment using acetaldehyde in ph=4 water solution found to happen over time "with or without the addition of ethanol" (they tried it both ways)...giving excellent yield of new product formed, 60% in 1 hour, and even greater yield in less time when they reduced the amount of acetaldehyde used to only 0.1% acetaldehyde solution! Just like the process I dreamed decades ago several times, to replicate the study as best as possible, letting solution sit in fridge for 3 hours with swirling once per hour.

Study calls for ph=4 water solution, which is what I dreamed...as that is the ph necessary for rapid new product creation yield according to the researchers, yield was slower at higher ph...not to mention acidic conditions are necessary to keep the natural LSH extracted from the seeds from re-arranging (decomposing) to LSA as will happen in neutral water, very fast in alkaline water, or when heated.

What was dreamed decades ago was Bigelow fresh mint/peppermint combo leaf sealed and packaged in foil along with 5 drops of peppermint extract. You can find it at your local grocery store in the herbal tea isle.

Fresh MG seeds you will need to grow or locate direct from a reputable grower, as the seeds sitting on racks in retail were found by the study to contain 3x less LSH vs direct from grower. If you find or grow good seeds, vacuum pack and freeze the extras, so they will retain their potency indefinately.

The study said "LSH is a labile compound, and therefore the variances in its concentration may be due to different age and storage conditions of the seeds rather than difference in plant metabolism." (1.71 LSH from producer seeds vs 0.54 LSH from retail rack seeds).

The sources were clear that the kykeon's other ingredient, mint (menthe pulegium) was fresh mint. Mint appears to have played a symbolic role in Eleusinian myth; being Hades' concubine, Mint was "dismembered by the jealous wife Persephone." See Wasson, "The Road to Eleusis", 111. The end.

Shown below, Dr. Shulgin in "Entheogen Review" describes how harmaline gains 2 hydrogen atoms from Vitamin C doner :shock: (same way Santo Daime brew their Ayahuasca for long periods) transforming all the harmaline in their brews into the stimulating, euphoric & colorfully visual anti-serotonin alkaloid tetrahydroharmine, via an Alchemy process. In a similar way LSH & LSA in the thread's recipe brew are transforming to their stimulating doubly anti-serotonin cousins 1-acetaldehyde LSH & 1-acetaldehyde LSA.

Courtesy, the Ultraviolet Catastrophe

 

[tregar]

The likely range in any mg species may fall between .005% and .079% total indole alkaloids in different batches of seeds. Freshly harvested seeds are best.

From the 2016 Polish morning glory study:

We found 1.71 LSH (lysergic acid hydroxyethylamide) from seeds bought from growers on-line vs 0.54 LSH (compound to IS ratio) from retail rack seeds found in the stores. 3x higher levels of LSH in seeds direct from growers. LSH is a labile compound, and therefore the variances in its concentration may be due to different age and storage conditions of the seeds rather than difference in plant metabolism.

Based on my dream experiences with FRESHLY harvested seeds right off the vine in the fall, the LSH compound to IS ratio is likely as high as 3.00, even higher then seeds bought from growers on-line, likely due to being picked super fresh & ever so slightly un-ripe (still black & hard though), having been fed miracle grow once a month. The seeds picked fresh are extremely potent based on my several dreams, and it is best to vacuum pack and freeze all the extra seeds picked right away so they will keep their super high potency indefinately.

Interesting thread: Unripe morning glory seeds (in the unripe seeds LSH:LSA certainly would be much more on the LSH side, effects very strong): Un-ripe Morning glory seeds - LSD, LSA, LSH - Welcome to the DMT-Nexus

Erowid report:

The unripened seed pods of the Morning Glory reveal a white, much larger, soft seed with some green in the middle of the kernel. I have found that this state of the seeds is more than twice as potent as the black dried seeds. 400 dried is similar to a little less than one hit LSD. 400 fresh is like about 2 or three hits.

My current favorite way to grow the Heavenly Blue morning glory (attached pics) is to plant 8 plants in a 17" wide x 15" huge tall beautiful Belize Chata Marsal Clay pot (shown in pic) with a piece of "rolled up welded-wire fence" inside the pot that will unwind automatically and fit the interior of the pot perfectly. I first fill the clay pot up with 3/4 miracle grow potting soil and 1/4 cow manure compost, both found at your local garden store. I mix it all together and add a handful of perlite to help water flow and aeration of oxygen in the soil.

The brand of wire fence is "Red-brand welded wire-fence" and it comes in rolls of 5 foot tall by like 100 foot wide, comes in a roll for only fifty bucks, you just use tin snips to cut off a piece, and then stick it inside your pot. The morning glories will climb the fence and produce thousands of seeds within the abundant number of seed pods formed at the end of the growing season in the fall. You can find the rolls of fence in the garden section at your local big box garden store. They have all different sizes.

The galvanized welded wire fence is so lightweight, you can even stack & wire tie another 5 foot section on top the first 5 foot section, for a total of 10 feet tall in all!

I then put the clay pot on the side of the patio (on top some 1 foot x 1 foot bricks to level it) so that it gets morning sun only, so the plants won't burn. I guarantee this method is cheap, easy, mobile, and allows many plants to grow in one single container with high quality soil, feed it once a month only with 1 tablespoon of miracle grow powder added to 1 gallon watering can with spout, this will keep the foliage down, but the flowers very large, and the lysergic acid amide levels very high. Super potent seeds produced this way at end of fall, which can be vacuum packed and frozen to keep their super high LSH/penniclavine potency indefinately. The teamwork between the high levels of LSH and penniclavine in the seeds is imho what produces the extraordinarily potent entheogenic & very euphoric dreams.

Note: Penniclavine (found in high amounts in the seeds, found to be CNS stimulating, Yui & Takeo) is a metabolite of agroclavine, and is active at the following brain receptor sites: Dopamine D1A, Dopamine D1B, 5-ht2a, Adrenal A2A, Adrenal A2B & Adrenal A2D, in comparison LSD (as far as adrenal sites are concerned) only has activity at A2A, but zero activity at A2B, A2C, and A2D.

 

[downwardsfromzero]

Just addressing this slight tangent:

Shown below, Dr. Shulgin in "Entheogen Review" describes how harmaline gains 2 hydrogen atoms from Vitamin C doner

Attached is my interpretation of the possible redox reaction between harmaline and ascorbic acid to yield THH and dehydroascorbic acid, plus the corresponding reaction between dehydroascorbic acid and harmaline to yield harmine and ascorbic acid. Curly arrows denote movement of electron pairs.

Is it perhaps relevant that these harmaloid molecules have nitrogen atoms capable of reacting with acetaldehyde?
[EDIT: Among all the harmala alkaloids the indole/acetaldehyde adduct is particularly pertinent to THH as that's the one with the most significant serotonin action.]
[EDIT2: In the first diagram of the putative harmaline/ascorbic acid, I realise that the ascorbic acid should be the other way up as a hydride shift is more likely from the 3-position.]

 

[tregar]

Yes, very interesting downwardsfromzero! Yes it appears relevant these harmaloids have nitrogen atoms capable of reacting with acetaldehyde. Thanks for your comments & diagrams above as I brought this up in post #56 to show just how easy it is to adduct acetaldehyde to LSH/LSA at the bottom indole NH group, just as 1992 adducts paper achieved.

Post #56:

The 1992 adducts paper specifically adducts acetaldehyde to indole at the NH group in one experiment using acetaldehyde in ph=4 water solution found to happen over time "with or without the addition of ethanol" (they tried it both ways)...giving excellent yield of new product formed, 60% in 1 hour, and even greater yield in less time when they reduced the amount of acetaldehyde used to only 0.1% acetaldehyde solution! Just like the process I dreamed decades ago several times, to replicate the study as best as possible, letting solution sit in fridge for 3 hours with swirling once per hour.

Study calls for ph=4 water solution, which is what I dreamed...as that is the ph necessary for rapid new product creation yield according to the researchers, yield was slower at higher ph...not to mention acidic conditions are necessary to keep the natural LSH extracted from the seeds from re-arranging (decomposing) to LSA as will happen in neutral water, very fast in alkaline water, or when heated.

Harmaline (C13 H14 N2 O) is an example of a betacarboline (class of indole alkaloid compounds) that when it gains 2 hydrogen molecules on it's indole --> transforms into tetrahydroharmine (C13 H16 N2 O), transforming from "sedating dreamy visual harmaline" to "stimulating & visually bright & colorful tetrahydroharmine". Harmaline does a complete 180 degree transformation with the addition of 2 hydrogen molecules on it's indole --> turning from tranquilizing to energizing.

This may translate over to LSA as well ie "the sedating qualities" :? of LSA into "stimulating qualities" like 1-acetaldehyde LSA and an "even more stimulating & visual" version of LSH --> into 1-acetaldehyde LSH.

Here are two link where Professor8 had success using vitamin C for the Reduction of harmaline to tetrahydroharmine (Reduction means addition of hydrogens). I remember you had also posted at the end of one of these threads downwardsfromzero back in the day.

THH - Harmala Holy Grail - Harmalas - Welcome to the DMT-Nexus

Conversion of Harmine->Harmaline->THH by simple boiling (and storage?) - DMT Discussion - Welcome to the DMT-Nexus

Professor8:

THH has the ability to raise your vibration in a most powerful, yet subtle way. It brings a crystalline prismy texture to spice and adds a super clear watery dimension to Aya, like looking down through 10meters of shimmering Caribbean Sea on clear blue day. It brings a dimension of pure light to the entheogenic experience and encourages entities & intelligences of only the Highest Order. If one is not accustomed to perceiving these experiences with a spiritual perspective most of the nuances & subtleties THH brings on are overlooked and remain unseen and one would better enjoy Harmaline as a house painter chooses a roller over a brush, its about preference & choice.

 

[downwardsfromzero]

Hehe, you've just reminded me - I still have that bottle of rue tea in the fridge. So much to do, so little time...
And you're right, I did suggest that harmala/ascorbate redox idea a couple of years ago already.


Here's something else to put forward:
What would be particularly valuable to confirm is whether or not the reverse conversion of the labile LSH → LSA decomposition can occur in the absence of the plant enzymes - and/or, perhaps, if it can occur in the presence of MG seed material. The plant makes that 1-hydroxyethylamide somehow.

 

[downwardsfromzero]

Post #56:[...]

I'm a teenie bit confused, as this seems to be post #56 in the thread!

I just re-read post #46, though, and that is a lovely story.

Perhaps something escaped me, but why do you persist in posting the picture of "her.10"?

 

[tregar]

tregar said:

Shown below, Dr. Shulgin in "Entheogen Review Journal" describes how harmaline gains 2 hydrogen atoms from Vitamin C doner, turning into tetrahydroharmine.

downwardsfromzero said:

Attached is my interpretation of the possible redox reaction between harmaline and ascorbic acid to yield THH and dehydroascorbic acid, plus the corresponding reaction between dehydroascorbic acid and harmaline to yield harmine and ascorbic acid. Curly arrows denote movement of electron pairs.

Is it perhaps relevant that these harmaloid molecules have nitrogen atoms capable of reacting with acetaldehyde?
[EDIT: Among all the harmala alkaloids the indole/acetaldehyde adduct is particularly pertinent to THH as that's the one with the most significant serotonin action.]

Hehe, you've just reminded me - I still have that bottle of rue tea in the fridge. So much to do, so little time...And you're right, I did suggest that harmala/ascorbate redox idea a couple of years ago already.

Here's something else to put forward: What would be particularly valuable to confirm is whether or not the reverse conversion of the labile LSH → LSA decomposition can occur in the absence of the plant enzymes - and/or, perhaps, if it can occur in the presence of MG seed material. The plant makes that 1-hydroxyethylamide somehow.

I'm a teenie bit confused, as this seems to be post #56 in the thread! I just re-read post #46, though, and that is a lovely story. Perhaps something escaped me, but why do you persist in posting the picture of "her.10"?

Yes it would be great if we could confirm the reverse conversion in the absence of the plant enzymes...yeah the plant does make the 1-hydroxyethylamide somehow. Very interesting to ponder! I only wish Dr. Shulgin were still alive to help answer questions like these. In TIHKAL, Dr. Shulgin also makes the following statement "we badly need more studies on tetrahydroharmine". He found it very interesting (he never got to try it) but much of what he knew about it he learned secondhand from Dr. Naranjo (the two knew each other). THH in Ayahuasca is strongly anti-serotonin, just like the following very strong anti-serotonin agents: 5-meo-dmt, ibogaine, LSD, mescaline, shrooms & bufotenine found in the dmt snuff's in the Amazon which give a 3 hour experience.

Posted "Her" only because she is one of my favorite DJ's at Friskyradio.com. As this is my crazy wacky thread, being an artist, I just wanted to input a little fun. Found the frisky site by accident and have been floored by all the amazing house/tech house/deep house/progressive house, etc. there...they have top 100 charts, mixes you can download and all mixes you can listen to in real time, fast forward thru even -- they are amazing -- would listen to "protonradio.com" for years, but it has gone downhill imho lately, and Friskyradio has saved my ears for eternity. Love the site.

Used to set up red & green 4.9mw robotic laser lights that would scan the dancefloor from left to right and program & run the 1200 watt microprocessor controlled intelligent robotic entertainment lighting luminaire fixtures which were way ahead of their time back in the day at a club in the late 1990's when underground music was everywhere. I was friends with the DJ and would spend countless weekends tripping out and hanging out in the DJ booth, working the lights and watching the women dance below, would borrow the DJ's vast record collections and make my own mixes...and shared them with friends...great times.

3) Intelligent Robotic entertainment lighting Luminaires of the late 1990's/early 2000's, lit up & scanned the dancefloor filled with beautiful dancing women.

 

[downwardsfromzero]

yeah the plant does make the 1-hydroxyethylamide somehow.

I was meditating on this while lying in bed either last night or this morning (time was always a tricky concept for me, antiserotonin or not )
In my view, the most likely biosynthetic route would be via N-lysergylalanine followed by oxidative decarboxylation, diagram attached. I guess we'll have to dig into the scientific literature for this one as well. Perhaps there's an old tracer study knocking around somewhere. Feed radiolabeled alanine to morning glories and see where the radioactivity turns up. Could also be just about feasible with C13 labeling and NMR.

[Thanks for the radio tip, I'm glad I asked now.]

 

[dragonrider]

Isn't it a fungus that colonises the plant, making the LSH?

 

[downwardsfromzero]

Isn't it a fungus that colonises the plant, making the LSH?

An endophytic fungus, yes. It's sort of like a reverse lichen in some ways. I'm not sure the fungus would survive in absence of the plant.

Looking at the biosynthesis of ergot alkaloids in Claviceps, it seems that lysergylalanine is produced from lysergic acid, but LSH maybe follows a different pathway from elymoclavine. This requires some further investigation.

[The wikipedia Ipomoea page is "interesting": Ipomoea - Wikipedia
There seems to be a dash of drug war propaganda going on.]

 

[tregar]

Excellent work downwardsfromzero! Chemical diagramming genius

Some people have been asking me who the girl in post #61 is...she is one of my favorite DJ's at frisky radio.com, Really great mixes over here, my favorite house radio channel...check it out:

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