Author Topic: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid  (Read 741 times)

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #20 on: September 03, 2010, 09:26:18 PM »
so what do guys think would it be possible to ferment lysergic acid amide with yeast and sugar and use the pdc pyruvate decarboxylylase enyzme to make the *active* acetyl aldehyde that conceivably attacks the amide to give lysergic hydroxylethylamide?
analagous to the synthesis of phenylacetylcarbinol?

Naf1

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #21 on: September 04, 2010, 12:52:53 AM »
Sure you can call me Data,

First off, while perusing the bluelight threads I noticed someone mentioned that the biosynthesis for LSH entailed acetaldehyde coming into contact with the ergine produced by the fungus in vivo at some stage and forming an adduct. Which is false as ergine is not produced by the fungus at all, analogous in some aspects to the biosynthesis of THC the labile adduct LSH is actually the only amide formed by the fungus and is cleaved to acetaldehyde and ergine easily upon extraction in aqueous solutions. Ergine not being a direct product of biosynthesis, knowing that not even the organism in question can put the pieces back together. You can start seeing it is not as easy as suggested, the very fact that it is an unstable (labile) adduct means the reaction equilibrium lays far to the side of the reactants acetaldehyde and ergine which are much more stable. The basic amide is actually more sucseptible to Schiff base formation, which may also provide a very active compound looking at its constitution providing it made through the body intact. As
it is very similar cinstitution to LSD, and could possibly provide good potency by virtue of being the same weight with similar spacial configurations ect. As suggested for the compound in the  paper you linked earlier jon.

Ergot alkaloids
IV. Contribution to the biosynthesis of lysergic acid amides

E. Kleinerová and J. Kybal
Folia Microbiologica Volume 18, Number 5, 390-392,
DOI: 10.1007/BF02875934

Analysis of the fermentation medium during the production phase of submerged cultivation of Claviceps paspali and model experiments carried out with an authentic sample of
lysergic acid ?-hydroxy-ethylamide showed that the only native amide produced under the conditions was lysergic acid ?-hydroxyethylamide while the simple amide and isomers
of the two, including the assumed diastereoisomer of lysergic acid ?-hydroxyethylamide, are formed secondarily.

http://www.springerlink.com/content/m111224152044076/

Now if we also look at the paper that was being passed around;


Tryptophan analogues form adducts by cooperative reaction with aldehydes and alcohols or with aldehydes alone: Possible role in ethanol toxicity
JAMES E. AUSTIN AND HEINZ FRAENKEL-CONRAT
Proc. Nati. Acad. Sci. USA Vol. 89, pp. 8439-8442, September 1992 Biochemistry

Quote
The strongly basic primary amino groups of lysine residues, N termini, and amino acids are known to react rapidly with acetaldehyde to produce Schiff bases [R-N=CH(CH3)],
which have been intensely studied and would not be able to interact with alcohols. However, much less is known about the reactions of the secondary ring nitrogens of
tryptophan and histidine with these reagents. The present study deals with the reactions of models for tryptophan lacking its primary amino groups: IAA and indole.

Quote
Data shown are for reactions performed at approximately pH 4, a pH resulting from the acetaldehyde (Table 1; Fig. 1). Aqueous reaction mixtures with pH from 5 to 7.4 and
containing as much as 99.9o water also yielded small amounts of product after a few days.

Note; They used ; 40% water: 40% ethanol: 20% acetaldehyde for 20mg of indole-3-acetic acid. They added 20% to the volume with lab grade acetaldehyde which lowered the pH to 4 upon addition!
Adding more water, to that will slow the reaction down to 3 days with only traces (small amounts of product produced). Lets talk kinetics, "Primary amino groups (-NH2), such as the N-terminal and lysine e-amino groups of proteins, react rapidly with acetaldehyde to form Schiff bases [-N=CH(CH3)], which are unable to react further with alcohols." Compared to; small amounts of product after a few days (and thats still with 20% of the volume of the reaction medium being lab grade acetaldehyde), Acetaldehyde boils at 20*C/68*F which is cooler than usual room temperature, if you have a peppermint oil or schnapps the trivial amounts of acetaldehyde present will be gone after the lid has been taken off for short periods thats if there was any present in your sample to start with after being processed commercially. Answer; the schiff base will form first with any acetaldehyde present, when using schnapps or peppermint oil ect with the carboxamide.

Quote
Acetaldehyde reacts readily under physiological conditions
with the exocyclic amino groups of nucleosides, and this
labile adduct becomes stabilized by condensation with ethanol
(1). We have initiated an investigation to establish
whether the same ternary reaction occurs with protein amino
groups. While the nucleoside reaction was suspected of being
mutagenic, there are grounds to believe that such protein
modifications might contribute to the toxicity of ethanol.

We are not talking about nucleosides! Although interesting as nucleosides go on to produce DNA and RNA after forming nucleotides, so being able to form adducts with aldehydes.
Especially acetaldehyde (the main metabolite of alcohol), becomes clearer as to the damage it can cause via mutagenesis of DNA precursors. But for our studies.....

Quote
Primary amino groups (-NH2), such as the N-terminal and
lysine e-amino groups of proteins, react rapidly with acetaldehyde
to form Schiff bases [-N=CH(CH3)], which are
unable to react further with alcohols. This well-known reaction
has received considerable attention from researchers
studying ethanol-induced hepatic injury and toxicity (2-5) but
is distinct from the cooperative reaction discussed here. Our
research focused instead on the secondary amino groups
(>NH) that are present in proteins in the imidazole group of
histidine, the indole group of tryptophan, and N-terminal
proline. To avoid the formation of multiple products through
Schiff base formation at the primary amino group of free
amino acids, we used N-acetyltryptophan and indole-3-acetic
acid (IAA) as models for tryptophan in proteins.

http://www.pnas.org/content/89/18/8439.short

Tregar threatened to use a pure aldehyde, but that never amounted to anything.....
Maybe a dry alcohol extraction of the LSH will form the corresponding acetal of LSH, and allow extraction as a somewhat stable compound? Any aldehyde maybe forming a schiffs base with ergine resulting in a compound with a very similar constitution to LSD? I do not like the theory that there is an adduct forming on the secondary nitrogen of the indole ring which increases potency, as N-acetyl-LSD for example is a very similar potency to LSD (slightly less potent;  ref1 ) with a very similar experience but can be told apart by the discerning connoisseur(probably because  it is not active until metabolized into LSD where it can bind to the relevant receptor). So the N-acetyl-derivative of ergine should show similar qualities, being not quite as potent as ergine. Also the N-acetyl derivative would require acetic anhydride, the aldehyde would produce  a compound with hydroxyethyl substitution on the indoles cyclic nitrogen.

So in reference again to the paper Jon linked, the LSD like potency comes from substitution on the amide nitrogen. Particularly substitution that allows similar interaction with the
receptor in question as the diethylamide moiety does.

REF1;http://books.google.com.au/books?id=Ec5hNgYWHtkC&pg=RA1-PA67&lpg=RA1-PA67&dq=ald+52+potency&source=bl&ots=BrP33g-v4f&sig=hHRy_2FotSqrBoyWdeiGl4actKA&hl=en&ei=lYiBTMTEEYb8vQOioMm2BA&sa=X&oi=book_result&ct=result&resnum=5&ved=0CCgQ6AEwBA#v=onepage&q=ald%2052%20potency&f=false

I again believe they were simply taking a good batch of ergine, that was possibly extracted better than there previous attempts, for example it is more likely in my opinion the excess R-(–)-carvone that would be present in mint oil could help retain the proper stereochemistry by becoming a chiral auxiliary with the amide possibly via transient Schiff base formation which could then make it through extraction without significant hydrolysis of the amide to lysergic acid, or any epimerization to either C-5 or C-8 as the R-(-)-carvone could 'hold' the ergine in the right configuration via steric hindrance. This could easily be tested by doing two extractions, one with R-(-)-carvone in mint oil and one with S-(+)-carvone from caraway seed oil (the caraway should force epimerization to the wrong isomer and be inactive if that is correct). And as such you could theoretically end up with three times as much(well three times the potency of the finished extract) (+)-d-lysergic acid amide (the active isomer) than a poor extraction. As stated ergine is just as sensitive as LSD to epimerization or hydrolysis, and same as LSD four different isomers can exist and only one active. And epimerization can occur easily in the presence of light!
« Last Edit: September 04, 2010, 01:12:22 AM by Naf1 »

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #22 on: September 04, 2010, 03:53:20 AM »
ok you cleared it up for me a bit.
 think the peppermint oil has some merit because there are so many amides that adduct (aldol style) and can form enols which could add to the amide

naf check this paper out it shows both radiolableled incoporpation of pryvate and alalinine into lysergic acid carbinolamade

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1178946/pdf/biochemj00680-0049.pdf


ait would to be snapps or some kind of wine because snapps has 1/2% ACO
wine does to the sherrys and the ph is 4 in wines so that may be better  
 
« Last Edit: Today at 11:32:38 PM by jon »  
 

but i think as you suggested there is something to that peppermint oil becuase it contains so many different aldheydes that can form very stable adducts and retain increased psychoactivity.


http://en.wikipedia.org/wiki/Menthone

what's interesting is it's tautomer i think the sterochemistry inverts when the enol attacks the amide

« Last Edit: September 04, 2010, 06:20:31 PM by jon »

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #23 on: September 04, 2010, 10:59:19 PM »
that link and this:
 show that it is possible to ferment lysergic acid amide into lysergic acid hydroxyethyl or methyl carbinol amide


Quote:
Chapter 17 THE BLOOD OF CHRIST

Todd knelt down, holding an ornately decorated gold chalice. A magnificent piece to behold, exquisite. It pulsated with energy, spirituality. "Sherom Teleqot Masecot," he began his prayers in ancient Chaldean, and then moved on to a higher prayer. "Ebatone Neahmeh Nohhoaayow..." the language of the gods. Reverent peacefulness engulfed him as the words came forth. He turned to face me and drank several large gulps. Then bowed his head in silence as he passed me the chalice.

"What is it?" I was totally caught by surprise; we had not planned on tripping for awhile. Things had been far too crazy lately.

"It's ancient wine. Just try a sip."

"I don't know..." I didn't want to have a repeat of my DMT experience. My mind wasn't as prepared as it should be prior to a journey. Also, I had never seen him this spiritual before a trip. He never prayed or used a chalice any other time. Usually he would non-ceremonially weigh out the doses on his lab scale, and then simply pass them out. No ceremony, no prayers. Why the sudden change?

"Just try a small sip. It is time for you to be initiated into the order, you're ready. But I would kneel and say a prayer first if I was you. This one must be taken very seriously." His head bowed slightly but he still kept eye contact.

I was curious so I knelt down, even though my instincts were telling me not to. What order? The brotherhood maybe? And what was in the chalice? It couldn't really be ancient wine, could it? I examined the liquid; it looked and smelled just like red wine. Why not? I cautiously drank a small sip. It was thinner than normal wine and had a woody taste. The most interesting part was the way it tingled as it went down. A warming sensation filled my throat and stomach. "Okay I drank some, now what is it?"

"It's Ergot wine." He smiled slyly, knowing he had gotten one over on me.

"ERGOT WINE! Oh my God!" I was in shock. "Ergot can kill people. I wouldn't have taken it if I would have known what it was. It's St. Anthony's fire! It can make you lose body parts if you touch it! Oh, my God!" My head was spinning. How could he have not warned me?

"I knew you would react like this, that's why I just told you to drink it. You get so afraid sometimes. There is no need to be; you are safe." A slight giggle escaped from his lungs.

"Are you sure it's safe? Where did you get it?" My heart was racing.

"I made it when I was younger. I did an alcohol wash of the ergot fungus with the wine. Then I corked the bottles up and stored them. The ergot fungus will feed on the sugars in the wine, giving it the woody taste. I let them age for about ten years. It is best to wait a little longer, but I felt it was an appropriate time to open one anyway. Every year it ages, it will become a little less potent and easier to control the dose."

"How do you know what a safe dose is?" I was skeptical.

"Ergot is a fungus and a precursor for LSD. Ergot is interesting because we really don't know what happens to the alkaloid concentration over time. It moves around, changes. So the dose is guesswork."

"Isn't Ergot what Socrates used to take at Eleusis?" I thought it was kind of cool to be taking something that the founders of our democracy used to take, but that our current democracy has made illegal.

"Yes, except for he did a water infusion of the ergot, instead of alcohol."

"I can feel it already." I took a deep breathe but couldn't ease my anxiety. "My chest feels tight and my heart is racing." My heart had never beaten that fast. "My hands feel like they're going numb. Are you sure I am going to be okay?" As I lay back onto the floor, to relax my chest became tighter, heavy. I started coughing and gasping for air. Time passed, I don't know how much.

"Here take a Valium. You will be alright, just breath sweety." He handed me the pill. Then picked up the chalice again and kneeled down beside me. He took several large gulps. After it was empty, he turned it upside down to show me that there was*n't any left. "See it's safe. You only drank a sip! Look how much I took!"

"But you can handle a lot more than me; you are three times my size!" I weighed about 110 pounds and stood about 5'8".

Todd on the other hand was a giant at 6'5", weighing somewhere around 275 pounds.

"Come on, let's go lay down on the bed where it is more comfortable." He reached down and grabbed my hand, helping me up off the floor.

The visuals were really starting to kick in now. They were thick and heavy like my breathe. Dark colors, red, purple, and blue. They overtook me; I could no long see my hand when I held it up in front of my face. A different world existed inside of me. A liquid oceanic playground for the mind. Would I come back from this space? Spiraling thoughts that made no sense. Fear of the unknown. Would I be okay?

My chest still felt heavy but I sat upright which seemed to make it a little better. My heart started to throb slightly. Every few breathes, I felt a sharp twinge along with the throb. Was the ergot causing the chest pain or was I? Was I having an anxiety attack? How could I tell the difference between a real pain and one that I manifested with my mind?

Instinctually, I started to chant my calming mantra, "Telelelelah-luu Letetwah," over and over again. I rocked with the words. "Telelelelah-luu Letetwah." I held my hands up, palms facing each other in prayer. The L's rolled off my tongue and took on new depth. They sounded like the echo of a thousand birds flapping their wings in the air. The mantra held me and kept me safe, like when a mother holds a child. I was going home to safe territory.

I began to sing songs from my soul, rooted deep within the divine. The songs carried me away with them, teaching me about the universe. At one point I saw the double-helixes of DNA swirling out of my mouth along with the words. Language gave birth to being. That's how I interpreted it anyway. Time was dilating. How long had I been floating on the breath of the universe:

Todd came into the room as I was floating back. "Oh, don't stop sweety. It's beautiful."

I was unsure about singing in front of him, so I backed off a bit. I chanted for a while, trying not to make a fool out of myself. I had to sound like a crazed lunatic, singing gibberish! Every now and then I would look over at him trying to gauge his reaction. He was sitting up, facing me, and getting very into it. His reaction was similar to Half-pints reaction. They were actually enjoying it! When I would stop he would look up disappointed, and think 'start again or 'keep going'. This went on for a while as time slowed.

I started to see holographic symbols, floating in a circle around Todd's head. I had never seen symbols before in a trip. They were translucent almost like glass. Empty space had taken on a form. They constantly rotated, allowing me to see all of their sides. A few of them looked like symbols from the zodiac. Others looked like Sanskrit, or Arabic. Some I have nothing to compare them to. Where did they come from? What did they mean?

Events started to become circular. "I feel like am singing, seeing, and going to the same places over and over again."

"Oh, you're stuck in the loop! It will just keep going, and eventually you'll come out of it." He lay back and closed his eyes.

Around and around I went, time was a circle.

Over and over and over again. Over and over and over again. Over and over and over again. Over and over and over again. Over and over and over again. Over and over and over again.

Finally I popped out the other side. It felt like eons had passed. I lay down beside Todd, cuddling up close to him. He and I were one, one body, one mind. We no longer needed to speak; linguistic devices were a hindrance to us now. We knew each others thoughts as we thought them. We could feel the depth of each other's love. It is an incredible gift from the universe to feel existence with no boundaries or doubts. One soul, at home once again.

We felt as if we knew everything, all the knowledge of the universe was at our fingertips. We were at the top of the cosmos, the simultaneous beginning and end, the eternal godhead. We could see in all directions at once.

My future and past were connected to my dreams. I started having unusual dreams around the age of eight. These dreams would reveal a sequence of events in my future. They were easy to distinguish from normal dreams because they had a different texture. More real. However, I never could tell when in the future they would occur. It could be in one month or two years. Whenever the event sequence did happen though, it felt like a deshavoo. I could see now that this phenomenon was me remembering who I am. Me remembering who and what we all are, divine co-creators.

Then the loop happened again. Around and around and around I went. Over and over and over again. Over and over and over again. Over and over and over again.

Again I came out the other side. This little voice in the back of my head, kept saying "your heart isn't beating right." It was strange. I felt as if my heart would sort of stop and I would roll out, far out into the ocean of the divine. Then I would feel/hear a loud bang and it would start beating again, really fast this time. I would in turn surf back in on the same wave that took me out. This whole sensation happened several times. I rolled in and out with the waves of universal consciousness.

It turns out that Todd actually was beating on my chest. But he didn't tell me about it until I came down. I guess my heart really was stopping, or at least slowing down! I think this is the closest I have ever been to death. There was safety in death, total security. Death is nothing more than a shift of cosmic life energy. Fear filled me and then I would let go, sort of release myself to it. My new/old form, God, overtook me. Love and happiness held me tight. It is almost like a caterpillar hatching out of its cocoon and turning into a butterfly.

"Here sweety, chew this up. It's another Valium. Your heart is beating way to fast. You need to calm down. Try to take deep breathes."

"Okay." I couldn't really talk; I was too high. I tried to breath, deep and slow. It seemed to help a little. I was afraid of overdosing. "It feels like my heart is stopping."

"You're okay, just breath. And drink some of this juice to keep your blood sugar up." He handed me a glass and watched to make sure I didn't drop it.

I drank some of the juice and cuddled up next to him again. How long had we been tripping for? I felt like I was ancient, floating on the cosmic time/space folds. Time and space are illusions, only here for our amusement. At the base of all being we are all one evolving consciousness. And we are all incarnations of that same self-reflecting divinity.

Out of all my journeys, ergot was my most difficult. Conversely, it was my most productive and therefore my best. I had had experiences before that seemed like near death. This time I really felt like I died. When Todd was pounding on my chest, it really felt like my heart was stopping. Despite the fear that it aroused in me, it brought me a sense of calmness. I know what death feels like! It isn't bad at all!

The chalice and prayers peeked my curiousity. Why had he done it this time and no others? What was the meaning of it all? He was so careful with his words, his humble demeanor, and even how he held the chalice as he drank. I had seen communion in church before and knew  
« Last Edit: September 04, 2010, 11:29:53 PM by jon »

Naf1

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #24 on: September 05, 2010, 12:09:57 AM »
Quote
think the peppermint oil has some merit because there are so many amides that adduct (aldol style) and can form enols which could add to the amide

Not enol, which is an ene-ol  ene = alkene, double bond and ol = alcohol, so alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. We need an enolate anion to form to proceed via aldol mechanism, which needs a base. How many enolates present in peppermint oil? can you say Schiff? (gazoontite) Also as stated acetaldehyde will leave quickly at room temperature in an open vessel, so if you have small amounts to start with....

Also with that paper you linked above, note they are adding radiolabelled amino acids to a fermentation medium containing c. paspali, in attempts to work out the biosynthetic pathway of LSH they are not incorporating amino acids into the molecule after it has been made. They are adding amino acids which are probably cleaved to pyruvate, which the fungus builds said compounds with and the hydroxyethyl substituent still exists without acetaldehyde hence it is formed via a different route(where the activation energy for the reaction is much lower, than trying direct addition of stable acetaldehyde with relatively stable ergine and hoping to produce unstable LSH.) .

Quote
The experimental conditions of alkaloid cleavage
described by Arcamone et al. (1961) lead to epimerization
at C-8, which not only decreases the yield of lysergamide
but also complicates its purification. Investigation of
alternative degradative procedures revealed that, on
heating the alkaloid in xylene both acetaldehyde and
lysergamide, free from isolysergamide, are obtained in
high yield. A possible mechanism for this reaction is
indicated in Scheme 1.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1178946/pdf/biochemj00680-0049.pdf

From the paper you linked, a great example of what I was talking about!

Quote
that link and this:
 show that it is possible to ferment lysergic acid amide into lysergic acid hydroxyethyl or methyl carbinol amide

That was very subjective could have been a strong batch of ergine.....

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #25 on: September 05, 2010, 12:46:58 AM »
naybe unstable at 100C but more stable then the reactants at stp.
sherry wines have .5% acetaldehyde and it does'nt boil out like co2 it's quite soluble in alcohol.
ergine is'nt as visual as that.

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #26 on: September 06, 2010, 11:59:49 PM »
confirmed it works.
used sherry cooking wine bleh!

soaked ground up ghanan seed (ergine content .1%)
vacum filtered and rinsed with red wine.
20 grams yeilded about 80 ml after all the washing took about 10 ml along with communion and experienced lsd like distorings of light and color some synathesia felt stimulated not relaxed but no lsd like edge i lasted 6 hours.
now we know how to make commumion wine for our own church i'll declare myself pope and force everyone who partakes to vow to poverty and give all thier world possesions the the church (me)
i think it will work.

« Last Edit: September 07, 2010, 12:03:13 AM by jon »

Vesp

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #27 on: September 07, 2010, 12:17:35 AM »
What is ghanan seed? that is, the genus and species?
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jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #28 on: September 07, 2010, 02:26:02 AM »
ghanan seeds on average contain .1% ergine so i cosumed maybe 2 mg of hydroxymethylcarbinolamide which half could have been alpha 8 ergine.
so the actives were ~1mg. whereas, ergine is active at 10 mg this felt like 70-80 mcg of lsd with some differences.
 it did'nt have the sharp anxiety edge of an lsd comeon.
i came on very subtilely and the effects were color intensification, "flickering" the lsd strobe, everything took some kind of vibrating resonance
it came on quick too like 20-30 minutes but subtle not powerful.
taking 4-500 mcg of strychinine would add to it as a more lsd like trip and improve it's qualities some.
it used to be standard 50 mcg's and 500 mcg strychnine you could all feel it in the back too the tension.
i think strychinine goes very well with commercial lsd because low doses of it improve sesnory expirience, color intesification, the "good anxiety"energy, etc.
it was arygeria nervosa the big beige colored seeds.
only weaker than the madagascar strain which i hear is the best.
also i think the enzymes in wine containing <l5% alcohol speed up the reaction, also tried it with fortified beer.
and it worked like a charm too.
one of the weirdest things was a sound comibined with light as intense as a camera flash

it was an interesting experience, there was no foggines the next day either, "natural lsd" is a perfect adjective.
« Last Edit: September 07, 2010, 04:41:04 AM by jon »

tregar

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #29 on: September 07, 2010, 04:31:56 PM »
You gotta admit the ergot wine stories are very intriguing. The story from Todd and Krystal above is a real trip. Fermentation and what not, there's some very interesting things going on. Thanks for the report as well Jon.

Just wanted to say excellent thread everyone...I knew about the bluelight study, and glad the study is being analyzed by the forum members here and all the contributions made in this thread. I'm going to go back and read this thread from from beginning to end.

Why all of the psychedelic researchers of the past have overlooked the fact that "mint" was an ingredient in the kykeon brew is beyond me. Heck, no one has even bothered to drink a cold water extraction of infected barley, however a guy on the entheogen.com forum did just that a couple years ago and tripped his brains out, seeing full on open-eyed hallucinations. Jonathan Ott was going to do just that, but chickened out at the very last minute.

This author below from the entheogen.com forum did the ICE cold CWE of infected wild barley (with some wheat/rye mixed in it?) found in the pacific northwest under the mountain known as Tahoma. Author claims 1.75 grams of claviceps purpurea was ground up under low light conditions (starlight), soaked for 3.5 hours in ICE cold water in the fridge, filtered through a very thin paper filter, with the ending 6 oz hypothetically consumed. I have more to say on this at the end of this thread reply by giving the experimental results of Peter Webster's experiments on converting ergotamine, ergotamine as you may recall is the principal toxic ergopeptine alkaloid in ergot that can be converted to ergine (LSA) with basification. Anyhow, Peter converted the contents of his prescription Gynergen tablets, which is 1mg of ergotamine tartrate each, to ergine/iso-ergine (LSA, iso-ergine) in a basified solution, the solution which Peter believes is very psychoactive once it is allowed to form the 3 drug conformations (d-boat LSA, d-chair LSA, and iso-chair LSA) over the course of an hour or more in solution. His Gynergen tablets (consisting of ergotamine) are not psychoactive at all in amounts even up to 5mg he said, but once he dissolved them into a solution basifying them first (using wood ash as the priests may have used), then adding ascorbic acid to make the freebase forms of the 3-conformations of the drug more bio-available in salt form, he experienced definate strong psychoactive effects. His trial consisted of consuming about 1200 micrograms of ergine-isoergine (LSA, iso-LSA) mixture. His experiment in Mexico where he consumed about 10mg of prepared morning glory solution was the equivalent of high dose LSD he stated. He speculates that if he were to consume an even higher dosage of ergotamine in solution (beyond 1200mg of the lsa/iso-lsa mixture) that it might actually approach the level of his past 10mg morning glory solution experience.

Author from entheogen.com forum experience with cold water extraction of 1.75g ergot:
Quote
SOTC describes the experience as being similar to, though visually far more intense then HBWR or MG, Complex geometry overlayed on backgound of colors, constantly changing like a tapistry, intermixed with very bright flashes of light (bubbles) and on ocassions beams of light. He describes the mental effects aside from that, and the auditory perceptions as being more or less lucid, which is what surprised him more than anything. This was barnone the most visual experience of the feline's life, and he had, in the course of wandering fields, consumed hefty dosages of 'godflesh' in times past, one species in particular noted for vivid visions, the feline found this to be far more intense.

I was the one that started the whole mess about the acetaldehyde and lsa stuff...based on a crude interpretation of the study I accidentally found below when cruising the net:

see Adducts_paper attached (which Jon posted in the beginning of this thread)

If you want to see a picture of the lysergic acid hydroxyethylamide molecule just look at the color photo in the middle of the book "LSD, my problem child" by Albert Hofmann. It looks very similar to LAE-32, which the people in a study found to be psychedelic at 1 to 2 mg, and was short lasting. A paragraph about LAE-32 is described in TIHKAL by Shulgin. It was not as strong as LSD, but still somewhat potent for a brief time nonetheless. The study participants still preferred the LSD over the LAE-32, they found LSD to be more therapeutic.

brief summary:
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Reaction of Indole with Acetaldehyde. A 0.2% solution of indole in equal amounts of water, ethanol, and acetaldehyde formed a product with 60% yield after 1 hour of reaction at ambient temperature. Omitting the ethanol (50% acetaldehyde in water mixture) had no effect. Decreasing the concentration of acetaldehyde to 0.1% increased the reaction rate and percent yield of product.

For preparative purposes, a mixture containing 20mg of IAA in 0.5mL of 40% water/40% ethanol/20% acetaldehyde was allowed to react at ambient temperature for 18 hours.

I'm not going to go into the whole adducts thing, as others here have gone into much depth, but will state that it gives a short lasting psychedelic state that does not seem to last as long as the normal morning glory extraction. The preparation in peppermint and everclear causes a state that comes on quick and feels much stronger than a normal preparation, but is too short lasting for me to really enjoy....perhaps taking a larger dose would overcome this. I still prefer the normal shamanic method in cold water without forming adducts or whatever with additional ingredients. But note that I have never taken a big dose of the adduct formed solution. It is definately strong when it comes on within 45 minutes, no messing around, and stays at that level for a couple to a few hours at a low dose...there could be much potential to this with experimentation, if someone were to get the experimental conditions just right. I'm going to have to look into Jon's wine experiments, sounds really good.

Why fresh morning glory extracts seem to work when prepared in a cold water solution and allowed to sit several hours (the same method used by the shamans)...is explained below by Webster...I had also briefly chatted with him on-line a long time ago, and he sent a link to his paper that I have also attached from earthrites. this method (preparation in plain cold water with a dash of d,l tartaric acid powder mixed in to reach a ph of 3 to 4) caused the only two very fantastic psychedelic states that I myself have ever experienced from morning glory seeds, with no nausea. In the distant past, I had done in dreams literally hundreds of acid hits at all different doses, and I found the short lasting state induced by the seed solution to be compatible in many similar ways.

In the first experience, I took about 6 grams of fresh morning glory seeds that I bought from a vendor on-line, crushed them inbetween two paper plates on a concrete floor with a hammer, then took the dust and added it to a coffee grinder and ground the seeds to a very fine dust, I then poured the dust into two large family sized lipton tea bags and stapled them shut. By the way, this is the same method used by "Hermes" from the old Lycaeum forum, he had lots and lots of very strong psychedelic experiences with this tea bag method, and let us not forget that the Shamans would also hammer the seeds and place them into a loin cloth and soak it in water for a time.

Hermes mentioned that the seeds needed to be less than a year old, and preferably the fresher the better, forget about using old seeds. Hermes used to prepare a lemon juice acidified cold water solution (using the empty tea bag method) of the Martha Stewart labeled heavenly blue morning glory seeds from K-mart. He would put on his headphones, lay back and close his eyes and very detailed visuals would develop that would intensify with the music he heard. He mentioned the music would sound just heavenly and broke out into tears from the experience once it was so beautiful.

I then poked a hole into a lid on a large mason jar and attached the tea bag strings to the hole on the lid and secured the hole with a square of duct tape. I then filled the mason jar with distilled water and a dash of d,l tartaric acid (easy to find on-line, used for wine making) to bring the ph to 3.5 (checked ph with a calibrated electronic ph meter)....then placed the mason jar with the tea bags floating in it in a fridge on a portable battery powered magnetic stirrer and let the water spin in the jar for several hours at high speed, it was all kept dark in the fridge. After several hours, I opened the jar and squeezed any juice out of the tea bags back into the water by pressing against the tea bags and the side of the jars with a large spoon, I then threw the tea bags away, and put the lid back on and allowed the contents of the jar to spin overnight on the magnetic stirrer in the fridge, again entirely dark. I wrapped foil around the jar to ensure that it was light proof when opening and closing the fridge door.

The next day I drank 1/2 of the solution, and then went to a shopping mall with my sp and about 2 to 2.5 hours after I had drank the solution I was feeling a very strong and most enjoyable psychedelic trip from the seeds, note that it does take a couple to several hours before you feel the effects of properly prepared morning glory seeds, the music in all the stores I walked into just sounded sublime, and very much enhanced, I was incredibly euphoric the whole time and could not believe how the music had sounded so much better for hours, the trip began to subside about 3 hours after it began. I also had incredible visual enhancement, it was a most enjoyable psychedelic state. The psychedelic state caused by the seeds is very euphoric and imho it would be very difficult to have a bad time on properly prepared seed solution. It seems to accentuate the positives and doesn't even allow negative mindstates to even begin to form, so in some ways it may be different from typical psychedelics.

This particular positive based psychedelic mind state would be perfect to use in the pavilion where the Eleusis ceremony took place for 2000 years in ancient Greece, in that ceremony it is theorized that inititates all were given a powerful psychedelic brew to drink (prepared by the priest) as there would be hundreds of new "initiates" in the hall taking a psychedelic for the very first time...if you think about it, you would want them to take a psychedelic which is low on the spectrum of causing "freak outs", you wouldn't want a person in there having a bad trip and freaking all the others out would you? A cold water extraction prepared from the nearby growing infected paspali grass would have the same alkaloid profile as morning glory seeds. Or, doing a cold water extraction on claviceps paspali from the infected barley grains growing would cause only the good water soluble psychedelic alkaloids to absorb into the water while leaving the poisonous non-water solubles behind. It is known that Plato attended the ceremony and when he had visions there, it is postulated that is how he came about with the Perennial Philosophy. You can read more about the Perennial philosophy from Aldous Huxley. Lots of well known famous Greek intellectuals attended the Ceremony at Eleusis and drank the brew. We know from the written hymns that the brew was composed of a solution of barley grains and mint. You never know, but some kind of maoi acting plant may have been added as well to further strengthen the psychedelic effects. The brew was kept a secret by the priest who handed it down to the priest in charge for some 2000 years. At one time, the sacred brew was leaked to a handful of Greek people who used it at a party and in doing so, they "profaned" the sacred brew. Death was the punishment for consuming the brew outside the ceremony or even talking about it could lead to a death sentence.

Report from a friend who is very experienced with ayahuasca:
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Just wanted to thank you for the Morning Glory thread. Yesterday I had my first experience with this Green Elder with a cold water extraction in phosphoric acid, pH 3. I shook my little muslin spice bag 4 times in the hour, filtered crudely through coffee filters and Kleenex, then put it back in the fridge until the next day. I used 8g. of "Ipomoea tricolor" from ******** **** , and the experience was wonderful. I had 1g. of raw rue seed 2 hours before, taken in yogurt so I wouldn't have to chew them or taste them. The experience lasted from 11am to 6pm, with a distinct afterglow period where I was totally baseline, but I was still full of energy. I wish I had explored CEV's more, but I got some impressive visions that were totally unlike anything I'd seen in Ayahuasca , and more like the paintings of Dali or Magritte (for example, a pyramid with an eye in the center floating on clouds was something I saw).

Unlike Ayahuasca , this WAS NOT SCARY at all and felt really nice in the body, and was easy on the mind.

Please read how you've inspired me! See the Plant World Forum: Yopo/Vilca as Medicinal Herbs. The cold water extraction seems to be generalizable to seeds with nasty seed oils, such as yopo and Syrian rue.

When I made Syrian rue with cold water methods, the liquid (which usually makes me retch just smelling or tasting it) comes out clear of any rue smell or taste, which all stays in the bag. I used a muslin spiced bag with a coffee filter folded up inside it containing the ground seeds.

Not only has the LSA thread revolutionized LSA prep, but also can make Syrian rue and yopo more user friendly...

One hour, shaken every 15 minutes, filtered with plain old coffee filters and Kleenex. Kept in the fridge until the next day. He smoked mapacho and caapi leaves from time to time and found the experience *very* interesting, lasting for 6 hours. Eyes closed visions (not just visuals, but fully-formed visions) were nothing like he had ever seen before with Ayahuasca -- totally different. He saw lots of the "eye" motif, with an eye in a pyramid against a brilliant blue sky and floating on clouds. He also had a lucid dream in which a phosphorescent snake encouraged him to try to follow him through a portal in the corner of his bedroom, but the snake slithered through, while he, the lucid dreamer, couldn't figure out how to perform the same trick. The 6-hour period was followed by another 5 of afterglow, and it continued, he said, into the next day very strongly.

He had no nausea of any kind, and no sedation from Heavenly Blues (Ipomoea triclor). He told me it felt very much like being sped up on lots of caffeine or Kratom . The day was very full and active, as opposed to meditative and serene at home, as with aya. He went all over town, cleaned house, did things he had postponed for months at home in the way of repairs and cleaning...l

A word of warning! I only drank 1/3 of the portion and got effects similar to yours one hour later. He thought it was a dud, and went to the store, and it hit him while he was standing in the checkout line of the supermarket. He said the body effects made it difficult not to just drop everything and start dancing and singing! He had another 1/3 two hours later, and the last 1/3 two hours after that. The visions came more or less later in the experience, but the body effects came early on. Effects were not sedating at any time. He was relaxed and super energetic.

It's hard to just lie down and achieve CEV's because it's difficult to remain still and calm in the beginning. CEV-observation is more conducive towards the end of the experience, he said, unless you especially adept at sitting or lying still long enough to trance into the CEV state amidst the excitement, which makes one want to dance around and sing!
Imho, the combination of properly prepared morning glory extracts combined with caapi/harmine hcl/thh should seriously be explored more, this is the way to go.

Hermes:
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Depending on seed quality, you should get some weak to decent effects from 8 grams, like mild reality bending, marked enhancement of aesthetic perception, insights, weak open eye visuals, moderate but subtle closed eye visuals (especially with music). I find that more satisfactory results are achieved with more seeds, like 14 grams or more. This much is needed to enter truly psychedelic territory. I wouldn't recommend this much if you haven't tried lower doses with the same seeds and method, however. LSA can cause significant vasoconstriction, causing restricted blood circulation to extremities. Make sure that your toes don't get numb or tingly on 8 or so grams first. And don't mix with other vasoconstrictives, like ephedrine or caffiene.

I usually just measure by Burpee bags. These are 1.8 grams each. I have used anything ranging from 3 to 12 of these. Strangely, the 12 bag trip was relatively weak. They must have been some old seeds. My strongest experience ever with MG seeds was with the Martha Stewart brand from K-Mart.

I had strong 4D lattice-like open eye visuals and warping and melting of furniture with only 400 seeds. There are about 32-36 seeds to a gram. The Martha Stewarts are more expensive than the Burpees. They are like $1.30 a bag or something close to that for a 1.2 gram bag. The Burpees are something like $0.88 a bag and each bag has 1.8 grams. That's $2.05 a gram for Martha Stewart seeds and $0.92 a gram for Burpee seeds. It seems to be a trade off.

My favorite way to go about this is to first wash the whole seeds in a bowl with a little water and a very small amount of liquid handsoap. I slosh them around and rub them a bit in the soapy water (not too long--could reduce potency). I then rinse them good with cold water in one of those screen vegetable strainers. This is intended to wash off any fungicide or other adulterants. I then dry the seeds well with paper towels. Then I grind the seeds in coffee grinder to a fairly fine consistency, but not to the point of being powder. The hulls should remain somewhat course, while the lighter colored inner stuff is pretty much powder. I then put this stuff into one or several empty tea bags. Don't overfill one. If the bags are small, use several. Next, put the bag(s) into a full glass of cold distilled water and use a spoon to press on them and make sure they are well-saturated with water. Let sit for 10 minutes in a cool dark place. Use spoon to squeeze and agitate the bag against side of glass some more to get more stuff out. Don't press too hard or you will break the bag and get seed mush into the water, which is undesireable. Leave for 10 more minutes. Squeeze again. Leave for 10 minutes. Squeeze. Remove bags after squeezing most of the water from them into the glass. You can suck on the bags if you want to get more stuff. I don't generally do this. Discard bags. Drink water. Get yourself into the mood with some good music and wait for effects. You might want to take a little ginger if you are worried about nausea. Usually I don't get any, but sometimes there is a little, probably partly from pre-trip anticipation anxiety.

For me, they seem to be similar in both duration and effect. The only real difference I notice is that LSA is a little more lethargic, at least in the early phase of the trip. LSD is a bit more speedy. With LSA, I am much more able to lay around or focus on one task like painting. I also noticed that it is possible to go to sleep while still tripping on LSA, which is impossible with LSD. I slept once on LSA and had incredibly visual dreams! These were the most beautiful visuals I have ever seen under any circumstances. I dreamt that I was being shown the entire unfoldment of the universe, with the evolution of man, and it was all represented on this incredible spinning wheel. It was indescribable. I want to go to sleep on LSA again and attempt to have a lucid dream. That would be nothing short of amazing!

Anyway, my LSA trips last 10-12 hours or so, with slight effects that linger for another 24 hours or so. And I usually feel something like an afterglow for a week or so afterwards. During this period, I am much more creative than usual and happier too. I also notice that colors look slightly more pronounced for a week or so in a very LSA specific way. I never noticed this on LSD.

Comfortably_Numb asked where I buy my seeds from. K-mart and Wal Mart have been typical sources. The most powerful brand of seeds that I ever tried were the Martha Stewart brand from K-Mart (I had strong effects, with good open eye visuals, on only 300 seeds! I used a water extraction with some added lemon juice on this occasion. I do not know if this helped). Burpee seeds work well too, but didn't seem as potent as the Martha Stewart brand. The Burpee seeds are less expensive. I have never tried bulk seeds. As far as I know, the ones that I tried didn't have any pesticides. Nothing was mentioned on the package that would indicate this. I did always wash the seeds just in case, however.

If anyone tries this, inform us about the results. Tell me if the tea-bag method worked for you.

If the taste bothers you, you can add something to the water, but I wouldn't guarantee that it will not reduce potency. The taste isn't that bad. Just drink it fast.

What is it with eyes anyhow? Does anyone else see eyes filling their CEVs or OEVs? I see eyes, eyes in triangles, wings, eyes in triangles with wings, cherubim, seraphim, pyramids, pyramids with wings and eyes and caducea, utchats, lions, owls, cobras, and generally anything related to the Western Mystery Tradition. The first great "vision" I saw was while on Morning Glories and listening to Mozart's Requiem. When the Lacrimosa began, I saw incredible Angelic forms and felt this incredible awe and love for existence. I think I stole a glimpse of the Beautific Vision itself. I cried and sobbed for hours, in pure ecstacy. I knew, however, that I only encountered the very periphery of the "Inner Kingdom," since the cherubs revealed neither their hands nor their faces, just three pairs of wings. I had never seen them before this, in religious paintings or otherwise. I had not read the bible or anything before this had happened. Afterwards, upon doing a bit of research, I saw that they are commonly encountered by mystics of various cultures, especially in the West. In particular, I saw them in a book on Islamic architecture, painted on the ceiling of a Mosque. These looked incredibly similar to those I saw, only very washed out and a far cry from the real thing. These things just can't be painted. They have to be experienced.

So, what sort of comparison would you now make between LSD and LSA? In my experience, they are difficult to tell apart. The taste in my mouth and the physical energy level are the only things that seem different. LSD causes a "taste hallucination" that resembles rusty iron, while LSA causes a taste somewhat like bee pollen. Also, LSA has a much more lethargic feel, at least in the early portion of the trip. Other than that, they are the same for me. Really, it seems like LSA is a little more visual for me for a given amount of mind alteration.

It always seems to me that with LSA, the highly visual phase is late in the session, long after body phase and introspective phase. I wonder if the occipital lobe (visual cortex if I am not mistaken) of the brain is one of the last regions of the brain through which the blood passes.

in fact, I have experimented with this combo (cold tea from 800 MG seeds + 50mg ephedrine) before and it made my extremites go very nearly totally numb. I had lots of intense tingling in my hands and feet, as if they had gone to sleep. During part of the experience, I actually had pretty significant pain in the veins in my hands. Besides, I noticed that for some strange reason, the ephedrine seemed to diminish the desired effects of the LSA. Really, ephedrine is a nasty drug no matter how you use it.

It seems to me that you will get less lethargy and nausea if you perform the water extraction and get a purer product. Those nasty nonpolar compounds seem to contribute a great deal to the lethargy, nausea, headache, tunnel-vision, etc. With a good water extraction, I get none of that.

As for visuals, I can't even begin to describe most of them. And my memory of them is likely not very accurate since it has been a few years. I tend to translate the experiences into a form that I can remember, as the real thing cannot be represented with sober thought. The visuals are beyond representation for the most part. All that I can give you are general themes.

I tended to see what seemed to be a four-dimensional lattice structure that appeared to be "behind" things, as if everyday reality were just a bright projection that obscured the real luminous hyperspatial structure behind it. Things tended to have eyes and feathers on them. Often what dominated the visuals was a winged eye in the center of my vision. Often, instead of wings, the eye was surrounded by colorful mandalic geometric forms or organic patterns like vegetation. But it was very common to see a serene eye in the focal point of my visual field with all sorts of fantastic forms radiating from it.

I also saw lots of angelic forms and gothic celestial architecture, particularly when listening to Mozart's Requiem on god headphones while tripping with my eyes closed.

I saw a vision of a pyramid, floating in the air, with the Eye of Ra on it, and with a sword piercing it from beneath. The sword was entwined with two cobras, as in a caduceus. And around this pyramid atop a snake entwined sword were four large luminous feathered wings, each one a distance out from each corner of the pyramid, coming from beneath the whole figure and reaching above it, almost as though the wings were guarding it. This whole figure has obvious occult meaning. I just wonder why the images are so typically Egyptian in character, at least for me.

I have found many things similar to my visions in the art of Alex Grey. The eyes all over things, the energy lattices, and so on, are all very similar to what I have seen. Have you seen Grey's painting called "Dying" ? That eye-filled vortex pattern is something that I have seen. It seemed to me at least while I was tripping that the winged eye that dominated things was my soul, maybe something like the "ba" of the Egyptians. I once saw it rising up to meet the light, as if I was underwater seeing the sun above the surface and my soul was flying up to join the sun.

I also once saw a great field of eggs, above which was a giant watchful eye, surveying the field of eggs. Some of the eggs were cracking, and the cracks were lined with peering eyes. Every exposed opening was filled with eyes. And I could see myself as one of these cracking eggs.

Another time, I saw myself as a red dragon, what seemed to be my true form in this hyperspace, flying up, seeking the Source.

All of the visuals have a quality that I can't describe well, verbally or with illustrations. Everything in that interior realm seems made of subtle energy and is luminous. It also often seems to have more than three spatial dimensions. It usually has a very detailed and very ordered structure, very mathematical, but arranged with a kind of structural harmony that is never seen in the physical world. The structures are beautiful beyond description. It is like visual music, with the sizes and positions shapes seemingly related by some kind of precise law that binds everything together in the most perfect harmony. The flawed forms of our world compared to those perfectly harmonious ones of that world are like the cacophany of a cocktail party compared to a symphony by Beethoven. Visual order like that has never been seen in physical form, in the natural world or in art. Fractal geometry sometimes resembles it, but still falls very short.

Peter Webster (from the book Sacred Mushrooms of the Goddess):
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So, we have the possibility that ergine (LSA) can be in one of three states: it can be ergine in the chair or boat conformations, or it can be isoergine in the chair conformations. And in many chemical and physical situations, the 3 forms are constantly converting themselves from one to the others, and achieving a typical equilibrium distribution. We therefore must consider that in an ergot preparation made according to our suggested method, and in morning glory seeds as prepared by Mesoamerican shamans, we are not dealing with pure chemically synthesized ergine or pure isoergine. Both pure compounds have been tested and found wanting by some investigators, including Dr. Hofmann.

The equilibrium mixture of ergine and isoergine may actually be the true psychoactive substance of the kykeon, and of ololiuhqui as well. Since ergine spontaneously changes to isoergine when in solution, over a period of perhaps several hours, any process to partially hydroluze the alkaloids of ergot such as our proposed recipe -- or even the Aztec ahaman's procedure for extracting ololiuhqui--should result in a mixture of the 3 states as represented here, (see photo of chemistry).
Chemist Peter Webster saids: Ingesting either ergine or isoergine as a pure compound, however, may not result in the equilibrium mixture arriving at brain receptors.

You know how with *dma, you don't feel "the magic" unless both the S and L isomer are present together and ingested at the same time...either one ingested on it's own will not cause the magic according to Shulgin. Even though those are isomers, and we are dealing with conformations here instead with LSA, maybe Peter is on the right track with all this 3 conformation to feel the magic stuff ? who knows.

Peter mentioned that a few milligrams of his MG syrup extract (A/b, A/b extracted?) glowed bright-blue Fluorescence...and was as powerful as high-dose LSD ... his extract producing "one of the most powerful psychedelic experiences I had known" (Sacred Mushrooms of the Goddess, March 2006).

First, he told lots of kids in Mexico where he was staying if they wanted to help him to go gather fresh morning glory seeds off the ground for him, and he would give them like a penny for each one they found, or something like that. He then extracted several kilos of seed using a simple process, purifying an alcoholic extract between organic solvents in the presence of ammonia and aqueous solutions of tartaric acid. After a couple days work, he obtained a nearly colorless syrup that exhibited the bright-blue fluorescence of active lysergic acid compounds.

This is how Peter made his very powerful extract:
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.. The procedure involved extracting finely powdered Heavenly Blue Morning Glories w/ Ethanol. Most ethanol was evaporated off in a rotovap, added a bit more water, basified the messy solution w/ ammonia (to make sure alkaloids weren't in the salt form) & extracted 3x w/ dichloromethane, combined extracts were extracted with w/ water containing 5% tartaric acid. The alkaloidal-tartarate solution was basified w/ ammonia and extracted w/ dichloromethane. Evaporate DCM leaving a light coloured syrup that fluoresced bright blue under blacklight...

Sounds like a double A/B extract.

Here is where Peter's theory (with pictures and chemistry) is located on the 3 conformations formed in liquid solution after the solution (such as cold distilled water, etc.) is allowed to sit or stir for some time:

See pages 24--35 of the earthrite's journal:

"Secret Recipes - Hofmann Symposium, Peter Webster, Ground Breaking Work on The Kykeon Mystery - Edited by Peter Webster and RevMEO"

http://earthrites.org/invisible-college/IC-Beltane07sm.pdf

Peter verified that his early on original wood ash kykeon hypothesis was correct by performing several experiments on his prescription migraine tablets Gynergen (each Gynergen consists of 1mg of ergotamine tartrate) since he did not have ergot available to him. He testified that for migraine relief, one can take even up to 5mg of the ergotamine and it would have no psychoactive effect.  This fact provided a control on his experiments. He performed three trials, using first one ergotamine tablet, then 2 and then 3 tablets. Since ergotamine tartrate-the actual compound in these tablets--is a much larger, and therefore heavier, molecule than ergine (LSA), a simple calculation shows that converting 1mg of ergotamine will ideally yield only a maximum of 4/10ths of a milligram (400 micrograms) of ergine and isoergine in their equilibrium mixture in solution (Peter states that this equilibrium of LSA or ergine to it's 3 drug conformations, d-boat, d-chair, and iso-chair...takes around an hour or more to happen in solution).

In the first trial, he heated 1 tablet containing 1mg of ergotamine with 200mg of hardwood ash (like the priest may have used) in 20ml of vodka in a kitchen double-boiler after 1 hour the alcohol had boiled off. He continued to heat this mixture for 2 more hours at around 50 degree C (122 degree F), then neutralized the mixture with vitamin C (ascorbic acid). Decanting the liquid from the residue of solids left by the wood ash, he then drank the result. A definite, but weak, psychoactive effect was noticed.

He then repeated the experiment with 2 and then 3 migraine tablets, the result was stronger and left no doubt in his mind that the partial hydrolysis process he hypothesized does indeed happen to ergotamine.
There is little reason to believe that if the partial hydrolysis process occurs with the ergotamine in a Gynergen tablet that it would not occur with the ergotamine and other ergopeptines in ergot.

In his experiment, he used vodka as a solvent, since in a Gynergen tablet the ergotamine content exists as tiny crystals and an alcohol-water mixture would enhance the low solubility of these ergotamine crystals.

Neutralising would make the brew more palatable, and in addition augment the solubility of ergine/isoergine (LSA-iso LSA) in body fluids since these alkaloids easily form salts with acids such as ascorbic, tartaric or even hydrochloric. The salts are far more soluble than the freebase alkaloids.

He suggest that in addition, to fully confirm our hypothesis, assayed ergot should be used and chromatographic analysis used to determine the ideal conditions necessary for a complete partial hydrolysis to ergine (LSA), and for the equilibrium with isoergine (iso-LSA) to be established.

In his final tests, he used 3 ergotamine tablets. With 3 tablets, the effect was, of course, even stronger, although at that level it was still not nearly the equivalent of his trial of morning glory extract in Mexico (which he found comparable to high dose LSD). He believes that the dose he used on that trial was much higher, perhaps as much as 10mg, and of course, the ololiuhqui extract contained a minor amount of other, possibly, psychoactive agents.

With 3 converted ergotamine tablets--ideally producing 1200micrograms of ergine-isoergine mixture in solution, he found the effect came on quickly after only 20 minutes. He said the effect, however, was not at all the same as LSD or peyote, he found it was more hypnotic and inward than the typical psychedelic experience.  The ergine - isoergine (lsa, iso-lsa) experience also seemed less dramatic to him, stating that it was more gentle and leads one to recline with eyes closed, whereupon mental processes seem kaleidoscopic and influenced strongly by set and setting.

He speculates that the experience may have well been just the type of drug that would have been suitable to use in a large gathering of persons such as at Eleusis, where most or all participants would have been previously inexperienced with psychedelic drugs.
« Last Edit: September 08, 2010, 02:23:31 AM by tregar »

lugh

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #30 on: September 07, 2010, 08:32:32 PM »
The subject of the shamanistic use of extracts of the seeds of Convolvulaceae was discussed on pages 240-257 of

The Botany and Chemistry of the Hallucinogens

by Richard Schultes and Albert Hoffman


https://www.wetdreams.ws/forum/ftp/lughwd/schultes-hoffmana.zip

 8)
« Last Edit: September 07, 2010, 08:42:05 PM by lugh »
Chemistry is our Covalent Bond

Naf1

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #31 on: September 08, 2010, 01:10:08 AM »
Firstly, awesome to see you here Tregar!

I just have one problem with the quote from P. Webster;

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So, we have the possibility that ergine (LSA) can be in one of three states: it can be ergine in the chair or boat conformations, or it can be isoergine in the chair conformations. And in many chemical and physical situations, the 3 forms are constantly converting themselves from one to the others, and achieving a typical equilibrium distribution. We therefore must consider that in an ergot preparation made according to our suggested method, and in morning glory seeds as prepared by Mesoamerican shamans, we are not dealing with pure chemically synthesized ergine or pure isoergine. Both pure compounds have been tested and found wanting by some investigators, including Dr. Hofmann.

But in fact we have the naturally occurring forms which are C-8 epimers; Ergine (d-lysergic acid amide), Isoergine (d-isolysergic acid amide) then the two possible other isomers which may not be seen in nature but are possible are C-5 epimers; l-lysergic acid amide and l-isolysergic acid amide. I was using the outdated d/l nomenclature, but you can see four different isomers as with lysergic acid;

Looking at the article, he was talking specifically about conformation, saying that Ergine has 4 different diastereoisomers as above but the actual molecule of ergine (8?)-9,10-didehydro-6-methyl-ergoline-8-carboxamide can take up two different conformations either boat or chair conformations on the d-ring both of which can interchange and would have a different activity regarding receptor uptake hence potency. Another reason the extraction would be crucial!
LINK

After some reading it seems there is really something to this, but we really need side by side tests! One extraction with acetaldehyde present and one without any present but the same general technique used. So then a definite answer to whether one is just a stronger extract than the other (maybe retaining stereochemistry and/or conformation so the end product is a lot stronger?) or is there definitely another compound being produced? If so what, as I have said the carbinolamide will not form easily in this case! It is more likely a Schiff base or an addition product attached to the indole nitrogen, if one looks at Schiff base formation that starts with nucleophilic addition of the amide to the carbonyl group followed by dehydration to the Schiffs base so we are talking about a Mannich base.  But really? Even P. Webster from the article that Tregar linked was under no illusions he was taking anything other than (8?)-9,10-didehydro-6-methyl-ergoline-8-carboxamide which is Ergine and stressing that the different conformations (boat vs chair) will play a large role in pharmacology and potency. He also brings up the point that a certain conformation of isoergine is able to stabilize itself via a hydrogen bond and prevents the same conformational changes, but more importantly because it has gained extra stabilization over ergine which is unable to participate in the same hydrogen bonding. It can affect equilibrium concentrations, he suggested to a 50/50 mixture opposed to LSD after equilibrium @ 88/12 active/non-active! I like that theory much more that the right stereoisomer of ergine in the chair conformation analogous to LSD would be super potent compared to a normal extraction.

@jon, sherry contains roughly 0.1 grams acetaldehyde per liter, so you are going to need over 2 gallons if you want to extract a gram (is the LSH really feasible?).

And also ;
Rectification
The alcohol obtained contains other impurities besides water. These impurities are further removed by fractional distillation. Low boiling impurities like acetaldehyde distill over as first fraction. The middle fraction contains about 93-95% alcohol and is called rectified spirit. Often, distillation and rectification is carried out in the same operation.

http://www.tutorvista.com/content/chemistry/chemistry-ii/carbon-compounds/ethanol-manufacture.php

Quote
I'm not going to go into the whole adducts thing, as others here have gone into much depth

I do have to say Tregar, that paper you quoted is for adducts on the indole nitrogen! the one on the ring! If you look at the pics above its the part that says HN on the bottom of the molecule, it clearly states for primary amines residing on the N-terminus they will react via a Schiffs base which is not what you want as amides generally react the same way.
« Last Edit: September 08, 2010, 01:12:27 AM by Naf1 »

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #32 on: September 08, 2010, 07:52:43 AM »
http://waterhouse.ucdavis.edu/winecomp/acetaldehyde.htm

@data, that book on nmr spectroscopy of alkaloids is interesting
« Last Edit: September 08, 2010, 08:00:12 AM by jon »

Naf1

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #33 on: September 08, 2010, 11:27:42 PM »
Nice link, seems I had the lower end of the spectrum with up to 500mg/L for sherry that smells like rotten apples.

Quote
Acetaldehyde (CH3CHO) is a volatile compound found in wine.

tregar

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #34 on: September 10, 2010, 02:18:15 AM »
Thanks for the warm welcome! Glad to be here. Huge Star Trek fan here as well, heh. If it weren't for star trek and star wars, I would never have gotten into science in the first place.

Naf1 said:
Quote
But in fact we have the naturally occurring forms which are C-8 epimers; Ergine (d-lysergic acid amide), Isoergine (d-isolysergic acid amide) then the two possible other isomers which may not be seen in nature but are possible are C-5 epimers; l-lysergic acid amide and l-isolysergic acid amide. I was using the outdated d/l nomenclature, but you can see four different isomers as with lysergic acid;
Very interesting.

Thanks Naf1 for the clarification on the adducts paper, that's correct, the paper talks about adducts added to the indole nitrogen, thanks. Persona had a long while back pointed that out to me as well, sadly the chemistry genius is no longer with us, suicide.

I respect the strength and reproducability each and every time of mescaline, mxxx, and lsd as entheogenic psychedelics, and have just sort of lost interest in the whole LSA thing, it was a really cool experience the two times it worked when prepared properly, but it is just so darn lethargic, perhaps some trials of taking it with 200mg of harmine or with 150mg of tetrahydroharmine would make it both fun AND stimulating, I have harmine and thh on hand. I have about four more reports from others who have taken MG extracts with either harmine or harmaline, and they all found it VERY visual and stimulating, one person actually compared it to "the best of mushrooms, lsd, and ayahuasca combined". These people all reached a +3 to +4 experience. Heck I was so impressed with the two "good" morning glory experiences I had when extracted with ph = 3.5 D,L tartaric acid powder then left to spin overnight in solution...taken the next day...that I even grew about 1/2 dozen morning glory plants, I then tried a water extraction of the very fresh seeds that I grew combined with peppermint/95% etoh/water, and was actually blown away by the potency. I should have tried just a plain tartaric acid water extract on them to compare to that trial, but sadly I didn't.  I collected all the seeds from the fresh plants and froze them all in a vacuum sealed baggie in the freezer to use in the future, however, due to space constraints I sadly threw them all away months later without even getting to try them again....and damn they sure were strong, way stronger than anything I had ever bought from a vendor.

Perhaps the "freshness" is the key to the morning glory psychedelic trip, as opposed to the ergine boat/ergine chair/iso-ergine chair theory? Or maybe it's both? Will we ever know?

I bet if Peter were to prepare a MG extract with seeds bought from a vendor that the trip would be no where near as potent as the 1960's trip he prepared using the fresh seeds the kids had collected for him off the ground from right where they fell off the plant.

Even Hermes mentioned that his best morning glory trip was due to the particular Martha Stewart variety (that must have been really fresh)...and that even the 12 bags of burpee seeds were weak compared to that particular variety.

I'm beginning to see a pattern here....the fresher the way better.

I just seem to have little patience anymore for trying to acquire "fresh" morning glory seeds....I had found a certain vendor who had great seeds, but when I tried the bulk seeds from several different places they all sucked, as did the burpee seeds, as hermes also found the burpees seeds lacking. It sucks to have to deal with such a "fickle" psychedelic when mescaline works each and every time. It's a crazy world and we all have to work so much at our regular jobs and what not that we have little time for fickle psychedelics..I'm all about maximizing free time wisely. I really hope that one day somebody cracks the secret of the brew prepared at Eleusis. This world is in a heap of trouble and if we don't embrace the psychedelics/spirituality soon we are all doomed. The "powers that be" will run us all into the ground, there is no balance anymore, no yin no yang, the creative spiritual people have been stepped on for way too long. The thread in this forum is the most intelligent I've ever read on this subject.

Peter Webster could be right about the whole ergine-boat/ergine-chair/isoergine-chair conformations being the magic behind the whole thing...although he admits his theory though good is not entirely satisfactory....just as Shulgin was right about the 50/50 proportion of R combined with the S isomers of mdma being the reason for the whole magic of mdma, as taking either just the R isomer alone or the S isomer alone does not cause the magic....so Webster just might be on to something.

He would have tried higher doses of his converted Migraine tablets except his procedure possibly caused side reactions to form which then caused the gastrointestinal issues he experienced with the 3 pill dose, so he never went further, shame. I would have really liked to hear about a 5 or even a 10 pill ergotamine dose converted experience.

Hey, does anybody know if the ergot alkaloids in the morning glory seeds are in the salt form or just what exact kind of form are they in ?....so....anyhow, I was wondering, when I extracted with d,l tartaric acid powder, and when hermes extracted his martha stewart seeds with lemon juice, and when d.d. extracted his seeds with food grade phosphoric acid, were we simply "aiding" the extraction by making the water acidic, or we were also converting the alkaloids to the salt forms? (which are way more bio-available to the body) Or were they already in salt forms to begin with?

p.s. I don't know if this matters or not, but if you do end up using a tea-bag style extraction with a magnetic spin bar running on high speed underneath the tea bag in the acidified distilled water, if you watch carefully, you can observe a tornado cloud of thousands of tiny white specs pouring from out of the tea bag into the water, looks just like a white tornado...what I like to do after this tornado subsides down after approximately 30 minutes, and before throwing away the tea bags (be sure to squeeze them well back into the water before disposing), is to then blend the water at high speed in a blender for several minutes to ensure that all of the tiny white embryos from within the seed have been chopped up totally, cause it's inside this tiny bean shaped white embryo that all the alkaloids lie. then put the jar of previously extracted and blender chopped water back in the fridge to sit or stir overnight.

...now Peter saids that this 50/50 equilibrium of isomers and conformations takes around an hour or more to happen at BASIC conditions, and since we are dealing with acidic conditions to further enhance not only the extraction process, but also the conversion of any of the free alkaloids (should they actually be in this state in the seed embryo) to the more bio-available salt form for the body, I believe for some strange reason that it is best to let the mixture sit or spin overnight in the dark fridge to allow plenty of time for this equilibrium process to be reached before drinking the solution. 99% D,L tartaric acid powder, (on-line used for wine making) just a tiny dash added to the extraction water works amazingly well for this process. Make sure the ph is around 3.5 to 4.0 if possible, use a good electronic meter, I wouldn't go below that ph.

Also, I don't know if this helped but the 1/2 dozen heavenly blue mg seeds were started in the spring, then the seeds were picked off in the fall, it is not an easy job picking all the seeds as you have to collect them one by one from the plant branches/flowers. Yes, there are thousands, but it is time consuming. I also grew the seeds in miracle grow, which may have helped boost the production of alkaloids, I have no idea. The taste of the water extracted fresh seed tea was way different then the taste of vendor bought seeds. The taste was more sort of like an acidic wine if that makes any sense. The water extraction of just 100 seeds was undeniably very potent, I remember drinking the mixture (after it had been spun in peppermint/everclear/water for a few hours) that I was watching a video interview with Scarlett Johansson that had background music playing, the music sounded so good that I kept backing up the video to replay it over and over, I was observing the entire interview from a deep psychedelic state, my emotional state as well as appreciation of humor was really hightened. it was quite fun.

The "metallic rusty iron taste" that Hermes is referring to when referencing LSD, is what's called a "taste hallucination" that the LSD causes, back in the mid-90's, I would always get this same "taste hallucination" in my mouth/tongue some hours after having dropped acid. Hermes said the fresh mg seeds produce a "bee pollen" taste hallucination on the tongue, he is exactly right about this, I could not have described it better.
« Last Edit: September 11, 2010, 09:29:50 PM by tregar »

NeilPatrickHarris

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #35 on: September 10, 2010, 12:32:11 PM »
i don't have much to add here except about talk of adding things to combat sedation.  back when doing cold water extracts of MG seeds (never had much luck with HBWR for some odd reason) i would add 50-100mg of caffeine and dissolve it in the CWE after filtering out the seed pulp.  it would synergize with the LSA extract and you could feel an energy surge throughout you kind of similar to LSD, it didn't make me shaky or really feel like caffeine, it felt like it synergized.  i found 100mg of caffeine added to it to be a bit much and 50mg was better.  what's weird is that sometimes i wouldn't add anything to it and would not be sedated all that much and was slightly energized by the seeds (just slightly, with a bodyload present).  the only change was the seeds, perhaps some seeds may have been older than others, stronger than others, who knows.  i gave up on LSA, the nausea and vasoconstriction was a bit much, at some points it would feel like somebody hooked up a vacuum cleaner to my legs and i couldn't even walk.  smoking a bowl would really amp up the visuals as well with this stuff, otherwise i was always "borderline" visuals the whole time like i was tripping and could almost feel the visuals wanting to come on but never really would unleash themselves until you smoke a bowl then the floodgates would open.  i used to take ginger to combat the nausea.  i'll put it this way, to this day - 8 years later - i still cannot eat ginger because i've gotten sick too many times doing the ginger/LSA combo and my mind relates ginger to those experiences now.  it sucks when i go to a japanese restaurant and they use a nice ginger sauce, i can't have any part of it.  same goes for LSA, the thought of it makes me cringe now.  good luck to all of you, there is a lot of promise here i will certainly agree with that.  but i'm going to sit this one out, i burned myself out years ago  :-\

tregar

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #36 on: September 10, 2010, 01:48:30 PM »
NeilPatrickHarris, that reminds me when you brought up vasoconstriction, that I vaguely remember burningcopal (the dreamer who did the cold water extraction) on claviceps purpurea and had visuals stronger than mushrooms, that he may have been feeling quite a bit of vasoconstriction...and that makes perfect sense, because really, the only water soluble psychedelic alkaloid in claviceps purpurea is ergonovine. I can't tell you how much ergonovine (ergometrine) is in morning glory seeds, but I know it's in there.

Perhaps what he was experiencing from his cold water extraction of claviceps purpurea ergot was only the psychedelic effects of ergonovine, which although psychedelic, causes too much vasoconstriction at high doses, when bigwood, jonathan ott, and the other guy decades ago took high doses of ergonovine, yes, they did hallucinate and have closed eye visuals and saw all sorts of spinning geometry, but they also had debilitating painful cramping of the legs, making it difficult to walk on the beach. Had it not been for the cramping, they would have concluded that Hofmann's theory was correct...that it was ergonovine that was the secret sacred brew.

That's where Peter Webster jumps in and theorizes that the Eleusian Priest used wood ash in water to create a water solution with a basic ph filled with purple claviceps purpurea from the barley grains that would convert/cleave all of the toxic ergopeptines to good water soluble ergot alkaloids like ergine and iso-ergine. What's interesting is that the color purple is thought to have been the color robes the priest wore, also a particular greek man was caught with "purple barley groats" on his mustache and was acting not normal, he was brought before a judge, who concluded that since he had the purple groats hanging from his mustache, that he had indeed profaned the sacred brew outside the ceremony, and was therefore sentenced.

My theory is different from Peter's in that I propose that the Priest actually did do a water extraction on claviceps purpurea (as Hofmann proposed in the book "The Road to Eleusis"), however, once they did that, then they adducted aldehydes onto the indole-nitrogen position to reduce the cramping effect of ergonovine, while still keeping it's psychedelic effects intact. No !*%!$#$ around with wood ash like Peter's theory, heh. keep it simple and do it just like the hymn saids. Mint was also a very popular herb in ancient Greece, used for all sorts of ailments. It was only natural for the priest to add it to the brew, and in doing so, caused fermentation or otherwise had added some alcohol and caused adduct formation onto the allready psychedelic ergometrine (ergonovine) molecule. Now all the sudden you've got something that's highly psychedelic at high doses but with alot less cramping since you adducted molecules onto the indole nitrogen.

Perhaps the priest only did a water extraction on claviceps purpurea...so then they would have a water solution of ergonovine (which is psychedelic but causes painful cramps at high doses)...so then they did some adduct magic on the molecule by adding in mint and causing adduct formation via fermentation or at least with a proper mix of water, mint and alcohol and what not allowed to stand for some time...to make a totally new molecule that then possessed little cramping activity?

It was very clear to me from the hymns that Mint was a vital ingredient in the mix...it had to do with the abduction of Persephone, it had to be in it. Just as ayahuasca requires cappi AND psychotria....The Sacred Eleusian brew required a water solution of ergot (to extract only the ergonovine) AND mint.

There are many names for ergonovine but just remember that it is the same thing as lysergic acid propanolamide, other names for it are ergobasin, ergometrine, etc....Some organization came to an agreement years ago, to just call it "ergonovine", so that's what I'll call it from now on. There is a color picture of it from Dr. Hofmann on one of the pages of his book "LSD, my problem child". It has 3 carbons on the amide Nitrogen, and 8 hydrogens.

Sansert (that medicine that used to be made by Sandoz) for migraines has 4 carbons and 10 hydrogens on the amide Nitrogen. It has a CH3 (methyl group) on the indole-Nitrogen at the bottom of the molecule. The methyl group reduces the drug's vasoconstrictive actions.

Sansert was reported to have profound LSD-like effects at the 20 mg dosage. Psychedelic effects could be felt from as little as 4mg (two of the tablets). ALD-52 (an LSD analogue) reported in the Sandoz archives by several people tested has a COCH3 (acetyl group - named as 1-oxoethy) on the indole-Nitrogen at the 1-position on the "bottom" of the LSD molecle. Notice how similar COCH3 is to acetaldehyde CH3CHO.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 ALD-52 was the active chemical in the "Orange Sunshine" LSD that was widely available in California through 1968 and 1969.  

If we are adducting and condensing an aldehyde chain of some kind onto the indole Nitrogen position, we may be fundamentally changing the pharmacological properties of ergonovine, lysergic acid amide, and the other water soluble lysergamides in the ergot. It seems to me that when you have several thousand participants all drinking a psychedelic potion, you want to have a substance that doesn't have a whole lot of "freak out potential", that is somewhat anxiety free and smooth to handle, whatever is being created may just fit the bill.

Novartis withdrew Sansert from the U.S. market after taking over Sandoz...however I've heard Sansert (l-methyl-lysergic acid) is still available from Canada. It's generic name is methysergide maleate. For those people that don't want to use psychedelics, so you use Sansert, think again, you are using a psychedelic. The hallucinogenic properties are slightly less than LSD or psilocybin but that is mainly due to two things. One, the Sansert dose is very low. Two, it's used every day so there is a blocking effect upon the receptors.

Methysergide is metabolised into methylergometrine in man, which is responsible for its psychedelic effects. Methysergide interacts with serotonin (5-HT) receptors. Its therapeutic effect in migraine prophylaxis has been associated with its antagonism at the 5-HT2B receptor. Furthermore, it is an antagonist at the 5-HT2C receptor and at the 5-HT1A receptor.

Axxaer:
Quote
I have tried methysergide (19mg) and it was very enjoyable. I found the psychedelic effects were indistinguishable from LSD.

Quote
Euphoria, hyperactivity, tachycardia, dilated pupils, and dizziness have been reported in a child with a dose of 20-24 mg of Sansert® (methysergide maleate).

One day, somebody should create a solution of LSD, add mint or perhaps even acetaldehyde, alcohol, distilled water, let it all spin for a day in the cold dark, then try it to see if the LSD becomes less anxiety ridden while also increasing the strength of the LSD.

Did the priest convert their water soluble solution of ergonovine to something that was just as psychedelic but nonetheless seriously reduced the vasoconstictive actions? I believe it was entirely possible and this process seemed like it would have been very easy to do....simply take your water soluble solution of ergonovine (the only major water soluble alkaloid in claviceps purpurea, as lsa is only in there in trace amounts)....and adduct a methyl group or aldehydes or what not on the molecule's indole nitrogen by adding in mint (possibly along with alcohol)....causing an entirely new highly psychedelic molecule...thereby reducing the drug's cramping activity several fold. Get the mixing conditions just right, and let it sit or mix for over a day, and you've got something new made in over 80% yield. I believe by simply stirring it or letting it sit for longer amounts of time would ensure high yields no matter what even if the beginning proportions of ergot, mint, alcohol and water were off.

The Lolium species (L. temulentum and L. perenned) are notoriously prey to the Claviceps fungus. The psychotropic reputation of darnel must therefore be attributed to its parasitic infection by ergot. Samples of ergot grown on L. temulentum and L. perenne collected in Germany, France, and Switzerland showed large variation in their alkaloidal composition. Some contained substantial amounts of ergonovine together with alkaloids of the ergotamine and ergotoxine group.
T
I surely don't have access to ergot. I don't live next to any agrarian plains. The telestrion where the Eleusis ceremony was held was right next to the famous agrarian plain...where barley grew and no doubt became infected. See, dead end.  Like I'm gonna get Dr. Nichols to run this one, heh.  
« Last Edit: September 12, 2010, 01:32:20 AM by tregar »

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #37 on: September 10, 2010, 08:54:09 PM »
very interesting tregar!

i did notice the wine soaked hawaiian woodrose seed solution gave a very relaxed trip very smart of you to corellate that to lad and it's dampened anxiety.
i think your on to something there.

tregar

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #38 on: September 11, 2010, 05:55:51 PM »
Thanks jon, wonderful thread you've started here. I too have noticed that the extractions that have been "adducted" onto the indole-nitrogen are indeed quite relaxing and way stronger...perhaps at the same time (stronger in a good way, just as ALD-52 is) it's even possible the vasoconstriction is being significantly decreased as well. All it took was for scientist to add a CH3 onto the indole-nitrogen ring of the ergometrine like molecule (sansert) to significantly reduce the vasoconstriction...ding ding allowing users to experience the profound lsd-like psychedelic effects (by taking 5 pills or more) without the vasoconstricting side effects.

Road to Eleusis:
Quote
A notorious scandal was uncovered in the classical age, when it was discovered that numerous aristocratic Athenians had been celebrating the Mystery at home with groups of drunken guests at dinner parties....there were physical symptoms that accompanied the vision: Fear & Trembling in the limbs, vertigo, nausea, and a cold sweat. Then there came the visions.....there was a sacred Rarian plain adjacent to Eleusis--that may have served as a source of ergot....It was Demeter's sacred barley, grown in the Rarian plain (next to Eleusis) that was the principle ingredient in the potion drunk by the initiates in preparation for the culminating vision. The formula for that potion is recorded in the Homeric hymn. In addition to the barley, it contained water and a fragrant mint called blechon (pennyroyal or a type of water mint was used). The grain was mixed with mint and water in urns, from which the sacred potion was then ladled into special cups for the initiates to drink their share.....lines 22 to 26 of the hymn have been lost. They may have contained further instructions for the drink and may have been destroyed intentionally.

This reply is a very long one, so bear with me, I'm trying to cram lots of valuable info in here. This is interesting: Peppermint oil appears to have about 0.04% isobutyraldehyde and 0.19% isovaleraldehyde, far more than is contained in beer.

Jon said:
Quote
did notice the wine soaked hawaiian woodrose seed solution gave a very relaxed trip very smart of you to corellate that to lad and it's dampened anxiety.
i think your on to something there.
Wine has an optimal ph (paper saids ph=4 is best) for these conditions to occur. Sounds like an acteyl or some other molecule group like acetaldehyde may just be adducting onto the indole nitrogen of the woodrose alkaloids, changing the pharmacological properties of all the psychedelic alkaloids in the seeds. ALD-52 has an acetyl group on it's indole-nitrogen. I would love to get ahold of some ergonovine and spin it in sherry wine (has loads of acetaldehyde) for a day and see what results...then do a followup experiment by adding drops of peppermint and repeat (spin again for a day) to see if it changes yet again.

As far as heavenly blue MG seeds are concerned:

Number of Seeds / Approximate amount of Ergonovine in milligrams (theoretical)

20 / 0.04 mg of ergonovine in the seeds
50 / 0.10 mg of ergonovine in the seeds
100 / 0.20 mg of ergonovine in the seeds
500 / 1.0 mg of ergonovine in the seeds

Approximate weight 100 seeds = 4 grams

Another study, this one from Weldon Witters, Rf values of extracts from three varieties of Ipomea.

Heavenly blue:

-----/-----/-----/----/ chanoclavine
0.47/0.28/0.15/0.23 elymoclavine
----------------------- penniclavine
0.67/0.18/0.23/0.28 ergometrine
0.76/0.70/0.40/0.52 agroclavine
0.62/0.75/0.47/0.26 lysegic acid amide

Pearly Gates:

0.21/0.12/0.10/0.42 chanoclavine
0.48/0.28/0.18/0.24 elymoclavine
0.44/0.22/0.46/----- penniclavine
---- /0.18/0.24/0.32 ergometrine
----/ 0.70/0.42/0.54 agroclavine
0.62/0.78/0.48/0.30 lysergic acid amide

I highly doubt that the priest back then were messing around with wood ash, as Peter found in his experiments to cleave the toxic ergopeptines caused possible un-wanted side reactions sparking gastronintestinal disturbances in his stomach which warranted his stopping stronger experiments. I just can't see them using wood ash either. The effects even with ergine/iso-ergine conformations would also be a lot less stimulating than ergonovine. Remember that he found his 1960's experience with fresh morning glory seeds (which likely had large amounts of ergonovine) to be way stronger than his ergine/iso-ergine experiments as well.

Please keep us updated on future dream tests, I will look into the matter on free time as well. I do believe that Hofmann was right in his theory about ergonovine being psychedelic, our job is to adduct that indole-nitrogen to make it even more potent, with decreased anxiety, along with decreased cramping...all 3 effects attacked by the addition of one simple adduct.

Ergonovine:
indole nitrogen R = H
amide Nitrogen substituent = CH(CH3)CH2OH
R=H

UML-491 (Sansert migraine medication) that has PROFOUND LSD like effects at 20mg:
indole nitrogen R = CH3
amide Nitrogen substituent = CH(CH2CH3)CH2OH
R=H

In case an aceteldehyde of some type is adducting onto the indole nitrogen, here are some other possible candidates:

acetyldehyde = CH3CHO
isobutyraldehyde = (CH3)2CHCHO
isovaleraldehyde = (CH3)2CHCH2CHO

remember, ALD-52 has the following acetyl-group at the indole-nitrogen = COCH3

White bread = 0.0225% isobutyraldehyde
Beer = 0.005% isobutyraldehyde
Apple juice = 0.000002% isobutyraldehyde
peppermint = 0.04% isobutyraldehyde

Peppermint oil appears to have about 0.04% isobutyraldehyde and 0.19% isovaleraldehyde (3-Methylbutyraldehyde):

TABLE 1
______________________________________
Comparative gas chromatographic analyses of the peppermint oils. Component A B C D E (%) (%) (%) (%) (%)
______________________________________

Isobutyraldehyde -- C4 H8 0
0.04 0 0 0 0
Isovaleraldehyde -- C5 H10 0
0.19 0 0 0 0
A-Pinene 0.73 0 0.10 0 0
B-Pinene 0.95 0 0.25 0 0.02
Sabinene 0.45 0 0.12 0 0.01
Myrcene 0.20 0 0.07 0 0.02
A-Terpinene
0.34 0 0 0 0.07
L-Limonene 1.49 0.11 0.68 0 0.30
1,8-Cineole
4.64 0.37 2.89 0 1.81
Cis-Ocimene
0.30 0.08 0.17 0 0.09
G-Terpinene
0.68 0.20 0.54 0 0.31
P-Cymene 0.18 0 0.15 0 0.05
Terpinolene
0.15 0.14 0.11 0 0.14
3-Octanol 0.24 0.14
1-Octen-3-ol
9.17 0.11 0.17 0 0.09
trans-Sabinese
1.04 1.04 0.12 0.18 0.98
Hydrate
L-Menthone 19.33 23.13 22.28 10.84 23.80
Menthofuran
1.84 2.02 1.95 0.50 2.30
Iso-menthone
2.63 3.30 3.11 2.04 3.16
B-Bourbonene
0.45 0.35 0.43 0.61 0.42
Linalool 0.22 0.23 0.18 0.32 0.33
Menthyl Acetate
5.14 5.15 4.59 7.54 4.42
Neo-menthol
4.04 5.04 5.75 6.48 5.31
B-Caryophyllene
1.62 0.89 1.37 2.07 0.60
Terpinen-4-ol
1.13 1.43 1.62 1.05 1.17
L-Menthol 41.11 51.35 46.87 63.57 46.77
Pulegone 1.25 1.09 1.48 1.63 1.36
Germacrene-D
2.12 0.37 1.92 0.70 1.89
Piperitone +
0.99 0.64 0.62 0.92 0.58
Viridiflorol
0.37 0.18 0.10 0 0.18

Albert Hofmann:
Quote
We analyzed ergot of wheat and barley in our lab and they were found to contain basically the same alkaloids as ergot of rye, viz alkaloids of the ergotamine (vasoconstrictor used for migraine prevention) and erogotoxine(toxic) group, substantial amounts of ergonovine (lysergic acid propanolamide) and sometimes traces of lysergic acid amide(LSA), As I said before, ergonovine and lysergic acid amide, both psychoactive, are soluble in water whereas the other (toxic) alkaloids are not.

Here is hoffman's evaluation of ergonovine when taken at his home when we wrote the book "The Road to Eleusis":

Quote
12:20 h: 2.0mg ergonovine hydrogenmaleinate, containing 1.5mg ergonovine base, ingested in a glass of water.

13:00 h: slight nausea, same effect as I have experienced always in my LSD or psilocybin experiments. Tired, need to lie down. With eyes closed I see colored figures.

13:30 h: the trees in the nearby forest seem to live, their branches moving in a threatening way.

14:30 h: strong desire to dream, unable to do systematic work, with eyes closed or open afflicted by mollusk-like forms and feelings.

16:00 h: motives and colors have become clearer, but bearing some hidden dangers.

17:00 h: after a short sleep I awoke by a kind of inner explosion of all the senses.

18:00 h: an unexpected visit forced me to become active, but during the whole evening I lived more in an inner than in the outer world.

22:00 h: all effects worn off, normal feeling.

He concludes the 10 hour experience has a potency of about 1/20th (at the 2.0mg dosage) the potency of LSD....hmmm sounds familiar? Sansert has been shown to be profoundly psychedelic at the 20mg dosage! ding ding...so taking ergonovine at the 20mg dosage (only if we adduct the indole-nitrogen first, to make the molecule stronger psychedelic wise, while at the same time decreasing anxiety along with vasoconstriction).

3 experimenter's effects when ingesting pure ergonovine, June 1979 Journal of Psychedelic Drugs:
Quote
In the January-June 1979 issue of the Journal of Psychedelic Drugs, Jeremy Bigwood, Jonathan Ott, Catherine Thompson and Patricia Neely report on their attempt to replicate Hofmann's finding in three experiments with ergonovine maleate, each time in one pastoral setting. They were following up Wasson and Ruck, who tried the same amount as Hofmann but "did not experience distinct entheogenic effects."

With Thompson acting as a guide, three of them took 3mg. of ergonovine maleate, which appeared as a slightly phosphorescent bluish solution in water. Fifteen minutes later they felt like lying down and looking at the sky; then there were "very mild visual alterations, characterized by perception of an 'alive' quality in inanimate objects." Most of this effect passed within an hour; walking along the beach, they experienced mild leg cramps. Bigwood saw eidetic imagery before going to bed, and the three "slept easily...awakening refreshed in the morning."

The three experimenters were "convinced that ergonovine was psychoactive, but only J.B. was persuaded the drug was entheogenic." They decided to try it again two weeks later in an increased dosage of 5 mg., but Neely took only 3.75mg. "Again, we experienced lassitude and leg cramps, more pronounced than in the earlier experiment." The psychic effects were more intense than previously, particularly eidetic imagery. "Now it was clear to all of us that ergonovine was entheogenic...The entheogenic effects, however, were very mild, while the somatic effects were quite strong. We had none of the euphoria characteristic of LSD and Psilocybin experiences."

To determine if higher consciousness alteration was possible, they tried larger oral doses of ergonovine maleate a week later. This time, Neely took a dose of 7.5mg and the others took 10mg:

"One of us (J.O.) described "flashes in periphery, ringing in ears, inner restlessness" 40 minutes after ingestion, and later noted "mild hallucinosis, cramps in legs and felt the cramping in the legs as painful and debilitating. The psychic effects did not increase with the same magnitude as the somatic effects...For what seemed like hours, we lay on our backs atop a small pumphouse, watching fluffy cumulus clouds pass silently above us. The effects were still quite intense six hours after ingestion. One of us experienced abundant eidetic imagery, rapidly-changing, colorful geometric patterns, undulating, never still. We all had a slight hangover the following morning."

My interest is once again back in this matter, thanks to your thread. Fresh morning glory seeds are likely quite high in ergonovine. If we can vastly reduce the vasoconstrictive effects of the ergonovine in the mg seed extractions by adducting the indole-nitrogen, then that means much larger doses of the solution can be taken without having cramping of the muscles, and adding a more relaxing mind-state. I have noticed the adduct prepared solution is significantly more stimulating than a normal mg water extract, perhaps it is the modified ergonovine (proven psychedelic) molecule that we are feeling the most.

I had proposed this theory about a year ago on a different small forum, but it went un-noticed by everyone. I'll admit it's not entirely satisfactory either, but if it were possible to get ahold of some ergonovine it could be tested quite easily. The indole-nitrogen is the part of the molecule receiving adducts of whatever form they might be...it's possible this new adduct is not only increasing the psychedelic potency of the molecule, but also decreasing anxiety while at the same time decreasing the vasoconstrictive effects. Perhaps the increased strength trip that begins within 45 minutes of taking a morning glory extract done with the adduct procedure, we are really experiencing the effects of the ergonovine taking on an extra adduct, which in turns give the more potent trip over a normal mg extraction.

Ergonovine (ergometrine) is just so close looking to sansert (which is very psychedelic at 20mg) on the upper half of the molecule, now if we could just add a methyl group (CH3) via chemical means or any kind of acetaldehyde molecule (easy mixing process using added water & alcohol) to the indole-nitrogen (easily done by following the adducts paper), we have a new creation with potent effects and decreased anxiety/vasoconstriction. Putting a methyl group onto the indole-nitrogen of sansert caused it to remain profoundly psychedelic while vastly decreasing vasoconstriction.

ALD-52 (1-acetyl LSD) and Sansert (methyl lysergamide) are two examples of man-made entheogenic molecules with attachments at the indole-nitrogen.

Monday, October 01, 2007 journal:
Quote
Methysergide (sansert) causes the fish surfacing reaction in the same way that LSD does, but a higher dose is needed. Fifty (50) ug/mL of UML-491 (methysergide) in the outside liquid gives approximately the same per cent of goldfish reacting as does 0.2 ug/mL LSD. Therefore, methysergide is about 250X less potent than LSD in goldfish.

For comparison with methysergide, goldfish intoxication proceeds when 0.2 ug/mL LSD is available to be ingested or absorbed by the fish gills. A larger dose of methysergide (sansert) is needed for fish and human effects.

Allgire:
Quote
For these headaches physicians prescribed opiates and also put me on a cousin of LSD known as Sansert (Methysergide maleate). This drug gives you hallucinogenic dreams. The doctor told me I had to take it. The dreams were really wild, a Technicolor acid trip every night. So my doctor basically prescribed a mild form of LSD to prevent my headaches.

Quote
Normal human subjects respond to an average threshold dose of 3.4 mg psilocybin, and an average threshold dose of 4.3mg or more of methysergide (Sansert). In other words, 25ug of LSD equates to 4.3mg of Sansert according to Jonathan Ott. Therefore, in human beings, psilocyin is 135X less potent than LSD, and methysergide is 170X less potent than LSD. Also in 1965, Dr. Abramson found that methysergide is 250X less potent than LSD in goldfish.

Claviceps Purpurea fungus: If no source can be found, you can make a field trip to obtain it from rye or other cereal grasses. Rye grass is the best choice. The ergot will appear as a blackish growth on the tops of the rye where the seeds are. They are approximately the same shape as the seeds and are referred to as "heads" or "ergot". From these heads or ergot sprout the Claviceps Purpurea fungi. They have long stems and bulbous heads when viewed under a strong glass or microscope. It is these that must be removed from the ergot, free from contamination, and used to inoculate the culture material.

(from Mixing the kykeon, final draft, by Peter Webster, published in ELEUSIS: Journal of Psychoactive Plants and Compounds New Series 4, 2000)
Quote
A likely possibility is that the priests had discovered how to spread an ergot infection
using a water solution of the honeydew produced. Early in the growth of ergot on grain, the
fungus causes the production of droplets of a sticky syrup on the grain heads, and insects
attracted to this exudation transmit the ergot mycelium therein to other developing heads of
grain. A solution of a few drops of honeydew in a litre of water produces a mixture that when
shaken or sprayed onto other developing grain heads readily spreads the infection.

burning_copal's ice cold water extract of "the deadly" 1.75g claviceps purpurea: there is no doubt in my mind that what he was experiencing was the effects of the water soluble ergonovine (the only major water soluble alkaloid in the fungus, as it contains only traces of the water soluble lsa), the other toxic alkaloids in the fungus are non-water soluble.
Quote
The feline found that the cold water potion, absorbed VERY quickly, within less than 30 seconds effects could be felt. The vascioconstriction was very apparent so the feline said, but not at all unpleasent . That was the first effect felt , followed shortly by the onset of beautiful closed eyed visuals ( so the feline said ) and then shortly after the open eyed visuals began, after each sip the feline found that the experience progressed over the course of a half hour or so.

The feline experienced very mild nausea, nothing notable at all in comparison to the snakevines ( Ipomoea , rivea etc ) The feline found that the coldwater potion had little to no taste what so ever, and did not induce a gag reflex.

After the entirety of the potion had been consumed by the feline, he sat back to experience it in its full glory, and truely glorious he found it to be.

While snakevines induce in felines ( and humans ) very beautiful experiences, they also induce somewhat of a ' drunken ' state , that is one looses a great deal of physical / mental co ordination when the dosage range is aproached where the visuals become quite intense. The feline found this to be entirely different. There seemed to be little to no loss in physical / mental co ordination, The feline felt for all practical purposes sober, but were it not for the bells, whistles, and wind in his ears, singing and talking ( he heard many voices ) and the absolute most radiant, and vibrant splashes of colors before the felines eyes, With his eyes opened, he experienced such beautiful visions, that he could not recall a experience where closed eyed visuals even approached the vividness. This was barnone the most visual experience of the felines life , and he had, in the course of wandring fields, consumed hefty dosages of 'godflesh' in times past , one species in perticular noted for vivid visions , the feline found this to be far more intense.

While he said he felt nearly sober the entire duration of the beautiful and powerful experience, he also experienced some extreamly profound things while he allowed his body to be completely stationary , and still. With his eyes closed, the feline experienced such profound rapture, meows failed to describe it, and words dont do a better job. There were times the feline thought he may have died , and steped through to the otherside, only to tell himself to open his eyes, and look around. And find that his body felt fine, his mind felt fine, but he was still enraptured in prisims of light. After several rounds of this , the feline resolved to not concern himself, he was not dying, and he finaly realised this, and simply alowed himself to experience the rapture. And to say anymore then ' He steped through the other side ' In such a complete and lucid way, really to say more does no good. No Meows No Words to describe it. Besides perhaps , Enraptured.

The feline finaly decided to allow himself some sleep as the experience was winding down. When he awoke, the typical ' afterglow' that follow consultion of snakevines, something the feline was very fermilar with , was present. Love, pure and simple, for everything.

The feline wondered, and I do now also, Why is this not spoken of more ? While the feline said, the vascioconstriction was certinaly apparent ( mostly because it came on so quickly ) He found it actually to be less intense overall then experiences with snakevines. While the visions induced were something snakevines never had even approached. And that aside, the general lack of a desire to vomit , would put the simple fungus , near the top of the feline's list, as perhaps at once, the most pleasent, and most profound entheogen, he has known.

In theory, suppose a cold water extract were done on claviceps purpurea and a bunch of ergonovine ended up in solution, would there be an easy way to add a methyl group CH3 onto the indole-nitrogen position, so that it would look nearly identical to sansert? This would certainly reduce the vasoconstrictive side effects of ergonovine while keeping the psychedelic effects intact, enabling much higher doses to be utilized....what sort of chemistry would be involved?

Ergot of Rye: (great info): http://www.botany.hawaii.edu/faculty/wong/BOT135/LECT12.HTM
« Last Edit: September 12, 2010, 06:25:41 PM by tregar »

jon

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Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #39 on: September 12, 2010, 08:50:09 PM »
In theory, suppose a cold water extract were done on claviceps purpurea and a bunch of ergonovine ended up in solution, would there be an easy way to add a methyl group CH3 onto the indole-nitrogen position, so that it would look nearly identical to sansert? This would certainly reduce the vasoconstrictive side effects of ergonovine while keeping the psychedelic effects intact, enabling much higher doses to be utilized....what sort of chemistry would be involved?



i guess the simplest answer to your question would be the ergot wine alluded to in an earlier paragraph.

i even think ald type compounds are about 50% more potent due to increased lipophillicity intersting indeed!
ii remember it took the equivalent of 2 crappy ghannan seeds to make me trip so i think there is a potency gain

also, the longer chain aldehydes would make more lipophillic adducts than acetaldehyde

whats interesting to note is you are correct the anedoctal reports i read on these expiriments report when successfull there is markedly reduced peripheral vasoconstriction, the expirience is more "bubbly" energetic, yet relaxing but there is also reports of bronchioconstrictiction from this derivative.
all anecdotal of course.


this is a report on brochioconstriction

It’s fantastic, until high doses are used and then that bronchoconstriction kicks in causing shortness of breath. That’s very unnerving. SWIM cannot stand it.

The best thing is to use a bronchodilator.

The safest to use in combination with LSH is probably theophylline, found in tea, but not in large enough quantities to be of use. You need theophylline tablets.

The other alternative is chocolate which contains theobromine. You need a lot of it though. You can make some chocolate milk and put about 2-3 times the recommended about of chocolate in it and it should effectively counteract most of the vasoconstriction and bronchoconstriction of LSH. It doesn’t work as well as theophylline does. The good thing about theobromine is that it’s not much of a stimulant so it won’t affect the stimulant effects of LSH much..

Caffeine is also a bronchodilator, but also a strong stimulant. It will alter the trip, making it much nicer at low doses, but at high doses of LSH, it’s not a nice combination, leading to extreme nervousness, excitability, pacing, etc. No fun.

Another option, although more dangerous, is to use mormon tea, or ma huang. Be VERY CAREFUL with ma huang. Ma huang contains ephedrine which is a strong bronchodilator. Unfortunately ephedrine has killed people. SWIM has not used this in combination with a high dose of LSH. He doesn’t feel it’s safe.

SWIM finds strong chocolate milk is a good choice. You can drink a few cups throughout the trip to ward off the vasoconstriction and bronchoconstriction effect of LSH and not worry about getting an overdose. People don’t die from drinking too much chocolate milk, but they do die from too much ma huang.


polytrip wrote:


but then in this thread
https://dmt-nexus.com/forum/default.aspx?g=posts&t=5733&p=5

they talk of using 15 hbwr seeds a large amount with little i'll effects using mint aldhehydes i thing that is smarter those aldehydehydes are either aromatic or longer chained and thus more lipophillic as adducts this is some interesting shit!
« Last Edit: September 12, 2010, 10:53:17 PM by jon »