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

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #40 on: September 13, 2010, 12:01:56 AM »
excellent post jon! i've asked ron69 to join if he wants to eventually and give us the lowdown on his experiences with the adducted-lsa only alkaloid from seeds, as he's had lots of experience with this. Thanks for pointing out the broncholidator side effect. Yes, I agree, the addition of a methyl group to ergonovine is simply out of the question, lets keep it to the adduction of aldehydes (easily done) just as ALD-52 has an acetyl group on the indole-nitrogen.  I know that hbwr seeds have no history of shamanic use...is it true they contain glycosides that could enter a cold water extract? or will an extract keep them out? I have no knowledge on the subject of hwbr, but was wondering if glycosides have anything to do with bronchiovasoconstriction.

jon said:
Quote
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!
very interesting!
« Last Edit: September 13, 2010, 01:06:50 AM by tregar »

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #41 on: September 13, 2010, 12:28:55 AM »
agreed we should let it ride until we can find some more wisdom on the subject

in my experience they usually just make you sick
yes they are washed along with water i never had any problems like turning blue i think it's in low concetratration.
it's like appleseeds for eg: you have to eat a lot of those to get sick.
most of the naseua is from the ergot alkaloids.
cyananogenic glycosides are usually boiled out cold water may just leave them alone.

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

just studying that thread i see variable results with bronchial/vaaswoconstriction with the mint tea expiriments but with the alcohol expiriments i see consistent success.
« Last Edit: September 13, 2010, 05:48:08 AM by jon »

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #42 on: September 19, 2010, 02:27:57 AM »
I agree, drop the mint and just use wine.

shulgin:
Quote
Methysergide, Sansert. This is the synthetic homologue of methergine (1-methyl) and is employed clinically as a treatment for migraine headaches. When the usual therapeutic dosage of two milligrams is scaled up by a factor of ten, there is a profound LSD-like response described by most subjects.

Have seen 100 of the 2mg tablets (canada) available for about a hundred bucks by prescription.

in theory, i think just doing a cold water extract on claviceps purpurea, then adding the contents of the cold water extract (ergonovine) to sherry wine (has the highest amount of acetaldehyde of all the wines) and letting it stir in the fridge on a battery magnetic stirrer for several days should create something similar to sansert, just instead of ch3 on the indole-nitrogen ring, there will be a stable ch3ch0 (acetaldehyde adduct) on the indole-nitrogen ring instead.

sherry wine has water, alcohol, and acetaldehyde, all 3 ingredients are needed to create a stable ch3ch0 adduct on the indole-nitrogen of ergonovine. I would imagine about 1 to 2 days worth of stirring would create about 80% or more of theoretical new pharmacological creation.

imho, this was what they were drinking, plain and simple.

The Road to Eleusis is one of my favorite books, available on-line to read.

An aside, but we do know for instance that cocaine when combined with alcohol in the liver transforms into an entirely new substance called coca-ethylene, and this was not even discovered until 1993! that was the secret to the famous vin mariani (drunk by Thomas Edison & even the Pope, thousands of celebrieties) the super potent wine with only small amounts of cocaine that was pre-mixed with wine and then when reaching the liver, turns into a 2 to 3 hour acting oral form of cocaine without acting on serotonin and dopamine as normal cocaine does, but only dopamine alone as it's new orally bio-available form. it only took say a dozen 1 gram bags of coca tea bags mixed into a bottle of wine back in the 1800's to create vin mariani.  although coca-ethylene is more euphoric (and very potent at low amounts) than normal cocaine, it is also more toxic.
« Last Edit: September 19, 2010, 03:25:21 AM by tregar »

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #43 on: September 19, 2010, 10:56:51 AM »
yeah i used to drink bourbon and snort 8 balls and wonder why i had chest pain.
shall we don it "vin alberto hoffman"?
« Last Edit: September 19, 2010, 05:36:15 PM by jon »

overunity33

  • Subordinate Wasp
  • ***
  • Posts: 218
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #44 on: September 19, 2010, 07:29:45 PM »
Hmm that explains why my vodka/30 coca tea bag black liquor shots made me violent, hypersocial and sick as a dog the next day.  Anyone got a good recipe for infusing coca tea into liquor that doesn't taste like asshole?

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #45 on: September 19, 2010, 07:40:17 PM »
you know we could make  the liquer chocolates?
those sell like hotcakes.
a good recipie would involve removing the cocaine from the mix.

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #46 on: September 20, 2010, 02:46:07 PM »
jon said:
Quote
shall we don it "vin alberto hoffman"?
;D
Sorry to get off subject, but to elaborate:
Overunity...here you go:

From "A Brief History of Cocaine" old edition:
Quote
When cocaine is consumed in the absence of alcohol, it is broken down into two metabolites, one called benzoylecgonine and one called ecgonine methyl ester. In 1990, separate groups of researchers, one in Barcelona and one in Miami, discovered that the combination of alcohol and cocaine produces a very unusual compound called cocaethylene--the stimulant effects are enhanced and prolonged--but much more toxic. That may explain why Vin Mariani, and the other cocaine-containing wines were so popular back in the late 1870's. The only requirement for the wine was that it contain 10 to 15% alcohol. One ounce of Mariani's tonic contained 6mg of cocaine. Two glasses of wine would have contained less than 50 mg of cocaine, equivalent to one 'line' of snorted cocaine. Even using today's sophisticated measuring techniques, 50mg of oral cocaine is barely enough to cause measurable effects in humans. However, in the form of cocaethylene (orally active), it is potent.
Would imagine that since there is about 5mg of cocaine per a tea bag back then, there is about three 8 oz glasses to a bottle of wine, so that would be about 3 tea bags per glass of wine or 3 x 3 = 9 tea bags per bottle of wine.  24.5 oz per bottle of average wine = (6mg x 24.5 = 147mg per bottle of wine) or 147mg/three 8 oz glasses = about 49mg per 8oz glass of wine. Overdoing it would definately cause the toxicity to rise, the book mentions wine only, as distilled spirits would cause too much toxicity.

Anyhow, back in the day, Bigwood, Ott and Neeley had it easy because all they had to do was pick up some ergonovine which was still available back then as a research drug, then they could run there experiments. shit out of luck these days, heh. This is why it is so easy to loose interest in this topic, because nobody really wants to mess around with ergot, much less have a readily available field nearby with infected grains. Gotta admit, the ice cold water 1.75g ergot dream consumption experience by b.c. is quite interesting. The stigma associated with ergot is so intense, that even years later no dreamer has even duplicated his findings (ice cold water extract only of the deadly claviceps purpurea).
« Last Edit: September 21, 2010, 12:42:57 AM by tregar »

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #47 on: September 20, 2010, 06:34:03 PM »
paspali is even better ergot for this the indole diterpenes if you look at thier structure they are clearly not very water soluble and those are the only offenders in paspali ergot.
there are a couple of ergolines that are'nt cataloged by the u.n. or the dea but i'm not saying which here back in the 90's it was ergocrystine then they caught on to that, but there are a few around.


« Last Edit: September 20, 2010, 07:02:00 PM by jon »

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #48 on: September 26, 2010, 05:32:46 PM »
Jon said:
Quote
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.

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.
I just measured the ph of the sherry wine (bleh too!) I've had sitting in the fridge for over 2 years, and the ph is exactly 3.8 to 3.9 when measured twice. It is at the perfect ph for these experiments.

Thanks so much for the report Jon....excellent !!! Judging from the adducts paper, with 80% water, and the rest alcohol in the wine and acetaldehyde you get about 27% product after 24 hours, so I would imagine spinning it all in the fridge for 3 days (72 hours) would yield over 78% of new product produced. As you mentioned sherry wines have about .5% acetaldehyde (the most acetaldehyde of all the wines).

When I get a chance I'll run some experiments as well.

I do have a portable battery powered magnetic sitrrer that works great for spinning solutions in the fridge.
« Last Edit: September 26, 2010, 05:35:46 PM by tregar »

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #49 on: September 26, 2010, 05:50:59 PM »
you can do a pinacol rxn on ethylene glycol and kick off acetaldehyde which you could bubble in.
lsd lsa whatever is a differrent substate than the one mentioned in that paper.
the indole nucleus is highly electron rich at n-1 and c-2 so it's possible it's more reactive.

Bluebottle

  • Subordinate Wasp
  • ***
  • Posts: 125
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #50 on: September 26, 2010, 09:13:24 PM »
I'm probably missing something obvious, but I need to ask; for the wood-ash hydrolysation experiments, why would the ergotamine hydrolyse to ergine, wouldn't the product of it make lysergic acid?
"And now we divide both sides by zero..."

Vesp

  • Administrator
  • Foundress Queen
  • *****
  • Posts: 3,130
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #51 on: September 26, 2010, 09:20:41 PM »
I think it depends on the conditions .. ergine is the amide of lysergic acid so if it were reacted long enough under harsh enough conditions it would probably produce lysgeric acid. I'm sure some lysergic acid does from along side the ergine.

Bitcoin address: 1FVrHdXJBr6Z9uhtiQKy4g7c7yHtGKjyLy

Bluebottle

  • Subordinate Wasp
  • ***
  • Posts: 125
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #52 on: September 26, 2010, 09:30:05 PM »
What I mean is looking at the structure, I can't see any reason for that other thing to come off first/preferentially. I've never heard of amines themselves hydrolysing and if so, I don't think they would so easily.
"And now we divide both sides by zero..."

Vesp

  • Administrator
  • Foundress Queen
  • *****
  • Posts: 3,130
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #53 on: September 26, 2010, 09:33:22 PM »
Oh! Yeah good point. It does seem like it would just produce lysergic acid I guess. Anyone know?
Bitcoin address: 1FVrHdXJBr6Z9uhtiQKy4g7c7yHtGKjyLy

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #54 on: September 26, 2010, 10:41:50 PM »
***why would the ergotamine hydrolyse to ergine, wouldn't the product of it make lysergic acid? ***
lsd chemistry is very subtle.
hoffman discovered that in alcohol with a lower ph it just clips off the complex side chain because the conditions are'nt strong enough to split the amide.

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #55 on: September 27, 2010, 12:12:26 AM »
I would love it if the liver would take the isobutyraldehyde in mint leaf and add that to form the new molecule in vivo, i'm gonna try drinking several cups of fresh mint tea then drink a small extract of mg seeds and see if in-vivo there are effects, if that does not work, then will try drinking sherry wine before taking the seed extract to see how that feels. Might even combine the mint tea and sherry wine before taking the seed extract. In simplicity as Jon had stated back on page 1, the liver is most likely taking lsa and acetaldehyde in the liver and forming in simplicity hydroxyamide.

the kykeon contained mint, so it's worth a shot drinking a bunch of mint tea then drinking a cwe of mg seeds to see if it has greatly enhanced effects without/with the addition of sherry wine to the liver.

The kykeon clearly contained mint:
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.

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

White bread = 0.0225% isobutyraldehyde
Beer = 0.005% isobutyraldehyde
Apple juice = 0.000002% isobutyraldehyde
peppermint = 0.04% isobutyraldehyde
peppermint = 0.19% isovaleraldehyde
peppermint = 41.0 to 51.0% L-Menthol
sherry wine = 0.5% acetaldehyde
« Last Edit: September 27, 2010, 12:52:26 AM by tregar »

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #56 on: September 27, 2010, 02:23:05 AM »
i'm not sure i think i just got a mixture of effects(ergonr and whatever adduct it produced) it was relaxing and stimulating at the same time it did'nt last as long as ergine which lasts 10 hours or more.
it was pretty nice.
spearmint would contain more aldehydes than peppermint so i would try that.
maybe just make a mojito with spearmint and mix it up and let it spin.

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #57 on: November 19, 2010, 07:11:27 AM »
this is a real interesting read
http://forums.mycotopia.net/botanicals/14769-low-light-morning-glory-wine.html

We know that alcohol is converted to acetaldehyde in the liver for a brief moment before the acetaldehyde is destroyed by aldehyde dehydrogenase enzyme.

Coca tea when mixed in wine back a long time ago was done to make Vin Mariani ( coca-ethylene was being formed in the liver discovered in the mid 1990s by researchers) , which potentiated the coca leaf alkaloids making them more orally potent.

When cocaine is consumed in the absence of alcohol, it is broken down into two metabolites, one called benzoylecgonine and one called ecgonine methyl ester. In 1990, separate groups of researchers, one in Barcelona and one in Miami, discovered that the combination of alcohol and cocaine produces a very unusual compound called cocaethylene--the stimulant effects are enhanced and prolonged--but much more toxic. That may explain why Vin Mariani, and the other cocaine-containing wines were so popular back in the late 1870's. The only requirement for the wine was that it contain 10 to 15% alcohol. One ounce of Mariani's tonic contained 6mg of cocaine. Two glasses of wine would have contained less than 50 mg of cocaine, equivalent to one 'line' of snorted cocaine. Even using today's sophisticated measuring techniques, 50mg of oral cocaine is barely enough to cause measurable effects in humans.

Apparently, N-(1-hydroxyethyl) lysergamide is an adduct compound formed from lysergamide (LSA) and acetaldehyde. This hints towards the idea that it isn't the most stable of compounds, but would be pretty easily formed by the combination of lysergamide & acetaldehyde under physiological conditions (mixing of the two).

Just a bunch of mindless ramblings.

Let us know if you've had any more experiences with the morning glory wine...curious to see if you had any more that turned out like the one you mentioned above--sounds promising.

The experience by space doubt sounds very interesting.

Albert Hoffman makes the claim that claim that ergonovine and lysergic acid hydroxyethylamide posses hallucinogenic activity--and these two compounds are allready found in amounts in the seeds.

lysergic acid hydroxyethylamide and ergonovine and others are probably good bets for producing most of the effects. But these are not as water soluble as d-ergine and d-isoergine in the seeds. So traditional water extracts and those that start with petro ether most likely produce a brew high in d-ergine & d-isoergine and little else. However...

Tartaric acid in the wine--or even adding a dash of tartaric acid to a cold distilled water extract may result in water-soluble salts of ALL the alkaloids. This should produce a much more well 'rounded' beverage.

I do seem to recall that hermes used to add a squirt of lemon juice or two to the extracts several times. Hermes was also known to do a three hour cold distilled water extract with minimal nausea once--still got the actives but kept the non-polar components from dissolving by using the tea-bag method. Although most of the time he used 30 to 45 min extractions...but the longer soak time in the fridge sounds promising--while most of the noxious non-polar compounds will remain inside the tea-bag.

Look forward to trying this in a dream and comparing it with plain cold-distilled water extract...but the cold wine extract in the fridge sounds quite promising--or even perhaps the cold-distilled water extract with dash of tartaric acid.

Interesting extract space doubt.

From a wikipedia article written by morninggloryseed

jon

  • Foundress Queen
  • *****
  • Posts: 1,883
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #58 on: November 21, 2010, 06:53:25 PM »
basically the carbinoylamine epimerises it and it breaks down to d-ergine in-vivo.

tregar

  • Subordinate Wasp
  • ***
  • Posts: 122
Re: n-hydoxyethylsergic acid amide and it's lsd equipotent n-butylhydroxylysergeamid
« Reply #59 on: December 01, 2010, 02:47:33 AM »
Yes, space doubt's brew is quite interesting.....remember reading about it years ago, it is simplistic and gets results...also leads to reflections on Krystle Cole's (Lysergic book) wine ergot sacrement that caused open and closed eye visuals that seem to mirror the powerful experiences the initiates were having inside the Telestrion at Eleusis. In the brand new book "Acid diaries", the last chapter is devoted to Eleusis, Hofmann's experiments with ergometrine (ergonovine), it's a good read.

Excellent post Jon!!

This coming spring hopefully going to be dreaming up some similar experiments to see if they get results.

Swim has 99.9% tartaric acid powder used in wine making, and when swim had mixed in a tiny dash with fresh cold water extracts of morning glory seeds in the past, they resulted in powerful experiences...it does make a difference. Just be careful to keep the ph at 3 or above, only a tiny amount of 99% DL tartaric acid powder is needed, be sure to use ph paper or meter.

There is a huge difference between trips when swim used the 99% DL tartaric acid blended in with the extraction, it does work, just as Hermes used squirts of lemon juice and had the most poweful experience that one time.

Excellent tips and research Jon.
« Last Edit: December 01, 2010, 02:50:48 AM by tregar »