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Activity of Ergolines in Ergot

Water and methanol are pretty different in terms of dissolving power. I wouldn't substitute anything; methanol is easy to acquire most places and Hofmann would have used water if it had worked, I'm sure - it costs less.
 
What about using the petroleum ether on an infusion (methanol or water) rather than on dried extract. And then siphoning off and saving the infusion which will have been refined by the petroleum ether.
 
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sekio said:
Water and methanol are pretty different in terms of dissolving power. I wouldn't substitute anything; methanol is easy to acquire most places and Hofmann would have used water if it had worked, I'm sure - it costs less.
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If you use sufficient agitation, all the lysergamides will infuse into the water.
 
I'm interested in the feasibility of baking water infusions of morning glory seeds in the oven, so that people don't have to choke down a foul liquid. I have two pieces of information that suggest it's possible to do this without destroying the lysergic acid amides.


"It seems like the ergoline alkoloids present in morning glories, Rivea Corymbosa, and Argyreia Nervosa seem to be resistant to heat." Visual Distortion | https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=6441


I prepared tea by crushing and boiling the seeds.
--
I opened my eyes and noticed that the carpet in my apartment was a luxurious shade of green interwoven with threads of vivid blue. It was almost like a small lake with ripples catching the gleams of the sun.

Stanley Krippner. The Ecstatic Adventure
 
I'm guessing there's a "destruction point", which is something a fair bit greater than the melting point? Does anyone know the melting points of ergine and ergonovine?
 
I was going through the citations listed and it occurred to me that there maybe a way to attack to NH2 without destroying the LSA molecule. A synthesis of lysergic acid from the amide maybe possible if the NH2 is reacted with Nitrous acid. The nitrous acid attack forms a diazo group intermediate that would become unstable in the presence of the of H2O resulting in a OH group substitution at the N=N. The subsequent lysergic acid can then be manipulated by traditional route.

screen shot

The reaction is for primary amines apparently leaving secondary amines unaffected so theoretically the indole ring remains untouched throughout. The production of Nitrous acid under reaction conditions would be by sodium nitrite in a proton transfer from a weak donation source such as Boric acid H3BO3 or some other acid that can be added to an alkaline salt to create an overabundance of OH- ions without attacking the LSA.

Obviously there would need to be an isolation of LSA from the multitude of ergolines found in traditional extract if the source for feedstock is HBWR seeds


red22 said:
I'm guessing there's a "destruction point", which is something a fair bit greater than the melting point? Does anyone know the melting points of ergine and ergonovine?
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ergometrine

Boiling Point: 635.2 °C

Flash Point: 337.9 °C

Melting Point: 235.36 °C

ergine

Boiling Point: 572.3 °C

Flash Point: 299.9 °C

Melting Point: 203.75 °C
 
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sekio said:
I have doubts you can "boil" ergot alkaloids!
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The proprieties were computer generated on the ACD/Labs’ ACD/PhysChem Suite software via the SMILES code, which a in general are reasonably trustworthy. I've not done data vetting previously because your the first to question the modeled result.

I went to the website and after plowing through pages of default function settings I found that there is a guesstimation program with what it describes as "provided with a calculation and margin of error". On viewing the equations for prediction of physicochemical properties used to generate the BP I would best describe them as an adaptation of Stein & Brown probability theory.

Your doubts would seem to be well founded, I had no idea such a respected software suite would be defaulting to probability theory without some kind of warning being attached to the analysis of the molecule. It maybe my fault for turning of the popup boxes.
 
Your doubts would seem to be well founded, I had no idea such a respected software suite would be defaulting to probability theory without some kind of warning being attached to the analysis of the molecule.
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This is why these are property prediction suites, not database lookups!

What I meant by my earlier comment was, I think if you heated ergine to 500C it would fragment into a million fucking pieces and some tar.
 
So, do you think you can bake an aqueous infusion in an oven at a low temperature in order to evaporate the water? What would you say the maximum temperature is?


I found a report of someone doing this.


Chop it up as fine as possible: a blender comes in handy. You may wish to chop then dry. A word of caution : try to avoid exposing your stuff to excessive heat. I dry in low heat oven. Heat and air destroy good compounds from upwards of 100 degs C. All this bit will depend on exactly what you are extracting.

http://www.erowid.org/plants/morning_glory/morning_glory_extraction1.shtml
 
Why is it that isopropanol can't be used in place of methanol/ethanol?
 
Here's something that says chanoclavine is "almost totally insoluble in water."* Chanoclavine is one of the ergoline alkaloids in morning glory seeds. Is anyone aware of sources for the properties of the ergoline alkaloids found in morning glory seeds? This would provide insight as to the cleanness of different types of extractions. Below is a list of these ergoline alkaloids from an analysis done on these seeds.

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Chao & Der Marderosian.

http://www.erowid.org/references/refs_view.php?A=ShowRefTopFrame&ID=7692&DocPartID=6807


*Peter Webster, Carl Ruck (ed) Sacred Mushrooms of the Goddess and the Secrets of Eleusis, Mixing the Kykeon Anew, p. 179
 
red22 said:
................................... Is anyone aware of sources for the properties of the ergoline alkaloids found in morning glory seeds? This would provide insight as to the cleanness of different types of extractions.
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I must be missing something here aren't these properties what we're taking advantage of to narrow the targets for extraction. Whats wrong with going with simplicity like acetone with a mild acid, citric acid/acetone or tartaric acid in methanol with a NP solvent rinse. On the other hand the fats could frozen out and filtered.

As long as resin glycosides are excluded by keeping water to a minimum and the fats that may contain some are removed I don't see the problem in getting to lysergic acid amide tartarate with the focus to build up feedstock to have a go at LSH.

Regarding this concept of LSH from LSA and Acetaldehyde in US 3060104, is this possible? wouldn't other sites on the molecule have more nucleophilicity then the amide nitrogen making it more likely that acetaldehyde would react elsewhere first.

Has anybody read a paper called Separation of ergot alkaloids by adsorption on silicates ?

Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague 4, 142 20, Czech Republic

Abstract
A mixture of ergot alkaloids (agroclavine, elymoclavine, chanoclavine, and chanoclavine aldehyde) was separated
from the Claviceps purpurea fermentation broth by adsorption on inorganic adsorbents containing silica. The
uptake of alkaloids depended on the concentration of adsorbent and pH. The adsorption capacity for of inorganic
materials increased with increasing content of inorganic oxides such as MgO and CaO in the adsorbent. Using
statistical thermodynamics, a simple mathematical model describing the multicomponent adsorption equilibrium
is proposed and a numerical method suitable for fast computer simulation of multicomponent adsorption was
developed.
 
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Docta said:
aren't these properties what we're taking advantage of to narrow the targets for extraction. Whats wrong with going with simplicity like acetone with a mild acid, citric acid/acetone or tartaric acid in methanol with a NP solvent rinse.
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Can you elavorate? What I had in mind was separating the clavine alkaloids from the lysergamides. Webster's literature says chanoclavine, one of the clavines, is insoluble in water (sekio's chanoclavine link confirms this). So I was thinking even a simplistic kitchen preparation would be able to eliminate this one ergoline -- and more, assuming there are other clavines that are poorly soluble in water. This would justify the "thin" water preparations that some people stand by (less side effects), as opposed to a crude preparation achieved by rigorously blending up seeds in water where the water insoluble chemicals will forcibly become suspended in the water. However, sekio brougt up another factor: these chemicals exist as both freebase and salts. This can change properties such as solubility.


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red22 said:
Can you elavorate? What I had in mind was separating the clavine alkaloids from the lysergamides. Webster's literature says chanoclavine, one of the clavines, is insoluble in water (sekio's chanoclavine link confirms this). So I was thinking even a simplistic kitchen preparation would be able to eliminate this one ergoline -- and more, assuming there are other clavines that are poorly soluble in water.................
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I got to say after having a good look lysergamides the structural complexity and stereochemistries make for some impossibly hard head scratching when it comes to how to getting at LSA alone. I understand what your saying with the clavines being insoluble where as the amides interact with or can be dissolved by water and other polar substances so you could say just use water but LSA freebase is subject to instability and oxidation.

I took at the LSA from the angle of subjecting it to the least amount of instability with the quickest extraction possible. I look at what LSA is soluble in that the others are not and how can I make it more stable as a salt. LSA freebase is soluble in acetone and so is tartaric acid but LSA tartrate salt becomes insoluble in acetone. So I like acetone maybe defatted several times with DCM. Or a more conventional A/B extraction.
 
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