Activity of Ergolines in Ergot

[red22]

Valuable paper:


Argyreia nervosa (Burm. f.): receptor profiling of lysergic acid amide and other potential psychedelic LSD-like compounds by computational and binding assay approaches.

Paulke A, Kremer C, Wunder C, Achenbach J, Djahanschiri B, Elias A, Schwed JS, Hübner H, Gmeiner P, Proschak E, Toennes SW, Stark H.

J Ethnopharmacol. 2013 Jul 9;148(2):492-7. doi: 10.1016/j.jep.2013.04.044. Epub 2013 May 7.

Institute of Legal Medicine, Goethe University of Frankfurt/Main, Kennedyallee 104, D-60596 Frankfurt/Main, Germany. [email protected]


Download

 

[red22]

I noticed that lysergic acid amide is a category of chemicals, in addition to being an individual chemical: lysergic acid amides a.k.a. lysergamides. It should also be noted that the ambiguity applies to lysergamide as well, as lysergamide can also refer to both the category or the chemical. Eckhart Eich uses the term ergine, which is a synonym for the chemical, lysergic acid amide. And Eich's information seems very professional. Is ergine a more scientifically accurate term? Should lysergic acid amide be considered outdated?


Eckhart Eich. 2008. Solanaceae and Convolvulaceae: Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economics Significance (a Handbook).

 

[dingophone]

I noticed that lysergic acid amide is a category of chemicals, in addition to being an individual chemical: lysergic acid amides a.k.a. lysergamides. It should also be noted that the ambiguity applies to lysergamide as well, as lysergamide can also refer to both the category or the chemical. Eckhart Eich uses the term ergine, which is a synonym for the chemical, lysergic acid amide. And Eich's information seems very professional. Is ergine a more scientifically accurate term? Should lysergic acid amide be considered outdated?


Eckhart Eich. 2008. Solanaceae and Convolvulaceae: Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economics Significance (a Handbook).

Lysergic acid amide is a perfectly valid name for the chemical; it is literally lysergic acid with an amide group. I don't think the name should be changed, as when referring to the group of chemicals one really should say lysergic acid amides. One doesn't confuse amphetamine with amphetamines, tryptamine with tryptamines, or isoxazole with isoxazoles. Calling lysergamide sounds a bit silly to me, but no reason for it not to be valid.But no harm in playing it safe and calling it LAA-11 or ergine!

 

[Docta]

....... Is ergine a more scientifically accurate term? Should lysergic acid amide be considered outdated?

When naming a chiral compound with two stereocenters such as Ergine. I like to use a single descriptive term that also conveys chirality and iso position that clearly defines configuration of the carbon @ 8 close to the carboxy group and 5 adjacent to the nitrogen atom. Using the names Ergine & LSA leaves no speculation on the chiral configuration. Terms like d-lysergic acid amide would be acceptable but seem a bit clunky so I just tend to go with the shortest abbreviation LSA.

I think Eich's use of the term "Ergine" is one of specific molecular configuration, not a denunciation of Lysergic acid amide as a nomenclature term or to bring into question it's validity as a naming word for the substance. As long as we know exactly what's being discussed any of the terms are OK.

 

[red22]

Thanks for the input, guys.

But no harm in playing it safe and calling it LAA-11 or ergine!

It's actually LA-111, but I was under the impression that this was a Sandoz "in house" code name.

All the ergot alkaloids are insoluble in water as the freebases

http://www.drugfuture.com/chemdata/structure/Chanoclavine.gif
chanoclavine

http://www.drugfuture.com/chemdata/structure/Agroclavine.gif
agroclavine

http://www.drugfuture.com/chemdata/structure/Elymoclavine.gif
elymoclavine.

http://upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Lysergol.svg/150px-Lysergol.svg.png
http://en.wikipedia.org/wiki/Lysergol
lysergol

AFAIK, none of these are active at 5ht2a.

By the way, do we know if any of the chemicals exist in the seeds as their freebases? Do you think that these chemicals are only fat soluble as their freebases?

 

[red22]

The "Summary" in the following paper isn't the entirety of this paper, is it? If not, can someone obtain it for us?


http://link.springer.com/article/10.1007/BF00401617

Psychopharmacologia
30. Mai 1968, Volume 13, Issue 1, pp 35-48
Die psychische Wirkung der mexikanischen Droge „Ololiuqui“ am Menschen
E. Heim, Prof. Dr. H. Heimann, G. Lukács

 

[red22]

Is anybody interested in an archive of information on morning glory seeds? I've gathered so many things, including the document I requested above.

Download it here.

What this archive contains:

human trials of isolated lysergamides
alkaloid-specific info
chemical analyses of morning glory seeds
morning glory seeds are infected with fungi related to ergot
naming issue, Ipomoea violacea/Ipomoea tricolor
publications
vasoconstriction and other somatic effects
cyanogenic glycosides
insight into extraction methods
is there a toxin(s) found in the fuzzy outer layer of A Nervosa seeds?
ololiuhqui, spelling and pronunciation
misc
cultivation
preparation method used by the mesoamericans
synthesis of lysergic acid amide
animals tripping on morning glory seeds
are morning glory seeds treated with a fungicide or a deterrent?
good resource for scientific articles

 

[EarthBounded]

Ahhh this has caught my attention

 

[red22]

I was surprised to see that the following statement in the following terrible Wiki on morning glory seeds actually had a reference. Would anyone mind evaluating it?

http://psychonautwiki.org/wiki/LSA_Adducts


It has been documented that Lysergic Acid Amide (LSA) is capable of forming adducts with various aldehydes.[1]

1. F. Arcamone, E. B. Chain, A. Ferretti & P. Pennella. Formation of 2,3-Dihydroxybenzoic Acid in Fermentation Liquors during the Submerged Culture Production of Lysergic Acid α-Hydroxyethylamide by Claviceps paspali Stevens and Hall. Nature 192, 552 - 553 (11 November 1961); doi:10.1038/192552a0
http://www.nature.com/nature/journal/v192/n4802/abs/192552a0.html

 

[red22]

bump

 

[tryp2fun]

I was surprised to see that the following statement in the following terrible Wiki on morning glory seeds actually had a reference. Would anyone mind evaluating it?

http://psychonautwiki.org/wiki/LSA_Adducts

It has been documented that Lysergic Acid Amide (LSA) is capable of forming adducts with various aldehydes.[1]

1. F. Arcamone, E. B. Chain, A. Ferretti & P. Pennella. Formation of 2,3-Dihydroxybenzoic Acid in Fermentation Liquors during the Submerged Culture Production of Lysergic Acid α-Hydroxyethylamide by Claviceps paspali Stevens and Hall. Nature 192, 552 - 553 (11 November 1961); doi:10.1038/192552a0
http://www.nature.com/nature/journal/v192/n4802/abs/192552a0.html

I read the abstract. It is hard to tell more without reading the entire paper, but the fact that the fungus produces lysergic acid α-Hydroxyethylamide in culture says nothing about the mechanism of formation of the compound. Biosynthesis often follows completely different pathways than chemical synthesis. Chemically, amides do not react with aldehydes in dilute aqueous solution, since amide nitrogens are only very weakly basic and nucleophilic.

 

[red22]

Chemically, amides do not react with aldehydes in dilute aqueous solution, since amide nitrogens are only very weakly basic and nucleophilic.

Very interesting. So you're saying that the idea of boosting the LAH content in an MG seed preparation could never be true?


For those just tuning in, we've already established that LAH seems to be naturally present in the seeds in high amounts, based on one chemical analysis; and that it probably decomposes before reaching the brain.

 

[red22]

Question. I plan on doing a basic water-based extraction of Ipomoea tricolor seeds soon where I will grind the seeds up in a NutriBullet; soak them in water for an extended period of time (any input on the duration would be appreciated); filter the solid bits from the liquid using a cotton straining bag, and evaporate the liquid in the oven. Would it be safe to expose the seed infusion to the oven temperature for hours upon hours? I put a Pyrex bowl in the oven earlier and set the oven to a low temperature and left it in the oven for a while. I took it out and pressed it against my arm and it felt like it was around 200 degrees Fahrenheit.

 

[sekio]

If your pyrex bowl was really 200f it would have left a welt.

It's impossible to say qualitatively about extraction yields. etc, unless you have a HPLC. Sorry but that's probably why nobody's answering your Qs.

And yes I think a quadricyclic C-N compound like agroclavine would be highly water insoluble as a FB.

 

[red22]

Thanks. I also asked you a separate question via PM...

 

[sekio]

To be 100% honest: again, I don't know about whether a specific extraction will or will not work with whatever method until you try it, and preferably HPLC it.

With the technique I posted you should be able to get some sort of residue that is enriched in alkaloids.It's very similar to Hoffman's tek, in fact it is functionally the same... Just follow the tek to the letter and see what happens?

The question being: if you took crude MeOH extract of morningglory/woodrose, remove alcohol, and defat with naptha, are alkaloids retained on paper? Probably, yeah. The alkaloid salts are insol. in naptha, it's just there to remove fats!

 

[red22]

And what I described in my PM* is exactly what you told me to do back on page 2?

And an additional question about this. Even though the indoles aren't soluble in the petroleum ether, they can still be moved into the petroleum ether if too much agitation is used, right? And instead of sitting on top of the coffee filter at the end of the extraction they would drip through... So the way to prevent this would be to simply place the tar in the petroleum ether and allow it to sit for a bit and afterwards just lightly shake it and then run the preparation through the filter. Contrarily, if one were to blend this preparation, they would have to wait quite a while before running it through teh coffee filter. Is this correct?

*So, if I took some morning glory seed tar-like extract and dissolved it in a generous amount of petroleum ether and allowed this preparation to drip through a coffee filter, the surface of the coffee filter material would be coated with indoles after all the PE had dripped through?

 

[sekio]

Even though the indoles aren't soluble in the petroleum ether, they can still be moved into the petroleum ether if too much agitation is used, right?

No, they're not soluble. Which means they don't dissolve. They won't "move" into the pet ether just because you mix it a lot, that is not how solubility works.

Follow the tek, it's not that hard!

 

[red22]

So, I have several articles that detail that sophisticated acid-base extractions were used when determining the chemical profiles of these seeds (example, below). Is it safe to assume that all the chemical extractions of these seeds don't remove a god damn thing as far as undesirable alkaloids? Indeed, an individual on another forum told me that one would need chromatography in order to get rid of undesirable ergoline chemicals. I look forward to hearing Bluelighters' opinions on this.

The ground seed material was extracted for 30 min with 25 ml of acetone-2% aqueous tartaric acid (7:3, v/v). The extract was filtered, and the residue re-extracted twice more for 10 min with 25 ml of the acetone-tartaric acid solution. The acetone was removed from the combined extracts in a rotary evaporator at below 35°. The aqueous residue was washed three times with 25-ml portions of methylene chloride-isopropyl alcohol (3:1, v/v). The pH of the washed aqueous extract was then adjusted to pH 7.7-8.2 with a saturated solution of sodium bicarbonate. The alkaloids were extracted from this with three portions of 25 ml methylene chloride-isopropyl alcohol (3:1, v/v) and the combined extracts were taken to dryness.

Amor-Prats D, Harborne JB (1993) New sources of ergoline alkaloids within the genus Ipomoea. Biochemical Systematics and Ecology, 21:455–462

 

[red22]

bump! see last post