Activity of Ergolines in Ergot

[Morninggloryseed]

good stuff. glad to read people still conduct this research/.

 

[King Kong]

Is the amide really the most nucelophilic position on LSA?
Shouldn't we first protect the nitrogen's indole with something like Cbz (which will also deactivate slightly the indole, I think)?

There is really too much speculation about those "lsd derivatives"...

http://herbs.maxforum.org/2012/10/17/we-were-wrong-about-lsh/

There is quite strange things on this forum. Like this: http://herbs.maxforum.org/2011/05/16/recommend-lsd-potentiators/#post3

 

[red22]

There's a paper that identified LAH as a "major component" of I. tricolor seeds: Gröger D. (1963) Über das Vorkommen von Ergolinderivaten in Ipomoea-Arten. Flora 153:373–382

I know this because another paper that I was able to obtain reiterates that fact: Genest K. Changes in ergoline alkaloids in seeds during ontogeny of Ipomoea violacea. J Pharm Sci 1966;55:1284–682 | http://www.erowid.org/references/refs_view.php?A=ShowDocPartFrame&C=ref&ID=7685&DocPartID=6800 (Last paragraph.)

Haven't been able to locate a copy of this, paid or for free. The following two websites have copies of this journal, but not the volume in question. http://www.sciencedirect.com/science/journal/03672530/198/6 | http://www.botanicus.org/title/b11691608

 

[red22]

Stanford University, Cornell University, and University of Michigan all have the above journal. Does anyone here, by chance, have access to those universities?

http://catalog.stanford.edu/view/360636

http://catalog.hathitrust.org/Record/000535883

 

[red22]

I obtained the above paper, thanks to endotropic :D

This is the only paper I've seen that identified lysergic acid hydroxyethylamide as a major component of morning glory seeds. Other analyses found lysergic acid hydroxyethylamide only in trace amounts. Shulgin says the following: "this material is quite unstable and is easily converted in the process of isolation."* To elaborate on that, Hofmann & Stoll state the following: "easily decomposes in a weak acid solution to form ergine and acetaldehyde."**

I'm unable to read the paper mentioned in the preceding post because it's in German, but going by this information, it can be presumed that their methods differed in such a way that allowed for a more accurate analysis of the seeds. Would somebody be able to translate this paper for us?


Gröger D. (1963) Über das Vorkommen von Ergolinderivaten in Ipomoea-Arten. Flora 153:373–382

https://docs.google.com/file/d/0B3BBccfPNsX8dEZEUHZoaXl1UkU/edit?usp=sharing


Chart from the paper. Note that lysergic acid methylcarbinolamide is a synonym for lysergic acid hydroxyethlamide.

*TIHKAL, p.313

**Stoll, A. and Hofmann, A. (1965) The ergot alkaloids. The Alkaloids, Vol. VIII, Manske (ed.), Academic Press, New York, Chap. 21, p. 747

 

[Morninggloryseed]

Makes a lot of sense to me as to why 'fresh' seeds have such a powerful psychedelic effect and the CWE I used to make seemed like an all together different psychedelic....and a not so good one. Although I am still not sure what that last point I made translates to...is the sacred brew of Mexican shamans because of ergine/isoergine in equilibrium or because LSH is extracted into water and you must drink before it breaks down to ergine and acetyl-aldehyde? Or is it a bit of both?

 

[sekio]

I bet you good money it's due to the ergine, if LSH breaks down in acid (viz. the stomach)

The paper is only moderately useful. Probably the best part are the Rf values for chromatography of ergot alkaloids.

It reports there are 0.01 to 0.05% alkaloids in seeds, some varieties have no alkaloids. Extraction with acetone-water-acetic acid mixture. Chromatography on alumina. He says you can find LSH naturally in saphrophytic cultures, C.paspali, etc. "Mild alkaline hydrolysis in a phosphate buffer at pH 8" convers it to LSA + acetaldehyde. (30min @ 70C)

1. Seeds of various Ipomoea-Species have been tested for alkaloids.
2. In seeds of I. rubro-caerulea Hook. and I. coccinea Linn. ergoline derivatives have been discovered for the first time. Some of the investigated samples did not contain alkaloids.
3. In the stem and leaves of plants cultivated in a greenhouse alkaloids were present (origin of seed: Porto, Portugal)
4. For the first time ergonovine and lysergic acid a-hydroxyethylamide have been detected in higher plants. [ed. - higher plants get it huhuh]
5. Methods are described for the chromatographic seperation of simple lysergic acid derivatives.

 

[red22]

Can somebody write elaborated instructions on how to perform the following procedure, minus the chromatography?


We started our extraction studies with Rivea corymbosa. Since we knew nothing of the chemical nature and sensitivity of the active principles, only neutral solvents were used and all extracts were evaporated carefully at low temperature. The finely powdered seeds were extracted with methanol, and the evaporated methanol extracts were defatted with petroleum ether. The defatted residue was tested for various kinds of alkaloids, especially for indolic compounds, since the indole structure was known to occur in psychotomimetic agents. Indeed, when paper chromatograms of this Rivea extract were developed by spraying with a benzene solution of p-dimethylamino benzaldehyde and subsequently treated with hydrochloric acid gas, violet-blue spots appeared, indicating the presence of indolic compounds. In order to assess whether this indole fraction actually represented the active principle, we collected some milligrams of this fraction from a great number of paper chromatograms and my laboratory assistant H. Tscherter and I tested it on ourselves. After my experience with LSD, I have become cautious: we started by taking doses as small as 0.1 mg., gradually increasing the dosage. With 2 mg. of this crude indole fraction we got clear-cut psychic effects: a dream-like state resulted with drowsiness and alterations in the perception of objects and colors. This showed that the indole fraction of the Rivea extract contained the psychic active principles.

Hofmann, A.: The active principles of the seeds of Rivea Corymbosa and Ipomoea violacea. Botanical Museum Leaflets (Harvard Univ., 1963) vol. 20, pp. 201-202
http://www.botanicus.org/item/31753003541189# (Must select desired volume from the drop-down menu.)

 

[sekio]

The finely powdered seeds were extracted with methanol, and the evaporated methanol extracts were defatted with petroleum ether.

Grind seeds in the cold under e.g. grain alcohol (I wouldn't use methanol if you're consuming the extract). Let it stand for a while. Seperate the liquid off of the seed chaff. This gives crude alcohol extract of morning glory.

Evaporate the alcohol, rinse the residue with naptha to remove fats, and redissolve it in grain alcohol for your consumption.

 

[red22]

How exactly does the rinse process work? Also, would you say that this adaptation is better than any method on the Internet?

 

[sekio]

How exactly does the rinse process work?

You add solvent to it and stir (shake, mix) it around and then remove the solvent.

Also, would you say that this adaptation is better than any method on the Internet?

Never done it.

 

[red22]

How exactly is the solvent removed. And any idea on the amount of time for the rinse?

 

[sekio]

1. Find some ergot-containing seeds. HBWR are best. And coffee filters, 2 containers, a dark, well-ventilated place.
2. Find some VM&P Naptha, or Hexane, or Heptane.
3. Find some methanol, 95% or better. (can use ethanol 95 too, or 151 proof, don't use 80 proof)
4. Smash the seeds up finely, so the particles are 0.5mm or less. If you can, use a fine sieve to make sure it's all really really small particles. Put them in a metal, glass or HDPE bowl.
5. Add enough methanol to cover the seeds, then 10 ml more for good luck.
6. Stir them around with a suitable stirring utensil made of glass, plastic or metal. Make sure it gets mixed well.
7. Allow to sit for 20 minutes to an hour (depending on how paranoid you are.).
8. Grab some cheesecloth, or a coffee filter. Filter off the alcohol solution into a new container. Rinse seed mush with more methanol. Discard seed mush after squeezing out as much alcohol solution as possible.
9. Allow the methanol to evaporate in a dark place. (leaving it in the sun will destroy the LSA)
10. When it's all evaporated you will have a gummy seed residue. Add enough naptha to cover it, plus 5-10 ml.
11. Scrape and smoosh the goop around so the naptha contacts all the stuff. Let sit for 10 mins.
12. Filter the naptha off, and discard it. The solid residue is enriched in LSA. Let it evaporate to get all the naptha off, again in a dark place.
13. Dissolve the residue in grain or drinking alcohol and consume it.

 

[red22]

99% methanol is easily ordered online. I'm still confused about the step that involves filtering the naptha. Do you mean evaporate the naptha? Thank you for taking the time to write that, by the way. Also, there are many types of morning glory seeds that contain lysergamides. The drug literature is behind the times. See pages 225, 226, 236, and 238 in the following book: http://en.bookfi.org/book/575809

 

[sekio]

The naptha won't dissolve everything, only non-polar fats. At that stage the LSA should still be as e.g. a citrate salt. So I mean exactly that, filter it by pouring the mixture into a coffee filter and retaining the alkaloids on filter paper as a solid.

This procedure in general is probably not worth doing unless you are extracting more than e.g. 50mg alkaloids, because you will lose some portion on e.g. the vessels and filter papers unless you are very meticulous.

 

[red22]

Eckhart Eich says that all convolvulaceae that contain ergoline alkaloids are in the tribe, Ipomoeeae (which is not to be confused with the species, Ipomoea, one of the members of that tribe). Argyreia, Turbina... they're all members of Ipomoeeae. So does that mean that the most accurate term for these seeds is Ipomoeeae seeds?

 

[16ValveHate]

Would somebody be able to translate this paper for us?

Well I could try, but it will take some time, and it will most likely not meet scientific standards.
I have no background in chemistry, and English is not my first language.
If that doesn't bothers you, I'll do it.

I will try to do at least one page a day, if life doesn't get in the way(wow it rhymes)
If something doesn't make any sense, please say so, it might be due to my translation, and I could try to figure it out.
If the quality is so poor, the whole thing is basically useless, please say so too.
Otherwise it's a waste of time.

Ok I start with only a few sentences for now, I have other things to do first, but I'll be back in a few hours and finish the first page:


Presence of Ergoline derivatives in members of the Ipomea genus

Until lately derivatives of Ergoline where only found in sclerotia and saprophytic cultures of several members of the Claviceps genus.
In 1961 Spilsbury and Wilkinson discovered the ability of fungi unrelated to Clavicipetaceae, to produce Clavinale alkaloids as well.
Even more surprising is the confirmation of Ergot alkaloids in several vascular plants, Hofmann and Tscherter (1960).

Both were able to isolate ergoline derivatives from “Ololiuqui”, a magic plant used by Aztec shamans.
It's use got already documented by spanish analist as early as the 16th century.
Today it still can be found used in magic rituals by some tribes of south Mexico(Hofman 1961, Hofman und Cerletti 1961).

Ololiuqui is not of consistent botany. Hofman examined 2 samples.
One consisted of brown seeds, called “badoh” by the native people, and was identified as Rivea corymbosa (Hall. f. =Ipomea sidaefolia HBK).
The second sample consisted of black seeds, called “badoh negro” by the native people.
This was identified as Ipomea violacea L..
Rivery corymbosa consisted of 0,01% alkaloids, and Ipomea violacea consisted of 0,05% alkaloids.

The spectrum of present alkaloids proved to be almost identical for both samples.
Aside from chanoclavine and elymoclavine d-lysergic acid amide and d-isolysergic acid amide were isolated as main components.
Rivea corymbosa furthermore contained lysergol.Whereas Ipomea violacea contained an alkaloid that couldn't be identified and which was fluorescent under UV-light.

According to Taber and Heacock (1962) the alkaloids are located in the embryo, whereas the husk and the resinous layer beneath are free of alkaloids.

Until now only 2 members of the Ipomoea family , both of Central American origin, have been tested for their alkaloid makeup.
Further research is needed to verify if other members of this genus produce alkaloids too.

It is not known if aside from the seeds other parts of the Ipomoea plants contain alkaloids as well.
The mechanism of production and biosynthesis of Ergoline in vascular plants is unknown to date. Further research will find the answers.


Own studies

The seed material used to carry out our studies was acquired from several botanical gardens in Europe.
The samples listed in the first table contained no alkaloids. The second table lists all alkaloid containing samples.

Samples with no alkaloids

0.5g of seed material was usually taken for analysis. Alkaloid extraction of the seeds and aerial parts of the plant was carried out using a variety of methods.
Most of the times we used a mixture of acetone/tartaric acid. For identification of the alkaloid mix methods of thin layer chromatography and paper chromatography were performed.
Adsorbing materials used include silica gel G”Merck”, soviet silicic acid and Al2O3 ”Greiz-Dölau” (I have no idea how to translate Greiz-Dölau, it might just be the manufacturer, and also I have no clue how I'm supposed to do lower case letters and numbers, sorry)

In Figure 1 and 2 a typical chromatogram is shown. The analysis of a sample from Porto(Portugal)
produced 5 under UV-light fluorescent spots on the plate(silica gel, solvent: acetone, ethyl acetate, dimethyl formamide=5:5:1).
Application of Van Urk reagent caused a violet blue coloration of the spots.
One spot , with an RF value of 0.03, and which was non-fluorescent under UV-light became violet blue as well.
The spots got labeled A-F(figure 1). The intensity of their coloration led to the conclusion substances B, C , D present the main components.

Substance A: Substance A had the same RF-value like chromatographed chanoclavine.
For further identification it was scraped of the plate, eluted and in several systems chromatograms were generated with chanoclavine on the same plate.
This resulted in one spot respectively.

Figure 1

Thin layer chromatogram made from seed extract of Ipomoea rubro-caerulae Hook.
(adsorbent silica gel G "Merck"; developed using solvent mixture 1).


Figure 2

Thin layer chromatogram made from seed extract of Ipomoea coccinea Linn.
(adsorbent Al2O3 "Greiz-Dölau"; developed using solvent mixture 2).



Table 2: Alkaloid containing Ipomoea varieties

Edit:Can someone who is familiar with this stuff please verify if this makes sense so far?

 

[red22]

You're doing a good job so far!


Presence of Ergoline derivatives in members of the Ipomea genus

Until recently, ergoline derivatives were only found in sclerotia and saprophytic cultures of several members of the Claviceps genus.
In 1961 Spilsbury and Wilkinson discovered in fungi unrelated to Clavicipetaceae the ability to produce Clavinale alkaloids as well.
Even more surprising is the confirmation of Ergot alkaloids in several vascular plants, Hofmann and Tscherter (1960).

Both were able to isolate ergoline derivatives from “Ololiuqui”, a magic plant used by Aztec shamans.
Its use was already documented by Spanish analysts as early as the 16th century.
Today its use can still be found in the magic rituals of some tribes of southern Mexico(Hofmann 1961, Hofmann & Cerletti 1961).

Ololiuqui is not of consistent botany. Hofmann examined 2 samples.
One consisted of brown seeds, called “badoh” by the native people, and was identified as Rivea corymbosa (Hall. f. =Ipomoea sidaefolia HBK).
The second sample consisted of black seeds, called “badoh negro” by the native people.
This was identified as Ipomoea violacea L..
Rivea corymbosa consisted of 0.01% alkaloids, and Ipomoea violacea consisted of 0.05% alkaloids.

The spectrum of alkaloids present proved to be almost identical for both samples.

 

[red22]

Edit:Can someone who is familiar with this stuff please verify if this makes sense so far?

Looks good to me. Keep up the good work. By the way, no one saw this comment because you didn't make a new post.

 

[red22]

sekio, how would distilled water work as an alternative to the alcohols? It would just take longer to evaporate, right?

Edit: Spring water or properly filtered water should be fine too.