Activity of Ergolines in Ergot

[Solipsis]

I'm inclined to agree. Non-polar washes are afaik just meant to clean possible pesticides or perhaps cyanoglycosides off the coatings. As far as undesirable alkaloids go, what would they be?
From what I understand, letting LSA products sit for a long time encourages degradation of the various LSA's to other compounds not initially present in the fresh seeds, or otherwise in more modest concentrations. Perhaps that is an assumption based on observing terrible effects from old seeds?
Firstly I imagine those theoretically nasty compounds are relatively similar in property to the desirable alkaloids so you cannot just purify that with any basic setup (I am saying that because ergolines are complex polycyclic compounds that I don't think can just lose part of that polycyclic structure), indeed chromatography is needed to separate considerably similar chemicals. And secondly I believe the LSA alkaloid composition can be somewhat complex to begin with, and that does not tend to bode well for keeping a clear picture of contents and separating that into desirables and undesirables. Again, unless there are usable differences in property / characteristics like polarity / solubility.

Anyway to begin with you need to know what you want to get rid of, otherwise how could you hope to achieve anything besides with luck? Is it even proven that fresh seeds already contain specific alkaloids that are mostly responsible for side-effects? Or is it just the basic LSA alkaloid itself and maybe various amide forms present, that can inherently produce those side-effects but just don't do that every single time. I am getting PD Dirty Acid debate flashbacks..

 

[red22]

Seems like there may be truth to the selectivity thing afterall.

Request: Somebody study these two articles and tell us how to decrease the amt. of all ergoline chemicals other than ergine in an extraction. Also, a person on another message board claims he was able to filter chanoclavine out of a C. paspali preparation using bentonite clay. Any truth to that?

Genest, K. A direct densitometric method on thin-layer plates for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds. Journal of Chromatography A. 15 February 1965, 19(3):531-9. DOI: 10.1016/S0021-9673(01)99495-6. DOWNLOAD

Chao, Jew-Ming; Ara DerMarderosian. Ergoline alkaloidal constituents of Hawaiian baby wood rose, Argyreia nervosa (Burm. f.) Bojer. Journal of Pharmaceutical Sciences. 1973, 62(4):588-91. DOI: 10.1002/jps.2600620409. DOWNLOAD

 

[red22]

Determining less toxic preparations of morning glory seeds is a pressing issue. See above post.

 

[red22]

Bump. How does one get an ergine-only infusion? Ice water, perhaps?

 

[MrHappyッ]

purify the extract with chromatography, keep only the LSA alkaloids, trash anything else.

Or just get your ergot from actual ergoty grain.

 

[red22]

I wasn't being completely literal. I want to know how the average person can take advantage of the different solubility properties of ergoline chemicals so they can use morning glory seeds in the safest way possible.

 

[red22]

Or just get your ergot from actual ergoty grain.

Morning glory seeds are a form of ergot too (see below information). There's nothing "actual" about the grasses aside from the fact that the grasses contain ergopeptines and morning glory seeds don't, at least not in significant amts. The traditional LSD precursor, ergotamine, is an ergopeptine. And C. paspali has the same chemical profile of morning glory seeds. Most forms of traditional ergot don't even contain significant amts. of LAA:

We analyzed ergot of wheat and ergot of barley in our laboratory and they were found to contain basically the same alkaloids as ergot of rye, viz. alkaloids of the ergotamine and ergotoxine group, ergonovine, and sometimes also traces of lysergic acid amide. As I said before, ergonovine and lysergic acid amide, both psychoactive, are soluble in water whereas the other alkaloids are not.

Albert Hofmann. The Road to Eleusis: Unveiling the Secret of the Mysteries. 1978. R. G. Wasson, Albert Hofmann, and Carl A. P. Ruck. Page 10. DOWNLOAD


Kucht S, Gross J, Hussein Y, Grothe T, Keller U, Basar S, König WA, Steiner U, Leistner E. Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides. Planta. 2004 Aug;219(4):619-25

Steiner U, Ahimsa-Müller MA, Markert A, Kucht S, Groß J, Kauf J, Kuzma M, Zych M, Lamshöft M, Furmanova M, Knoop V, Drewke C, Leistner E (2006) Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants. Planta 224:533-544

Ahimsa-Müller MA, Markert A, Hellwig S, Knoop V, Steiner U, Drewke C, Leistner E. Clavicipitaceous fungi associated with ergoline alkaloid-containing convolvulaceae. J Nat Prod. 2007 Dec;70(12):1955-60

Markert A, Steffan N, Ploss K, Hellwig S, Steiner U, Drewke C, Li SM, Boland W, Leistner E. Biosynthesis and Accumulation of Ergoline Alkaloids in a Mutualistic Association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean Fungus. Plant Physiol. 2008 May;147(1):296-305. doi: 10.1104/pp.108.116699


Full copies available in my MG seed info archive: http://www.bluelight.org/vb/entries/7141-morning-glory-seed-information-archive


Overview of the research:

edit: hidden for length

NSFW:

Taber WA, Heacock RA (1962) Location of ergot alkaloid and fungi in the seed of Rivea corym- bosa (L.) Hall. , “Ololiuqui”. Canad J Microbiol 8:137-143

Taber WA, Vining LC, Heacock RA (1963a) Clavine and lysergic acid alkaloids in varieties of morning glory. Phytochemistry 2:65-70

Dobberstein RH, Staba EJ (1969) Ipomoea, Rivea and Argyreia tissue cultures: Influence of vari- ous chemical factors on indole alkaloid production and growth. Lloydia/J Nat Prod 32:141-147

Taber WA, Heacock RA, Mahon ME (1963b) Ergot-type alkaloids in vegetative tissue of Rivea corymbosa (L.) Hall. f. Phytochemistry 2:99-101

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

Mockaitis JM, Kivilaan A, Schulze A (1973) Studies of the loci of indole alkaloid biosynthesis and alkaloid translocation in Ipomoea violacea plants. Biochemie und Physiologie der Pflanzen 164:248-257

Boyes-Korkis JM, Floss HG (1992) Biosynthesis of ergot alkaloids: Some new results on an old problem. Prikl Biokhim Mikrobiol 28:843-857

Bacon CW, Porter JK, Robbins JD, Lutrell ES (1977) Epichloë typhina from toxic tall fescue grasses. Appl Environ Microbiol 34:576-581

Morgan-Jones G, Gams W (1982) Notes on Hyphomycetes. XLI. An endophyte of Festuca arundinacea and the anamorph of Epichloë typhina, new taxa in one of two new sections of Acremonium. Mycotaxon 15:311-318

Glenn AE, Bacon CW, Price R, Hanlin RT (1996) Molecular phylogeny of Acremonium and its taxonomic implications. Mycologia 88: 369-383

Bacon CW, DeBattista J (1991) Endophytic fungi of grasses. In: Arora DK, Rai B, Mukerji KG, Knudsen GR (eds) Handbook of applied microbiology. Soils and plants, vol 1. Marcel Dekker, New York, p 231

Porter JK (1995) Analysis of endophyte toxins: fescue and other grasses toxic to livestock. J Anim Sci 73:871-880

Petroski RJ, Powell RG, Clay K (1992) Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte. Nat Tox 1:84-88

White JF Jr (1997) Systematics of the graminicolous Clavicipitaceae. In: Bacon CW, Hill SH (eds) Neotyphodium/grass interactions. Plenum Press, New York, pp 27-39

Clay K (1990) Fungal endophytes of grasses. Annu Rev Ecol Syst 21:275-297

Powell RG, Plattner RD, Yates SG, Clay K, Leuchtmann A (1990) Ergobalansinine, a new ergot- type peptide alkaloid isolated from Cenchrus echinatus (sandbur grass) infected with Balansia obtecta, and produced in liquid cultures of B. obtecta and Balansia cyperi. J Nat Prod 53:1272-1279

Jenett-Siems K, Kaloga M, Eich E (1994) Ergobalansine/ergobalansinine, a proline-free peptide- type alkaloid of the fungal genus Balansia, is a constituent of Ipomoea piurensis. J. Nat. Prod.57:1304-1306; Erratum: Correction of the species: I. asarifolia (Desr.) R. & Sch. (2004) J Nat Prod 67:2160

Tofern B, Kaloga M, Witte L, Hartmann T, Eich E (1999) Occurrence of loline alkaloids in Argyreia mollis (Convolvulaceae). Phytochemistry 51:1177-1180

Kucht S, Groß J, Hussein Y, Grothe T, Keller U, Basar S, König WA, Steiner U, Leistner E (2004) Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides. Planta 219:619-625

Steiner U, Ahimsa-Müller MA, Markert A, Kucht S, Groß J, Kauf J, Kuzma M, Zych M, Lamshöft M , Furmanova M, Knoop V, Drewke C, Leistner E (2006) Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants. Planta 224:533-544

Schardl CL (1996) Epichloë species: fungal symbionts of grasses. Annu Rev Phytopathol 34:109-130

Schardl CL, Leuchtmann A, Spiering MJ (2004) Symbioses of grasses with seedborne fungal endophytes. Annu Rev Plant Biol 55:315-340

 

[red22]

Bump. How does one get an ergine-only infusion? Ice water, perhaps?

Adsorbent minerals: http://www.bluelight.org/vb/entries/7584-how-to-remove-toxic-alkaloids-from-ergot


Can anyone translate this German article, which is one of the only reports on the effects of isolated ergine in humans:


...euphoria, synesthesia and altered time experience were observed.

Heim E, Heimann H, Lukács G. 1968. Die psychische Wirkung der mexikanischen Droge „Ololiuqui“ am Menschen. Psychopharmacologia (Berl.) 13, 35–48. DOWNLOAD

...

 

[serotonin2A]

Morning glory seeds are a form of ergot too (see below information).

Morning glory seeds are certainly not a form of ergot. Ergot is a species of parasitic fungus from the genus Claviceps. Morning glory seeds are produced by plants from the Convolvulaceae family. Morning glory seeds may contain ergot alkaloids due to infection by a parasitic fungus, but that does not make them a form of ergot.

 

[red22]

I wasn't literally saying that they are a form of ergot. The drug of morning glory seeds is a combination of two biological entities. When people speak of ergot do they always say "we harvested ergot-infected grass", or do they just say "we harvested ergot."

Perhaps I could have phrased my original statement better...

 

[serotonin2A]

I wasn't literally saying that they are a form of ergot. The drug of morning glory seeds is a combination of two biological entities. When people speak of ergot do they always say "we harvested ergot-infected grass", or do they just say "we harvested ergot."

Perhaps I could have phrased my original statement better...

You can do both types of harvesting, what it is called depends on what is actually collected. If you collected rye that was infected with ergot then you would literally be harvesting rye that was infected with ergot. If you seperated the sclerotia from rye and collected the fungus, then you harvested ergot.

 

[red22]

rEQUESTS:

Strickland JR, Oliver JW, Cross DL (1993) Fescue toxicosis and its impact on animal agriculture. Vet Hum Tox 35:454-464

Strickland JR, Cross DL, Birrenkott GP, Grimes LW (1994) Effect of ergovaline, loline, and dopamine antagonists on rat pituitary cell prolactin release in vitro. Am J Vet Res 55:716-721

 

[red22]

Request:

Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high
Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW
Forensic Science International
April 2015, Volume 249, Pgs. 281–293
DOI: 10.1016/j.forsciint.2015.02.011
http://www.fsijournal.org/article/S0379-0738(15)00074-2/abstract

 

[red22]

I have a pertinent question.

Otto Snow in LSD speaks of obtaining an extract of ergot that contains "prevalently" ergine and isoergine, however I'm having trouble identifying the processes he's referring to. I looked at Grawert 1980, part of which is included earlier in the book, but said article doesn't mention ergine once, and it was too complicated for me to understand if the process connects to what Snow says in the below quote. This article mentions charcoal and bentonite (mentioned in the quote), so I assumed that Snow was referring to it.


The usual procedures of extraction with suitable organic solvents, such as benzene, chloroform, methylene chloride and the like, or absorption with the known absorbent means, such as charcoal, bentonite and the like, under alkaline conditions, may be used for the separation and isolation of the mixture of the obtained alkaloids. The mixture, in which lysergic acid amide and isolysergic acid amide are prevalently present, can then be hydrolyzed with alkali, in known manner, to lysergic and isolysergic acid (J. Chem. Society, 1934, p. 674, and 1936, p. 1440).

LSD. Otto Snow. Thoth Press (2003). Pg. 178. Bolding added.


Grawert, W; Schiedt, L.; Neumann, B.; Heidenbluth, K; Dauth, C; Schirutschke, R.; Müller, M.; Process for the Isolation of Ergot Alkaloids from Culture Suspensions; 1980; US 4,237,291

This article can be viewed here: https://www.google.com/patents/US4237291?dq=4,237,291


Additionally, please note the request for a new analysis of morning glory seeds in the previous post.


By the way, the ergine hypothesis stated in this video was the original topic of this thread, which went by the wayside (which is understandable as I didn't summarize it and people aren't wont to read long linked-to articles). Perhaps somebody wants to weigh in on this hypothesis (epimers and conformations; structural comparison to LSD...) https://www.youtube.com/watch?v=NJS25nEcdZg

 

[yessa]

Sorry to bump such an old thread.
But it's the best thread about this topic on the net I could find so far!

If any of you is still interested in this topic, I would like to see if we could find anything new.
Some time ago I started a similar thread on the Nexus (https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=75332)

Just as a short sidenote:
It seems the famous quote from "The ergot alkaloids", that LSH easily decomposes in an acid solution, is nothing but a really bad translation error!
It actually seems to be quite stable in acidic environments, except for epimerization.
What LSH really cannot stand is high temps and alkaline environments.
Although I don't know it's behaviour in very acidic environments, like PH 0 in the stomach. One would have to test this.
But they could find LSH in human blood and urine after ingestion of the seeds. So it seems like it can find it's way into the blood, even through the stomach.
(if anyone is interested in more info, and citations to the corresponding papers, just look in the linked thread, as I don't want to spam everything here)

It's really a pity Hofmann isn't in this world anymore, otherwise I would have been sure, he could have shed some light on the topic, what he thought about LSH.

 

[Limpet_Chicken]

These alkaloids, at least those with a double bond which can epimerize are VERY sensitive to PH. And probably the best way to strip the alcohol would be to line (externally) the flask with Al foil to exclude light, as well as the still head, condenser, etc. and distill in the cold using a vacuum of sufficient strength to strip the alcohol under reduced pressure, cold, and rather than using a capillary bleed connected to the outside atmosphere (when doing a vacuum distillation, they can and probably will, unless distilling very small quantities of distillate) bump like crazy (boil uncontrollably, spitting upwards, and potentially throwing undistilled contents of the still pot directly up into the still head and condenser) and thus contaminating your distillate with the unpurified contents of the still pot) To circumvent this, the usual way is to use a capillary tube with a very fine bore. One can be bought, or made. The latter by either taking a broken thermometer (alcohol, preferably, rather than mercury since one does not want Hg all over the place, or in your distillate), subject it to purge via vacuum in an EMPTY pot (not the flask your using for your distillation) to remove any residual thermometer contents, alternatively employ a blowtorch at a distance to heat a glass pasteur pipette and SLOWLY, steadily, pull it down to a thin, thin whisker (making sure to insert this inter a thermometer adapter with the wide end first, so as not to break the capillary, they are very fragile made like this.)

The principle is to introduce, pulled via the vacuum a fine stream of air bubbles which give a nucleation point and prevent the sudden localized flashboiling that causes bumping (normal bumping chips don't work under vacuum since all the air adsorbed onto the surface is removed by the low pressure environment of the interior of the flask) although according to at least what I have read a magnetically spun stirbar works. But this I have never tested, never having had to use this way, and often heating things in metal (steel/iron) based oil or water baths which of course both distance the magnet of the stirrer from the flask and stirbar inside it and are ferromagnetic themselves, so its always made sense for me to use glass capillaries)


Also not all of the ergot alkaloids are liposoluble. Indeed in Kren and Kvac's 'the genus claviceps' it has an amusing (for everyone but the chemists in question' that for a long time they looked for the oxytocic factor of ergot in the nonpolar phase, after basing, assuming it would be there. It wasn't. It was hydrophilic and they had been chucking it in the aqueous fractions straight down the drain

 

[Limpet_Chicken]

Also, albeit my edition is old, but it does state that ergine is without biological activity.

 

[yessa]

Also, albeit my edition is old, but it does state that ergine is without biological activity.

Lol, then your edition really has to be old. There have been quite some human trial studies on ergine in the 50s and 60s. And prior to that Hofmann himself had tested it.
There's no doubt that ergine shows biological activity. It's just that there is serious doubt it shows a "psychedelic" activity.
The studies mainly concluded that it acts as a sedativum and yields a state of apathy.

Are you a chemist? As I'm not quite sure what you wanted to tell with the post above (a bit above of my head). An extraction of LSH?

I think Gröger basically showed a good way to get the alkaloids without destroying the LSH.
All newer research I found on this topic basically still used his procedure (with little changes).
The main point is surely: Do make the alkaline extraction step as short as possible and only use quite low PH values and certainly no heat.
Also Hofmann stated that it's the alkaline step in the extraction which kills the LSH (if you don't handle it properly).

BTW: If you're a chemist, I would be very interested, what you think about what could happen to again expose LSA to acetaldehyde in an alcohol.
TLCs showed that there is a molecular change happening, but noone knows into what.
This molecular change did not happen, when there was 50% of water in the alcohol.
All the chemists I know so far in unisono claimed that it is very unlikely that the product could again be LSH. But what molecular change could it be?

 

[tregar]

I've read this thread from beginning to end, here is a brand new thread as well:

"Potent LSH & penniclavine fresh from morning glory vine & relation to Eleusis in ancient Greece"

Lysergamides - Potent LSH & penniclavine fresh from morning glory vine & relation to Eleusis in ancient Greece

Update 7.24.2022: LSH extract tek: 500 Heavenly blue morning glory extract in 1oz everclear + 1 oz wine, imagine your best 3 hit LSD experience x 2...

www.bluelight.org

and this as well you might find interesting, has to do with morning glory seeds and why were added to wine by ancient Aztec and Mayans:

At-home conversion of LSD to 1-acetaldehyde LSD in 1 step (similar to but beyond even ALD-52)

Lysergamides - At-home conversion of LSD to 1-acetaldehyde LSD in 1 step (similar to but beyond even ALD-52) like upgraded version of LSD

Update 10.16.2021: THH or Tetrahydroharmine + 1-acetaldehyde LSD (similar to ALD-52) combo, like high dose mescaline with pics: https://www.bluelight.org/xf/threads/thh-or-tetrahydroharmine-1-acetaldehyde-lsd-similar-to-ald-52-combo-like-high-dose-mescaline.910640/ :love: :love: :love...

www.bluelight.org

 

[tregar]

This is a very good thread by Red22, read all 5 pages.

Update 7.6.2022:

500 Heavenly blue morning glory extract in 1oz everclear + 1 oz wine, imagine your best 2 hit LSD experience x 2

500 Heavenly blue morning glory extract in 1oz everclear + 1 oz wine, imagine your best 2 hit LSD experience x 2 - Botanicals

Growing Magic Mushrooms, Mushroom spores, Ayahuasca, Magic Mushroom, Cultivation, Magic Mushroom Cultivation, Psilocybe Mushrooms, Cactis and Cannabis, including research, legislation, media coverage, bibliography and lots of links

mycotopia.net