Ergot Season is comming: Lysergic Acid from Ergot

[Lilienthal]

Ok, everything said me thinks... We don't want to move this thread to the Couch, do we? BTW, no chance regarding the signature... People would start signature wars...

[Dr_Heckyll]

MaDMAx, you mustn't read what you want to read, you must read what is written; here is what I exactly said, and it leaves two options for you:

If you want to be an A+ Analyst you should get a critical mind of your own and get your facts straight...or move your rotten ass out of here, DEA agent MaDMAx.

I was hopeing that you would take my initial (admittedly somewhat caustic) critique as an opportunity to strike me back within the frame of a heated flaming scientific debate. Knowing more about you now, I understand that you had no choice but to take it personal. It never was my intention for our dispute to case ripples throughout The Hive, but after you changed your signature I had to make a move. Of course, as soon as I found out that you changed yours back to normal mode, I followed your good example.

Let's move one; we're both not visiting The Hive to fight some guerilla civil war against one another. Maybe it'll make you feel better when you see it as a learning experience: I guarantee you that what happened to you here by the evilness of Mr. Jive will happen to you again in life. But next time you will be better able to cope with unfair treatment, won't you?


Happiness, health and wealth through chemistry...

[Buster_Hymen]

How viable would the extraction of LSA from morning glory and/or Hawiian Baby Woodrose seeds be, relative to ergotamine?

  \\|//
    ô¿ô    --  Anger management? Fuck that!
    \O/
      '''

[Dr_Heckyll]

Don't they mainly contain lysergic acid amide? I think the average percentages are quite well known, just not to me by heart. I would have to look for it. The method I described would have to be modified, but the key step, adsorption on charcoal, would facilitate things here, too. Take the lysergic acid amide content, and a pessimistically-realistic recovery rate of 25% and you get your lysergic acid yield.


Happiness, health and wealth through chemistry...

[Rhodium]

Heckyll: LSA = LysergSäureAmid = Lysergic Acid Amide

[bujinkan]

madmax, could you tell us some about the origins of the ergot samples? how far apart from each other were the samples taken?

[locrian]

I was hopeing that you would take my initial (admittedly somewhat caustic) critique as an opportunity to strike me back within the frame of a heated flaming scientific debate.

How was referring to MaDMAx as "DEA agent MaDMAx" something that would trigger a "heated flaming scientific debate" or something "within the frame" of one?  That's a personal attack that has nothing to do with science, so why would you expect a scientific answer?  You're bullshitting because you can't admit you acted like an asshole, which is unnecessary and unbecoming.  Why can't you just be a gentleman about your points, disproving or contrary as they may be to others?  Is it necessary to talk shit?  Is it necessary to accuse (and yes that's how anyone would have taken it)?  I got respect for both of you cats, so lets all try to avoid this bullshit in the future and keep things scientific (no calling peeps DEA, ok? - the scientific facts about the graph was more convincing than posting "DEA agent MaDMAx"). 

Anyways, that being said, - good job on the reply, you are pretty convincing in your points.  Swinl just may try something of this nature soon - results would be posted.  This makes me wonder about Catcher in the Rye, now, you know?  Kid goes a little mental?  Dosing perhaps?  j/k Peace.

[Dr_Heckyll]

Rhodium: Heckyll: LSA = LysergSäureAmid = Lysergic Acid Amide

I know, Rhodium, but earlier in the thread I was defining lysergic acid as LSA. Should have probably chosen LA for lysergic acid. Well, stone my...


For every molecule there is a moron thinking it will be a great drug

[hCiLdOdUeDn]

I believe HBWR seeds contain ~0.04% LSA and Morning glory seeds contain ~0.01-0.02% LSA. To get just 1 gram LSA you would need 2.5KGs of HBWR seeds and 5-10KGs morning glory seeds.
hcildoduedn

[bujinkan]

Madmax while i am impressed by your experiment, and i respect you as the A grade researcher that you obviously are, i think that there should really be more analysis before we close the door on unmodified natural ergot strains.

however, ive always thought that cultivation is the way to go..and selectively cultivating ergot in order to make it more effecient may not be as difficult as one would expect.
Madmax, if i was in your position i would analyze ergot samples until i found one that produces a satisfactory amount of alkaloids, then i would attempt to isolate high producing strains using agar. of course, theres a lot to be discovered here.
agar ideas 

Post 226926

(cyril: "Re: ergot and agar", Tryptamine Chemistry)

and of course, growth mediums.

Post 246869

(bujinkan: "Re: ergot and agar", Tryptamine Chemistry) (and further threads)

or, there is the remote possibility that we could mutate ergot strains ourselves.

Post 246873

(bujinkan: "Re: ergot and agar", Tryptamine Chemistry) the Ethyleneimine idea is interesting. 

the point im trying to make here is that while natural ergot sampling is fine, i believe it should be looked at as a first step to better, more efficient way of obtaining lysergic acid via cultivation. Heckyll, even you must admit that for the large scale, wild ergot collection becomes less feasable. this in no way says that lysergic acid from wild samples isnt great for small projects, but self sufficiency may also be an issue, since as madmax's experiments are alluding to, alkaloid production in ergot MAY (emphasis on MAY so that you dont call me an agent) vary widely dependant on who knows what kind of variables.

there....now can we all return to the peaceful utopia that tryptamine chemistry once was? 
 

[Dextrose]

Swim has seen quite affordable bulk seeds recently...
// Dex

[Dr_Heckyll]

[BeeLoyal]

hello , I must apologize for not having a reference, but i have read that european strands of claviceps purpurea have significant amounts of alkaloids , while many other strands of claviceps are useless.

this is a statement of facts i read.  I will be happy if someone actually can find a confirmation.

beeLoyal
The war isnt over!

[terbium]

Sweet dreams ... and good bye!
Don't forget to shut the door on your way out.

PS: there is one last thing you should know: indole, the heart of all tryptamines, smells like, well, faeces (means shit)
Did you read that in the Merck Index? I certainly doubt that you have ever actually smelled purified indole. Have you ever even been in a lab?

[Yachaj]

One of the few good remarks of Uncle Fester in his LSD book was this one at page 5/6:

"Sources Of The Lysergic Amides

Let me begin this chapter by nuking an oft-chanted mantra, this mantra being the claim that a person can grow ergot fungus in a culture medium and get it to produce lysergic acid amides to feed into LSD production. This claim as seen in Psychedelic Chemistry and other publications I read while in college is pure BS. It is truly unfortunate that nature does not cooperate in this manner, since this would obviously be the best way to set up a large-scale production operation, as the logistical complications of crop growth and harvest would then be eliminated.
Let me give a science and literature reading lesson to those who have made these claims. See Proceedings of the Royal Society of London, Series B, Volume 155, pages 26 to 54 (1961). Also see US Patent 3,219,545. You will note while reading these articles detailing how to get lysergic amide production in a culture medium that these guys had to scour the globe to find that rare strain of claviceps fungus that will cooperate in this manner. The vast majority of claviceps fungi just will not produce these alkaloids while being cultured. See the following articles to convince yourself of just how futile it is to collect a wild strain of claviceps and try to get it to produce lysergic acid amides in culture: Ann. Rep. Takeda Res. Lab Volume 10, page 73 (1951); and Farmczco, Volume 1,
page 1 (1946); also Arch. Pharm. Ben. Volume 273, page 348 (1935); also American Journal of Botany, Volume 18, page 50 (1931); also Journal of the American Pharmacy Association Volume 40, page 434 (1951); also US patent 2,809,920; also Canadian Journal of Microbiology, Volume 3, page 55 (1957), and Volume 4, page 611(1958) and Volume 6, page 355 (1960); also Journal of the American Pharmacy Society Volume 44, page 736 (1955). With this matter disposed of, it is time to move on to what actually are viable sources of lysergic acid amides for the production of LSD..."

So far Fester. Unfortunately there is one US patent which he doesn't cite: 3038840. Look it up and you will see in an instant why Claviceps paspali is much better. This fungus produces lysergic acid in aerobic surface culture! (extra bonus: the patent cites a simple 'virulention' technique which re-activates lysergic acid biosynthesis in paspali strains which almost have lost that quality).

Another interesting quality of this funny fungus is that it does not keep the alkaloids in its mycelium (like psilocybians do), no, it excretes the acid in the medium! (*). According to the patent, the lysergic acid can be extracted from the medium with a simple A/B protocol. So you do not need to go through the hassle as described in Am. patent 3183172 for isolating psilocybin (of which the freebase is soluble in water, so A/B doesn't work properly but only yields the less stable psilocin).

In post no. 339507 I described a simple medium for paspali surface cultivation which doesn't need much sterile precautions. It enables mycelium production in the very same container which is later used for the A/B.

The virtue of the addition of peroxide to growing media was first published by K.L. McAlpine in The Orchid Review of January 1947, p. 20-22, and further developed for basidiomycetes by <www.mycomasters.com>. In my experiments with C. paspali the pinkish color reaction is not hurt in any way after the addition of H2O2 (the fungus decomposes it as usual - I suggest to buy the manuals from <www.mycomasters.com> if you want to know all the details - do not inform the author about the fungus you would like to use it for if it is not an edible one).

From old notes I can present a medium which is even better than the one in post no. 339507, that is if you live in an area where the temperature does not exceed 20 centigrade or so: a contamination proof solid-to-liquid medium for areobic surface cultures.

It goes like this: prepare a maltose+marmite medium as described in post no. 339507 but add 20g/l (2g/100ml) of gelatin. Pour in cultivation containers (marmelade jar, sep funnel etc.). Allow to soldify in fridge, then put at roomtemp (<20 centigrade or gelatin will liquefy). Inoculate with bit of fungus and leave it alone.

Now what happens is that the fungus will decompose the nutrients, the peroxide and the gelatin in about 2 weeks. The result is a nice watery liquid which can be A/B'd

Determine the lysergic content of the medium by a reagent test (I think Keller reagent but I will have to look that up). Isolate & purify by TLC. Extract the strip of TLC paper you need and purify further.

What I have done so far is the cultivation of paspali on described media, and seen the pink reaction. I have not performed the extraction or the TLC test. Perhaps later, in a country where that is legal to do. I do not possess the knowledge to process the lysergic endproduct further but I hope one of you beez has and will publish results.

P.S. C. paspali Stevens&Hall is not a very restricted fungus. Especially in Eastern Europe and I believe even Germany are culture banks where you can buy it.

(*) McLuhan was right!
bibliopharmacophile

[Yachaj]

In his book THE CHEMISTRY OF MIND ALTERING DRUGS, Daniel M. Perrine writes about paspali (p.277):

"Meanwhile, the biologists had found a better way: in 1964, they observed that a strain of Claviceps paspali under saprophytic cultivation in fermenters would produce an abundant quantity of paspalic acid [see: Kobel, H.; Schreier, E.; Rutschmann. J., Helv. Chim. Acta, 1964, 47 1052]. (C. purpurea will only grow on grain in a field.) And soon it was discovered that paspalic acid easily isomerized under basic conditions to lysergic acid; conjugation with the indole ring being under these circumstances more thermodynamically favored than with the carbonyl [see: Troxler, F., Helv. Chim. Acta, 1968, 51, 1372] To the present day, this probably remains the most efficient and economical way of obtaining lysergic acid.
(...)
It is likely that the LSD so widely available in the United States (at least on college campuses and at rock concerts) comes from a few clandestine laboratories in San Francisco and, perhaps, on the East Coast, each with a few tanks of fermenting C. parpali—cultivation of which is only one or two orders of magnitude more sophisticated than fermenting yoghurt. After all, it can be done by biologists. Instructions on how to cultivate Claviceps are given in Smith, M. V., Psychedelic Chemistry, Loompanics Unlimited: Mason, MI 48854, 1981. A more reliable source of information, chemist Alexander Shulgin, tells me that specimens of C. paspali are readily available from the U.S. Department of Agriculture. And, of course, as with yoghurt, once you have a sample of the fungus it reproduces indefinitely. You can endow other clandestine daughter labs. This and the fact that LSD is so astonishingly potent (1 g = 10,000-20,000 doses) probably accounts for the fact that there has been no discovery of any clandestine LSD production in the United States by any police agency in almost two decades”

An even more intriguing possibility is quoted in Jonathan Ott's book PHARMACOPHILIA OR THE NATURAL PARADISES (ISBN: 1-888755-01-06), p. 125/126:

"…there are considerable strain variations in alkaloid production by ergots, which may contain the visionary ergonovine [Merck Index 12:3694] and at least two known ergolines of almost certain visionary activity, which have yet to be tested in human beings: elymoclavine and lysergic acid-N-(1-hydroxyethyl)amide. (...)

The latter, likewise found in ololiuhqui and related seeds (...) is known from Claviceps paspali Stevens and Hall parasitizing Paspalum distichum L., in which it can be readily converted into ergine [vide: E Arcamone et alii, “Production of lysergic acid derivatives by a strain of Claviceps paspali Stevens and Hall in submerged cultures” Nature 187: 238—239, 1960]. Moreover, it has been shown that some strains of C. paspali in saprophytic culture are capable of transforming this natural hydroxyethylamide of lysergic acid into its close relative, the diethylamide, or LSD [vide: F. Arcamone et alii, “Production of a new lysergic acid derivative in submerged culture by a strain of Claviceps paspali Stevens and Hall” Proceedings of the Royal Society 155B: 26—54, 1961]. It thus appears likely that there exist strains of ergot which produce L5D itself, and that this will eventually be shown to be a natural product."

Any comments?
bibliopharmacophile

[bujinkan]

One of the few good remarks of Uncle Fester in his LSD book

i dont understand, are you being sarcastic?


Thanks for your ideas on culture mediums and techniques, it would be nice to know just how much of the alkaloids are being produced in these settings.

[BeeLoyal]

(comment for Yachaj´s last Post) If such a strand of C. Paspali exists I would gladly trade my golden eggs laying chicken for a growng culture.  

anyways for more serious matters,

I read your posts Yachaj , and I read the patent 3038840, it was very helpfull. but I feel that my insecurities have still left me with grey areas in my comprehension of the subject.

1. Virulention : I would please like to have more information on the exact procedure of mutating Claviceps Paspali , to make the LSA producing Claviceps Paspali.

2. would C. Paspali collected from the Paspalum Dilatatum (Dallis Grass) be good as starting specimen for the agar cultivation procedure?

3. THIS ONE IS A NEWBEE QUESTION!    where should i look for to find ARTICLES? the above mentioned articles from NATURE, HALVATICA , Proceedings of the Royal Society of London ,  and all other mentioned periodicals and such.  please i really want to read them but as I am no scientist have never had to look up this kinda sh1t.  WHERE DO U LOOK UP THIS STUFF?
online sources would be appreciated for these.
  -

4. how would u go about using collected Claviceps Paspali from plants as a start? would u grow it on agar?  and what the hell is this Agar ?   I am not a native english speaker and fail to understand what agar is, and so pictures or acurate descriptions of how to make a it in various forms (i gathered that many types exist). for example how would u make Potato-glucose-agar

5. after making the nutrient medium, what part of the agar colony would u add to it? how much of it per liter? would u just mix it in the solution and let it incubate? and if so does the solution look uniform or are there solids on the bottom? A Picture will be great.

6. after the production of the culture and Alkaloids, how would u go about extracting them?   YES I am asking this even after reading the Patent. 
the lysergic acid can be extracted from the medium with a simple A/B protocol.
sorry for being such an ignorant fool, but what is an A/B protocol? what do A,B stand for?

7. after collecting the Alkaloids in crystals form, how would u go about converting all to LSA and ISO-LSA, and would u then feel its needed to make purifications procedure to convert ISO-LSA into LSA as described in Rhodium´s site before starting for final synthesis?
there is also mentioned in the patent a "known way" of Alkaline Hydrolysis that is supposed to be in "(J. Chem. Society, 1934, p. 674 and 1936, p. 1440.)  what are the specifics of this know way and please how do i find the original article?

8. In the patenet description they always refer to the MgSO4 * 7H2O  what do they mean?  is it  MgSO4 / H2O    1/7  in proportions?

9. what is the pink reaction u are refering to ?  and how would i go about doing the TLC test? (funny, can u imagine i still dont have any experience with TLC, or any chromatography), how is the keller reagent used to test LSA quantities in medium?

I know my questions are those of a 6 year old but if u answer them ill sell u my sister hehehe.

BeeLoyal

The war isnt over!

[Yachaj]

Bujinkan, I am not sarcastic but merely refering to the fact that Fester never made LSD nor ever cultivated any fungus ever, but still makes a living by selling 'information'. According to an interview with him in George magazine <www.georgemag.com>, December 2000, p. 116-119&125-127 he no longer does empirical drug research because he is threatened with the '3 strikes and you are out' law (he has already 2). Perfectly understandable, but he doesn't state that in his books. Duh!

BeeLoyal,
1. info is in the patent text (UV etc). But ATCC 13893&13984 probably do not need to be revived (their pinkish / fleshcolor just beneath the white fluffy hyphae is OK and I am told that that is because of the lysergics. But like I wrote I have not performed a reagent color test.

2. No idea. Isolate astrain, make Van Urk reagent and find out! 

3. University library (cheap), <www.scirus.com/?s> (expensive)

4. isolating fungi from the wild: <www.fungi.com> <www.mycomasters.com>

what is agar: , <

http://www.uct.ac.za/depts/botany/pstgrd/enrico/seaweed/agar.htm&gt

;

4b. Read the patent text & utfse utfse utfse UTFSE UTFSE UTFSE UTFSE!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
OK: first A/B, then TLC, find a useful colorimetric reagent from which the desired alkaloid can be liberated and do just that. Zubrick's The Organic Chem Lab Survival Manual (ISBN 0-471-38732-0) informed me about everyting I needed to know about TLC, and Trout's Notes #FS X-7 title SOME SIMPLE TRYPTAMINES (available via books@troutsnotes.com) contains the most extensive list of recipes for colorimetric reagents for TLCing bioactive tryptamines I have ever seen. Not much about lysergics, but you migh get an answer if you use the email adress&order the book).


5. Unfortunately I am at loss here. But I think this is something for Rhodium  (if you are lucky)
bibliopharmacophile

[Rhodium]

3: The journals the articles are published in can be found at your nearest university library.

3 (the other question #3): Agar is a nutrient mix used to grow fungus, bacteria etc. Buy from a biochem supplier.

7: MgSO4*7H2O is magnesium sulfate which has crystallized together with seven molecules of water. It is called Epsom Salts. Can usually be bought at a pharmacy or at a chem supplier.