LSD Biosynthesis

java · Consumer

mnmguy
(Stranger)
04-12-02 14:48
No 296124
Re:LSD Biosynthesis?!

Okay, found this on some ethnobotany site:

"It has been shown that some strains of Claviceps 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 LSD itself, and that this will eventually be shown to be a natural product."

This from Ott's "Pharmacophilia" pp125-126

... and then the guy adds the following:

"Forgot to point out that lysergic acid-n-(1-hydroxyethyl)amide (a natural morning glory alkaloid) was added to the solution that the culture was sumberged in.

Apparently ergot, in much the same way psilocybe spp. mycelium converts tryptamine --> 4-OH-n,n-DMT, can biosynthesize its OWN nifty alkaloids. This would certainly make LSD (bio)synthesis a snap compared to building the molecule from ergotamine tartrate."

If this is true, I think we're on to something. Comments please?

Dr_Greenthumb
(Stranger)
04-13-02 13:15
No 296477
Re:I suppose if you figured out what atoms the ergot ...

I suppose if you figured out what atoms the ergot enzymes added and where, you could infer from that what the fungus would create from LSA. Does anyone know the how ergot adds what onto which molecule?

Or, I suppose one could attempt to extract the LSD from ergot grown on an LSA laced substrate. This idea is too promising not to look into...

nevry
(Stranger)
04-13-02 14:05
No 296494
Re: LSD Biosynthesis

i found this lying around on my hardrive:

ftp://65.30.231.7/11/alkaloids-biosynth.pdf

it doesn't really give alot of specifics, but it does show the basic idea.

- nevry.

mnmguy
(Stranger)
04-13-02 14:15
No 296497
Re: I suppose...

So assuming that this is true, that claviceps papsali would produce LSD when fed an LSA laced substrate, how difficult would it be to separate out the LSD from the other ergot alkaloids in the final product. Could one simply A/B extract the total alkaloid fraction from the culture medium and throw the whole thing into a chromatography column? I am not familiar with chromatography procedures and their limitations. Thanks so much.

spectralmagic
(Hive Bee)
04-13-02 19:46
No 296601
Re:Uh oh...

nevry, that had better not be your or a friend's server!

Check your PMs.
To Bee, or not to Bee... ;-)

paranoid
(Hive Bee)
04-13-02 23:37
No 296676
Re:interesting

Well, if the genes responsible for the production of the appropriate LSA precursors could be determined, extracted, and spliced into the ergot genome then the natural enzymes present could convert it to LSD.
On the other hand, the genes from the ergot responsible for producing the enzymes that convert the LSA to LSD could be isolated and spliced into the morning glory genome.

Easier said than done, but interesting nonetheless.

However, since LSD is easily danaged, other provisions would be necessary to ensure the molecule isn't degraded as quickly as it is produced.

halfapint
(Ubiquitous Precursor Medal Winner)
05-06-02 21:56
No 305633
Re:HorrorShow

As a theme for fiction (forgive if this is off topic) it seems like a real scary room to enter, the lab for severe genetic manipulation of ergot spp. The subject species are robust, even within the hardy fungi. Since the reasons they have evolved a sophisticated and complex chemical weapons factory (to produce some of the most potent and subtle neurotoxins in the natural world) are not known, it could turn out to bee injudicious to arbitrarily start carving up their genome. I'm not superstitious nor paranoid; I just make it my habit, to go around looking for things to worry about.

Is the title "Production of a new lysergic acid derivative in submerged culture by a strain of Claviceps p." a deliberate understatement, or what, if they were talking about LSD? That's surely amenable to environmental optimization, without gene splicing of ergot.
a half a pints a half a pound a half a world a half a round

Rhodium
(Chief Bee)
05-07-02 07:16
No 305740
Re:Acid bioterrorism

Horror Show? Such as genetically engineer E. coli bacterium to produce LSD, and then accidentally release them into the environment (city water supply) so that everyone coming into contact with the infected body of water develops their own LSD-producing bacterial culture in their gastrointestinal system - everyone goes boinkers, and the source of the LSD found in the bloodstream of all the affected people cannot be determined until it is to late and the bacterial strain has spread to a large portion of the population. It would also be impossible to eradicate it, as the strain can not be specifically targeted by antibiotics, and killing off the entire E. coli population in the world is out of the question, as that would do even more harm than good.

Ok, that's the synopsis. Where is Stephen King when you need him to write a complete movie script?

The sequel is pretty obvious - In "Acid Bugs II" the E. coli strain once again escapes into the environment, and this time not restricted to E. coli, the gene plasmids transfects other single cell organisms just like antibiotic resistance is carried across different species. Finally, when introduced into blue-green algae, the entire animal population of the world is at risk of going insane, as the LSD concentration in the oceans rise exponentially, as the new genes bring such an advantage to the plankton as all species which usually eat it gradually gets more and more incoherent in their actions until they cannot feed themselves - will the earth be covered in a thick slime layer of blue-green algae floating on an ocean which has turned into an aqueous solution of LSD, or will our heros save the world in time?

Acid Bugs III - coming soon to a theater near you. This time the LSD-producing genes has mutated to take advantage of the chlorinated hydrocarbons from the pollution of the environment, synthesizing a halogenated LSD analog 100 times as potent as the original, and which is not biodegradable...

halfapint
(Ubiquitous Precursor Medal Winner)
05-07-02 09:33
No 305772
Re:That's it, you got it!

Anyway what mnmguy has taught us, is to include ground-up MG seeds, or their extract, in our ergot culture medium. That makes it worthwile to stick the ergot extract straight into HPLC preparation. It's a good bet, that about any ergot strain selected for high alkaloid production, would pull the neat trick reported to yield LSD. Worth a test, far easier than the sythesis if it works.
a half a pints a half a pound a half a world a half a round
Sidearm n. Flask neck tube.

timnickbear · Fri Aug 19, 2005 4:13 am

I have emailed bear recently and I would like the pdf references if you can provide them...here is the email...I will link him to the info if it is found. Thank you.

Seems Bear that you are right again; I have a reference to back up your theory that there is LSD occuring naturally- where an ergot fungus finds wet morning glories and has a trippy lunch of sorts.

"It has been shown that some strains of Claviceps 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 LSD itself, and that this will eventually be shown to be a natural product."

This from Ott's "Pharmacophilia" pp125-126

Would you please scan and send me copies of your references.

... and then the guy adds the following:

"Forgot to point out that lysergic acid-n-(1-hydroxyethyl)amide (a natural morning glory alkaloid) was added to the solution that the culture was sumberged in.

Morning glory seeds contain varying amounts of ergine (amide) but not the hydroxyethylamide, (the alkaloid Hofmann thinks is the active agent in the grain-based Eluseum brew). It is is found naturally, along with the ergonovine group in c paspalum.

Apparently ergot, in much the same way psilocybe spp. mycelium converts tryptamine --> 4-OH-n,n-DMT, can biosynthesize its OWN nifty alkaloids."

I don't think psilocybin musrooms require any tryptamine in the substrate to produce psoilcin. The mushroom makes the tryptamine intermediate as part of the process.
--

Cheers,

Bear

java · Consumer

From Artificial To Natural Drug
Jonathon Ott

Excerp

In 1972 Andrew Weil published "The Natural Mind" in which he alleged that natural drugs in plant form were inherently safer and more healthful than what he called 'synthetic' drugs (meaning artificial compounds, which are distinguished from natural products by not having been found in plants or animals but rather originating from chemical synthesis -many natural drugs may be, and frequently are, synthetic, having been prepared by chemical synthesis or semi-synthesis, rather than simply being extracted from natural sources) [WEIL 19721].

.......as read here, http://leda.lycaeum.org/?ID=16853

will look to see if the journal citation can be located.....

Proceedings of the Royal Society 155B: 26-54, 1961

Radiumhero · Fri Aug 19, 2005 10:45 pm

Well once swirh was thinking about growing this mushroom growing on corn
only know its german name -.- ( Mutterkorn ) wich contains a very high concentration of lysergacid ... thought about getting out on the field harvesting some of those shrooms putting them in an incubator on a medium like "agar agar"
or simpler ones , keeping the stuff clean ( ne bacteries ) will be the thoughest part
so swirh didnt want to go that way ..

joe_aldehyde · huxleys associate

before anyone attempts cultivation of claviceps purpurea, swij suggests that he gets familiar with the toxicological properties of the relevant toxins. you don't want your extremities to fall off, would you?

Radiumhero · Sat Aug 20, 2005 6:11 pm

Swirh knows the rather toxical properties of the shroom , ( pregnant women used it to kill their babies and died theirselfe ) of course id never attempt to take this shroom orally , the ergot-alkaloyds will be extracted for futher use ....

joe_aldehyde · huxleys associate

you don't even need to eat it, they readily permeate the skin...use gloves and respiratory protection when collection ergot fungi.

java · Consumer

joe_aldehyde · huxleys associate

when you read radiumheros post, java, you will see. german "Mutterkorn" stands for c. purpurea.

java · Consumer

You're correct....sorry I wasn't clear in what I read it was in german hence didn't catch the drift ...........java

Note: however I found this, hence confusing.....

Substance

Name of the Substance: Secale cornutum(Claviceps purpurea).
English common name :Ergot of Rye
French common name
German common name: Mutterkorn

however nothing to do with corn fungus.......

joe_aldehyde · huxleys associate

no problem, as long as you don't start bitching "OFF TOPIC!!!" as i do sometimes Wink

timnickbear · Wed Aug 24, 2005 9:47 am

I believe that the reference says Claviceps paspali...doesn't cause gangreen. I would like the references please...

nubee · Master Archiver

sounds good ! Surprised

hahas · Wed Aug 24, 2005 11:39 am

nowhere in the article is LSD mentioned, in any way, and what was said in the original post was wrong. and the closest relative to it that was added to the culture was tryptophan (for the better).

half of the product from this freak, lab developed strain of Claviceps, was thought to be the d-alpha-hydroxyethylamide. the rest, although they had at least 37.75 grams of it, was not characterized, and no analysis or spectra was given. they only say that the IR is similar and that the cpd. "could be transformed almost quantitatively into isolysergic acid amide by allowing a 6.5% solution in 66% aqueous methanol to stand for 1 h after addition of a few drops of 0.1N NaOH."

Radiumhero · Thu Aug 25, 2005 1:13 am

Swirh Heard that the shroom is rather hard to cultivate and chooses its new owner very carefully ^^but those who master to cultivate him will earn rich fruit
think swirh has a pdfon this ... hell search for it

... bee safe