lysergic

[bujinkan]

BozAkium...why bother? Festers book is a cave drawing compared to the info here on the web.
I don't see why you're giving formula so much shit,and just when it was getting interesting too. then again formula, this post is probably redundant, and if you really want to learn you should access the serious chem forum. (it also means that you wont be able to spread more inane comments since they check your post before it gets put up.)

[paranoid]

I don't think anyone was giving 54 a hard time, just some fair warning about the difficult journey of making LSD.

[slappy]

The synthesis of LSD is not very hard, provided that you have a good organic chemistry background, and alot of first hand experience.

All of those old methods suck, big time. We have much better reagents nowadays. POCl3 dehydration? I don't think so. Thanks to the progress made in peptide synthesis over the last 20 years, we have a beautiful selection of amide coupling reagents available to us. And since this reaction is a simple amide coupling, we should use some of these gentle reagents. So all you need is your Lysergic Acid and your Diethylamine. From there I would go for the following routes:

PyBrOP coupling, catalysed by HOBt in DMF, Acetonitrile, or N-methyl-2-pyrrolidone. Used with a gentle base like TEA or DIPEA. Low temps, high yields.

You can also use a Carbodiimide coupling reagent, although the urea formed can cause problems with the workup. I would use the polymer bound ones, as the urea formed will remain bound to the solid phase, and can be removed by simple filtration.

Of course this would all be carried out at low temps, with the proper lighting precautions, etc.

As a general rule, this type of reaction can be carried out in just about any dry polar aprotic solvent, and with any coupling reagent. BOP, PyBOP, AOP, PyAOP, PyClOP, HBTU, TBTU, etc. would all work just fine.

[formula54]

just an abstract i found: unrelated to the order.

FORMATION OF A LYSERGIC ACID DERIVATIVE DURING THE PARASITIC DEVELOPMENT OF A STRAIN OF CLAVICEPS PASPALI.
P. Bianchi, E.B.Chain
Infected florets were collected 5 weeks after innoculation. Infected tissue was seperated. The ground tissue was extd. with 2% tartaric acid in 70% Me2CO for 12 hrs. The suspension was filtered and the Me2CO was removed in Vacuo at 30deg. The turbid soln. was extd. with light petroleum ether to remove fats, the pH adjusted with NH4OH and the soln. reextd with CHCl3. The CHCl3 ext. was evaporated to dryness in vacuo at room temp., the dry ext. dissolved in .5 ml CHCl3 and chromatographed. (54 notes that this was performed using wild infected grain: earlier they appearantly tried infecting P.dilatatum with C. paspali (strain F550), but the infections were deemed 'abnormal'...which explains the next entry:
Reisolates of the fungus derived from the abnormal sclerotia derived from st. F550 produced the same alkaloid, but quant. yeilds varied widely.

-swis54

[formula54]

ARTIFICIAL CULTIVATION OF ERGOT.
Jan Kybal, Jiri Protiva, Karin Strnadova
The cultivation was performed in 1000ml flasks filled with 600 ml. of medium composed of sucrose7.5, sorbitol 2.5, citric acid .05, NH3 0.54, Ca(NO3)2.4H2O 0.15, MgSO4 0.025, agar 0.05% and tap water.  The pH was adjusted to 6.0, the medium was sterilized at 1 atm. for 35 min., and innoculated with 20 ml innoculum of a 48 -hr. culture of claviceps purpurea isolated from the sclerotia paratizing on on rye and grown in 3deg Be.malt infusion on a rotary shaker at 25deg. The flasks were agitated and incubated at 25deg for 22 days. the mycelium was seperated, washed with H20 and dried in an air stream at room temp. it contained 14% ergotamine.
-swis54

[slappy]

Claviceps is toxic, and will eat away your skin if it gets on you. Ergot cultivation, like LSD synthesis, is easier said than done.

[hest]

Slappy is it a joke ??
I'v been growing claviceps on agar a couple of times. Its much easyer to handel than psilocybe.

[terbium]

Claviceps ... will eat away your skin if it gets on you.
Pre 1950s or so, ergot was commonly gathered by sending children out into the fields to pick the infected grain heads.

[formula54]

intresting...ive always wondered what exactly st anthony's fire was... is it like gangrene? or does ergot release poisonous chemicals?
terbium, ive heard that too...maybe it isnt as poisonous as originally thought.

-swis54

[Rhodium]

Ergotamine alkaloids causes constriction of the blood vessels in your extremities, causing gangrene. That is St Anthony's fire.

[flipper]

Maybe a stupid question but how do I use these coupling reagents.

slappy(Hive Bee)11-29-01 12:52 No 242024 Re: lysergic

The synthesis of LSD is not very hard, provided that you have a good organic chemistry background, and alot of first hand experience.

All of those old methods suck, big time. We have much better reagents nowadays. POCl3 dehydration? I don't think so. Thanks to the progress made in peptide synthesis over the last 20 years, we have a beautiful selection of amide coupling reagents available to us. And since this reaction is a simple amide coupling, we should use some of these gentle reagents. So all you need is your Lysergic Acid and your Diethylamine. From there I would go for the following routes:

PyBrOP coupling, catalysed by HOBt in DMF, Acetonitrile, or N-methyl-2-pyrrolidone. Used with a gentle base like TEA or DIPEA. Low temps, high yields.

You can also use a Carbodiimide coupling reagent, although the urea formed can cause problems with the workup. I would use the polymer bound ones, as the urea formed will remain bound to the solid phase, and can be removed by simple filtration.

Of course this would all be carried out at low temps, with the proper lighting precautions, etc.

As a general rule, this type of reaction can be carried out in just about any dry polar aprotic solvent, and with any coupling reagent. BOP, PyBOP, AOP, PyAOP, PyClOP, HBTU, TBTU, etc. would all work just fine.

New routes from ET to LSD

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/et2lsd.txt)

[formula54]

didnt you just answer your own question?
-swis54

[flipper]

No.
How do I know how much reagent I have to use.

[Rhodium]

The document you linked does provide you with all the amounts... Foe example, with BOP:

Proposed LSD synthesis procedure:

1eq. LSA is dissolved in a suitable solvent(must be fairly dry) at RT, 1.05 eq BOP-reagent is added. 2eq. of diethylamine is added and the rxn is stirred at RT until it goes to completion(15min-2hr). The solvent is removed under vacuum and the residue partitioned between EtOAc(or other suitable solvent) and saturated NaHCO3(or NH4OH). The layers were separated and the organics were washed with NaHCO3 (or NH4OH), H2O, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo to remove the solvent and excess diethylamine. The crude LSD, which should be fairly pure, is then further purified by chromatography and converted to the tartrate salt.

[flipper]

But not with ByProP.

[Rhodium]

Do you have any lysergic acid and all the needed equipment available, so that it any meaning with anyone of us figuring the exact reaction details out for you? I would guess that a slight molar excess of any peptide coupling reagent is always used to form amide bonds.

[formula54]

Why are you so intent on using ByProP? this is lsd chemisty not meth...we cant afford to fuck around, its hard enough as it is! Use BOP.
!

[flipper]

It's just a question. You guys have a lot of unreleased anger . Try some Yoga. Why Is it so difficult to answer a question. Damn. If it is so easy to do then why is it so difficult to do a little favor and answer this question instead of getting mad and frustrated. Are you quys on prozac or something.
I'm Just very interested and wan't to know everything. Is that a crime?

[foxy2]

"How do I know how much reagent I have to use."

No one really knows the answer.

You have to look for procedures using the respective coupleing agents to perform similar reactions and compare them.  This should give you some indication as to whether or not yours will work.  Don't expect people to start extrapolating in a very specialized segment of organic chemistry.


The fact that you ask that question in the way you did indicates that you are not even close to being prepared to attempt this synth.  Go to the library and find at least 5 references where they use ByProP to produce amides, preferably dialkylamides.  Get familiar with these and then come up with your own procedure!!

Do Your Part To Win The War

[Rhodium]

We don't know everything off the top of our heads, but we can find out with a literature search, but before we go through that trouble we would pretty much like to know of it is of any use that we do that job, or if the information will just lie around unused.

I always answer the questions that I already know the answer to, but I only do literature searches for people when I feel that the result is actually going to be used.