A question about the hydrolysis of ergot alkloids...

Ned Flanders · Sun Mar 20, 2005 1:14 am

I would like to know if this reaction is sensitive to impurity, the reason being I was wondering if the hydrolysis could be done directly to a water extraction of HBWR seeds, neutralized to ph 5-7 with HCl, and the resulting lysergic acid absorbed on activated charcoal per Patent GB1107156.

wyndowlicker · Member of the Month

Hey now,

Its one major bitch to get good LSA from HBWS.Its not an ergot alkaloid
by the way.What do you mean by a water extraction?explain your steps more than that.Ill take a look at the patent.You should give some concideration to fermentation of clavaceps purpurea or paspali, and extracting from there.The first step is always the hardest.

W.L Laughing

Ned Flanders · Mon Mar 28, 2005 11:09 pm

O.K., I should have been more clear about what I was thinking of. The patent I listed is a method of getting small amounts (380mg/liter was listed in the examples) of lysergic acid out of a fermentation broth by absorbing on activated charcoal.

Take your kilo of HBWR seeds, and soxhlet under vacuum with water. Add your KOH to the extract, heat at the proper temperature under an inert atmosphere until the alkaloids have hydrolysed, neutralize with HCl, (not sulfuric, we don't want it to precipitate here) and absorb it on charcoal as described in the patent. I just don't know if the tannins or other junk in the seeds would react with the alkaloids or lysergic acid under the reaction conditions to an extent that would make it impossible to get a useable yield.

I wonder what they were doing with a fermentation broth with lysergic acid in it? Did they find a strain that produces lysergic acid itself, or did they hydrolyse the whole damn impure mess, like I was thinking one might be able to do?

mk-1 · Fri Apr 01, 2005 3:59 pm

from what I know about activated charcoal it will absorb junk as well.
I think your best bet to go would be to first extract with a non-polar solvent to get as much junk out (maybe 2-3 times), then extract under soxhlet with ethanol or what not (water seems to me like a bad choice, but i guess every bee to his self). hydrolisis occurs better with either high molar amounts of KOH with or without sodium dithionite (http://12.162.180.114:90/synthetika/hiveboard/tryptamine/000476652.html)
or with Tetrabutylammonium hydroxide with or without K/NaOH (http://rhodium.moppy.net/www.rhodium.ws/chemistry/paspalic.lysergic.html)
About aborbtion on charcoal, i dont know. I know it does absorb junk, but if u dont have junk then u dont need to worry about it.

From what I know, the best bet to purify ergine from HBWR without chromatography, would be to first extract with a non polar solvent a few times, then extract the alkaloids in ur favored way. then evap to drynes, dissolve in hot metanol and stick in the fridge. Ergine will xtalize from methanol. This way u could get a clean enough sample wihtout the need for chromatography, then u could proceed to hydrolisis and absorbtion on charcoal or whatever... but it would be a good idea to clean the sample every stage of the way...

Just my thoughts on the subject...

Ned Flanders · Fri Apr 01, 2005 11:06 pm

A link to the refernced patent:

http://l2.espacenet.com/dips/viewer?PN=GB1107156&CY=gb&LG=en&DB=EPD

Water would seem advantageous because it's cheap, non-flammable, produces no smelly fumes, is entirely OTC, and ergine is soluble in it. The absorbation on charcoal is done in aqueous solution, so you could simply neutralize and absorb. According to the patent, you can isolate practically pure lysergic acid from an impure solution this way. You can wash the charcoal with water before eluting to remove water soluble impurities. The question isn't whether the charcoal will absorb impurities, but would they be eluted from the charcoal along with the lysergic acid.

Assuming that the extraction method described in the patent works as described, I don't see why this wouldn't work.