Sciencemadness Discussion Board - Ergotamine extraction

Ergotamine extraction

beerwiz - 20-9-2014 at 07:09

Have some ergot extract with 50% alkaloids and tried to do an alkaloid extraction.
Added 100ml water to 20g of the powder and basified to pH 11.5.
I then added 100ml Naphta and got what seems to be an emulsion after stirring with a spoon by hand for 2mins. The upper naphta layer is mixed with liquid brown drops/bubbles.

Should I still separate the naphta layer and then wash with a 2M HCl solution followed by basification to then filter out the alkaloids or should I take another approach?

I'm at a loss on how to proceed with the alkaloid extraction any assistance is welcome.

forgottenpassword - 20-9-2014 at 07:57

I very much doubt that ergotamine is soluble in naphtha. Why did you not research the extraction method before you attempted it? You should look on google patents -- it is an extremely well researched and patented area of chemistry.

beerwiz - 20-9-2014 at 09:43

After about 20 minutes, what seemed like an emulsion fully separated and I was able to do a clean separation. Proceeded forth with and HCl wash and separated the HCl. I then basified the HCl to pH 9 and saw crystals forming but I used too much aqueous HCl and what I got is suspension of crystals. I will wait a day or so for them to settle and then decant. Any tips are appreciated.

forgottenpassword - 20-9-2014 at 09:59

The only tip I could give you is that ergotamine is insoluble in petroleum ether/naphtha.

beerwiz - 20-9-2014 at 10:15

Quote: Originally posted by forgottenpassword

The only tip I could give you is that ergotamine is insoluble in petroleum ether/naphtha.

Even when it is aqueous with an alkaline pH?

forgottenpassword - 20-9-2014 at 10:41

Yes.

Actinium - 20-9-2014 at 10:53

in the literature it talks about using U.V. while looking at a chromatography column to seperate the different mixtures seeing how Ergotamine glows under such device.
Crudest way to seperate is using ethyl acetate eluted thru an active alumina column following the path with a U.V. lamp and allow to drip into 10x Petroleum ether.
Here is a Patent method based of the LEK Tovarna Farmacevtskih of 1972.
Another method is the use of Bentonite which can be found at the Hydro store as "Hydrotone".
Also you have not given any information relevant to the source?
Ergot is a very broad term. Is it dried mycelia, Sclerotia, is it wild or domesticated?

beerwiz - 20-9-2014 at 11:26

Quote: Originally posted by Actinium

in the literature it talks about using U.V. while looking at a chromatography column to seperate the different mixtures seeing how Ergotamine glows under such device.
Crudest way to seperate is using ethyl acetate eluted thru an active alumina column following the path with a U.V. lamp and allow to drip into 10x Petroleum ether.
Here is a Patent method based of the LEK Tovarna Farmacevtskih of 1972.
Another method is the use of Bentonite which can be found at the Hydro store as "Hydrotone".
Also you have not given any information relevant to the source?
Ergot is a very broad term. Is it dried mycelia, Sclerotia, is it wild or domesticated?

It is dried and powdered sclerotia which is then extracted and concentrated to contain 40% alkaloids. I'm trying to extract the pure alkaloids.

"Process for isolation of ergot alkaloids from ergot US20070161795A1"

Following this patent I will now attempt:

Mix the powder with toluene 85% and 15% ethanol and filter and discard the filtrate.
Add 120 proof ethanol to the toluene and ethanol solution, separating and keeping the aqueous layer. Make the aqueous layer alkaline to pH 7.3 with 5% NaOH and extract with toluene again. Evaporate most of the toluene under vacuum at no more than 35 Celcius until you see crystallization. Filter the crystals and dry them in a vacuum dryer at 60 C at 50 mbar of negative pressure. Or completely evaporate the toluene, but yes scraping off the powder from a round bottom flask is a pain through the small neck opening.

aga - 20-9-2014 at 11:39

Quote: Originally posted by Actinium

Another method is the use of Bentonite which can be found at the Hydro store as "Hydrotone".

I dunno what an Alkaloid is, but i do know what "Cat Litter" is : mostly Bentonite.

Unsure if "Cat Litter" is what it's called outside the UK.
It's the dry granules you put in a tray for the cat to piss on.

Actinium - 20-9-2014 at 12:00

Quote: Originally posted by aga

Quote: Originally posted by Actinium

Another method is the use of Bentonite which can be found at the Hydro store as "Hydrotone".

Here in the good Ol' US of A we have cat litter as well and yes cats tend to piss on it time to time.
As far as Bentonite, it comes in a variety of forms and different salts.
The Hydroton is the commercially available for of expanded agrregate. I remember reading a process years ago that used such in aqueous solution of mycelia to filter and recuperate.

@ O.P., you do realize that you need a good Kg of Sclerotia to get any amount of usable tartrate and by usable I mean meager and if you actually manage to extract it.

beerwiz - 20-9-2014 at 12:38

Quote: Originally posted by Actinium

Quote: Originally posted by aga

Quote: Originally posted by Actinium

Another method is the use of Bentonite which can be found at the Hydro store as "Hydrotone".

@ O.P., you do realize that you need a good Kg of Sclerotia to get any amount of usable tartrate and by usable I mean meager and if you actually manage to extract it.

I'm aware of the bentonite method but it is difficult to filter out. I prefer a simpler process.
Yes, the yield is a meager 2-2.5%. What do you think of my extraction method, got any tips before I experiment with another 20g of product?

Nicodem - 20-9-2014 at 13:17

Quote: Originally posted by beerwiz

What do you think of my extraction method, got any tips before I experiment with another 20g of product?

My tip is to learn chemistry first and waste precious material latter.

Why would someone use "naphtha" for the extraction of something like ergot alkaloids? "Naphtha" is essentially as polar as ligroin, petroleum ether, or any plain alkane.

Actinium - 20-9-2014 at 19:11

I agree with Nicodem, especially when dealing with this compound. Ergolines are temperamental and when mishandled tend to isomerize into inactive product. Pet Ether is great to separate product from solution. there is so much literature out there its ridiculous. the U.V. lamp is mentioned in many papers. David E. Nichols used a centrifuge to separate while using the U.V. to watch the fraction move thru the tubes, saw it in a documentary a while back.
Did you pick all this Ergot? just wondering, as I have my own private patch that I pick at every summer although I didn't go this year.

beerwiz - 21-9-2014 at 01:25

If it isomerizes it's no issue there's a simple procedure to convert to the active form. I have a friend who picks tons of it and processes it with his milk machines. The centrifuge is good but unnecessary, you get a similar effect with a sep funnel. I wonder if the UV will damage the molecules, I suppose a short 2-3 second burst won't do much damage.

[Edited on 21-9-2014 by beerwiz]