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Acid-Base extraction of Morphine and Methylmorphine from Poppy Seeds

C

C_Tripper

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Joined
Feb 19, 2008
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Hi all! Not sure whether this fits here, but I thought it may as well go here for now, mods move at your discretion.

Was reading some science papers dealing with poppy seeds, and came across an interesting one:

Morphine and codeine in poppy seed
Michael D. Grove, Gayland F. Spencer, Marjorie V. Wakeman, Harvey L. Tookey
J. Agric. Food Chem.; 1976; 24(4); 896-897.
First Page Full: PDF (229k)

Basically, they list an extraction method to remove the surface alkaloids present in commercial poppy seeds, which GCMS revealed to be comprised of Morphine and Methylmorphine (Codeine).

Their method was as follows (paraphrased, just to give a general overview):
- Wash with a pH 2 solution of water and HCl
- Wash with distilled H20
- The water washes were freeze-dried, redissolved in
H2O (50 ml), and made alkaline to pH 8.5 with NH40H
- The alkaloids were then finally extracted using a chloroform-isopropanol mixture (3:1)

They then proceeded to use GCMS to work out how much alkaloid was present, etc.

Now, I was wondering whether this is actually a viable method of extracting the alkaloids from the poppy seeds, as opposed to the so-called "tea"?
 
You have to be on top of your chemistry to try this. Not many people would find this useful. To boot the extracted amount wouldn't be more then tea.
 
The only part in which I'm not sure how to replicate outside of our labs at uni would be the final step, with the CHC13-i-PrOH extraction. Gotta do some reading, find out exactly why they've used that mixture. I assume it's simply being used as a solvent, in which case its possibly able to be replaced with a more readily available solvent, no? Any more advanced chemists wish to shed some light :)
 
Why not use the standard AB used for opium that is so popular in asia for heroin production?
 
sure you can extract morphine from seeds, if you have a fuckton to begin with (talking about xxxlbs). I believe growing a single poppy though, yields way more product =D
 
rave23 said:
sure you can extract morphine from seeds, if you have a fuckton to begin with (talking about xxxlbs). I believe growing a single poppy though, yields way more product =D
Click to expand...

Obviously, hehe. Although some of us aren't talking about extracting marketable quantities here. I mean, 500g of the seeds (from a bulk supplier near me) gets you nodding so god-damned hard it's not even funny, and that's just a basic extraction using water as the solvent.
 
I've had good luck doing methanol extractions of the pods, followed by an A/B.
 
I've always wanted to just selectively breed poppies to up the trace hydromorphone content to something that competes with the morphine content, and maybe tweak it until the 3-methylmorphine content becomes 6-methylmorphine somehow.
 
For surface-adherent alkaloid on seed exterior only, then don't bother with an A/B, use calcium hydroxide.

Add saturated solution of slaked lime to the liquid solution obtained from washing the seeds, it will form an insoluble calcium morphinate salt by virtue of the acidity of phenolic hydroxyl groups, which precipitates out and the morphine can be liberated from this by standard means, acidification with dilute acid. The calcium phenate salt can be used in extractions from pods too, such as MeOH extractions, hydroalcoholic (aq. or wet methanol works good here too) extractions, or stewed pods ala pod tea can be extracted this way too.

I prefer to do several extractions using wet, slightly acidified methanol, containing a little hydrogen chloride first, evaporating most of the solvent, distilling it off and saving it for redistillation and recycling (although MeOH is pretty cheap if you buy in small-bulk quantities, say,a few five gallon or a couple of ten gallon drums will last most people a bit. Or if you want to reduce both your operating costs and your solvent use, as well as having far less to recycle, or indeed cut use down so much in
the right circumstances that the slops can simply be burnt, after you know theres nothing left in there worth having,and the quantity insufficient to bother fucking around setting up the still, even more so if your inclined towards vacuum distilling it off to save time. This, is where getting a Sohxhlet extractor comes in. They are a piece of glass that mates with a suitably sized flask*, typically quite a large joint size, and contains the substrate to be extracted in a porous 'thimble'; and when in use, the solvent in the flask is heated, to volatilize it, sending it percolating round through the substrate until it condenses a sufficient quantity to reach a drain, which then sends the solvent, with its (less volatile) extractive back down into the flask, bypassing the substrate.

The solute stays within the flask, and the solvent is sent back for another round of extracting, having been freed of much of its solute burden, to go back and collect some more. Lather, rinse, repeat.

Makes for a very efficient technique for extracting plant/fungal/animal tissues, and solid reaction products containing byproducts, or they also, can be used effectively in reverse, to leach in slowly, a reagent which will dissolve in the chosen solvent, to the flask, adding it in a controlled manner. Not by any stretch of the imagination a tool which is vital and indispensable in the lab, but having one sure as shit makes life easier! I've never regretted getting mine, although I'd like a couple more, a far larger one and a moderate sized one, as well as, maybe, just maybe, one that could be used with my microscale kit, (think 5-10ml flask sizes, and things like one piece two-neck 5ml pear shaped flask with side arm, and integrated column w/vac takeoff etc, 5 and 10ml long-necked partly-round flasks, with flat bottoms, etc. The one-piece thing looks SO damn cute haha=D Only cost me something like <$6, too)
 
dread said:
Holy incomprehensibility, batman.
Click to expand...

its written like that to confuse the delicious human scientists, robin... i mean to confuse the scientists, robin, em i dont know what ya mean, laad.

will robin finnd out batman's deathly vampirous secret? or has clarkey kent from limerick revealed his public and mysterious "superhero" identity? tune in next time i sart talking shitel you might just find out,
 
butane said:
I've had good luck doing methanol extractions of the pods, followed by an A/B.
Click to expand...

The point is at the beginning you use a slightly basic alcoholic solution (pH~9) to extract the alkaloids and stir at reflux. Then you evaporate the alcohol and redissolve the extract in basic aqueous solution (pH~11) to separate morphine in its morphinate form from the rest of alkaloids, after filtering off the solids you bring the pH down to about 9 again to precipitate morphine freebase out of the aqueous solution and then simply extract it with an organic solvent. Basically it's a modification of the original method with lime.
 
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