As a disclaimer I have not tried any of these two main procedures I am about to describe, but am perfectly capable of doing so. Once I have anything interesting to share in regards to separating active alkaloids from whatever chemicals cause wood lovers paralysis I will share. But there are sub-questions in here. Of course this is all in the name of scholarly learning (possibly with the end result of even being able to ellucidate a novel neuro-muscular blocking agent for use in anaesthesia that doesn't affect breathing.....or so the hippies can get something useful out of wood lovers without falling off their bicycles, or suffering dangerous catatonic paralysis.)
There are two main teks for Psilocin extraction I have read; described briefly as follows.
One is A/B. Extract in acetic acid soln ph 4. Heat to 70C. Cool. Titrate to ph 8-9 with weak base. Quickly extract with either Xylene or Chloroform or DCM. Clean up freebase from here into ascorbate or other salt as desired or leave as freebase.
Second is to wash with acetone. Discard acetone. Wash with chloroform, discard chloroform. Extract with methanol or methanol/ aqueous. Evap for xtals? Is this a salt or freebase, forgot the final workup (assuming a salt based on the following observation.)
Couple questions here. One is that I have seen both these procedures spelled out by people who have pictorially demonstrated xtals (first) or vouched for (second).
Heres a question. Both procedures have been described using chloroform. However one uses it as a freebase extraction solvent, the other as a solvent to wash away undesireable compounds. This seems completely contradictory. My only explanation could be that in the biotic material the alkaloids are present as salts in the cellular matrix and thus are not extracted by chloroform in salt form. Can anyone verify this explanation? Or speak to the veracity of said procedures?
The meat of this thread would be to test these procedures on wood growing strains that produce WLP, to see if either procedure, or both, isolate actives and discard the neuro-muscular agent.
Supposing the agent is aeruginascin, as is the working theory given that positively charged methonium moeties are present in nuero muscular agents, such as Suxamethonium, we may be on to something.
Being positively charged here should make it immune to being extracted as a freebase under the same conditions as Psilocin, I would presume. A weak base at pH 8-9 should not strip the positive methonium charge inherent to that baked in third methyl. Presto? Procedure 1 eliminates WLP?
Now, as for procedure two, I do not see why acetone or chloroform would strip away a methonium version of Psilocin, given that these two solvents will leave positively charged salts alone, which is why they are used for washing salts of waxes/lipids. So in the end of this procedure the compound that produces WLP may still be present.
If my assumptions are correct, this experiment could provide hobby chemists with the ability to deduce whether or not aeruginascin is indeed what is causing WLP.
Alternative is to wait on real publications and journal articles to produce a paper where someone uses pure synthetic aeruginascin to produce such evidence.
Lastly and unrelated to the above, a long lost person with chemical knowledge I had reason to trust once told me to "precipitate psilocin from solution with iodine." I was very curious but he seemed to tease this as easily discoverable. He suggested using OTC iodine antiseptic solution, which is Iodine and Sodium Iodide in 47% alcohol. I am not sure if he suggested doing this in an aqueous salt or freebase solvent, I remember trying to pick details but was left with nothing. My internal mental library does not immediately provide me with answers. If anyone with chemistry knowledge is sparked by this concept please speak up.
There are two main teks for Psilocin extraction I have read; described briefly as follows.
One is A/B. Extract in acetic acid soln ph 4. Heat to 70C. Cool. Titrate to ph 8-9 with weak base. Quickly extract with either Xylene or Chloroform or DCM. Clean up freebase from here into ascorbate or other salt as desired or leave as freebase.
Second is to wash with acetone. Discard acetone. Wash with chloroform, discard chloroform. Extract with methanol or methanol/ aqueous. Evap for xtals? Is this a salt or freebase, forgot the final workup (assuming a salt based on the following observation.)
Couple questions here. One is that I have seen both these procedures spelled out by people who have pictorially demonstrated xtals (first) or vouched for (second).
Heres a question. Both procedures have been described using chloroform. However one uses it as a freebase extraction solvent, the other as a solvent to wash away undesireable compounds. This seems completely contradictory. My only explanation could be that in the biotic material the alkaloids are present as salts in the cellular matrix and thus are not extracted by chloroform in salt form. Can anyone verify this explanation? Or speak to the veracity of said procedures?
The meat of this thread would be to test these procedures on wood growing strains that produce WLP, to see if either procedure, or both, isolate actives and discard the neuro-muscular agent.
Supposing the agent is aeruginascin, as is the working theory given that positively charged methonium moeties are present in nuero muscular agents, such as Suxamethonium, we may be on to something.
Being positively charged here should make it immune to being extracted as a freebase under the same conditions as Psilocin, I would presume. A weak base at pH 8-9 should not strip the positive methonium charge inherent to that baked in third methyl. Presto? Procedure 1 eliminates WLP?
Now, as for procedure two, I do not see why acetone or chloroform would strip away a methonium version of Psilocin, given that these two solvents will leave positively charged salts alone, which is why they are used for washing salts of waxes/lipids. So in the end of this procedure the compound that produces WLP may still be present.
If my assumptions are correct, this experiment could provide hobby chemists with the ability to deduce whether or not aeruginascin is indeed what is causing WLP.
Alternative is to wait on real publications and journal articles to produce a paper where someone uses pure synthetic aeruginascin to produce such evidence.
Lastly and unrelated to the above, a long lost person with chemical knowledge I had reason to trust once told me to "precipitate psilocin from solution with iodine." I was very curious but he seemed to tease this as easily discoverable. He suggested using OTC iodine antiseptic solution, which is Iodine and Sodium Iodide in 47% alcohol. I am not sure if he suggested doing this in an aqueous salt or freebase solvent, I remember trying to pick details but was left with nothing. My internal mental library does not immediately provide me with answers. If anyone with chemistry knowledge is sparked by this concept please speak up.
