Backfolding is a common phenomenon that can be observed in stretched molecules when one end is able to interact with the other in any way. There might be H donor groups that interact with H acceptor groups, or there might be some p - p interaction.
Drawing psilocin with the sidechain folded back to the 4-OH where the H is shared by the nitrogen and the phenol I got a quasi 8-membered structure. When I compare this to the structure of LSD, the nitrogen might be in an similar position. I drew the protonated form, because this is the form that interacts with the Asp at the 5-HT receptor. -Hmmm, not bad, I thought and tried the same with the phosphate ester.
I drew it that way so the sour P-OH shared its H with the nitrogen. The resulting structure with a 10-membered scaffold shows (at least on the paper) exactly the same conformation like LSD. I was astouned!!! Is it only accidentally or is it of any relevance?
It is a shame that nobody really knows what molecule is really responsible for the action. If you eat 4-AcO-DMT or psilocybin, I bet that there are actually two active compounds that do the job in your brain, the esters and the free phenol. And it seems to be impossible to say what effect results from what compound
Intravenous application might be the only way to feel the effect that is mainly caused by the esters.
An other way to elucidate this, would be the comparison of binding data of the esters and the free phenol. Actually no one did it, -at least not to my knowledge.
Have a look at the drawn structurs and tell me what you mean. I was so fascinated by that idea and the similarity with LSD. Probably there’s something really wrong in my considerations. Every comment is welcome.
Drawing psilocin with the sidechain folded back to the 4-OH where the H is shared by the nitrogen and the phenol I got a quasi 8-membered structure. When I compare this to the structure of LSD, the nitrogen might be in an similar position. I drew the protonated form, because this is the form that interacts with the Asp at the 5-HT receptor. -Hmmm, not bad, I thought and tried the same with the phosphate ester.
I drew it that way so the sour P-OH shared its H with the nitrogen. The resulting structure with a 10-membered scaffold shows (at least on the paper) exactly the same conformation like LSD. I was astouned!!! Is it only accidentally or is it of any relevance?
It is a shame that nobody really knows what molecule is really responsible for the action. If you eat 4-AcO-DMT or psilocybin, I bet that there are actually two active compounds that do the job in your brain, the esters and the free phenol. And it seems to be impossible to say what effect results from what compound
Intravenous application might be the only way to feel the effect that is mainly caused by the esters.
An other way to elucidate this, would be the comparison of binding data of the esters and the free phenol. Actually no one did it, -at least not to my knowledge.
Have a look at the drawn structurs and tell me what you mean. I was so fascinated by that idea and the similarity with LSD. Probably there’s something really wrong in my considerations. Every comment is welcome.