Mushrooms / Psilocin and Psilocybin Workthread

[Mindlusion]

Hehe well for starters -NH is a much better nucleophile than -OH, you can apparently acetylate such amines with a very benign acetylating agent as ASA. Where -OH acetylation will require more, a base to deprotonate (or for nucleophilic catalysis) and your industry standard acetylating agent.

It shouldn't be necessary, however, to acetylate. Its not hard to keep the -OH protonated, psilocin is neutral and is soluble in the appropriate organic solvent as per the literature.


i've always thought that potential H-bonding interaction had a lot to do with psilocins potency, maybe easier to bypass MAO or increase BBB permability (hiding the polarity, like you said DFZ)

 

[Loveall]

I think this internal interaction hides some of the polarity of psilocin. So the slope seen with increased ionic strength in the graph there may relate to that. What does a similar plot for o-cresol vs. m-cresol look like? Or 4-OH indole vs. 5-OH indole? I'll have to sleep on this one.

I couldn't get o-cresol vs. m-cresol to work in the simulation since they don't seem to be zwitterions. However, based on your suggestion I added 6-OH-DMT to our list of 4-OH-DMT (psilocin) and 5-OH-DMT (bufotenin). As expected 6-OH-DMT is a lot more resistant to change when salting water, supporting your proposal of self-cylisation interactions :thumb_up: :

 

[downwardsfromzero]

Good stuff, Loveall. I really appreciate what you've been working on here.

Might as well run for 7-OH DMT as well, to account for electromeric effects.





(My dear little ego has been jumping for joy since Mindlusion replied :lol: )

 

[Loveall]

A new entry seems to have popped up for psilocybin at PubChem (or at least I had not seem it there before),

In water, 2.0X10+3 mg/L at 25 deg C (est)
US EPA; Estimation Program Interface (EPI) Suite. Ver.3.12. Nov 30, 2004. Available from, as of Dec 22, 2005: Chemicals under the Toxic Substances Control Act (TSCA) | US EPA

I added this estimation of 2mg/ml to the wiki.

The EPI suite software looks interesting. There is more info here. Seems like it could be a useful scientific tool, but be warned that it is published by a government.