The Church of Psilomethoxin is a religious organization that claims to have create a compound, 4-HO-5-MeO-DMT, or psilomethoxin, through feeding 5-MeO-DMT to Psilocybe mushroom substrate. They base their logic on a process by Gartz to add other substances to the mushroom substrate in order for the natural enzymes to 4-Hydroxylate those compounds.



Maybe due to steric hindrance from the methoxy group in the adjacent carbon or for other various reasons, evidence shows this biotransformation is NOT happening in the case of psilomethoxin. This sample has been tested several times by GC-MS according to the church itself, as well as by Usona institute using UPLC-HRMS.

At our lab we have recently tested a sample from this church, and published an article with our results. We DID NOT find any psilomethoxin, neither 5-MeO-DMT, only psilocybin and psilocin (and traces baeocystin). We have used an MRM method that looks for characteristic fragments from different compounds. These fragments are very predictable and we could have detected this sample with a very high probability if it was present, even without a reference standard.



The arguments the church uses to defend themselves are unscientific, and put in legal risk their members. Even though we obviously disagree with the war on drugs and believe every conscious adult should be able to decide what to do with their own bodies, we do not condone the founders of a church to lie in order to sell a product to their followers that does not contain what they advertise. Even if they are not consciously scamming people, it is still an unscientific position they are holding and despite the evidence pointing against their claims, they dig their heels and continue spreading misinformation. Please be mindful when interacting with such people.

This already sounds like a rat catcher story. Take 2 things with a strong reputation and make people believe you combined them in one. Makes up a good internet story. Glad that your lab is double checking on stuff like this.

is the experience different from regular mushrooms?

I've heard about this getting debunked. Seemed farfetched from the start to me. Thank you for pursuing authentic and actually valuable information, endy.

One love

Unfortunately there are many psychedelic cults. This might be another of them. Never heard of them or the substance. Thanks for using the scientific method.

Intetesting. Thanks for sharing your report.
I'm left with more questions than answers.
Can such a molecule exist?

Perhaps they simply assumed it was the case because of infusing the substrate, but found out later after testing.

Their putative molecule, if it existed, would still be covered by the Federal Analog Act in the USA, as well as catch-all tryptamine bans in other juridictions.

Yes, although it would likely be quite susceptible to oxidation, as well as somewhat difficult to synthesize. I think it was only ever mentioned speculatively once by Shulgin and people have run with that and taken it as gospel. Why they haven't tried synthesizing the 4-hydroxy-Mickey Mouse yet that he mentioned in the same paragraph is beyond me...

https://en.wikipedia.org...thoxydimethyltryptamine remarks that Marc Julia made it via a ten-step synthesis starting with orthovanillin, which would be beyond the scope of this discussion. The paper, Julia M, Manoury P, Voillaume MC; Bulletin de la Société Chimique de France 1417-1423 (1965) "No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines", seems rather hard to dig up as well. [EDIT: found it - thanks, MAPS!]

Here's a summary of what appears to be all the known pharmacology of the group of compounds from the Julia et al paper. The following animal tests therein described appear to suggest that the 4-hydroxy-5-methoxy compound may be inactive:The corresponding 4-benzyloxy derivative was seemingly about a tenth of the potency of 5-MeO-DMT in the rabbit hyperthermia assay. This tells us precisely exceedingly little to nothing about the human pharmacology of either compound. Would they have deliberately omitted mentioning a compound which approached the potency of LSD-25, however? Would they have mentioned the untimely deaths of any of the creatures concerned? Well, it seems I was correct about the compound's instability:While the catalytic removal of the benzyl group proceeded smoothly, isolation and purification proved to be exceptionally difficult on account of their ease of oxidation. The compounds would rapidly discolor blue or red and this great instability possibly explains their weak activity in the hyperthermia tests.

Thus, the lack of discoloration already appears to prove that The Church of Psilomethoxin material cannot be what they claim it to be.