Tryptamines Psilomethoxin Church

[xdrc]

There is an experienced clandestine analytic chemist on DMT-Nexus (and related websites) who did experiments with spiking ps. cubensis substrate with 5-MeO-DMT. I think he was mostly doing work with HPLC-MS or GC-MS, but I don't remember and can't find his posts now. Apparently, Hamilton Morris also talked in his Patreon podcast about having been given a sample of that church, and finding no 5-MeO-4-HO-DMT. It has to be said that currently no analytical sample of that compound exists, last being made in France in 1965 or so (I think the paper has never made it to the digital age, but if someone may try to access it: Julia M, Manoury P, Voillaume MC (1965). "[No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines]". Bull Chim Soc Fr (in French): 1417–23), so it is going to be rather hard to proof existence/non-existence of that compound without isolating it and completely characterising the structure. I was given to understand by Dirk Hoffmeister that PsiH (the 4-hydroxylating enzyme in ps. cubensis) is not yet understood enough as to give predictions whether or not 4-hydroxylation with 5-methoxy substitution is feasible or not. Note that their group did work on 5-Methylpsilocybin, but making 5-Methylpsilocin synthetically and only using the phosphorylation enzyme.

I think there is legitimate doubts to have about the church of psilomethoxin. Their claims are entirely based on bioassays, mostly in microdosed quantities. Placebo is real.

 

[JackARoe]

I think it always comes back to the myth that these drugs only work if you have a “shaman” (aka ex felon trying to clean you out) to help you facilitate and integrate the experience. We are our own guides, we chose our destiny. The moment you give up your right and self agency a lot of bad things can happen.

Lots of myths with Shamanism. Not sure when it became about a person flying to South America to trip with a native. Shamans were the trippers, the recipient usually were not tripping based off what I know. The Shaman is the healer, not the guy that doles out the drugs. At least that is the notion I had through the years even before these ayahuasca packages. Sessions with people seem to be a different story among the natives. There does seem to be tripping in groups. But Shamanism is not that.

I always love the conclusion, we are our own Gurus and we are our own Shamans. LSD was release in public and people had to be their own guide. Not every tab of acid taken by a person came with a personal babysitter or instructions. And I am one to believe that is how Nature really wanted it. Not a vacation package. lol

 

[Latherdome]

I think there is legitimate doubts to have about the church of psilomethoxin. Their claims are entirely based on bioassays, mostly in microdosed quantities. Placebo is real.

Placebo is real, but i can easily differentiate psilomethoxin from psilocybin microdoses blind. I made 6 capsules of sub-150mg, 3 being psilomethoxin as provided by church, 3 being my psilocybe cyanescens forage. The color differs. Never took more than 45min for me to say which i’d eaten from the paper bag without looking, confirmed by counting what was left.

This experiment has been almost my only interruption of almost 2 straight months of almost daily Pm microdosing: no tolerance effect as with psilocybin.

The church has tacitly acknowledged that analytics may remain equivocal absent a reference sample, which they estimate may cost $30-40K to synthesize. Note also that they mix undisclosed amino acids to the fumarate salt of 5 they feed the psilocybes, trade secret, perhaps explaining different results of 3rd-party attempts.

 

[xdrc]

Placebo is real, but i can easily differentiate psilomethoxin from psilocybin microdoses blind. I made 6 capsules of sub-150mg, 3 being psilomethoxin as provided by church, 3 being my psilocybe cyanescens forage. The color differs. Never took more than 45min for me to say which i’d eaten from the paper bag without looking, confirmed by counting what was left.

That is no proof for the existence of 5-MeO-4-HO-DMT. Aside from 3/3 not being statistically relevant, who says that "undisclosed" additions may not result in different effects? From what I've heard, the churches samples were analysed to consist of unchanged 5-MeO-DMT, but I haven't seen the results myself. Trade secret idc, this is a cult with too many red flags to count. If it has good results for you - placebo, psilomethoxin, other constituents - that is nice for you, I personally only care about the question whether or not ps. cubensis can 4-hydroxylate 5-MeO-DMT, for which there is no good proof currently.

 

[Latherdome]

That is no proof for the existence of 5-MeO-4-HO-DMT. Aside from 3/3 not being statistically relevant, who says that "undisclosed" additions may not result in different effects? From what I've heard, the churches samples were analysed to consist of unchanged 5-MeO-DMT, but I haven't seen the results myself. Trade secret idc, this is a cult with too many red flags to count. If it has good results for you - placebo, psilomethoxin, other constituents - that is nice for you, I personally only care about the question whether or not ps. cubensis can 4-hydroxylate 5-MeO-DMT, for which there is no good proof currently.

Granted there’s no proof. I wrote why i still think it’s likely legit here:

Re cult, my definition includes some attempt by leadership, often charismatic, to control thought, behavior, speech by adherents. This is nowhere evident. This thread has wandered a bit, but for the record the church involves no shamans, sitters, or dogma, though they have integration support groups, Zoom services, local meetups for "hikrodosing" etc. They send you sacrament for you, sovereign, to do with as you please, letting it do the talking.

 

[Didgital]

800 dollars

That's stupid expensive. I generally really dislike psychedelic capitalism

So it can be extracted out no problem but can’t withstand the demands of a GC/MS? I call BS

Me too, why wouldnt they just use HPLC which is non destructive? Or honestly might need NMR because afaik the reference standard if psilomethoxin probably arent available.

Do you have any guesses that explain my experience

Could it be some other chemical? I would actually suspect it's quite active and probably pretty potent. I'm also really curious how these mushrooms dont have any psilocybin. I assume inject mushroom with another tryptamine it should still be synthesizing psilocybin? Unless it's not a psilocybe species?????

 

[Didgital]

$30-40K

40k to synth a reference sample? Highly doubt that. I've had exotic cannabinoids custom synthesized by Cayman on a few occasions, the most expensive was 12k for something called b-oh-hhc. I'm sure some china/india lab do it for much less although its riskier. I do think the synth is probably a bit more involved then a condensation reaction, but if 4-hydoxy-5-methoxyindole is available, it could likely be done in kg quantities.



Also guys, I think the only real way to know is to actually try it, which I am hereby committing to right now.

I've a few questions though in best way to proceed. Would I need to convert into a water soluble salt? Um is it best to inject mycelium or right into fruiting body? How much should I dope I dunno, let's say a small mason jar?

 

[Latherdome]

Fumarate salt solution (water) of 5-MeO-DMT plus undisclosed amino acids injected as uniformly as possible into substrate after first flush. Lower fruiting temps below normal optimal. Same amount of 5 as you would expect the strain to produce of the usual alkaloids per flush. Given enough 5, this suppresses production of the usual compounds for the new. I have not tried this (forager), cannot provide more detail. Just what I've gleaned from multiple sources either well placed or good fakers.

The first synthesis was by Marc Julia of Pasteur Institute in 1965, 10-step process starting from ortho-vanillin. Hamilton Morris said it would take a month or more. $30-40K is a quote from chemist; not saying the best quote.

 

[Didgital]

Ya know I did find a very similar synthesis and it looked pretty daunting, but I also dont fully understand why they did it the way they did. I dont like to get too much into synthesis on here, but I'm sure there is a better way. Ortho-vanillin isnt even an indole. I really dont see why it cant be made via the antony speeter in the same way that 4 aco or psilocin are

 

[Jabberwocky]

Per Shulgin himself:

Dear Dr. Shulgin:

I have been puzzled, why this compound (4-HO-5-methoxy-N,N-dimethyltryptamine) wasn't included in TIHKAL -- for me it looks very appealing. Have you by the way, ever looked into cathinone (beta-keto-amphetamine) analogues of some of the psychedelic amphetamines (DOB, TMA-2, etc.) The MDMA-analogue (Methylone) is active indeed, do you think the 2,4-5-substitution pattern could be applied onto the CATs?

_Anon_

Dear _Anon_,

I totally agree with you.

4-Hydroxy-5-methoxy-N,N-dimethyltryptamine would be a fascinating compound to explore. The reason it's not in TIKHAL is that it is virtually unknown. The only report of it in the chemical literature was a paper published by Marc Julia's group at the Pasteur Institute in 1965. They reported the synthesis and physical properties of the compound but to my knowledge it has never been explored in any way. The synthesis is quite a frightening thing. It starts with ortho-vanillin and takes approximately 10 steps to get to the 4,5-HO-MeO-DMT. I'm not surprised that no one has pursued the compound.

However there is a very interesting study that took place in Leipzig about 15 years ago. Jochen Gartz, a mushroom explorer whom I know quite well, has done some fascinating studies with Psilocybe species by raising them on solid media containing strange tryptamines that are alien to the mushroom. Apparently the enzymes that are responsible for the 4-hydroxy group of psilocin are indifferent to what it is they choose to 4-hydroxylate. He has taken things like DPT or DIPT and put them in the growth media and the fruiting bodies that came out contain 4-hydroxy-DPT or 4-hydroxy-DIPT instead of psilocin. In fact, he has a patent on the process. These active compounds are made by the mushroom so they really are natural and yet they never have been observed in nature. I'll give you even odds that if you put spores of a psilocybe species on cow droppings loaded with 5-MeO-DMT you would come out with mushrooms containing 4,5-HO-MeO-DMT. This way you avoid a 10 step synthesis by growing a psychoactive mushroom that contains no illegal drug.

Your idea of making analogues of the psychoactive amphetamines with the carbonyl that is characteristic of CAT would probably be a disappointment. Cathinone itself is rather unstable because there is a primary amine and a ketone in the same molecule. It will tend to dimerize and become inactive. In the example of METHYLONE (as with methcathinone) the amine is a secondary amine and the compound is quite stable. But all of the psychoactive amphetamines (except for MDMA) are primary amines.

- Dr. Shulgin

With magic mushrooms being legal in Colorado and Oregon, we can probably expect experimentation resulting in lots of novel tryptamines.

 

[Jabberwocky]

Ya know I did find a very similar synthesis and it looked pretty daunting, but I also dont fully understand why they did it the way they did. I dont like to get too much into synthesis on here, but I'm sure there is a better way. Ortho-vanillin isnt even an indole. I really dont see why it cant be made via the antony speeter in the same way that 4 aco or psilocin are

Because the methoxy and hydroxy functional groups are at the correct places on the benzene ring.

 

[Didgital]

Because the methoxy and hydroxy functional groups are at the correct places on the benzene ring.

Yeah, but you'd have to build the indole ring and then the amine out of the aldehyde and methylate it as well. Anyway no more synth talk, I'm just gonna inoculate some amd see if it different

 

[Jabberwocky]

Yeah, but you'd have to build the indole ring and then the amine out of the aldehyde and methylate it as well. Anyway no more synth talk, I'm just gonna inoculate some amd see if it different

I sent you a PM.

 

[Dead Machination]

I think it's pretty obvious that a lot of these new "churches" are just trying to skate around federal law. Even if the owner, priest or shaman or whatever has legit good intentions, when they start charging fees that could get you a nice used vehicle, it definitely makes it LOOK like the intention is to sell drugs for a profit. I've never heard of a church that REQUIRES payment, that's not very "churchy", it's more akin to a business. My mother-in-law is active in a real church, and they drove around and gave out their sacrament to members, for FREE, if they didn't want to come because of COVID.

I wonder if any of them are using legal RCs, and that's why they feel so comfortable about operating the way they do. Just a guess.

I just looked up the ayahuasca church in Kentucky, for the service is that they provide, and the amount they charge, the profit margins are grotesque. Buying in bulk, one could quite literally buy enough aya ingredients to trip whenever they wanted for the rest of their life.

I love tripping, and I believe that everybody should have a complete access to any psychedelic they want. I think these "churches" are praying on people who want to try psychedelics, but don't necessarily have a "hookup", or aren't willing to commit a felony.

I live really close to that facility in Kentucky, and I find it really strange that if I were to do ayahuasca in my home, just a few miles away, I'd be committing a felony. Yet I could drive over there and pay a four digit number with no 1's to do the same drugs with some sketchball dude, who isn't even a doctor or anything, legally. I also legitimately believe that psychedelics produce spiritual experiences, and are a crucial part of my growth and development as a person, I believe that as wholeheartedly as any "church" member, so what's the difference? I guess it's just a bunch of money, apparently you really do pay for your beliefs.

 

[Jabberwocky]

I've never heard of a church that REQUIRES payment, that's not very "churchy", it's more akin to a business.

You've never heard of the Church of Scientology?

They require payment.

 

[Dead Machination]

You've never heard of the Church of Scientology?

They require payment.

Yeah, and they're not very "churchy" either.

They're like a drug church without the drugs.

 

[xdrc]

Two important things which were pointed out to me regarding psilomethoxin:

a) 4,5-dihydroxytryptamine is a known serotonergic and noradrenergic neurotoxin.

10.1007/BF00306720

It was found that local injections of 4 ~µg of either of the three compounds [4,5-DHT; 5,6-DHT; 5,7-DHT]into the ventromedial tegmentum and into the grey matter of the spinal cord produced extensive and probably rather selective damage to the ascending and descending indolamine fibre tracts and - - although to a lesser and variable extent - - the noradrenaline and dopamine systems.
[...]
The same amounts of 5,6-DHT or 4,5-DHT caused larger necrosis and tissue damage (about 1.0 -1.5 mm in diameter) at the site of injection. This indicates that general and unspecific cytotoxic effects are exerted by lower concentrations of 4,5-DHT and 5,6-DHT than of 5,7-DHT.
[...]
4,5-DHT and particularly 5,7-DHT cause significant damage also to the NA-containing axons, thus being less specific for indolamine neurons than 5,6-DHT.

b) 5-MeO-DMT can be demethylated in human metabolism to bufotenin, which makes it likely that psilomethoxin may be dealkylated to potential neurotoxic metabolites as well.

10.1016/j.bcp.2010.02.020

Depending on CYP2D6 status, MAOI co-administration and 5-MeO-DMT dosage, systemic exposure (AUC) to bufotenine was 2–24% of the systemic exposure to 5-MeO-DMT (Tables 4 and 5), indicating potential involvement of bufotenine metabolite in complex pharmacological effects of 5-MeO-DMT.

I'd like to point out that I'd love seeing psiH making 5-MeO-4-HO-DMT, as that would be a cool enzymatic reaction, and I'd love seeing 5-MeO-4-HO-DMT being a cool and benign compound. But there are serious doubts to either hope. What I hate seeing is some pseudo-science cult scamming depressed neo-hippies out of money and making false claims.

Regarding synthesis of psilomethoxin, Marc Julia made the respective 5-MeO-4-BnO-indole precursor from o-vanillin, via the respective ortho-nitro-nitrostyrene and reductive cyclisation. Since 1965, there are many new methods for synthesis. I'd assume Hemetsberger indole synthesis for instance saving some steps otherwise required for nitration at the right position. I'd like to point out that this note on synthesis omits too many details to be of use to anyone who doesn't know how to generally synthesise these type of compounds in the first place.

Regarding the pharmacology of the disubstituted tryptamines they made (with 4,5-substitution, those were: 5-MeO-4-BnO-DMT, 5-MeO-4-HO-DMT, 5-MeO-4-HO-T, 5-MeO-4-BnO-T and 5-MeO-4-BnO-DET), the following (translated from French) is pointed out:

Julia M, Manoury P, Voillaume MC (1965). "[No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines]". Bull Chim Soc Fr (in French): 1417–23)

The pharmacological study was carried out by Doctor J. Jacob, M. Cl. Lafille, Mlles C. Barthélémy and P. Echinard-Garin, in the Pharmacology Laboratory of this Department. We would like to thank them again. The detailed results will be published elsewhere. Let us point out that: the only active compounds in the test of temperature elevation test in rabbits (research of psychomimetic action) were the 5-methoxy-4-benzyloxy (4783 TC), 5-methoxy-6-hydroxy (4680 TC) dimethyl tryptamines and 5-methoxy-6-hydroxy-diethyl tryptamine (4786 TC), all three of which are about 10 times less active than 5-methoxy-dimethyl tryptamine (4,334 TC).

Rabbit temperature elevation test is outdated, and I'm not even sure how good it works on tryptamines. Also, those are quite broad statements without seeing the actual paper, which I couldn't find searching for the authors. But it may be that 5-MeO-4-HO-DMT is not even particularly active. I'd welcome insights on that.

 

[SpiralusSancti]

Fumarate salt solution (water) of 5-MeO-DMT plus undisclosed amino acids injected as uniformly as possible into substrate after first flush. Lower fruiting temps below normal optimal. Same amount of 5 as you would expect the strain to produce of the usual alkaloids per flush. Given enough 5, this suppresses production of the usual compounds for the new. I have not tried this (forager), cannot provide more detail. Just what I've gleaned from multiple sources either well placed or good fakers.

The first synthesis was by Marc Julia of Pasteur Institute in 1965, 10-step process starting from ortho-vanillin. Hamilton Morris said it would take a month or more. $30-40K is a quote from chemist; not saying the best quote.

In this day of age I would go for a liquid culture of truffles fed with all kinds of goodies than lab tested.

THAT’S THE WAY OF A psypixeipsipsopaspipsmastixr TRUE RELIGION one and only whit toads eating 4-ho-5-meo-DMT truffles and shitting UNTESTABLE nano-tryptix DMT spirit doing all da talk after you drop 3, 6 & 9mg of acid. Don’t believe it, try it for yourself!

 

[JackARoe]

Re cult, my definition includes some attempt by leadership, often charismatic, to control thought, behavior, speech by adherents. This is nowhere evident. This thread has wandered a bit, but for the record the church involves no shamans, sitters, or dogma, though they have integration support groups, Zoom services, local meetups for "hikrodosing" etc. They send you sacrament for you, sovereign, to do with as you please, letting it do the talking.

I am guilty of making the thread wander. But I do think as far as answers we know we have a church distributing a psychedelic to its members. The chemistry question remains as to what it is. Totally enjoying the banter though so thanks for all the info.

I do remember reading about someone on the Nexus that injected mushrooms with 5-MEO-DMT. There may be a whole thread on it. I have not seen it in a while.

 

[Didgital]

I am guilty of making the thread wander.

Its wandered, but in a good way!