4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin

[Coschi]

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

So... how would one of you guys go about doing this?

What do you think about it?

[apothecary]

I reckon this has been covered before, incl links to other forums where people have attempted adding tryptamines to substrate.

U T F S E.

[Coschi]

Gee cheers matey

Edit: if your referring to http://www.shaman-australis.com/forum/inde...?showtopic=9886 yeah great interesting reading, but i'm no chemist, i'm no mycologist, and this doesn't give any guide on how to actually 'load a substrate with tryptamines'. I came across it on Ask Dr Shulgin, it certainly sounds like an interesting concept that i thought i'd mention, also someone else might read this (who hadn't previously seen it) and be interested themselves, you know spread the word and all that

Thanks for being so fucking helpful Apo

Edited November 2, 2006 by Sphinx

[apothecary]

You're welcome?

If you want to know the answer to your questions, then you can look it up (including several pages of dicussion on what everyone thinks about it).

[apothecary]

If I can find it in less than 5 minutes, why can't you.

Or do you want all your questions answered without any effort on your part?

http://www.shaman-australis.com/forum/inde...?showtopic=9611

[apothecary]

http://www.thenook.org/forum/index.php?showtopic=46362

Do you want me to hit the shroomery and find even more threads that make you look even lazier?

[Coschi]

http://www.thenook.org/forum/index.php?showtopic=46362

Do you want me to hit the shroomery and find even more threads that make you look even lazier?

No no thankyou that's quite enough the one mentioned above is actually just what i was looking for, thanks SO MUCH BUDDY!!!!!

[apothecary]

You can be as rude as you like, but it won't get you anywhere, and being rude because you expect people to answer questions when they already have been is gonna get you less.

I pasted those links to prove to you that they exist and I'm not just being a prick, but next time I doubt you'll get much help from anyone like that.

[Coschi]

I'm sure we've done this before..

I was flicking around the net, i saw that, i thought 'gee that sounds interesting'. I like to discuss things as part of my personality, I also like to share things. I wasn't aware that this was so common knowledge, so i posted it, thinking perhaps someone would read it and find it interesting, and I could get an answer - like i said i like to discuss so my instinct when i read that was to post a question rather than search around for answers. Not that big a deal imo, you see an extra line on you screen, one a week its gone shit man how dare i do such a thing

[apothecary]

Maybe for you it's one line a week and then it's gone. Realistically, those of us who use the search engine only stand to gain a dilution of the previous knowledge set.

Nevermind. Obviously you're gonna just keep posting questions like this with little regard or respect for the research others have already put in to it, so I'll just leave this be.

[Coschi]

Maybe for you it's one line a week and then it's gone. Realistically, those of us who use the search engine only stand to gain a dilution of the previous knowledge set.

Well well well.. your point has been made

I'm not being sarcastic actually now i see your point, as many times as i've seen you say UTFSE (which i clearly don't respond too well to ) i haven't seen you mention why exactly. Since you are a 'searcher', i'm pretty much your mortal enemy huh

Well in future i may actually make an effort - a suggestions though, UTFSE many people won't respond well to, your better off just saying what said above

[Hyphal]

Play nice people...

[AndyAmine.]

AFAIU its fine to post such things Sphinx, jst post them in a thread that is already going in that direction. like the thread you mentioned above.

It may only be on line a week but what if everyone did that, then there would be over 500 lines every week.

[apothecary]

Well well well.. your point has been made

I'm not being sarcastic actually now i see your point, as many times as i've seen you say UTFSE (which i clearly don't respond too well to ) i haven't seen you mention why exactly. Since you are a 'searcher', i'm pretty much your mortal enemy huh

Well in future i may actually make an effort - a suggestions though, UTFSE many people won't respond well to, your better off just saying what said above

Yeah so next time maybe consider other points of view than your own before acting the way you did :/

Like Andy wisely said, nobody will complain if you revive an old thread, in fact people prefer it that way because it keeps the information together and flowing. (and will also revive the information for new people to see)

And consider, most of the people who use SAB aren't posters, they're searchers (otherwise this would be a much busier forum).

Edited November 2, 2006 by apothecary

[Amulte]

OMFG!

now children! take it to PM or start a new thread about this (UTSE just incase there is one ofcourse) but shit. i understand the point very well but 7 posts of bitching??? seams like somones making an example. and now i imagine it will go on with nothing in relation to this thread but UTSE.

be part of the solution and not part of the problem, take it to the person and the mod, the mod can merge threads and delete needless posts. i see absolutely no point of making a public spectical, if the goal was the educate others about UTSE then make a pinned thread in everywhere about doing so.

[Coschi]

HAHAHAHAAA good call man

my bad, really, my bad

[Fenris]

Hey GCF thats an interesting avatar you have today is that an American Indian thunderbird or a depiction of the less well known Cornish Owlman? Or am I totally off?

[Fenris]

Thats cool, I wonder what cultural/spiritual significance the horned owl had to them.

[phloom]

Maybe you would find this info on google easily, but if you cant pm me n i'll send you the file.

From the Journal of Basic Microbiology 29, Jochen Gartz, "Biotransformation of tryptamine derivatives

in mycelial cultures of Psilocybe";

Abstract:

Mycelial cultures of Psilocybe cubensis capable of forming psilocybin and psilocin de novo display a high

capacity for hydroxylation of tryptamine derivatives at the 4-position. A specific biotransformation of

added synthetic N,N-diethyl-tryptamine was found. Thus high amounts of 4-hydroxy-N,N-diethyltryptamine

(up to 3.3 %) and a minor quantity of 4-phosphoryloxy-N,N-diethyltryptamin(e0 .01 -0.8 %) were

isolated from fruiting bodies of Psilocybe cubensis in corresponding experiments. This is the first example

of a directed biosynthesis of tryptapine substances by fungi.

An effective biotransfomation of N-methyltryptamine was also demonstrated with surface cultures of

Psilocybe sernihnceata. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified

in the biomasses.

No alkaloids could be found in the culture medium.

[phloom]

Wow GCF, Mayan ay! nice....ive never seen that type of Mayan design before.

[FungalFractoids]

I reckon this has been covered before, incl links to other forums where people have attempted adding tryptamines to substrate.

U T F S E.

LOL

I UTFSE'd and this was the only relevant thread that came up... Good thing the OT posted it, eh?

[FungalFractoids]

You can be as rude as you like, but it won't get you anywhere, and being rude because you expect people to answer questions when they already have been is gonna get you less.

I pasted those links to prove to you that they exist and I'm not just being a prick, but next time I doubt you'll get much help from anyone like that.

Why even run a forum if you're gonna take that sort of attitude??? Seriously, go start an entheogenic search engine or something... Not everyone is leet as you. I just happened to hear about this elsewhere and thought I'd check out your forum for some extra info, your attitude must be very off=putting for inquisitive newcomers...

[blangschpeer]

If people have heard it all before then why even bother posting an annoyed response, either add something without bitching like a helpful community minded soul or just let the noobies discuss it. It's not like any harm is being done.

[Monk]

This is a fairly old wound to be picking at, but I believe this spat had a lot to do with the context of the original post. There was quite a few extraneous topics being posted at the time that had already been covered well in the forums. This type of thing is annoying to the searchers among us when a simple search for info turns up 30 threads of diluted information. After all, that's one of the main points of forums. They serve as a searchable log of information exchange among like minded folks. If they become unsearchable due to tons of redundant material, they lose one of their main functions and then it's just social hour. So, while I think it would be good to bring up an old topic (especially this one ) to see if anyone has anything new to add, it really should be done in the original thread.

[blangschpeer]

If they become unsearchable due to tons of redundant material, they lose one of their main functions and then it's just social hour. So, while I think it would be good to bring up an old topic (especially this one ) to see if anyone has anything new to add, it really should be done in the original thread.

Point taken, I can see how it would be annoying trying to pinpoint exactly what you're looking for if the place were a glorified chat room.

That said, a little more leaniency should be afforded to newcomers, if a thread can be cleaned up or merged then so be it. Not many people will stick around if they're made to feel like an idiot for trying to contribute.

All in all though, I too would love to hear if there have been any further developments in this field, I recon some pretty interesting developments in the medical field will happen via this method.