using Mushrooms to synth intresting tryptamines

[Neoshaman]

Not sure if thsi has already been discussed didn't find it on the serach engine but i'm sure most here will find it quite an intresting topic wasn't sure if it belonged in mycology or chemistry but anyways

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

http://www.cognitiveliberty.org/shulgin/blg/index.html

[TheDudeAbides]

so this compound would be classified legal ?

[Chiral]

I've read that passage a few times and understand that by using say phalaris grass dried as a substrate one can increase tryptamine levels in the fruits growing on them...trials are still being conducted...one person at the nook has confirmed it did work and although the flushes were not great...possibly because spores where used as opposed to coned culture.... the potency was riduculous strong.

H.

Edit..I remembered also that some people where using MHRB in powdered form mixed in with the WBS and as an additive to the substrate with some success too.

Edited June 1, 2009 by Hunab Ku

[Monk]

I've read that passage a few times and understand that by using say phalaris grass dried as a substrate one can increase tryptamine levels in the fruits growing on them...trials are still being conducted...one person at the nook has confirmed it did work and although the flushes were not great...possibly because spores where used as opposed to coned culture.... the potency was riduculous strong.

H.

Edit..I remembered also that some people where using MHRB in powdered form mixed in with the WBS and as an additive to the substrate with some success too.

Yep, at least a couple people there doing these experiments ;)

Also, some are adding Anadenanthera colubrina seed to their wbs jars. It gives ridiculous potency and possibly some kind of 4,5OH thingy, but there's no one who wants to have it GC/MS tested at the moment.

[Alchemica]

Interesting!

Edited June 7, 2009 by The Alchemist

[Chiral]

thanks for posting that...i;m reading Mycelium running at the moment and have gained a lot valuable insight into how these wonderful organisms help the world... the chapters on Mycoremediation and mycopesticides are nothing short of mind blowing....I encourage everyone to read these chapters at some point their life and see how amazing a natural organism it is.

One question I have running around my mind about the above article is...could one say a mushroom that didn't contain any Psilocybin and cultivate it with the radioactive tryptamine method...could that mushroom then be encouraged to produce a form of tryptamine or psilo...take a button mushroom for example and grow it out the way they are describing....be an interesting experiment...as if it worked I'd love to know if the spores of said mushroom where to carry DNA or the embodiment of the mother shrooms now newly accumulated alkaloid into its genes for reproduction....or would it carry that and the mushroom became a non psilo/trypatamine carrying shroom again through spores.

H.

edited for spelling.

Edited June 5, 2009 by Hunab Ku

[alkatrope]

I would suspect that such mushrooms would lack the required enzyme/s. Otherwise I don't see what's stopping them producing it from tryptophan.

I don't think it's something that would get carried to offspring either way. The parent having experience with a new substrate isn't going to alter its DNA to code for new enzymes.

[Green Chemist]

WOW that is so cool. Good find. Makes me want to g back to uni to study molecular biology and mycology. Fungus gotta love them

[Dr Green Thumb]

Not sure if thsi has already been discussed didn't find it on the serach engine but i'm sure most here will find it quite an intresting topic wasn't sure if it belonged in mycology or chemistry but anyways

http://www.cognitiveliberty.org/shulgin/blg/index.html

Thanks so much for this post, I never knew that was possible. SWIM will have to do some research into this. You wouldn't know if there are papers out with a technique for this?

[Slybacon]

Can the enzyme that facilitates the chemical process be created in a lab or extracted naturally and as such avoid the ten steps to arrive at your desired chemical outcome????

And what would be the proposed result of lacing cow dung with nndmt? I'm guessing 4-ho-NN-Dmt?

So then would more complex Tryptamines like 4-ACO-DET(DMT) that are suspected to be converted into Psilicin in your body become 4-HO-4-ACO-DET(DMT) perhaps to complex to come under the current analog laws. Maybe the perfect legal mushrooms, particularly if they do convert to Psilicin. Maybe Torsten would be able to clarify if this chem would be classified under or analog laws????

Edited December 8, 2009 by Slybacon

[alkatrope]

Can the enzyme that facilitates the chemical process be created in a lab or extracted naturally and as such avoid the ten steps to arrive at your desired chemical outcome????

I don't see why not, but seems easier to just grow the fungus in a substrate impregnated with your precurser?

And what would be the proposed result of lacing cow dung with nndmt? I'm guessing 4-ho-NN-Dmt?

Yes, aka psilocin.

So then would more complex Tryptamines like 4-ACO-DET(DMT) that are suspected to be converted into Psilicin in your body become 4-HO-4-ACO-DET(DMT) perhaps to complex to come under the current analog laws. Maybe the perfect legal mushrooms, particularly if they do convert to Psilicin. Maybe Torsten would be able to clarify if this chem would be classified under or analog laws????

 

This compound cannot exist. Each position on a benzene ring can only have one substituent, so it can either be 4-HO or 4-AcO, but not both. And as mentioned, the AcO is hydrolized to HO in the gut anyway.

[Slybacon]

 

Thanks for that

[t st tantra]

snu's book says dmt is not a very good substrate for these fungi and that just using tryptamine would give more efficient results.so the acacias that contain very simple typtamines [not including dmt] should work better than those containing dmt.think because of the enzyme reactions available to it the mushroom can use tryptamine more efficently and productively than dmt.

t s t .

[Neoshaman]

snu's book says dmt is not a very good substrate for these fungi and that just using tryptamine would give more efficient results.so the acacias that contain very simple typtamines [not including dmt] should work better than those containing dmt.think because of the enzyme reactions available to it the mushroom can use tryptamine more efficently and productively than dmt.

t s t .

 

theres a thread going can't remember if its here or AE about using that concept to up the alkaloid production in ceratin cactus( injecting or feeding precusors ) intresting concepts I quite like the idea so theoretically if one was to put one of the 5meo compounds into the subtratewhat would be the end result such as a subtrate with moxy in it would result in the mushroom producing ??????4HO-MIPT i guessing is this right ?????????????????????

............high tryptamine is good if so i wonder if one could make a peatlostylis ( butterflly bush ) based subtrate or work some shredded plant matter into the subtrate at least from memory the tryptamine levels are fairly high and the majority of that is straight tryptamine

[Slybacon]

??????4HO-MIPT i guessing is this right ?????????????????????

 

If this is right , you would want to be way careful with those mushies. Shulgin reports 20mg of 4-HO-MIPT to be more active then 50mg of 4-HO-DMT.

Edited December 8, 2009 by Slybacon

[Neoshaman]

If this is right , you would want to be way careful with those mushies. Shulgin reports 20mg of 4-HO-MIPT to be more active then 50mg of 4-HO-DMT.

 

[alkatrope]

so theoretically if one was to put one of the 5meo compounds into the subtratewhat would be the end result such as a subtrate with moxy in it would result in the mushroom producing ??????4HO-MIPT i guessing is this right ?????????????????????

 

Finding it a tad hard to decipher your post, but sounds like you're asking what would result from adding something like 5-MeO-DMT to the substrate?

I don't know if substitution on the 5 position affects the activity of the enzymes, but if not it would make sense you'd end up with 4-HO-5-MeO-DMT.

MiPT is N-methyl-N-isopropyltryptamine.. The mushrooms will not produce this, this is substitution on the Nitrogen which is a completely different story. The fungus simply adds a hydroxy on the 4-poition of the ring. But if you added MiPT to the substrate it would make sense you would end up with 4-HO-MiPT.

[Neoshaman]

Finding it a tad hard to decipher your post, but sounds like you're asking what would result from adding something like 5-MeO-DMT to the substrate?

I don't know if substitution on the 5 position affects the activity of the enzymes, but if not it would make sense you'd end up with 4-HO-5-MeO-DMT.

MiPT is N-methyl-N-isopropyltryptamine.. The mushrooms will not produce this, this is substitution on the Nitrogen which is a completely different story. The fungus simply adds a hydroxy on the 4-poition of the ring. But if you added MiPT to the substrate it would make sense you would end up with 4-HO-MiPT.

 

Sorry yeah moxy =5 meo-mipt yeah but thanks for clarifying that was still the answer to the question i wanted wether it was viable to use substances in the 5meo group but what i'm gathering from your answer is straight tryptamines i.e MIPT, DIPT ,DMT etc are what needs to be used ?

[alkatrope]

Well I haven't seen anything to suggest that you can't use 5-MeO substituted tryptamines to result in a 4-HO-5-MeO-trypatmine.

[Neoshaman]

Well I haven't seen anything to suggest that you can't use 5-MeO substituted tryptamines to result in a 4-HO-5-MeO-trypatmine.

 

in the original post which i copied from ask Dr Shulgin ,the chemical 4,5-HO-MeO-DMT is mentioned while i imagine very little reserch on its nature exists it is possible right which means I mistated the chemical which would be produced 4,5-HO-MeO MIPT

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.

more here http://www.cognitiveliberty.org/shulgin/blg/index.html

so someone tell me T your probably going to be the best one for this would such a compound be trapped by analouge and homolouge laws

Edited December 11, 2009 by neoshaman

[Alchemica]

A few people seem to be interested in the original article mentioned by Dr Shulgin:

Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

J Gartz

Journal of Basic Microbiology 29(6) (1989) 347-352

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-diethyltryptamine (0.01-0.8%) were isolated from fruiting bodies of Psilocybe cubensis in corresponding experiments. This is the first example of a directed biosynthesis of tryptamine substances by fungi. An effective biotransformation of N-methyltryptamine was also demonstrated with surface cultures of Psilocybe semilanceata. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified in the biomasses.

No alkaloids could be found in the culture medium.

Save a copy if you desire it, might be removed at some stage.

Biotransformation_of_tryptamine_derivatives_in_mycelial_cultures_of_Psilocybe.pdf

Biotransformation_of_tryptamine_derivatives_in_mycelial_cultures_of_Psilocybe.pdf

Biotransformation_of_tryptamine_derivatives_in_mycelial_cultures_of_Psilocybe.pdf