DMT->psyilocin

stratosphere · Sun May 29, 2005 4:56 am

are there any established (or hypothetical) routes from dmt to psilocin or other 4 subsitituted dmt variants (e.g. nitro, halo)?

i assume the subsistitution at the 4 position blocks an enzyme that degrades dmt and is responsable for its short life relative to psilocin?

left · Sun May 29, 2005 5:58 am

One reasonably easy, albeit not exactly precise way was shown by Gartz. Simply feed DMT to psilocin producing mushrooms, and they'll happily convert it for you.

A cleaner route, and one which is more suited to large scale conversion, would be to isolate the relevant enzyme from the mushroom, immobilise it in gel and feed DMT through it in a column. This is a very common procedure in biochemistry, and can easily be done by someone with even an undergraduate knowledge of the field.

MargaretThatcher · Sun May 29, 2005 6:52 am

stratosphere · Sun May 29, 2005 8:31 am

well left the biochemical pathway is an interesting possibility. but leads me to alot more questions. any articles you could guide me to would be greatly appreciated.

just to list a few questions
1)is there just a single enzyme responsible?
2) what would you have to feed into the column besides dmt, presumably oxygen?
3)is the enzyme present in the mycelium, so you would not have to go to the trouble of fruiting the mushrooms?
4)how much dmt would a given amount of psyilocybin biomass be able to convert?

and finally any specifics on the isolation of the enzyme and running the bioreactor etc.

nubee · Master Archiver

why would one want to do this ?? dmt is rarer than psyilocin which accourns in shrooms is it not ??? (which grow much easier and quicker and in number than dmt plants...) Question

stratosphere · Mon May 30, 2005 12:45 pm

i would argue the assertion that dmt containing plants are more difficult to cultivate in quanity then psilocybin containing mushrooms, depending on climate of course.
for instance bundle flower is easily grown in mass in many parts of the US, its a weed and is perfectly legal until you extract dmt from it. now wether or not there is still an advantage if you were to follow the biosynthetic pathway remains to be seen.
practicality aside as a fan of chemistry im always curious how you might go about turning one compound into another

loki · guinea pig

http://webdoc.sub.gwdg.de/diss/2004/jensen/jensen.pdf

here's a very comprehensive pdf on the topic, the synth it describes is pretty involved but doesn't look out of teh reach of well equipped swims, maybe it could inspire something. the route is very interesting in how it proceeds, it makes the ether equivalent of indole and then oxidatively isomerises it with ammonia and then it re-closes it.

anyways, i hope this helps. I don't believe that it is possible to oxidise the 4-position on dmt, unless one first breaks the dmt quite extensively, and even then, the writers of that paper claim that no combination of reagents allowed them to avoid cyclising into a azole ring.

left · Tue May 31, 2005 10:14 am

I'll try to answer some of the questions, but am not an expert; merely an amateur who has done extensive research into a related matter. (see below for my interest)

stratosphere · Sun Jun 05, 2005 7:46 am

all very interesting. to quote shulgrin "if you put mickey mouse in you 4-hydroxy mickey mouse out". once agian a example of enzymes doing what are reagents can't.

while all conceptouly doable without a fantastically equipped laboratory, i think with all the unknowns this seems like something that would need the assistance of a unversity lab to get the kinks worked out. damn, i really want to try it though.
i think ill keep researching this. thanks left.

Alice · Tue Jul 19, 2005 6:06 pm

well i heard that DMT rich substracts yeld way more potent shrooms (check shroomery.org)
DMT rich substracts yeld shrooms up to X2 X3 times potent than controls
true that tryptophan rich substracts also yeld more potent shrooms but tryptophan is part of shroom pcilocibin/cin biosynthesis so thats not relevant

anyway its hard to belive that shroom brakes dmt to tryptophan and then use it for biosynthesis of pcilocibin/cin.....
seems that there is indeed "indole 4-hydroxylase" kind of enzyme in the shrooms...

wel another "holly grail" to search for

slowly · Sun Sep 04, 2005 2:20 am

... sorry for my english
---text from Rhodium: 4-Hydroxydimethyltryptamine (Psilocin) from DMT C.R. Acad. Sci. Paris 275,613(1972) See also C.R.A.S.P. 269,51(1969) and BSC 1523(1959).

Mix 0.01 M dimethyltryptamine, 0.02 M phosphate buffer pH 7.2 containing 5 mM ascorbic acid, 0.02 M disodium EDTA and 0.01 M ferrous sulfate (CuCl may substitute) and add with stirring at 20-22ш 0.02M H2O2 (0.01 M may increase yield). Let reaction proceed to completion (2 hours or less) and extract with ethyl acetate. Dry and evaporate in vacuum to get about 30% yield of psilocin. The product, which contains the other OH-DMT's as well, can be chromatographed on silica thin layer with t-butanol-acetic acid-water (ACS 22,1210 (1968)) or on a 5% alumina-Nickel column or 10% alumina-Nickel plate with CHCl3-methanol and the psilocin eluted with methanol.

---thiss some original: C. R. Acad. Sc. Paris, t. 269 (7 juillet 1969).

Serie G - 51

CHIMIE ORGANIQUE. - Synthese de la psilocine a partir de dimethyl trypta-mine. Note (*) de MM. MARC JULIA et FRANCOIS RICALENS, presentee par M. Jacques Trefouel.

Le reactif de Fenton-Cier oxyde la N-dimethyl tryptamine en position -4.

II a etc recemment montre [(*), (2)] que la psilocybine 1 a et la psilocine 1 b etaient synthetisees a partir de tryptophane ou de tryptamine par diverses souches de psilocybe. L'hydroxy-4 tryptophane n'est pas incorpore mais la N-methyl et la N-dimethyl tryptamine le sont (3). La psilocine est phosphorylee dans ces conditions. Ces resultats font conclure qu'entre le tryptophane et la psilocine les intermediaires sont dans 1'ordre : tryptamine, N-methyl tryptamine, N-dimethyl tryptamine, hydroxy-4 dimethyl tryptamine, psilocine, psilocybine.

(....)

On a employe le systeme hydroxylant de Fenton-Cier ( Cool

. La N-dimethyl tryptamine en solution aqueuse (0,01 M), tampon phosphate (0,2 M), pH 7,2 contenant de 1'acide ascorbique (o,oo5 M), de 1'acide ethylene diamine tetracetique (0,01 M) (sel disodique) et du sulfatc ferreux (0,01 M) a etc traitee a 20-22° par de 1'eau oxygenee (0,02 M). On a d'abord laisse la reaction se poursuivre avant d'extraire a 1'acetate d'ethyle. L'extrait concentre est alors examine en chromatographie sur couche mince. On a employe tout d'abord le systeme silice, t-butanol-acide acetique-eau (3). La possibilite de formation de complexe entre les groupes phenol et aminc de la psilocine et les ions metalliques nous a conduits a utiliser comme adsorbant de l'alumine chargee avec un sel metallique. Le chlorure de nickel (6H2O) (10 % par rapport a l'alumine) a permis une separation bien plus efficace. On a ainsi constate la formation, dans 1'oxydation, d'un produit se comportant comme la psilocine authentique. On constate aussi l'absence de bufotenine (hydroxy-5 dimethyl tryptamine).

C. R. Acad. Sc. Paris, t. 275 (18 septembre 1972)

Serie C - 613

CHIMIE ORGANIQUE. - Hydroxylation de la N, N-dimethyltrypt-amine en psilocine, etude de certains des facteurs qui gouvernent Vorien-tatinn. Note (*) de MM. MARC JULIA et FRANCOIS RICALENS, presentee par M. Maurice-Marie Janot.

On a etudie l'effet des concentrations en eau oxyge'nde ou EDTA, du pH et de la nature du melal sur les rendements et les proportions des quatre isomeres. Le rende-inent total a varie de 3,3 a 70 % et la proportion d'isomere-4 (psilocine) de 2 a 85 %.

Dans le cadre d'etudes relatives aux effets d'orientation, exerces par des fonctions presentes dans le substrat, sur 1'hydroxylation aromatique radicalaire (1), nous avons approfondi 1'etude deja amorcee (2) sur 1'hydroxy-lation de la N, N-dimethyltryptamine (DMT) par 1'eau oxygenee en presence do sels ferreux, d'acide ethylene diamine tetracetique (EDTA) et d'acide ascorbique [methode do Fenton-Cicr (:l)]. L'hydroxy-4 dimethyl-tryptamine avait etc dosee et isolee mais avec un faible rendement
(3,3 %).
Les rendements en produits hydroxyles ont ete considerablement augmentes : 14 % par rapport au produit de depart (conversion), et 19 % par rapport au produit consomme (rendement) tout d'abord en travaillant sous azote. Les quantites plus abondantes ainsi obtenues ont permis de mettrc en evidence la presence des quatre hydroxy-N, N-dimethyltrypt-amincs isomeres en -4, -5, -6 ot -7 ou l'isomere-4 (psilocine) predomine largomont (60-55 %). Si onsnite on modifie le reactif de Fenton-Cier [(2), (3)] a pH 7,2 en divisant par diuix la quantite d'eau oxygeneo (modification A), les autres quantites etant conservees, on observe une augmentation (de 14 a 20 %) de la conversion et surtout une augmentation de 19 a 60 % du rendement en hydroxydimethyltryptamines; la proportion d'isomere-4 dans ce melange diminue un pen mais reste predominante.
In 2-nd part says how up yeld, who frends with french may you translate please