|
Some of these posts are very old and might contain outdated information. You may wish to search for newer posts instead.
|
RigaCrypto
Hidden Heart

Registered: 06/22/06
Posts: 23
Last seen: 15 years, 1 month
|
Addition of 5-MeO-DMT to mushroom substrate
#6368972 - 12/14/06 02:08 AM (17 years, 5 months ago) |
|
|
For my next cultivation I'm planning to add some 5-MeO-DMT to my mushroom substrate. However I need some advice from those who have experience with adding tryptamines:
1. As suggested in the shroomery tek, I'm planning to add about 70-80mg to a PF cake. Is this a reasonable amount?
2. The 5-MeO-DMT I have is freebase. Should I turn it into a salt? Would a citrate salt work? What would be the solubility of the resulting salt?
3. Should I add the 5-MeO-DMT solution at the beginning or when the cake is colonized?
4. Any special procedures or substrate composition in order to make it work?
5. Finally, can anyone speculate as to the nature and pharmacology of the resulting compounds? Might it be 4-HO-5-MeO-DMT? Maybe 4,5-MDO-DMT? What additional properties does the 4-HO group add(like immunity to MAO)?
|
fastfred
Old Hand



Registered: 05/17/04
Posts: 6,899
Loc: Dark side of the moon
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: RigaCrypto]
#6369006 - 12/14/06 02:32 AM (17 years, 5 months ago) |
|
|
The 5-methoxy group will prevent 4-hydroxylation IMO. I highly doubt that 4-hydroxylase will do an addition ortho to a methoxy group. It's also specific to the 4 position, so I don't think it would hydroxylate anywhere else on the ring.
So I wouldn't think that 5-meo-dmt would be a good additive.
-FF
|
RigaCrypto
Hidden Heart

Registered: 06/22/06
Posts: 23
Last seen: 15 years, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: fastfred]
#6369027 - 12/14/06 02:55 AM (17 years, 5 months ago) |
|
|
Maybe so. But Dr. Shulgin thinks it may be otherwise. To quote him,
"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. "
His full answer can be found at
http://www.cognitiveliberty.org/shulgin/blg/index.html
|
fastfred
Old Hand



Registered: 05/17/04
Posts: 6,899
Loc: Dark side of the moon
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: RigaCrypto]
#6369147 - 12/14/06 05:08 AM (17 years, 5 months ago) |
|
|
I would hate to dispute Shulgin, but I just don't see it happening. He just guesses even odds and cites Gartz's work with 4-hydroxylating DPT and DIPT. If you look at those compounds they don't have any substitutions on the indole ring. They are both just tryptamines with additional groups attached to the nitrogen.
Adding functional groups to the benzene ring totally changes it's electronic structure. The 4 position on DMT (which does get 4-hydroxylated) is going to be totally different than the 4 position on 5-methoxy-DMT.
It is true that a methoxy substitution is usually considered an ortho/para director, but the bulk of the methoxy group is going to hinder any enzyme mediated ortho ring substitution.
I would bet that 4-hydroxylase is highly specific for tryptamines without indole ring substitutions. Otherwise take serotonin (5-hydroxytryptamine, or 5-HT) for example. 5HT has almost the same situation as 5-meo-DMT. It just has three less methyl groups. If 5-meo-dmt could be 4-hydroxylated then 5HT likely would also.
If it was then you'd probably get 4,5-HO-DMT. Plenty of people have talked about using 5HT in substrates, but I've never seen anything come of it. 5HT is cheap and easy to get.
Here is what Shulgin has to say about 4,5 substitutions... ----------------------------------------------------------- The two aromatic ring positions that are associated with human psychedelic activity are the 4-position (of psilocybin fame) and the 5-position (of 5-methoxy-this-and-that fame). Here is a compound with both positions oxygen-substituted (with the methylenedioxy ring that is so effective in the phenethylamine world) and it has not been looked at in man, to my knowledge. I snooped around in the literature associated with this kind of DMT substitution, and the world of di-oxygen substitution to be found at these two potent focal points is almost unknown. -----------------------------------------------------------
So it certainly would be novel to get a 4,5 substituted tryptamine. 4,5-MDO-DIPT is known to be active BTW. I just don't see it happening via 4-hydroxylation in this biosynthetic pathway, but of course I could be wrong.
-FF
|
RigaCrypto
Hidden Heart

Registered: 06/22/06
Posts: 23
Last seen: 15 years, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: fastfred]
#6369230 - 12/14/06 06:21 AM (17 years, 5 months ago) |
|
|
I've only found one thread discussing addition of 5-HT and no actual experiments carried out. Maybe you can give me some links?
I agree that it's a slim chance but that's no reason not to do it. If it doesn't work it would set me back 80mg of 5-MeO-DMT, big deal. I don't really like the stuff anyway.
I'm trying to make sure though that if I do it I do it correctly, not having it fail because procedure errors. I'm curious in particular whether to add it in freebase or salt form.
|
fastfred
Old Hand



Registered: 05/17/04
Posts: 6,899
Loc: Dark side of the moon
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: RigaCrypto]
#6370401 - 12/14/06 01:15 PM (17 years, 5 months ago) |
|
|
Quote:
RigaCrypto said: I've only found one thread discussing addition of 5-HT and no actual experiments carried out. Maybe you can give me some links?
Sorry, try a few different search terms. There are a ton of threads. Most of them are "What if I add this or that to the substrate?" There's threads on all manner of tryptamine additives. You probably won't find much usefull info there though.
Quote:
RigaCrypto said: I'm trying to make sure though that if I do it I do it correctly, not having it fail because procedure errors. I'm curious in particular whether to add it in freebase or salt form.
I think it would be hard to figure anything out using small amounts. What you would want to do is add your addative in a large excess so that it would monopolize the biochemical pathway. That way you wouldn't have to deal with the psilo's or worry about enough product being present.
Here is a chart that might be usefull...

As you can see uptake of larger tryptamines is highly reduced. You might expect 5-meo-dmt to be similar to DMT, i.e. very slight. So of your 80mg perhaps 10mg (if you're lucky) might be taken up by the myc.. Then even if all that is converted to something you'll end up with 10mg of a drug with unknown properties mixed with perhaps 40-50g of wet mushrooms. It would be really hard to figure anything out from that mixture, unless the product turns out to be highly toxic... 
I'm not trying to shoot you down, just trying to give you a realistic estimation of what might happen.
As far as salt vs. freebase I don't think it would make the slightest difference. The salt would just dissassociate in the moisture of the substrate and the freebase would establish equilibria with any normally present ions. Using the salt would just slightly increase the salt concentration. Once the myc tries to uptake it it will become dissolved and equilibriated in any case. You could probably fool around with the osmolarity of the solution to force some more into it if it were a liquid culture, I don't see anything make much of a difference in a normal substrate though.
Anyway all I've said is drunken foolery and could be totally wrong or not actually make sense, but it does to me at this moment.
-FF
|
MattEx
Psychonaut

Registered: 01/01/05
Posts: 110
Loc: New Zealand
Last seen: 16 years, 5 months
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: fastfred]
#6370440 - 12/14/06 01:27 PM (17 years, 5 months ago) |
|
|
Ya, personally i'd stick with Tryptamine or 5-HO-Tryptamine (aka Serotonin). I'd be very interested to see a bioassay of 4,5-diHO-DMT (i'd rather a synthesis for exact results, but cool to do it via our fungus friends).
|
RigaCrypto
Hidden Heart

Registered: 06/22/06
Posts: 23
Last seen: 15 years, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: fastfred]
#6370634 - 12/14/06 02:31 PM (17 years, 5 months ago) |
|
|
Quote:
fastfred said:
Sorry, try a few different search terms. There are a ton of threads. Most of them are "What if I add this or that to the substrate?" There's threads on all manner of tryptamine additives. You probably won't find much usefull info there though.
From what I've read tryptophans have been established as ineffective, whereas tryptamines worked, including added in vegetal material. I haven't found anything relevant involving the addition of 5-substituted tryptamines. By the way, there's a buddy of mine who's going to try the 5-HT addition too.
Quote:
fastfred said:
I think it would be hard to figure anything out using small amounts. What you would want to do is add your addative in a large excess so that it would monopolize the biochemical pathway. That way you wouldn't have to deal with the psilo's or worry about enough product being present.
Thanks for the graph. That's a good point you made. Do you have more details about the experiment? According to that graph, tryptamine would be the ideal additive for mushrooms. But as I recall from a thread some people had results even with addition of small quantities of Mimosa root bark, which would suggest that even alkyltryptamines can be assimilated.
I might postpone the experiment until I have a larger quantity of 5-MeO-DMT.
Quote:
fastfred said:
It would be really hard to figure anything out from that mixture, unless the product turns out to be highly toxic...
Anyway, I wasn't planning to be as brave with drug testing as Dr. Shulgin, although he's lived to a respectable age. I was thinking more along the lines of enlisting the help of an animal to test for toxicity first, then starting small.
|
hjalmar
chemist, autist


Registered: 10/27/04
Posts: 295
Loc: Belgica Secunda
Last seen: 1 year, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: RigaCrypto]
#6370745 - 12/14/06 03:08 PM (17 years, 5 months ago) |
|
|
Quote:
Anyway, I wasn't planning to be as brave with drug testing as Dr. Shulgin, although he's lived to a respectable age. I was thinking more along the lines of enlisting the help of an animal to test for toxicity first, then starting small.
Thin layer chromatography is less hasslesome and more ethical.
Use 5-Meo-DMT and "untreated" psilocybe extract as standard.
If you don't have Erhlich's reagent, I'm sure you could make the spot visible using a short wave UV light.
Otherwise I'm sure iodine vapours or KMnO4 spray will let you distinguish the tryptamine spots too, if you have the Rf values of psilocybin and 5-MeO-DMT for a given solvent (I hear n-butanol/acetic acid/water 90:5:5 works fine) without the typical Erlich colour reaction.
Or maybe even use Marquis reagent? (9 parts conc. H2SO4 to 1 part formaldehyde)
|
hjalmar
chemist, autist


Registered: 10/27/04
Posts: 295
Loc: Belgica Secunda
Last seen: 1 year, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6371266 - 12/14/06 06:03 PM (17 years, 5 months ago) |
|
|
BTW I agree with FastFred that the 5-methoxy group will probably hinder enzymatic ortho-substitution.
But it would be nice to try. There is very little information known on 4-OH-5-MeO-DMT except that it is extremely unstable. Maybe the phosphorylated compound will be more stable.
I doubt you will see the difference between a mouse on psilocybin or a mouse on the new compound, as you don't know how much of the new compound will be present, nor its activity. Extrapolating the activity level and quality from 5-MeO-DMT and psilocybin isn't always viable, there are enough examples of compounds in TiHKaL to prove that (eg. 4-MeO-DMT and pyr-T).
It could well be that some 4-OH-5-MeO-DMT is formed but much less than expected due to the steric factors mentioned.
Thus, your mouse will tell you nothing. Only TLC is a viable alternative to qualitatively determine it.
Cheap too
TLC plates and n-butanol are very common, non-hazardous (the alcohol) and completely unwatched. You should be able to order them through most scientific supply outlets.
|
RigaCrypto
Hidden Heart

Registered: 06/22/06
Posts: 23
Last seen: 15 years, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6372613 - 12/15/06 12:58 AM (17 years, 5 months ago) |
|
|
Animal testing would be just for screening for toxicity. Basically if the poor animal is okay after it comes down, then the compound should be safe for testing on myself starting with very low doses and gradually incrementing. I don't expect the animal to write a trip report, just to prove that the compound is not very neurotoxic.
|
MattEx
Psychonaut

Registered: 01/01/05
Posts: 110
Loc: New Zealand
Last seen: 16 years, 5 months
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: RigaCrypto]
#6372784 - 12/15/06 03:40 AM (17 years, 5 months ago) |
|
|
It's very unlikely it would be any more toxic than bufotenine (5-HO-DMT). I'd bioassay it .
|
hjalmar
chemist, autist


Registered: 10/27/04
Posts: 295
Loc: Belgica Secunda
Last seen: 1 year, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: MattEx]
#6374452 - 12/15/06 03:06 PM (17 years, 5 months ago) |
|
|
You can't prove if a compound is neurotoxic by checking if the animal dies or "looks ok when it comes down" ??
If I were to give a reasonable dose of the potent neurotoxin 4-chloroamphetamine to a mouse, it will survive yet it will suffer irreversible damage at the serotonin receptor sites. I'd like to see you differentiate that mouse from say two healthy ones.
If I was to give a mouse LSD, it will probably react pretty weird for the next days, as there must be some trauma factor included. Yet LSD is not neurotoxic.
Read the reasons why Shulgin tests his compounds on himself, and not on an animal. Because you can't differentiate if the animal is having toxic reactions or is just being under the influence.
Generally the simple tryptamines are not neurotoxic at moderate dosage levels. What you should do is use Shulgin's method for bioassaying unknowns, which is pretty safe imho.
Start out with an extremely low dosage, eg 10 mg dried mushroom. A week later (or at least a couple of days) double that dosage. Do this until you have found the treshold level.
Stop here, and establish treshold level of regular mushrooms, and compare.
This will tell you much more then your mouse ever will.
|
hjalmar
chemist, autist


Registered: 10/27/04
Posts: 295
Loc: Belgica Secunda
Last seen: 1 year, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6374495 - 12/15/06 03:17 PM (17 years, 5 months ago) |
|
|
slighty off-topic but this remembers me of one of the funniests paper I've ever read in a peer-reviewed journal. It was written by a couple of forensic scientist who are on the DEA payroll. They actually stated they were able to differentiate between several hallucinogens and MBDB by feeding them to newly hatched chickens.
The report went something along the line of :
chicken A on 2C-B wiggled around a bit chicken B on MBDB also wiggled but had sideways twitching chicken C on mescaline twitched in a different way
They guys were actually very serious about this. 
Honestly I'm sure that when I give whatever hallucinogenic to a newly hatched chicken it will wiggle and twich.
They didn't even consider that different dosage levels may cause different twitching as to make identification of the compound very hard...
|
MattEx
Psychonaut

Registered: 01/01/05
Posts: 110
Loc: New Zealand
Last seen: 16 years, 5 months
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6374548 - 12/15/06 03:44 PM (17 years, 5 months ago) |
|
|
There is /some/ basis behind that, such as the ratios of 5-HT2A vs 2C activation, where 2A I seem to remember is more likely to induce "wet-dog" shakes. So you would have so many shakes per hour period, and this could be your measurement.
However it's a pretty fucking lousy and inaccurate way of testing. As you say, dosages also would fuck around with it a lot.
|
ExplosiveMango
HallucinogenusDigitallus


Registered: 07/12/05
Posts: 3,222
Last seen: 14 years, 6 months
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: MattEx]
#6374939 - 12/15/06 06:29 PM (17 years, 5 months ago) |
|
|
Am I correct in reading that nearly no DMT is uptaken by mycelium? Why would this be the case? Where does the DMT go when the mycelium metabolizes the substrate?
-------------------- Know your self. Know your substance. Know your source. The most distorted perspective possible is the perspective that yours is not distorted.
|
hjalmar
chemist, autist


Registered: 10/27/04
Posts: 295
Loc: Belgica Secunda
Last seen: 1 year, 1 month
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: MattEx]
#6374966 - 12/15/06 06:38 PM (17 years, 5 months ago) |
|
|
This paper could shed some light on the subject:
Quote:
Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe.
* Gartz J.
Institut fur Biotechnologie der AdW, Leipzig.
J Basic Microbiol. 1989;29(6):347-52
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.
My uni has no access to the journal. Does someone happen to have it available?
|
captaintrps
Stranger
Registered: 08/08/06
Posts: 29
Last seen: 16 years, 10 months
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6377217 - 12/16/06 04:13 PM (17 years, 5 months ago) |
|
|
would 5-meo-dipt work? i have some of that, if not, what is the best tryptamines to use? id love to try this out
|
fastfred
Old Hand



Registered: 05/17/04
Posts: 6,899
Loc: Dark side of the moon
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: captaintrps]
#6377475 - 12/16/06 05:59 PM (17 years, 5 months ago) |
|
|
> would 5-meo-dipt work?
I don't think any tryptamine with a functional group in the 5 position will be 4-hydroxylated. It would be really interesting if such compounds could be created, but I don't think it would work that way. So I don't think serotonin or any 5-HO or 5-MeO compounds would work.
-FF
|
fastfred
Old Hand



Registered: 05/17/04
Posts: 6,899
Loc: Dark side of the moon
|
Re: Addition of 5-MeO-DMT to mushroom substrate [Re: hjalmar]
#6377522 - 12/16/06 06:18 PM (17 years, 5 months ago) |
|
|
> Thanks for the graph... > Do you have more details about the experiment?
Sure, it's from... "Biosynthesis of Psilocybin: Part II. Incorporation of Labelled Tryptamine Derivatives." Agurrel, S. and J.L.G. Nilsson. Acta Chemica Scandinavica 22(4): 1210-1218 (1968).
Here is another table from the paper. This is the real meat of the article.

This tells you a lot about what's going on. They just prepared radioactive isotopes of the various precursors and then extracted the psilocybin from the myc.. They then measured the radioactivity of the psilocybin which tells how much of the radiolabeled precursors were incorporated into the final psilocybin. One thing to remember is that the data doesn't take into account any precursors that were transformed into other things. For example, if the 4-OH-Tryptamine was made into norbaeocystin rather than psilocybin that would alter the results, but you couldn't really see that effect in the data.
> Thin layer chromatography is less hasslesome and more ethical. [than animal testing]
All a TLC is going to give you is a Rf value. That won't tell you anything about what the compound is (since you won't find a literature Rf value for totally undescribed compounds anyway) or if it's toxic or not. With mushroom extracts you're going to get 4-5 spots on a TLC plate. If a 5th or 6th spot shows up that might be interesting and might lead you to think that another compound is present, but it's not really going to tell you anything else.
The chances of making something highly toxic is pretty small, but then again you are creating something you expect to be highly potent without knowing what it's exact effects might be. I think using a mouse to test toxicity would be a good idea. It's far less ethical to test something out on a human, even if it's yourself. > Am I correct in reading that nearly no DMT is uptaken by mycelium?
Yes.
> Why would this be the case?
The easy answer would be that it's larger. However psilocin is larger yet, but is uptaken well.
If you look at the chart you'll notice that it seems that N-methylation decreases uptake, see N-methyltryptamine vs. N,N-dimethyltryptamine. It also looks like 4-hydroxylation sometimes increases uptake, see 4-OH-tryptophan vs tryptophan, and sometimes decreases it, see 4-OH-tryptamine vs tryptamine. Perhaps the effect is due to carboxylation or polarity or the formal charge.
> Where does the DMT go when the mycelium metabolizes the substrate?
Only substances the the myc absorbs will get into the myc. Other things will just remain in the remaining substrate and build up around the myc.
-FF
|
|