5-pro-DMT

[Solipsis]

Hi everyone

there seems to be a novel compound on the loose, 5-propionyl-N,N-dimethyltryptamine or 5-pro-DMT.
Google does not provide any info nor does any other site I've seen.
There is a topic about 4-pro-DiPT, where Nuke suggests there may be
hydrolysis to 5-HO-DMT like with 4-AcO-DMT to 4-HO-DMT, only it might be slower due to the moiety being bigger. Of course, besides the possibility
of being a pro-drug (no pun intended), the parent compound may exert
activity itself.

Personally I'm pretty scared of the thought of long-lasting variations on psilocin or bufotenin, the normal 5 hours of psilocin have a huge impact and I wouldn't be interested in extending the state... the afterglow is enough on its own.

There is a one man rumor there is only one source for this compound currently, which doesnt seem very credible to me. Anyway it does make it more special that I have found a source somewhere.
I must say I'm very intrigued and even though the suggested metabolism puts me off, it seems to me the possibility of toxicity is not that big as with some more complex and freaky new compounds. I know, the logic is worthless and substitution on the 5 position could render the impact on the body very big considering 5-MeO-DMT. Also, 5-HO-DMT is probably not a very nice substance so somewhere I do doubt there is much promise to 5-pro-DMT.

If someone has any information on this or chemical/pharmacological speculation that is not as bad as mine - please, shout out!

 

[dread]

I'm guessing 5-pro-dmt wouldn't be orally active..?

 

[nuke]

Why not? It would probably be de-esterfied to 4-HO-DMT, which should be active, and it would also be more lipophilic than 4-HO-DMT.

 

[Solipsis]

Why not? It would probably be de-esterfied to 4-HO-DMT, which should be active, and it would also be more lipophilic than 4-HO-DMT.

I think you mean 5-HO-DMT, I made the same mistake typing the opening post for a second!
But my thoughts indeed seem to be compounded by yours.
I'm just wondering if a stretched out bufotenin experience wouldn't be physically harmful since bufotenin itself has a reputation of giving your
body quite a whopper (right?).
And I'm not talking about some kind of burger, even if our discussion has made me hungry...

 

[Jabberwocky]

why couldn't they have made 4-pro-DMT

what were they thinking

 

[nuke]

Oh, right you are. This may still be active too though, if it makes it into the brain and then the propionyl group is cleaved.

 

[Jabberwocky]

well it could be injected yes if it is to be destroyed in the stomach?

is bufetenine destroyed by MAO?

 

[hamhurricane]

i would be a lot more interested in a bufo analog than another psilocin one, sure its nice that 4-ho/po/aco/pro-xxx ALWAYS seems to be a winner, believe me i love them with a passion, the chances of 4-pro-dmt not being great are pretty slim.

5-pro-dmt on the other hand is a complete mystery and isent that why we love these chems so much? the unknown%) also i and many other have searched for a bufo preparation or ROA that produced the magic effects such a minority of people report with no luck, i think 5-ho/po/aco/pro-xxx will eventually yield at least a few worthwhile materials.

 

[nuke]

well it could be injected yes if it is to be destroyed in the stomach?

is bufetenine destroyed by MAO?

It's a mystery, bufotenine seems to be munched up by MAO-A orally, but it's possible the bulky propionyl ester might not be a substrate for MAO-A. I would personally wager on it not being orally active.

There is an interesting study that indicates bufotenine as an MAO-A inhibitor, however:

...the magnitude of endogenous MAO A inhibition was PTZ > yohimbine > bufotenine > quinine > flumazenil > isatin.

http://www.ncbi.nlm.nih.gov/pubmed/9246908

On a tangent: Another interesting perhaps orally active possibility is 5-MeO-4-HO-DMT, whose synthesis is briefly alluded to in PiHKAL.

 

[Riemann Zeta]

I would never want to take a bufotenine-ish compound, be it bufotenine proper or a pro-drug, too many peripheral side effects to be worth the effort. Why not just take 5-MeO-DMT and get the fabulous effects of, well, 5-MeO-DMT, skipping all the extraordinary peripheral side effects of the 5-OH- analogue.

 

[MattPsy]

I think the point is that the peripheral effects would be probably be reduced over it's parent OH compound, 5-HO-DMT (Bufotenine).
Different pharmacokinetics, distribution in the body; lots more of it should get into the brain, which means less floating around the rest of the body causing nasty peripheral actions. That said it's unlikely to have less peripheral effects than 5-MeO-DMT - this will probably cut it out of the choices of many immediately, as 5-MeO-DMT is not exactly known to be gentle as far as peripheral effects go (or psychological ones for that matter)..!

 

[Solipsis]

Yes, good point.
But is it understood that peripheral side-effects of 5-HO-DMT originate all over the body, or is it an indirect effect in the sense that the brain and rest of CNS cause problems in the rest of the body?
If the action of this 5-pro-DMT is much restricted to the brain, it would be very important to know if nasty side effects are produced right there or if they would be avoided by this pharmacological deviation.

 

[cegli]

I'm really excited to see a couple reports on this one. The bufotenin Big and Dandy is such a mess and this might make it a bit more clear how bufotenin really works in a human body. I wonder how much the propionyl will affect it though? This is a very interesting compound for them to choose.

5-Methyl-DMT is active and somewhat pleasant according to this: http://www.erowid.org/archive/rhodium/pharmacology/5-me-dmt.txt

Maybe some of the other 5-substituted analogs will be interesting.

 

[Solipsis]

I may try and synthesize 4-PrO-DMT sometime, actually I can't find anything about it, has no one ever done this before? Seems so simple, if one can acquire 4-HO-DMT.

If I can't get that, I guess I will propionylate 4-HO-MET to make 4-Pro-MET. If successful and active, Prometheus could be a good name.

I don't mean to talk about synthesis, I wonder how much is known about the compound(s).

 

[dread]

4-Pro-MET will very probably be pretty much identical to 4-Aco-MET. Perhaps a bit more potent due to higher lipophilicity... but that'll probably only hold true if administered parenterally, ie. bypassing first pass metabolism.

 

[Solipsis]

How do you figure? Altered pharmacokinetics can significantly alter the subjective effects can they not? And the di-O-propionyl morphine has had some great results, I heard it can be better than di-O-acetyl morphine (i.e. heroine as you probably already know). If I believed it would be thát similar I might not want to make it. But it just might be a little souped up or enhanced in effects relative to the HO and AcO versions...

It seems I will be able to get a small quantity of 4-HO-DMT so it seems more than worth the modest effort to try this. Pretty much all the 4-AcO tryptamines were thought to be identical in effect to the 4-HO counterparts but we all know the subjectively experienced difference claimed by plenty of people.

If it's up to me I will try and make 4-Pro-DMT and also 4-Pro-MET if successful, and try them titrating. I suppose the dangers would be pretty minimal of that considering the precursor is the physically harmless 4-HO-DMT as long as I quench properly. I believe 4-Pro-DiPT was tried without adverse effects so nothing disastrous will be expected to happen. Shulgin was fine when trying much riskier compounds by titrating and stopping in time, right?

I don't know if I want to do a real purification or try and selectively oxidize the remaining 4-HO-tryptamine. What are your thoughts on that?

I'm hoping on some criticism that can help me confirm what I think of this plan or reject it.

 

[dread]

How do you figure?

Well, heroin when taken orally is pretty much identical to morphine. In the case of hallucinogens, every trip is different anyway, so it will be really really hard to tell if there is a subtle difference between two different substances: it's hard to say if you will perceive a difference in effects only because you know you are taking a different substance.

 

[Solipsis]

Perhaps so, it might be hard to say but there is still some consensus in 4-HO vs. 4-AcO comparisons in PD. I get placebo effects but I believe the chance is reduced when you don't know certain things about a drug on forehand, take it, then afterwards read and post about certain differing properties about it, right?

At least it seems to come up and come down differently which positions you in another way even if the active metabolite is the same I suppose.

Maybe one needs to smoke 4-AcO's and 4-Pro's then? I don't think insufflation is gonna work.

 

[Xorkoth]

Yeah, for me, 4-HO-DMT and 4-AcO-DMT are very different... I am absolutely convinced I could easily tell them apart in a blind test. 4-AcO-DMT is like smoked DMT, but slower and longer and as a result much less extreme. 4-HO-DMT is not much at all like DMT... more like mushrooms (of course), but also different from mushrooms.

The point is, I think it's likely that many people (though not all) could definitely tell a difference between 4-HO-DMT and 4-Pro-DMT. It seems that some people find very little to no difference between the AcO and HO tryptamines, whereas some find quite significant differences.

 

[Solipsis]

Looking at 4-AcO-DMT and 4-Pro-DiPT my conjecture would be that 4-Pro-DMT will be very stretched out and therefore smooth and laid-back, while qualitatively much like DMT. One of the big values of 4-AcO-DMT seems to be that it's much more dilated than smoked DMT giving you time to get into the experience rather than it blowing over your head.
The rush of the impossible happening in your mind is marvellous, don't get me wrong, but since it's a little too much too fast it can be interesting to see it all happening not so fast.

4-Pro-DMT might be like that even more so, quite possibly without a real defined peak at all but subtly coming and going. Let's hope it's interesting and maybe therapeutic in between and it can be of value.
Let's not forget that if we go double blind we would probably be lost in a sea of similar substances, still we feel pretty certain that there is quite a spectrum of psychedelia to be discovered with research PEAs and tryptamines.

Hopefully it's not too evident that I'm protective to the point of ignorant about my future pet project... You might understand how excited I am about the prospect of finding something novel that is even remotely interesting.

Oh well, even if it's a subtle difference, 4-substituted tryptamines - especially -DMT - is an excellent territory to be in! It's not undeserving of refinement.