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Tryptamines 4-AcO-DMT vs. Psilocin


Nov 12, 2007
ask :]
are there actual differences? user reports seem to suggest that there are, but they both metabolize to psilocin... explanations?

also, do all 4-ho tryptamines metabolize to the same chemical as their 4-aco counterparts?
Yes. The idea that there are no differences comes from what we now can be pretty sure is the inappropriate labeling of 4-AcO-DMT as a mere prodrug of psilocin (4-ho-DMT, which is what I think you're referring to when you say psilocybin or 4-po-DMT.) The 4-AcO form is almost certainly active on its own, as made evident by its immediate full-spectrum effects when administered intravenously (i.e. the user doesn't have to wait for body enzymes to deacetylate the 4-AcO-DMT before they start tripping heavily.) It may very well be that the 4-AcO-DMT ultimately gets converted into psilocin, but both the activity of 4-AcO-DMT on its own and the rate at which the theorized conversion occurs probably influence the subjective differences between it and 4-ho-DMT. It may be that 4-po-DMT has its own independent effects as well. In my opinion 4-AcO-DMT is indistinguishable from MUSHROOMS because, though I've had mushroom experiences that were distictly diffent from my experiences with 4-AcO-DMT, the range of varience in subjective effects of many different mushroom batches is sufficiently broad to comprise the effects of 4-AcO-DMT.

[EDIT]: I've tried both 4-AcO-DMT and synthetic 4-ho-DMT and the latter is more manic, stimulating, and chaotic.
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i have tried 4 aco dmt as well as 4 ho dmt.
Unfortunately the 4 ho dmt was always consumed thru and by mushroom.
Mushrooms have a mixture of chemicals do it is hard to compare the two,

4 ho converts into a more stable 4 aco tryptamine. it requires a couple more mg than the 4 ho.

I find synthetics to be alot different than natural substances. I prefer synthetic chemicals ober the natural though. We can clean up and alter chemicals ourselves improving natures mixture, or at least isolating one substance.

The 4 aco dmt was mellow and very comforting. IT lasted 4 hours whereas i have had mushrooms trips go from 6-14 hours.

I think they all convert into the same. Your nody is a like a glass flask doing chemistry.
I read in TIHKAL that it converts into the same , but i think the answer was not definite. (?)
I find it hard to believe that 4-aco-dmt is as brutal towards the ego as mushrooms are. I've done my fair share of mushrooms, 50-60 trips or somewhere in that neighborhood. I haven't tried 4-aco-dmt but I have read it has a very forgiving nature and its hard to really be annihilated in the same way that mushrooms do so well.
mushrooms always have the chance of chaos wheras
all synthetic shrooms analogs rarely or never give me chaotic or lost trips.
4 aco has all the positive aspects that shrooms have , but just realxing and fun
It turns into the same stuff... right? I mean with mushies you run a slight risk of hell, but otherwise...
I've had the chance to take a lot of trips on 4 aco-dmt and it has become one of my favorites. Like it has been already said it can be a lot smoother and gentler than shrooms in a certain dosage range, but can become very heady and intense as you increase the dosage. The come up is usually very smooth, sedating, and without any nausea. The visuals are quite spectacular and remind me of a combination of shrooms and nn-dmt, although the visuals are definately more dmt like than shroom like. The duration for me varies widely depending on the dosage and can be anywhere from 4-7 hours. The trip ends abruptly for me, one second i'm trippin hard the next i'm completely sober and the trip is over. I really love this stuff, I'm glad I was able to stock up on this one.
its not at all clear that shulgin's theory that 4-aco's are just prodrugs is at all accurate.

stories of people IVing 4-aco-DMT and it being active almost immediately plus stories of people who have tried both 4-aco-dmt and synthetic 4-ho-dmt (me for one) and finding a difference subjectively between the two, would suggest that 4-aco-dmt is NOT a prodrug to 4-ho-dmt.

The counter-theory is that 4-aco-dmt IS a prodrug it is just the case that the absorption rates drastically affect the subjective experience (I can buy that but you still have a story to tell about routes like smoking and IVing).
I personally believe that Shulgin jumped the gun when he said that 4-AcO-tryptamines are just prodrugs that metabolize to 4-HO-tryptamines... he isn't god, and what he says might not always be true. I have tried 4-AcO-DMT and pure 4-HO-DMT pretty extensively, especially 4-AcO-DMT, as well as mushrooms themselves, and I can say with absolute certainty that I experience dramatically different effects from each, especially from 4-AcO-DMT. To me, the AcO feels like smoked n,n-DMT, but slower. The headspace is just plain different, as is the physical feeling. It consists of a high-frequency buzzing, whereas 4-HO-DMT and mushrooms do not.

I have used a lot of psychedelics and I am definitely able to tell different substances apart. Sure, each trip is different, but when you've taken lots of trips on thingss, you can start to tell them apart from other things because even though each trip is different, there are many similarities between trips on a single substance. I can say with confidence that if you handed me a sample of 4-HO-DMT or a sample of 4-AcO-DMT, I could tell them apart within the first few minutes of starting to come up. They are, quite simply, two different drugs.

Likewise, people tend to believe that 4-PO-DMT (psilocybin) metabolizes to 4-HO-DMT (psilocin), but I really don't buy that any of the esters besides the hydroxy just metabolize into the hydroxy. Perhaps they do, but I believe they have their own effects as well.
^ I agree with everything you said besides the last point. Its not that I disagree, per se, but I just don't know about the PO's pharmacology. I wouldn't be surprised either way.

I definitely agree with a difference in subjective effects between the aco and the ho.

Hey xorkoth, would you feel comfortable with the hypothesis that this difference in subjective effects is a difference in absorption/metabolism? (and thus that the aco does indeed eventually metabolize into the HO could be true in conjunction with the data that they are different subjectively).
^^ I could buy that hypothesis if there were some evidence (which there may be, I don't know). Is there evidence that the AcO ester does not have any effects on its own? If not, then I'm not sure why people would come to that conclusion. Why couldn't it have its own effects? It's a 4-substituted tryptamine.

All I know is that for me, the two are totally different drugs which seem to affect me differently entirely. They both come on at the same incredibly rapid rate (10-15 minutes even orally). It just doesn't seem like there is time for it to metabolize into 4-HO-DMT before the effects start, and when the effects start, they are not the effects of 4-HO-DMT. When I take mushrooms by different methods with different absorbtion rates, I achieve the same types of effects, even if the faster absorbtion methods provide a slightly different style of trip. Likewise, when I take a substance rectally vs. orally (very different absorbtion rates), the differences are many, but the nature of the trips remains the same.

It's my opinion that the reason the idea that 4-AcO-Ts and 4-HO-Ts are essentially the same drug came about because someone, somewhere, who people listened to decided that they must be the same, and people went with it. It's like another idea that some well-respected older members of the online community have spouted, that all or most of the 4-substituted tryptamines are essentially the same thing. Because to me, they're all totally separate drugs. Sure they have some similarities, but they're all unique. I feel that the same is true of AcO vs. HO esters of 4-substituted tryptamines.
I agree with your line of reasoning. I think 4-aco-Ts can cross the BBB.

Some people think they cannot (ie shulgin). Hence the theory that they must metabolize first.

Reports of people IVing 4-aco-dmt and it being active almost immediately would suggest that the aco can actively cross the BBB at least by some MOAs.
Does anyone know if the acetoxy desacetylation can be done in vitro???

Also i think the key piece of evidence in this debate is the matter of dosage i regularly see people describe the dosage of psilocetin 10+ mg higher than psilocin, that alone seems to be strong evidence that one is more than a prodrug of the other.
Simply comparing the effects of plain 4-hydroxys and their 4-acetoxy counterparts should be a dead giveaway that they're more than just prodrugs. It's entirely possible, even likely, that the acetoxy is metabolized to a hydroxy, as that is known to happen with heroin, but I would wager that most of it reaches the brain unchanged. Again, the effects of heroin are far different from those of morphine. Perhaps differences in people's abilities to metabolize the acetoxy ester contribute to wider variability in their effects from person to person as compared to the simple hydroxy, something I've also observed. As hamhurricane pointed out, if the acetoxys were prodrugs, the doses as compared to the hydroxy should be the same, minus the molecular weight of the acetyl group, but this is clearly not the case. I don't understand why there was ever a question about it in the first place as the differences are blatantly obvious.
butane said:
Simply comparing the effects of plain 4-hydroxys and their 4-acetoxy counterparts should be a dead giveaway that they're more than just prodrugs.

You know, this is exactly what I think. I wonder if the reason that a good number of people say that they're mostly indistinguishable is because there are a number of older reports around from people who had tried each once, maybe twice. They then wrote their reports as if they were fact, when in reality they had not had enough experience with the compounds to make that sort of generalization about the similarity of their effects. I know that before I ever tried any of the more obscure psychedelics, my perception of the 4-substituted tryptamines was that they were all essentially the same with maybe slight differences, other than duration. Then when I tried them I discovered that they are all unique and I wondered how someone who gave them a reasonable series of trials could possibly think they were all the same.
butane said:
Simply comparing the effects of plain 4-hydroxys and their 4-acetoxy counterparts should be a dead giveaway that they're more than just prodrugs. It's entirely possible, even likely, that the acetoxy is metabolized to a hydroxy, as that is known to happen with heroin, but I would wager that most of it reaches the brain unchanged.
A quick glance at my first post in this thread will show I agree with the consensous here about the full and independent activity of 4-AcO-DMT as 4-AcO-DMT. However, for the sake of fun quibbling allow me to play devil's advocate and say that the simple fact that the 4-AcOs and 4-hos are contrasted with one another is not sufficient to infer that the AcO is not a prodrug i.e. is not fully active on its own. The best, and only strong evidence of that is the immediate activity of the AcO via the IV route (the rest of the reasons for thinking that are mostly pragmatic, as there are a number of coincidences between independent reports of qualitative difference that are easier to explain if the AcO is fully active on its own, but this is hardly definitive.) The reason I say this is because the rate of absorbtion clearly affects the subjective experience of other drugs. Everyone agrees the experience of smoked or IVd DMT is distinct in QUALITY, not just "quantity," from even extremely high oral doses (who knows why exactly, but it is.) The reports that IM doses of DMT are far more comparable to oral doses than smoked or IVd doses indicates that the rate of absorption factors heavily in subjective qualitative experience independently of the presence of an MAOI. On this interpretation of the AcO as a prodrug, the qualitative differences--for example, that the AcOs are "smoother" than the hos--are a reflection purely of the slower absorption of the drug due to conversion time. Also, a prodrug is not necessarily completely inactive, only significantly less active than its "active" metabolite. So as devil's advocate I can also say that the AcO's small but not entirely insignificant independent activity in tandem with its slower rate of absorption is sufficient to explain the qualitative differences between it and the ho while maintaining that the AcO is still a prodrug.