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Miscellaneous The Big & Dandy Psychedelics of the Future Thread

MattPsy said:
Acetoxy is just a ester - esters are derived from hydroxys.

The ester is stripped off in the body (hydrolyzed) to leave the hydroxy group. This is why 4-AcO-DMT feels the same as 4-HO-DMT (Psilocin).
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i feel it pertinent to point out that the whole 4-ester stripped off in the body to leave the 4-HO thing has never been proven, and although very likely to be true, may be only part of the story. many ppl report perceived differences in the effects of the ester vs ho versions, leading some to postulate activity of the ester-bound compounds, or possibly a seperate metabolism chain as of yet undocumented. it could very well be the slower onset of the compound due to the chomping process, or it could very well be a different compound at work.

ill also add that i find ald-52 to be the quickest comeup of any lysergamide ive tried... weird...
 
Anyway, 4-AcO-DMT does not feel exactly like 4-HO-DMT at all, for a lot of people, like myself. My thought, which is also speculation, is that they do convert to the hydroxy but are also fully capable of passing the BBB themselves. I think probably some people convert them so quickly that what they're getting is primarily the hydroxy, but others get more of the acetoxy into the brain. I find 4-AcO-DMT quite different from 4-HO-DMT even comparing pure synthetic 4-HO-DMT to it, they're easily distinguishable. Most people I know find the hydroxy and acetoxy to be at least marginally, but consistently, different each other with all of the tryptamine variants. For me it's been the most dramatic difference with the DMTs.
 
is putting a silicon atom into a drug considered a dead end or something?

im imagining a structural analog of 2c-e or 2c-p, where the carbon bonded to the ring at the 4 position is replaced by a silicon. wouldnt that be like a slightly heavier 2c-e(p), without the bulk of adding an additional carbon to the chain?

*why not apply it to the whole 2c-t series? i barely passed hs chem, but im learning; perhaps this kinda chemistry es muy dificil?

***also, if anyone has any book recommendations on sar and how the molecule sits in the receptor id be very grateful.
 
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whatever happened to 5-ethoxy-dmt? shulgin mentioned it during a talk.

and someone on another forum mentioned 1-acetyl-pro-lad... sounds like the bees pajamies
 
I love the way you think! Ive been asking about adding silicon to the 4 position of a psychedelic phenethylamine since before time.

nepalnt21 said:
is putting a silicon atom into a drug considered a dead end or something?

im imagining a structural analog of 2c-e or 2c-p, where the carbon bonded to the ring at the 4 position is replaced by a silicon. wouldnt that be like a slightly heavier 2c-e(p), without the bulk of adding an additional carbon to the chain?

*why not apply it to the whole 2c-t series? i barely passed hs chem, but im learning; perhaps this kinda chemistry es muy dificil?

***also, if anyone has any book recommendations on sar and how the molecule sits in the receptor id be very grateful.
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Isn’t -SiH2- a strongly reducing group? If you look at the element’s role in biology, silicon always occurs in its oxidized form iirc
 
I am not even an organic chemist much less an inorganic one. According to this article, silicon will substitute for carbon.

http://blogs.sciencemag.org/pipeline/archives/2012/11/07/silicon_in_drug_molecules_not_quite_there


Now here’s a subject that most medicinal chemists have thought of at one point or another: why don’t I put a silicon into my compounds? Pretty much like carbon, at least when there’s only one of them, right? I’ve done it myself – I was working on a series of compounds years ago that had a preferred t-butyl group coming off an aryl ring (not anyone’s favorite, to be sure). So I made the trimethylsilyl variation, and it worked fine. We had some patent worries in that series, and I pointed out that a silicon would certainly take care of that little problem, but it was still a bit too “out there” for most people’s comfort. (And to be fair, it didn’t have any particular other advantages; if it had stood out more in activity, things might have been different).
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here is a paper that suggests it has applications..

The incorporation of silicon and synthesis of organosilicon small molecules provide unique opportunities for medicinal applications. The biological investigation of organosilicon small molecules is particularly interesting because of differences in their chemical properties that can contribute to enhanced potency and improved pharmacological attributes. Applications such as inhibitor design, imaging, drug release technology, and mapping inhibitor binding are discussed
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http://pubs.acs.org/doi/abs/10.1021/jm3010114
 
lol, what about n,n-di-silyl-tryptamine?

si has more mass, but a lower electronegativity, iiuc
 
I would try the silicon version of 2c-d for sure. In fact I would try all the versions. Also a MXE-doped with silicon thingy
 
nepalnt21 said:
lol, what about n,n-di-silyl-tryptamine?

si has more mass, but a lower electronegativity, iiuc
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...and that is the problem. Silicon is, in fact, less electronegative than hydrogen.

Silanes are highly reactive/unstable; organic compounds with silyl groups can serve as potent reducing agents, which also means that they are readily oxidized to silanols upon contact with water. Many silanes even tend to be pyrophoric, i.e. they will just spontaneously ignite when exposed to air at room temperature.

Trimethylsilyl groups (where the silicon is shielded by four carbon substituents) and especially trimethylsilyl ethers are more stable, but they might be too bulky to be of use in most psychoactives.
 
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Does this also apply to thioethers? Then a version of 2C-T-9 where the one central carbon in the tert-butyl-group is replaced by a silicon would come to mind.
Hodor said:
a vendor is going to introduce "5-MeO-APB" to the market soon, although I am unsure whether the "5-MeO" refers to the 5-position on the aromatic ring (which would make it an analogue of MMDA), or whether it is actual 5-MethOxy-6-2-AminoPropyl-Benzofuran, which would be an analogue of MMDA-2.
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In fact Shulgin made 5-MeO-6-APDB and simply called it "F". So 5-MeO-6-APB would be the aromatic version, wouldn't it?
"Aroma F" would be a catchy name for that one! :D

Also is there a reason why there are no dicyclopropyl-tryptamines around? Like DcPT, 5-MeO-DcPT or 4-HO-DcPT. I think they might be interesting if they are possible.
 
well, what happens when you put an electronegative atom on the amine of a tryptamine; something like: n-fluoromethyl-n-methyl-tryptamine?

i think i remember a bit of conjecture in tihkal that the methyl may be all that is needed to get into place, so long as the other n substitution can protect the nitrogen from getting chomped (im paraphrasing)

iirc, fluorine is the most electronegative element, and creates the strongest organic bond... am i just littering?
 
thinking about arylcyclohexylamines:

what about the cyclohexanone in the 2'-oxo compounds? can this be a cychohexanethione? any reason to think it might be toxic?
 
it'd be a shame for this thread to be 'pruned'... even if its been pretty much me and a coupl'uthers posting lately.

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on one of the slides of a.c.h. presentation that jason wallach and hamilton morris did at m.a.p.s. had a bunch of hypothetical structures...

one of them had an allyl? (i think) instead of the aryl.

ones with the 2'-oxo seem to be hits, often...

maybe 2'-oxo-AllylCM would be tight?

????????????????????
truly, id be most excited to try anything ketamine with the 2 (phenyl) substitutions.

i mean, we dont know if the bromine will be too heavy unless we try...
 
It won't be, because it's bumped. :)

I would love to see 2C-AL... 2C-allyl. 2C-E is a fucking gem, 2C-P is also epic... add to the carbon chain and it might be great, no? I'm surprised no one has ever tried it.
 
4-propionoxy-N,N-dimethyltryptamine - anyone knows something about this? It's said to be an 4-AcO-DMT analogue..., - and this one is a phantastic Molecule, really outstanding!
 
Very interesting. So psilocin is 4-hydroxy-N,N-dimethyltryptamine. Psilocybin is 4-phosphoryloxy-N,N-dimethyltryptamine. And 4-AcO-DMT is 4-acetoxy-N,N-dimethyltryptamine. Basically this is a previous unheard-of group on the 4th position. It's tough to say whether it would be substantially different from psilocin, as with psilocybin the group is too polar to be able to pass the BBB and is converted to a hydroxy, but with 4-AcO-DMT, the difference in effects makes it pretty clear to me that at least in some peoples' metabolic systems, it is able to pass the BBB and produce a similar yet unique effect.

Either way this is really cool, as I like 4-HO-DMT more than 4-AcO-DMT and if it just is a simple prodrug, I'll be excited. And if it's its own drug, I'll be even more excited. :)
 
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4-propionoxy-DiPT was made before but I don't think it was widespread enough for anyone to come to a conclusion whether it's different from the 4-AcO.

https://www.bluelight.org/vb/threads/388877-The-Big-amp-Dandy-4-PropO-DiPT-Thread

Psilocybin doesn't cross the BBB because it's too polar, not because it's too nonpolar. I don't think 4-PrO-DMT would have trouble crossing the BBB. It wouldn't surprise me if the effects were subjectively different from 4-AcO-DMT.
 
Ive read about some weird lamp that can somehow stimulate brain waves..
Its supposed to give a dmt like effect by just sitting in the light in emits.
 
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