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So I thought of some interesting ways to manipulate the tryptamine backbone...

T

thizzkid

Bluelighter
Joined
Jan 28, 2013
Messages
121
Hey there BL, its been a while with my studies and all haha.


So I realize my title is actually not correct and this suggestion wouldnt be modifying the backbone itself, but I digress....I love doodling random structures in class when the subject matter is stuff I already know and one of the theoretical drugs I drew up the following structure (http://imgur.com/LgVT6wE)

The way it is drawn, the two hydroxys at 4 and 5 can be substituted with anything imaginable (MeO, Aco, Indene, etc.) or not be included at all, like a piperidine version of dmt, but they are there just to show the variable sites of interest.

The real interesting thing about this molecule is its combination of being a piperidine and also having the indole based backbone of a tryptamine.

Just out of absolute curiosity, does this chemical seem like it would be stable? I have no clue how to go about making such a drug but it seems like it is almost certainly psychoactive, and with such a spread of hydrophilicity and lipophilicty, I would bet its absurdly potent. The only real issue would be steric hindrance I imagine, but what are some other peoples thoughts? This is purely a hypothetical discussion and I cant stress that enough. There is just as equal likelihood that something like this would be dangerous, or not work at all but for the sake of science I would love to hear bluelights take on this.

Much love and I look forward to responses!:)
 
LgVT6wE.png



thizzkid said:
The real interesting thing about this molecule is its combination of being a piperidine and also having the indole based backbone of a tryptamine.
Click to expand...

You say it has an indole backbone, so I'm gonna assume that it was just a mistake that the indole-nitrogen is missing, right?


The closest Shulgin ever did in that direction in Tihkal is this:


tihkal24.gif


There are 3-4 differences:

- the 5-ho is missing

- Pyrrolidine instead of Piperidine

- 2-carbon-bridge instead of 1-carbon-bridge

- (the missing indole-nitrogen that i've already mentioned and that's likely just a mistake)


Here's Shulgins quote:

(with 20 mg, orally) "This substance proved to be quite unlike psilocin and bordered on the bizarre. There was a latency period of about three hours after ingestion before the onset was noted. Visual disturbances were minimal; no alteration in colors or objects occurred. The nature of this compound was characterized by the heightening of the intellectual process, but not to the extent seen with psilocin. The entire experience was more 'stimulant-like' rather than hallucinogenic. A very unpleasant ride. Have no desire to go deeper or, indeed, to look at the other cyclic analogs."
Click to expand...
 
This is an EXTREMELY bad idea.

4,5-dihydroxytryptamine is a neurotoxin, less potent than the more well known one 5,6-dihydroxytryptamine, but still very neurotoxic.

While we cannot be certain that this neurotoxicity would live on with N-subsituted analogs, it's quite possible it would.

And even if it were active in addition to being a neurotoxin, it would probably suck; the N-cyclic typtamines don't seem to be any good.

What a coincidence you posted this, I was just about to make a post as to why 4,5-MDO-tryptamines are a very bad idea because they're likely to be metabolized into this.
 
There are many problems with this proposed compound. The compound is not a tryptamine derivative, but rather an analog of gramine, which acts as a mitochondrial toxin. Gramine and analogs (ie, indolemethylamines) are not very active at 5-HT2A, and are even less active without the indole nitrogen. Its hard to predict the potential neurotoxicity of this compound because it might not be a SERT substrate (required for dihydroxytryptamine toxicity).
 
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Whoops, I somehow didn't notice that the ethylamine chain was shortened and the indole nitrogen was gone. I need to work on being more observant. Still though, whether it behaves more like gramine or tryptamine, it doesn't seem like it's going to be anything you want in your body.
 
0_Forget said:
Whoops, I somehow didn't notice that the ethylamine chain was shortened and the indole nitrogen was gone. I need to work on being more observant. Still though, whether it behaves more like gramine or tryptamine, it doesn't seem like it's going to be anything you want in your body.
Click to expand...
^When I wrote that the proposal has major issues, I was referring to the OP and not to your post. Your prediction is not unreasonable, but I'm guessing that there might be enough of a structural difference to eliminate the possibility of neurotoxicity.

EDIT: I modified my post so it isn't confusing.
 
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Shoot whoops I will clarify that the first responder is correct: I meant there to be a nitrogen there to make that an indole structure so my initial image is incorrect, sorry about that. Although whether there is a nitrogen there or not I wouldn't be surprised to end up with a neurotoxic compound.

Again, in the original post I did not mean for the 4/5 positions to be the focus. I appreciate your guys imput thus far, and again this is theoretical. I am not at all looking to put something like this in me, just having some fun theorizing:)

So yea the focus is on the nitrogen that I DID draw. it is meant to be an indole backbone so again my apologies, but for the other theorists here, focus your eyes to that top nitrogen. It doesnt have to even include a 4 or 5 - sub, I just put those there to broaden the discussion to include psilocin type substitutions, etc. But with the piperidine ring, what kind of difference would we expect?

That TiHAKL entry is really interesting, and is kinda what I would expect branching toward pyroline or piperidine types of cyclic variations, since what I know of piperidines is solely 3-meo-pcp and that is quite a stimulating drug. But, not to diss Shulgin or anything 'cause he's the man, but his opinion is only a small sample number and it's only one of many possible compounds that have just been proposed so lets expand our what ifs a little more just for shits and giggles :)

Im thinking drop the 5'-hydroxy and leave the 4;'-hydroxy but with an indole backbone and the piperdine N-substistute. What kind of profile would we expect from a drug like this? It sounds scary honestly haha but these things are fun to think about.

First off; is a piperidine ring there even stable?
 
Oh shit I really drew this wrong...Ill post another picture when I can but yea the ethylamine chain is also supposed to be there, so thats anopther mistake. Again just imagine the tryptamine molecule with the amine switched to a cyclic nitrogen of some sort.
 
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