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4,5-MDO-tryptamines?

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blowjay

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Jan 7, 2010
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Thought I would just make a new thread instead of derailing older thread more. Or something.

http://en.wikipedia.org/wiki/4,5-MDO-DiPT

http://upload.wikimedia.org/wikipedi...5-MDO-DiPT.svg

I am wondering why DMT or for that matter anything that is a recreational tryptamine with 4 or 5 sub'd isn't being investigated much further. I feel like he ran out of umph with Tihkal. I mean seriously the MDO would add so many more options to the list of things to try.

Anyone know about legality of these? Does this circumvent anything because I don't recall any 4,5-MDO tryptamines being scheduled. Would be hard to argue them as analogs for any compound I would reason.
 
The SAR should be different enough from alpha-methylated phenethylamines to suggest that this might be barking up the wrong tree. For example, the simple tryptamine homologue of amphetamine, amt, already releases serotonin copiously (in addition to DA and NE). It's unclear what, exactly, the methylene-dioxy substitutions would do.

ebola
 
The 4,5-methylenedioxytryptamines are, I assume, active via conversion to the 5-methoxy-4-hydroxytrypamine in vivo. The latter class is a rather famous target, but is quite difficult to synthesize.

I say this because of the sole report on these compounds:
http://www.erowid.org/library/books_online/tihkal/tihkal28.shtml
Nothing much happened for about 3 hours, and then I suddenly shot up. [...]
Click to expand...
 
atara said:
The 4,5-methylenedioxytryptamines are, I assume, active via conversion to the 5-methoxy-4-hydroxytrypamine in vivo. The latter class is a rather famous target, but is quite difficult to synthesize.

I say this because of the sole report on these compounds:
http://www.erowid.org/library/books_online/tihkal/tihkal28.shtml
Click to expand...

I was always under the impression that not everything in PIHKAL and TIHKAL is necessarily from Shulgin's research group - several of the experiences are from other literature.

From the limited exploration of the MDO tryptamines and the commentary in TIHKAL, I wonder if he even synthesised them, never mind explored them with his group.
 
4,5-MDO-tryptamines are a difficult synthetic target from a chemical point of view, even for Sasha--though he managed to hack into them nevertheless.
 
Would you agree that they are an order of magnitude or two harder to make than extracting DMT from mimosa hostilis root bark?
 
literate said:
Would you agree that they are an order of magnitude or two harder to make than extracting DMT from mimosa hostilis root bark?
Click to expand...

What bearing does that have on the ability of Sasha or any other reasonably skilled chemist to synthesise MDO tryptamines?

Of course they're an order of magnitude harder than simple extractions.
 
My thought was that perhaps having proportionally fewer people with both the high level of skill and chemical raw material resources necessary to synthesize such compounds has hampered their widespread availability.

I am sure it is not out of range of the our Chinese chemical compatriots, however. The second factor is the actual level of effectual desirability of partaking of said compounds. (ie, are they good or not? i really don't know)
 
Thats the point in bringing this up. I feel like he was sorta BS'ing a little with those. Like I said, feels like he ran out of steam or just skipped them. I was just trying to gauge others opinions on the activity. In my limited opinion, I think they should 'all'(most) work in the 4,5 positions if they supposedly did for the single example I posted.

This could have no actual truth in it but my personal observations of the activity of the MDO on phens and the activity observed from 4 and 5 OH or MEO subs on tryptamines certainly presents a possible argument. I mean it is an MDO on DiPT, how much more random could it be? Why the hell would he think DiPT would be the one to start with? The standard IMO would have been onto DMT because he just moves up in size but the iso first is just weird.

I was just wondering if anyone had tried or heard any more about his. Seems fairly unexplored and I could see it going somewhere if activity was found to carry over to all 4,5 MDO's.

It is a bit generalizing to say that they should be active, but the 4 or 5 substituted trypts gives me a feeling that they are.
 
scrath that i forgot it did say he did try the 4,5 mdo dmt. I am wondering if maybe the activity decreases with the mdo. MDMA requires a higher dose than meth, fuck it study time.
 
blowjay said:
Thats the point in bringing this up. I feel like he was sorta BS'ing a little with those. Like I said, feels like he ran out of steam or just skipped them. I was just trying to gauge others opinions on the activity. In my limited opinion, I think they should 'all'(most) work in the 4,5 positions if they supposedly did for the single example I posted.

This could have no actual truth in it but my personal observations of the activity of the MDO on phens and the activity observed from 4 and 5 OH or MEO subs on tryptamines certainly presents a possible argument. I mean it is an MDO on DiPT, how much more random could it be? Why the hell would he think DiPT would be the one to start with? The standard IMO would have been onto DMT because he just moves up in size but the iso first is just weird.

I was just wondering if anyone had tried or heard any more about his. Seems fairly unexplored and I could see it going somewhere if activity was found to carry over to all 4,5 MDO's.

It is a bit generalizing to say that they should be active, but the 4 or 5 substituted trypts gives me a feeling that they are.
Click to expand...

The concerned is o-Demethylation to neurotoxin metabolites... The tryptamine diones are nasty things and have the tendency to induce monoaminergic neurotoxicity. If the active dose is low enough, they may be interesting to explore, but it's hard to say.
 
specialspack said:
I was always under the impression that not everything in PIHKAL and TIHKAL is necessarily from Shulgin's research group - several of the experiences are from other literature.

From the limited exploration of the MDO tryptamines and the commentary in TIHKAL, I wonder if he even synthesised them, never mind explored them with his group.
Click to expand...

I am pretty sure that he synthesized it, considering that he gave the synthesis in the same excruciating detail as the others. And I am pretty sure that the report linked is about 4,5-MDO-DiPT, and not about some other compound, as I am pretty damn sure Shulgin keeps all his ducks in a row.
 
nuke said:
The tryptamine diones are nasty things and have the tendency to induce monoaminergic neurotoxicity.
Click to expand...

Hmm, 4,5-dimethyl-DMT then?

Why Sasha made the conscious decision in tihkal to focus on N,N-disubstitution molecular tinkering instead of tryptaminic aromatic substitution (which was the mainstay of pihkal) puzzles me, unless he was so enamored of DMT itself that he got sidetracked. i dunno.
 
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