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I Like to Draw Pictures of Random Molecules

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Thioamides exhibit significant delocalization rendering the amine function no longer very basic, which would likely make the molecule inactive.

toastmann's oxazolidine would isomerize to the 4H rather than 2H, as the imidate is a more stable isomer owing to amide-like delocalization around the OC=N bonds. It seems to make more sense as an oxazole, though, as diarylmethyl- is a rather common DRI motif.
 
V3luZgw.png


was just pondering how I would make a "legal" mephedrone replacement

fuck me right? loved and hated that drug...
 
klfiend said:
V3luZgw.png


was just pondering how I would make a "legal" mephedrone replacement

fuck me right? loved and hated that drug...
Click to expand...

What's wrong with 3-MMC (3-methylmethcathinone)? I thought it was good overall.
 
Phosphindole tryptamine analogues: Possible avenue for drug discovery?

So, I was thinking tonight, a logical (at least to me) step that one could take in discovering some new active tryptamine analogues would be to examine the phosphindole analogues of conventional psychedelic compounds such as DMT. I have checked around, and I cannot find any mention of such compounds being explored, or even synthesized for that matter. Does anyone see anything immediately wrong with this idea? If not, what are your thoughts on it? I have included an image of one such possible compound, just to illustrate it for the casual reader.

jy4.png
 
I don't think "phospindole" is a known compound, but it's possible, I guess. Wierd heteroaromatics (e.g. borabenzene) tend to behave less... nicely than the CNOS analogs.
 
"phosphindole" does return about 15,000 hits on google, but none of the results seem like they'd be too relevant here.

also, silabenzene would be a better analogy here than borabenzene, no? neither one seems too hopeful as far as SAR is concerned, though.
 
Well, phosphindoles are a known family of compounds, and they are stable without the ridiculous stabilizing structures required for things like silabenzenes and borabenzenes. Phosphorus does indeed share some characteristics with nitrogen, and is in the same column on the periodic table. I think you would have much more luck with a phosphindole DMT analogue than a silabenzene DMT analogue (yes, I know I drew some of the homobenzenes a few pages back, but that was more for fun than anything), especially since from my understanding, you would require something like this to stabilize it[1]:

24hs.png


Now, I'm not going to say that I know 100% that something that looks like that will not be active, but I can say that my level of surety vis-a-vis the inactivity of the aforementioned compound is about as close to certain as anyone could be without actually tasting it. I doubt it would cross the BBB, and if it did, it would almost certainly be too sterically hindered to bind to 5-HT2A.

The phosphindole, on the other hand, I believe to have much more promise. Considering a similar compound, known as dimemebfe[2], using oxygen instead of phosphorus in place of the pyrrole nitrogen, has been synthesized, and sampled to positive result[3]. Similarly, the benzothiophene analogue of various tryptamines has also been synthesized and tasted, to some positive reviews, although I cannot seem to find references to this at the moment, but I will post them once I remember where they are.

All that being said, it seems that the tryptamines are somewhat tolerant to substitution of the nitrogen while retaining affinity for and efficacy at the 5-HT2A receptor. Therefor, it would seem logical to me that the phosphindole analogues of at least a few well-known tryptamines should at least be considered as candidates for novel psychedelic compounds.
 
atara said:
Big problem with phosphindole is that it is almost indubitably toxic as hell, and susceptible to hydrolysis if that weren't enough. Reduced phosphorus (i.e. not phosphate/esters) basically never appears in biological systems.
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You are absolutely correct, and there is a good chance that it may be quite toxic. This is why I said it might be useful to take a look at it as a possible avenue of exploration. To me, this would involve animal testing of the compound to ensure that it wasn't a horrible poison. I really do appreciate your contribution though, I'm glad you commented about the possible toxicity, the last thing we need is some irresponsible person to read this thread, synthesize it, do 0 testing, slap some brand name like "SyntheTRIP TRIPLESTACKED B34NZ" on it, and start selling it as the next LSD or something.
 
So, I was messing around in ChemDraw today and....

I was wondering if anyone thought this compound would seem interesting?

 
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Somehow I doubt it. The 2 and 5 positions on the 2C- series don't handle a lot of steric bulkiness - certainly not whole tryptamine molecules glued on.
 
I like the second one, the DMT-esque one with the cyclobutane ring in place of the pyrrole ring, but you are missing one carbon in your sidechain, at least if your goal was tryptamine-style SAR as I imagine it was.
 
SeenSoFar said:
I like the second one, the DMT-esque one with the cyclobutane ring in place of the pyrrole ring, but you are missing one carbon in your sidechain, at least if your goal was tryptamine-style SAR as I imagine it was.
Click to expand...

Ah yes sorry about that.

Just looked it up and apparently the scaffold is called benzazetidine. Couldn't find a DMT derivative on SciFinder though. Not one with a dihydro quinoline scaffold either.
 
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