Psychedelic Tetrahydrobenzoindolamines (RU-23306, 3-AMTBI)

[crmt28]

These compounds seem to be really interesting!

There's RU-28306 which is basically DMT with an extra carbon atom.
There's a really short discussion here on Bluelight.

Molecule: n,n-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine

I couldn't find any info, apart from these papers:

• Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites.
• The Development of Indoleamine Derivatives Selective for Subtypes of Serotonin Receptors

Unfortunately, these papers are quite old and don't mention 5-HT2 subtypes.

However, the 5-HT2 affinity seems to quite similar to DMT.

Does anyone have any idea if it would act as a psychedelic?

Racemic partial ergolines (PEs) RU 27849 and RU 28306 showed diminished potency compared to TRYFs at 5-HT1 sites, but were equipotent to homologous TRYPs at the 5-HT2 site.

There's also 3-aminomethyl-THBI, which is more potent, and seems to be a more worthwhile compound. But there's no information about it anywhere else.

Molecule: 3-aminomethyl-1,3,4,5-tetrahydrobenz-[cd]indole

It seems to be 4-5x more potent than tryptamine:

However, the partially constrained non-ergoline-like analog 3-aminomethyl-THBI is significantly more potent (4-5 times) than the two homologous compounds (tryptamine and the partial ergoline RU 27849). This suggests that it may be worthwhile to examine totally rigid analogs of the non-ergoline-like conformations attainable by 3-aminomethyl-THBI, particularly those that overlap with possible conformations of the tetrahydropyridylindole RU 28253.

This one is probably not psychedelic, since it's just a tryptamine analogue.

But I think we could have some really interesting compounds based on that, like these DMT/Psilocin analogues.

N,N-DMT-BIMA / N,N-DMT-OBIMA (Cool names!)

What do you guys think? There seems to be a lot of potential on these compounds.

 

[black53]

Similar stuff was already posted - http://www.bluelight.org/vb/threads...-molecules?p=12413300&viewfull=1#post12413300
And I think you'd have more luck in http://www.bluelight.org/vb/forums/155-Neuroscience-and-Pharmacology-Discussion

 

[Solipsis]

Moving it there actually,

PD > NSP

Too theoretical and advanced for PD.
Welcome to the forum tho

 

[bolinas]

Now that it's posted here, just wait 6 months for China to pump it out

 

[ebola?]

...:/

ebola

 

[blueberries]

I came up with this one, as I'd had theories about them for ages now:

 

[Transform]

I wonder if the simple act of adding the additional ring system would prevent MAO metabolism and therefore make N,N-DM-THBIMA active as-is...

 

[crmt28]

Looks like it won't be affected by MAO, but will probably more like psilocin than DMT.

Also, I just came up with these molecules. Sounds to be the most promising of the bunch. It's psilocin closed on the oxygen, just like the 2C-x-FLY series.

N,N-dimethyl-1,3,4,5-tetrahydro-5-oxabenzo[cd]indol-3-methylamine / N,N-dimethyl-5-oxabenzo[cd]indol-3-methylamine

 

[Hiltoniano]

Is there any recent SAR data on with these types of compounds?

 

[Solipsis]

Why would those oxygenated ones be better than 4-MeO-xxT to which IMO it should be more similar than to psilocin? They're ethers..

I like the constrained DMT idea though, they are also quite lyserg like in structure...

 

[adder]

3-(dimethylamino)methyl-THBI and its 5-methoxy analogue could be active as psychedelics given that 5-methoxy-beta-methyl-T has an even higher affinity to 5-HT2A receptors than plain 5-MeO-T does (2.2 nM vs. 4.8 nM both against [125I]DOI, source 1, source 2), it should translate well to N,N-dimethyl analogues and I doubt that it could change functional activity much in case of beta-methyl analogues.

 

[Solipsis]

Does beta-methylation prohibit MAO from nomming on tryptamines?

 

[Zeds(NCO2CH2CH3)2]

Yes it will greatly reduce Mao activity I believe, but all dimethyl alpha methyl tryptamines have poor psychedelic activity, while alpha methyl tryptamine is highly Potent for example.

All of these structures are close BUT I would suggest the alpha methyl non methylated counterparts of the above-

At times in chemical space we seek to use the direct comparison/replacement method and yes the above do look like lsd, however, sometimes adding one space component then removing another works better(sometimes) due to the "long arm" effect non cyclic analogues have on transmembrane domain recruitment..

Zedsdead

 

[crmt28]

How come we don't have any significant research on beta-methylated tryptamines? The only thing I could find was a single a single paper from David Nichols.