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Tcb-2

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LuxEtVeritas

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any idea on this compound TCB-2
Chemical Name: (4-Bromo-3,6-dimethoxybenzocyclobuten-1-yl)methylamine hydrobromide

High affinity 5-HT2A receptor agonist (Ki values are 0.73 and 0.75 nM for rat and human receptors respectively). Potently stimulates IP3 accumulation in NIH3T3 cells stably expressing rat 5-HT2A receptors (EC50 = 36 nM).
 
Looking at those Ki values its Nichols benzocyclobutane analog of 2CB (Conformationally Restricted Hall. Phen. Analogs...). U sure about that name? That structure has a double bond in the cyclobutane ring, making it anti-aromatic, doesnt necessarily mean it couldnt exist tho.

Whats the T for in TCB-2?
 
That's interesting, I've never heard of it. Google hasn't either, apparently. Do you have the structure?
 
On the first page of that document, by any chance does potency go in this order: fig. 3, fig. 1, fig. 4 and fig. 2, in descending order of potency (fig 3 most, fig 2 least, that is)
 
2>1>3>4, though racemic 2 is about the same potency as 2CB (1), R-(2) is somewhat more potent. On page 4 they give the ED50 for R-(2) as similar to LSD. Which suprised me, looking at the Ki values (i dont know much pharmacology) which are 0.66 for 2CB and 0.35 for R-(2) on rat 5HT2 receptors.

Edit: The first step in the synth of 2 looks like a bitch, have no idea how you'd get that starting material!
 
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Really? I was way off. I was basing that off of how closely they'd line up if you sat an image of LSD on top of them. I think FnB thought of that idea originally.
 
Yeah i thought that was a really good idea, suggesting that a tetrahydronaphthylamine would be a really good one, then vanadium posted that nichols paper from 10 years ago! Still cant believe that! No activity?!

Edit: LuxEtVeritas, yeah i got that, meant that looking at the Ki values i'd have expected it to be a couple times more potent than 2CB, whereas the ED50 values suggest its about 200 times more potent. I guess receptor binding values are misleading in this case (i know they dont always correlate that well, and i guess 1/2 the Ki doesnt mean twice the potency?)
 
dorothyperkins said:
Looking at those Ki values its Nichols benzocyclobutane analog of 2CB (Conformationally Restricted Hall. Phen. Analogs...). U sure about that name? That structure has a double bond in the cyclobutane ring, making it anti-aromatic, doesnt necessarily mean it couldnt exist tho.

Whats the T for in TCB-2?
Click to expand...

The but-ene is sort of a peculiarity in nomenclature, because the "cyclobutane ring" shares 2 pi bonded carbons - i.e the two that are part of the benzene ring. There are only 3 double bonds total so it is still aromatic by Huckels' rule criteria.

A fourth double bond conjugated in the "cyclobutane" part of the molecule would be known as benzocyclobutadiene.

That may be a little confusing, so some formuals help. Unsubstituted benzocyclobutene formula is C8H8. The anti-aromatic benzocyclobutadiene would be C8H6.
 
Well, it's not a PEA, and from my conversations with the DEA and what I've seen their scientists say in court papers about their criteria for inclusion, I'd say no.

What will the DEA say, though?

You think they'll decide in our favor on anything? They could hand out million dollar bills everytime they rule in our favor and they'd still have all the million dollar bills and I'd have none.
 
dorothyperkins said:
Isnt everything within the US analog act!?
Click to expand...

sometimes it kinda feels that way :\ :p


this one would be hard pressed to not be considered included...which why that was more tongue in cheek

interesting to see a PEA derivative being on par with LSD
 
"this one would be hard pressed to not be considered included"
Huh!? it probably is or isnt included?

As for the amphetamine ive no idea weather the extra methyl would help any more. One way to find out, though synth would be a bitch!
 
Now, close that 2-position methoxy into a furan ring, and replace the Br with a CF3 and you have a real winner.
 
probably would be considered an analogue, certainly enough so not to want to be on trial testing that it is not, though they will always have to prove human use so if you synthed some and were not distributing they could not do anything but likely take your shit -- just keep a couple of mice in a cage to show your real intention =D
 
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