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Author Topic: Analogues of 2C-BCB (TCB-2)  (Read 200 times)

timecube

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Analogues of 2C-BCB (TCB-2)
« on: December 18, 2009, 08:14:30 PM »
I recently came across the structure of 2C-BCB, which is purportedly similar in potency to LSD and Bromo-DragonFLY.  The structure is relatively new, first synthesized in 2006 if Wikipedia is to be believed.

I wonder how some of its analogues would behave.  Obviously the equivalent 2C-B analogues would likely show interesting activity, particularly 2C-T-7 and 2C-G.

It seems reasonable that the methylenedioxy derivatives (see attached) would show increased potency as well, but I'm not sure what that would actually translate to.  They may just be horrible neurotoxins.  To my knowledge, they've never been synthesized.

Tsathoggua

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #1 on: March 30, 2010, 05:52:23 PM »
Has TCB-2 been bioassayed in vivo yet? or better yet, in humans?

Affinity and potency mean bugger all if its not activating the correct secondary messenger pathways intracellularly, downstream of 5HT2a agonism.


Look at 2,5-DMA  which is functionally selective for IP3 turnover and does not posess psychedelic properties, being a plain stimulant in man, vs selective agents such as 2C-N, functionally selective for PLA2/arachidonic acid release, which is indeed psychedelic.

Any info yet on functional selectivity of the Nichols cyclobutanamine series?
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timecube

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #2 on: March 31, 2010, 02:57:25 AM »
A few RCs have made TCB-2 available at rather exorbitant prices, so a few scattered bioassays exist.  They seem to indicate that the compound is psychedelic at doses >1.5 mg.

When I originally made this post, my understanding of pharmacology was quite a bit more limited.  Conformational restriction is important in 5-HT2 receptor activation.. basically the flatter the molecule stays the better, which is why LSD binds so well.

There's no indication that I know of to suggest conformational restriction is important in MDx-style activity, so combining MDMA and TCB-2 separately would probably produce more interesting effects than any of the analogues I suggested, although it may be potentially unsafe as I do not know if TCB-2 is a centrally active stimulant as well.

Enkidu

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #3 on: March 31, 2010, 05:53:05 AM »
Your cyclobutane MDMA analog could have some potential. So what if conformational restriction isn't 'important,' i.e., isn't required (I mean duh we already have MDMA). You can still try to enhance the potential of the drug through conformational restriction. Isn't that what 5,6-methylenedioxy-2-aminoindane is about? (Which I happen to bet is better i.v.)

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #4 on: April 01, 2010, 01:52:42 AM »
The substance Enkidu linked to I believe will show higher activity then the cyclobutane variation posted because the MDAI eliminates the stereo center of the MDMA molecule strengthing the chain substantialy.

My knowlage of pharmacology is abit limited as well but as I understand it basicly the stiffer the chain on these form of compounds the better off one is in terms of potency.
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Enkidu

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #5 on: April 01, 2010, 05:52:28 AM »
^ No, there's a big difference between the 5-HT2A receptor, the SERT/DAT, and the VMAT2. In short, yes, the 2-aminoindane doesn't have a stereocenter, but that doesn't necessarily make it more potent. I just means that the best you can do is no stereocenter, which actually COULD make it less potent..

Dr.Methoxy

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #6 on: April 09, 2010, 06:59:10 PM »
TCB-2 was designed to bind perfectly to the 5-HT2A.

MDA is a serotonine reuptake inhibitor and slightly binds to 5-HT2A. If you add a methyl you'll get MDMA. The methylated compound don't bind to 5-HT2A that's why MDMA is better. Sorry but your MDMA analogues are not interesting...

jon

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Re: Analogues of 2C-BCB (TCB-2)
« Reply #7 on: April 14, 2010, 06:26:58 PM »
that's true that aminoindane analouge is shit with no euphoria.
a lot of this stuff looks neato on paper but in reality it be crap.
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