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25x-NBF/C/B/I

Anon0631

Anon0631

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As far as I can see. There haven't been any useful reports of 25i-NBF in human subjects but the data suggests that it should be active and of a similar potency as 25i-NBOMe. I assume the same would be true of 25b/c/d/etc-NBF.

What about the 2-chlorobenzyl, 2-bromobenzyl and 2-iodobenzyl analogues of 25i-NBF? Would they be likely to be active?
 
I thought some of these were trialled in Heim's thesis?

Chemically speaking, Cl/Br/I are much different than F, which is really closer to a hydrogen than a chlorine.
 
The 25I-NBF is in the recent review of psychedelics by Nichols. There is essentially no difference in binding of NBF and the unsubstituted N-benzylphenethylamines. That is, the fluorine acts like an H, not an O. The 2-halobenzylophenethylamines were not made, but the 2-halobenzyl quinazolinediones were made by Ralf Heim, and the halogen had little to no effect on binding to 5HT-2a receptors. Also, 4-halo substituted N-benzyls of 2C-B were made by Glennon (J. Med. Chem. 1994,37,1929-1935). The 4-Br and 4-I derivatives have similar binding to the unsubstituted N-benzyl, but other substituents in the 4-position were detrimental.
 
dingophone said:
So basically they'd be possible routes to go if the NBOMe's get banned? ;)
Click to expand...

The unsubstituted N-benzyls are active, but about 20-fold weaker than NBOMes, so at the 10-15 mg level sublingually. I find their effects to be much more interesting than the NBOMes, and much shorter duration, about 3-4 hours max. The binding data suggest the NBFs would be similar to the NBs, but to be safe it would be best to do a titration starting at a very low dose, say 50-100 ug.
 
Just pondering out loud now. What about replacing the 2-MeO in 25i-NBOMe with a 2-NO2 to make 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-nitrophenyl)methyl]ethanamine?
 
Off the top of my head I would be worried that nitroaromatic compounds can be toxic if the nitro moiety is not protected enough from enzymatic metabolism. Isn't it too 'reactive' a group? Could it not be metabolized to nitroso compounds which would be bad news for your DNA for example?
With DON or 2C-N or 25N-NBOMe there are 4 ring substitutions instead of two which would make it much harder to create a conjugated system, right? Not sure what reason there is to accept those drugs as 'probably safe' and not the compound you suggest.
I am talking from some intuition way down below so let's wait for someone who can say if we can even speculate about such generalizations and if my suspicions could mean something.
 
You mean ethoxy?

Why? If you find something that works, what you want to do is try to find analogues that match the pharmacophore the best. Longer 2-position homologues might not be a good idea because if the moiety is flopping around too much it could hinder proper binding. If you want to develop on that position I suggest that the group be constrained, like it is in the NBMD structure.
It would make a benzofuranyl group just like in 6-APB, but it remains to be seen if that pi-bond works, otherwise you'd get dihydrobenzofuranyl like in 6-APDB.

Speculation about SAR is one thing, but in the end it would just have to be tested to make conclusive claims.
 
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