NBOMe substituent on psychedelic amphetamines

[marzipan93]

Does anyone know if there has been any work done to follow up on the 25I-NBOMe PEA analogs, specifically, with the 3-carbon amphetamines? If this substituent gives a 15x potency increase as well as more intense visuals (compared with the parent molecule: 2C-I), what would happen with the DOX series or the TMA series?

I have searched around, but I can only find one reference in the journals. I don't own a subscription to said journal, so I can't get to the paper without going to the library, and I am too lazy for that.. The referenced compound was the DOI-NBOMe analog. I am sure that all they do is list the IC-50 for the seretonigenic activity, which doesn't say much other than potency guestimations when compared to other IC-50s.

With the potency of the 25I compound giving a dose around 500ug-2mg (down from 20-25mg for 2C-I), the 3-carbon analogs could be dangerously potent. DOI is at 2-3mg, so if the SAR trend is maintained, we get something around 100ug for this N-benzyl substituent.. LSD potency. This substituent has also been implicated in a few deaths, so the danger is real.

I am interested in the TMA-2-NBOMe analog. TMA-2 is around 35mg, so this one sould be in range of the 25I analog (500ug-2mg). The 2,4,5-scaffold is the same as 2C-I, but qualitatively, I prefer TMA-2 many times over 2C-I. And considering the suprising results with the N-Me-TMA-2, this might be very interesting indeed.

I apologize to the staff if I am breaking rules here... I'm new, and I honestly can't tell if this is not proper after reading the rules. If this isn't the proper forum for this kind of talk, I can go elsewhere.. just let me know.

 

[sekio]

The original paper which characterised the 25x-NBOMe family also touched on the DOx analogs. as well as a few other ones - FLY analogs (more potent) and tryptamines (much less), and a-methylation on the benzyl group as well as N-methylation (all methylation decreases potency).

41 = 2C-B
35 = DOB
231 = 25B-NBOMe
234 = DOB-NBOMe

As you can see DOB-NBOMe isn't actually that much more potent than DOB, whereas 25B is 100s of times more active than 2C-B.

Subjective tests have revealed that NBOMe-mescaline (345-trimethoxy-PEA) was a flop - not active like the 25x series - so I highly doubt TMA-NBOMe would pan out. Maybe 25O-NBOMe? (FWIW, 2C-O series sucks, compared to other substs there. I would rather see 25T2-NBOMe )

The SAR with the NBOMe series is very tricky and not everything is what it seems. There is definitely no 1:1 corresponence where you can just plug a N-benzyl on a PEA and have it be a "super" version.

 

[Hammilton]

With the more dangerous 4-methylthio analogues, perhaps this would be a good way to increase potency to the point that MAO inhibition was irrelevant and make them safer.

 

[ebola?]

People have written off psychedelic NBOMe-amphetamines as "too weak", but I think that this is quite hasty. A compound presenting a fruitful subjective experience with an active dose of 10-20 mg is way more valuable than a physiologically difficult and/or experientially flawed psychedelic with an active dosage in the microgram range.

With the more dangerous 4-methylthio analogues, perhaps this would be a good way to increase potency to the point that MAO inhibition was irrelevant and make them safer.

Good point, but because the 25X-NBOMe compounds don't feel particularly similar to the corresponding 2CXs, there is no reason to expect retention of the 'magic' of the 2CT-series.

ebola

 

[ebola?]

I'm going to fix the topic name (you named an n-benzoxy-methoxy substituent, which doesn't make sense (you can't have an oxy methoxy )).

ebola

 

[Hammilton]

Maybe the magic will be even better!

you could have benzylperoxy... Not super likely to go BOOM but maybe if you hit it hard enough.