Cause for oral inactivity of 25C-NBOMe?

[Aetherius Rimor]

Been researching this chemical recently, however nothing I've read has explained the cause of the oral inactivity.

DMT for instance is broken down by MAO, so taken orally with an MAOI allows it to work.

Is the cause known for the breakdown of 25C-NBOMe? Is it in the stomach, or the intestinal tract that this occurs? Is there any possible ways to prevent the breakdown like DMT has using some other substance?

 

[cannibalsnail]

Some acid or enzyme probably cleaves the N-benzyl ring resulting in the original 2C compound remaining (pure speculation). Its probably in the stomach or small intestine because plugging works.

 

[Epsilon Alpha]

Could be an pH thing too, not really sure how stable that compound is or its absorption kinetics. But, it could easily be protonation of the nitrogen that's responsible.

 

[skillet]

It's stable to any physiological pH. Also more lipophilic than 2C-C (cLogP 4.1 vs 2.0) and possibly slightly less basic (calc. pKa 9.1 vs. 9.7, I guess because though it's a secondary amine, it's benzylic) so it should be even more readily absorbed. This would also make it more likely to diffuse into hepatocytes, so I'm guessing first-pass metabolism is the reason.