N-hydroxyamphetamine , N-hydroxymethamphetamine really active?

[yoyoman]

Both of these especially the meth version are available by many chemical companies. I've heard N-hydroxy versions of MDMA and other Shulgin compounds were nearly identical to the non hydroxy versions.

I've read conflicting answers to whether or not these would be active. If so it would make for a good analog (for RC companies to sell, although to prevent degradation maybe N-acetoxy-amphetamine etc might stabilize them?).

What do you guys think? It would be nice if N-hydroxy-N-ethylamphetamine was made and sold. I've read it can be complicated to find an answer if its a tertiary amine - but if N-hydroxy-MDMA works why wouldn't the meth/ethyl ones work?

Maybe they would be shorter lived... an old hive post came up with someone claiming racemic N-hydroxyamphetamine was more potent than d-methamphetamine.

 

[adder]

Such hydroxylamines are quickly metabolized into the corresponding amines, so they should be virtually no different from those amines. As another example, similarly to N-hydroxy-MDMA exerting the same effect as MDMA, N-hydroxy-p-CA showed the same neurotoxicity as p-CA and it was proven it is quickly metabolized to p-CA (https://www.ncbi.nlm.nih.gov/labs/articles/4441415/).

 

[white55]

Another example would be hot-7.

 

[Seppi]

Those hydroxylamines are believed to be toxic and are produced from amphetamine/methamphetamine in humans during the first step of FMO3-mediated oxidative deamination. They remain bound to the enzyme during biotransformation because they're also substrates for FMO3.

Edit: Reference for most of what I've stated here: https://www.ncbi.nlm.nih.gov/pubmed/10027866

 

[belligerent drunk]

Personally I would not want to take an N-hydroxy compound, because hydroxylamines are quite reactive in not the most pleasant ways.

 

[Wiserthanearlier]

Interesting thread. I too read conflicting info on this

 

[yoyoman]

What about ALD-52 or 1P-LSD? Doesn't the acetyl or whatever is stuck on the N get reduced to a hydroxy? isn't there still an -OH attached to the nitrogen like with psilocin/4-aco-dmt?

Just wondering what other simple prodrug options there could be.

 

[Weltmeister]

1P-LSD is said to be much different than ALD-52/LSD yet still substantially similar effects (if that makes sense)

Effect wise 1P-LSD is closer to LSD than ALD-52.

 

[Xorkoth]

AL-LAD is definitely a different substance uniquer from LSD, and is not a prodrug for LSD.

Effect wise 1P-LSD is closer to LSD than ALD-52.

This varies based on the individual, my guess is it's because of individual body chemistry, or even placebo/expectation (though I disagree with writing off peoples' subjective experiences because of thinking we know everything - personally I find them to have differences from LSD and each other, while remaining mostly the same).