5-APBD and Metabolites

[Ryouge]

Does anybody have any information on the pharmacology of this chemical and the metabolism routes in takes into the body?

I'm wondering how similar to MDMA/MDA it is. I really can't find much information at all on the chemical, but it just felt so similar to MDA/MDMA that I'm wondering how similar it acts.

Thanks!

 

[sekio]

I'm wondering how similar to MDMA/MDA it is.

Very - APB and MDMA differ by essentially 1 atom.

 

[ebola?]

Would we expect to ring-opening catabolism, yielding alpha-methyl-dopamine (and n-methyl-alpha-methyl-dopamine) a la MDxx?

ebola

 

[sekio]

Given that we don't see e.g. 2c-E being converted to the phenol (carbon-carbon bond breaking being rather unfavourable), I expect not.

If anything the APBs would open to a 3-hydroxy-4-hydroxyethyl-amphetamines.

 

[Psychedelic Jay]

Same type of dopamineric poisons I presume...

 

[sekio]

Not neccesarily - the 3,4-dihydroxy compound is toxic probably because of its ability to easily oxidise to a quinone and back. You can't neccesarily say the same for the ring opened AP(D)Bs.

I'm not sure if the aromatic benzofurans would open - maybe only the dihydrofurans. The furan ring is a lot more stable then a methylenedioxy ring.

The rate of ring opening would likely be fairly low in any case given that acetals are orders of magnitude easier to break than plain ethers; tetrahydrofuran is not metabolised appreciably to butanediol in vitro, for instance.

Either way there's no concern of alphamethyldopamine being formed.

 

[Psychedelic Jay]

So those are not as reactive?

Doesn’t look dramatically less scary to me.

 

[sekio]

The catechol (a-methyldopamine) can be oxidised to a quinone and back (redox cycling), which is thought to be the cause of oxidative stress, but the hydroxyethyl compound would be irrversibly oxidised to a carboxylic acid.

Related compounds like 3-MeO-4-Me-amphetamine are considered oxidatively nontoxic compared to MDA by Nichols' studies. And so are sompounds like the presumed metabolic products of mephedrone and e.g. 4-hydroxyamphetamine. The 3- and 4-fluoroamphetamines also lack the ability to form a toxic quinone as fluorine is not generally metabolically removed from aromatic rings.