any info on o-acetylephedrine?

[Phanerothyme]

(not sure if this is the best forum, move if see fit)
I saw this mentioned in a post in the stimulants of the future thread, and I came across a post on a different forum that gave a little info on it. If this is as easy to synthesize as it seems to be, why do you never hear about it? Does anyone have any info on it? Are there any published journals or studies on it? Any info appreciated.

 

[Swerlz]

i can find some stuff on N-acetylephedrine.. but not much on o-acetylephedrine besides a pubmed article on blood pressure in rats and a russian pdf

 

[fasteddie]

"Uncle Fester" claims that it's starting material.

Hasn't every conceivable ephedrine derivative been researched to the nth degree by some or another drug company, hoping to find a weight control drug?

 

[morphiquet]

i think o-acetylephedrine would have a quite short half-life and the remaining ephedrine could then cause unpleasant side effects.

i'd rather think of o-benzoylephedrine as this compound would have 3 advantages over the first one:

better metabolic stability (longer half-life)
presumably cocaine-like properties, suggesting from a look on its structure
more easily obtainable precursors (hopefully that doesn't offend the forum rules)

 

[hussness]

I have a journal article on O-acetylephedrine. I think it's from the '40's though. Pm me if you want it.

 

[fastandbulbous]

O & N-acetyl ephedrine interchange quite easily depeding upon the pH of the solution they're in (<7 ie acidic results in O-acetylephedrine where >7 ie alkaline favours the amide formation). I came across this many, many years ago and I think it was an OK stimulant - I don't have any 'real horror show' memories of it as I do of ephedrine (and I mean many - lots of drug fillee waters have flowed under the bridge since then!) with not too much of the hideous ephedrine feel - think that's to do with the dose required - 20mg - not producing enough ephedrine metabolite to bugger it all up.

Having an acetyloxy group on the benzylic carbon improves BBB penetration & prevents direct action on receptors that ephedrine has (benzylic OH groups seem to increase noradrenergic activity in preference to dopaminergic - esterify it and you push it more towards the dopamine activity).

If I remember it's not that stable - my sample stunk of acetic acid after a few weeks without the benefit of an airtight contaner including dessicant

 

[Phanerothyme]

i think o-acetylephedrine would have a quite short half-life and the remaining ephedrine could then cause unpleasant side effects.

i'd rather think of o-benzoylephedrine as this compound would have 3 advantages over the first one:

better metabolic stability (longer half-life)
presumably cocaine-like properties, suggesting from a look on its structure
more easily obtainable precursors (hopefully that doesn't offend the forum rules)

Any chance this is the structure of o-benzoylephedrine?

 

[Phanerothyme]

I have a journal article on O-acetylephedrine. I think it's from the '40's though. Pm me if you want it.

I want the journal but im a mere greenlighter, ill pm you if i ever get up to BLer status. Unless theres another way you could get it to me.

 

[hussness]

I can email it to you if you provide me with an address, or upload it to any ftp or whatever. By the way, that is the structure of o-benzoylephedrine, although it is lacking stereochemical information.

 

[fastandbulbous]

Is it the paper concerning the way the acyl group migrates from O to N under different conditions eg pH? If it is, that's OK, but if it's something different, could I perchance scrounge a copy if I send you my e-mail address?

 

[hussness]

^The title of the article is "The Constitution of Acetylephedrine and Acetylpseudoephedrine, and it's by Welsh. Surprisingly, I can't find the journal title anywhere. But I think it's probably the one you already have even though I'd be happy to send it anyway, just in case.