para-hydroxyamphetamine

[Ham-milton]

Does anyone know if this one is specifically scheduled? It's approved for use in optometry for dilating pupils (in combination with a tropane, I think, I can't remember for sure).

Anyway, I kinda think that this won't have much recreational potential, but then again, we have codeine addicts...

If this isn't specifically scheduled, it'd make it the only amphetamine approved and regularly used that isn't scheduled.

I gotta say, I'm interested in tasting it just *because* it isn't.

 

[nuke]

I don't believe it's scheduled (in the USA anyway), however you'd shoot yourself in the foot trying to buy any quantity of it because the ether (PMA) can easily be made from it.

Everything scheduled in the CSA is listed at:
http://www.usdoj.gov/dea/pubs/schedule.pdf

edit: The drug 'metyrosine' might also be of interest to you, it's indicated for excessive amounts of catecholamines.

 

[Ham-milton]

Is metyrosine something you think might be recreational?

For some reason I can't see the structure on my computer. Is it working when I post it? I don't know what the problem is. I just see a grey block???

Is metyrosine a ketone?

EDIT: I see the image now. I don't know what the problem was still. Anyway, I don't think it'd be much of a stimulant without the methyl group there.

Anyone else have ideas?

And how exactly does it reduce catecholamines? Meth-style depletion or toxicity?

 

[nuke]

the methyl group is there (actually two methyl groups if you exclude the rest of that carboxylic acid). my guess is that it probably causes cathecholamine depletion by neurotoxicity, but it's hard to tell, sometimes these things can inhibit things like tyrosine hydroxylase or DOPA decarboxylase.

 

[MattPsy]

It would even pass the BBB, with that big polar carboxylic acid hanging off it? And the para-hydroxyl group?
I somewhat doubt it.
If it did though then yeah I suspect the same as nuke.

As for p-OH-amph. I suspect it would be neurotoxic. I certainly wouldn't be eating it, anyway.

 

[Ham-milton]

Okay, I see it (I'm a little baked and that's definitely not the normal PEA style of drawing) and I was a little confused.

It doesn't look like something that'd be enjoyable, but I don't think it fits the substitution pattern you see in other neurotoxic PEA's.

 

[LuxEtVeritas]

Metyrosine is i believe the opposite of what one wants...

 

[LivingOnValium]

Isn't parahydroxyamphetamine one of the amphetamine metabolites which is suspected to cause psychotic behaviour?

 

[dorothyperkins]

[QUOTE = PIHKAL]A major metabolites of amphetamine is 4-hydroxyamphetamine, from oxidation at the 4-position. It has been long known that with chronic amphetamine usage there is the generation of tolerance, which encourages ever-increasing doses to be used. When the daily load gets up around one or two hundred milligrams, the subject can become quite psychotic. The question was asked: might the chronic amphetamine user be methylating his endogenously produced 4-hydroxyamphet-amine to produce 4-methoxyamphetamine (4-MA), and maybe this is the agent that promotes the psychosis? To address this question, several studies were done with normal subjects, about 20 years ago, to see if 4-MA might produce a psychotic state (it didn't at the highest levels tried, 75 milligrams) and to see if it was excreted to some extent unchanged in the urines of these normal subjects (it was seen even at the lowest dosage tried, 10 milligrams). It produced excitation and other central effects, it produced adrenergic pressor effects, and it consistently produced measur-able quantities of 4-MA in the urine, but it produced no amphetamine-like crazies. And since the administration of up to 600 milligrams of amphetamine produced no detectable 4-MA in the urine, this theory of psychotomimesis is not valid. [/QUOTE]

As for the effects of 4-OH-amphet, i've no idea, and i dont know how likely it is that its methylated in vivo. I thought metabolism of methoxy PEA's was by demethylation?

And its probably not possible to methylate the OH of 4-OH-amphetamine without completely methylating the amine. Unless you protect it.

 

[Ham-milton]

I'm pretty sure that amphetamine psychosis is the result of problems with dopamine usage, not the result of any metabolites.

 

[nuke]

Okay, I see it (I'm a little baked and that's definitely not the normal PEA style of drawing) and I was a little confused.

It doesn't look like something that'd be enjoyable, but I don't think it fits the substitution pattern you see in other neurotoxic PEA's.

Any amphetamine with the possibility of 6-hydroxylation and ability to cross the blood brain barrier has the potential to be neurotoxic, it seems like.

From this book:

Metyrosine inhibits tyrosine hydroxylase

http://www.accessmedicine.com/content.aspx?aID=944910&searchStr=liver metabolism

It may make it into the brain via an amino acid transporter. Studies on pharmacokinetics indicate that monoamine levels in the plasma return to normal within 5 or so days of cessation.