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Substituted Aminorex as PEA analogs

haribo1

haribo1

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Nov 29, 2006
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Hi,
The cyanate route to aminorex is well known but both AR & 4MAR are strictly controlled in the UK... however, if you ring-substitute them, then there are no laws. Anyone prepared to guess on the activity of ohhhh... the 3,4 methylenedioxy version of aminorex. Plain aminorex is supposed to lie midway between S-amphetamine & methamphetamine in potency so maybe the stuff is stronger as well! Nice to keep things legal, I always say.

H1-)
 
Well, I'd say it'd have to be a 'suck it and see' test as I don't have much on the absolute conformation of the aminorex derivatives, so how the ring substituted ones would fit into the 5HT2a receptor is a mystery.

The methylenedioxy derivative would have a good chance of being active from what I know of DAT & SERT binding though
 
Well, the p-F was active, was it not? Just need to find the appropriate 1 phenyl 1 hydroxy 2 amino ethane... tricky. Cannot see a simple way of converting a benzaldehyde to it, either. Any ideas on that front?
 
4-methylaminorex is unusual in that all four stereoisomers are active. The double bond in the oxazoline ring shifts around the ring under some conditions so maybe the isomers interconvert in vivo?

Anyway yeah I've always thought the 3',4'-methylenedioxy analogues of aminorex and methylaminorex looked promising.

From the original paper, the 4'-fluoro, 4'-chloro, 4'-bromo, 4'-trifluoromethyl, 3'-trifluoromethyl, 4-methyl and N,N-dimethyl analogues of aminorex all showed pretty strong anorectic activity in rats, and the 3',4'-methylenedioxy and 3',4'-dimethoxy analogues were active although weaker. So theres lots of potential for developing useful new compounds from aminorex...
 
haribo1 said:
Well, the p-F was active, was it not? Just need to find the appropriate 1 phenyl 1 hydroxy 2 amino ethane... tricky. Cannot see a simple way of converting a benzaldehyde to it, either. Any ideas on that front?
Click to expand...

Noradrenaline. Turn the dihydroxy into a methylenedioxy and Robert is your mother's brother
 
I guess, although how good are those DBM methods... always looked like a messy, low yielding pain in the arse... going via the nitroalcohol and reducing with, say, DIBAL (or something simpler) would give the desired product...
 
Last edited:
>>From the original paper, the 4'-fluoro, 4'-chloro, 4'-bromo, 4'-trifluoromethyl, 3'-trifluoromethyl, 4-methyl and N,N-dimethyl analogues of aminorex all showed pretty strong anorectic activity in rats, and the 3',4'-methylenedioxy and 3',4'-dimethoxy analogues were active although weaker. So theres lots of potential for developing useful new compounds from aminorex...>>

Would we expect any to have the nightmarish neurotoxicity of the 4-halogenated amphetamines?

ebola
 
^ Don't know, but until proved otherwise I think a sweeping generalization along the lines of "if in doubt, take nowt" is the best approach.

One big potential problem with the aminorexes is their ability to cause a condition known as pulmonary hypertension. I's mediated via the 5HT2b receptor, so para-halogenated aminorexes do give me a bit of cause for worrying
 
haribo1 said:
Well, the p-F was active, was it not? Just need to find the appropriate 1 phenyl 1 hydroxy 2 amino ethane... tricky. Cannot see a simple way of converting a benzaldehyde to it, either. Any ideas on that front?
Click to expand...

SWIM has heard reports from the bees who has tasted trans-p-F-4-MAR.
The potency was a dissapointment (almost the same as 4-MAR AFAIR), and so was the effect, which i quote "is probably the worst stimulant you could think of".
Still the bioassays were very sparse and only a very few trials were made.

SWIM has never tasted this compound, but still find this compound interesting, since the bioassays were very subjective.

The DOB/2C-B-homologue of 4-MAR was attempted by a bee, but ring closure of the corresponding norephedrine intermedia was impossible.

Deeper synthetic details will be left out, of respect to the forum rules.
 
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