• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

4-ear

Status
Not open for further replies.
S

stillhead

Greenlighter
Joined
Oct 4, 2007
Messages
11
Has anyone had any experience with 4-ethyl aminorex?

I can't find anything on it anywhere.
 
I don't have a whole lot of knowlege of how this works, but wouldn't an extra carbon there allow it to form a ring (attaching to the phenyl)?

I don't know a whole lot about conformationally constrained stimulant analogues (seen some with MDMA types I know- TDIQ was one that looked interesting). 4-MA seems to be so much more euphoric without the physical problems (someone who's tasted it will need to chime in here), perhaps an ethyl in place of that methyl will decrease the physical even futher, and only slightly dampen the euphoria.

I don't know that the physical problems associated with it are bad enough the loss of euphoria is a valuable sacrifice.
 
Ham-milton said:
I don't have a whole lot of knowlege of how this works, but wouldn't an extra carbon there allow it to form a ring (attaching to the phenyl)?
Click to expand...

Well from my understanding, no it wouldn't, simply because adding another carbon to the methyl chain doesn't make it electrophilic enough to give it a reason to attach to the benzene ring. Same reason why Br2 will put an anti addition across an alkene, but there won't be a reaction when added to benzene. There are ways to 'force' the reaction to happen, but that's another topic. Most (all?) reactions occur only when there is a drop in energy and losing the aromaticity would cause a raise in energy. Although I still have a heap to learn so I might be missing something...
 
4MAR is an excellent (can I say the best?) stimulant I've ever tried. I HATE methamphetamine & cocaine, regular amphetamine is OK, dextroamphetamine better still... but they don't match up to 4MAR.
 
immaturepoop said:
Most (all?) reactions occur only when there is a drop in energy and losing the aromaticity would cause a raise in energy. Although I still have a heap to learn so I might be missing something...
Click to expand...

Nope, you're perfectly right. A simple alkyl chain will not attack an aromatic ring without proper activation. Period.
 
Rather than 4-EAR, I would take a look at 4S,5S dimethylaminorex. From what I can glean, it's stronger than 4-MAR or AR by a factor of 5. Cyanate route from pseudoephedrine would do it. It wouldn't be listed as being controlled although the CsA laws in the US might well apply.
 
haribo1, I assume the cyanate route from pseudoephedrine gives only that enatiomer, is that right? I vaguely remember reading something about physical issues with dimethylaminorex use and vaguer still something about a safe(r) isomer. Is this it?

Ham-milton said:
perhaps an ethyl in place of that methyl will decrease the physical even futher, and only slightly dampen the euphoria.
Click to expand...

That more or less what I was hoping too. My reasoning is that if a 4-methyl reduces the cardiotoxicity of aminorex then a 4-ethyl is hardly likely to reintroduce that factor back into 4-ear. I should say that I am not in the least bit qualified to be making these assumptions. Seriously!
 
Last edited:
4-ethylaminorex is certainly active, the patent lists the p-chloro derivative of 4-EAR as one of their especially preferred compounds, but thats the only information I can find about it.

Could have some potential as 4-MAR itself is a lot more MDMA-like than most dopaminergic stimulants, and with MDMA itself extending the alpha methyl to alpha ethyl to make MBDB results in a compound with less stimulant effects and shorter duration but retaining the empathogenic and euphoric effects.

Seeing as one criticism thats sometimes made about 4-MAR is that it lasts too long and the stimulant effects are too strong when its taken in large doses, the 4-ethyl analogue might be well worth a look.
 
I mentioned that specific isomer because the cyanate route causes a stereo-inversion of the benzyl alcohol, because it's 5 times stronger and because it is not listed as an illegal compound. Chronic use can lead to heart problems, but (at least to me) it's not something I would take more than, say, monthly...
 
afaik pseudoephedrine in the cyanate route gives amide only, but 3,4-dimethylaminorex was flagged as both cardio- and hepatoxic elsewhere anyway so not much interest to me tbh
 
No, any isomer is possible with the cyanate route. The carbonyl reacts with the benzyl carbon throwing off the hydroxyl as water. That's how come it causes a stereo-inversion.

You know, those p-F analogs must be VERY nasty because the option of making something legal & 5 times stronger would certainly attract someone.

The issue of Microgram states that they don't tell you the synthesis because it would make life easier for chemists... then they give you the references!

Bandil made p-F 4MAR from aldehyde and if you look at his synthesis & then read the DEA commentary... you have a very DETAILED write-up of the route.

KOCN + HCl --->HOCN<---> OCNH (i.e cyanic and isocyanic exist in equilibrium in solution. It's the isocyanic acid that adds to the nitrogen.
 
Status
Not open for further replies.
Top