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Adas
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thumbup.gif posted on 6-9-2012 at 07:42
Modified Phenylethylamine as antidepressant?

Hi guys!

I have read about Phenylethylamine used as an antidepressant on a drug forum. Most people claimed, that it is metabolised too fast and either large quantities are needed, or you must also take MAOI (taking more than 1 gram PEA can create toxic metabolites, from what I've read).

But despite its very short duration, they said that it has perfect anti-depressant properties (and it is a body's natural compound).

I wondered if it is possible to make a compound that has relatively long half-life and slowly metabolizes into PEA. It would be a great help for those suffering of depression, IMO.

Let's discuss this!



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Rich_Insane
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[*] posted on 6-9-2012 at 08:12


I wonder if N-acetylation might allow for the creation of a prodrug. Or perhaps substitution on the phenyl portion might make it more difficult to metabolize...
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[*] posted on 6-9-2012 at 17:24


PiHKAL anyone?



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jon
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[*] posted on 6-9-2012 at 18:27


l- dopa does the same thing trust me i got some and i know.



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[*] posted on 6-9-2012 at 18:44


L-DOPA is the prodrug that crosses the BBB. But I've heard mixed reports about its effectiveness.



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[*] posted on 7-9-2012 at 06:13


L-DOPA is the prodrug of dopamine, not PEA...

Maybe 2-amino-3-phenylpropanoic acid would be a good prodrug of PEA.



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jon
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[*] posted on 8-9-2012 at 10:53


using the l-dopa analogy sounds plausible indeed.
less h-bonding sites too, looks like it could breakdown, and cross the blood brain barrier with ease.



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[*] posted on 8-9-2012 at 11:40


Phenylethylamine is one carbon away from phenylisopropylamine, which is not so easily broken down by MAO. And amphetamine definately has an anti-depressant effect, no doubt. Phenylethylamine will be taken off the market soon enough, however.
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[*] posted on 8-9-2012 at 11:45


Well, we used to try to get lots of tyrosine into the pipeline. Body uses it to produce dopamine. Cheap, works fairly well, some effectiveness at alleviating Parkinson's symptoms.
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9-9-2012 at 07:25
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[*] posted on 9-9-2012 at 19:36


What about this?
http://en.wikipedia.org/wiki/%CE%91-Ethylphenethylamine



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[*] posted on 22-9-2012 at 12:36


There is a nomenclature problem inherent in this question.

Phenethylamine has the structure C6H5-CH2-CH2-NH2

The generic term Ethylphenethylamine gives no clue as to what actual structure you are referring to. Ethyl where? N-Ethyl(which might be assumed)? Ortho, Meta, Para...Ethyl? 1-Ethyl?

Turns out you are referring to 1-Phenyl-2-Amino-Butane. An analog of 1-Phenyl-2-Amino-Propane....AKA Amphetamine.

Wikipedia may refer to this material simply as Ethylphenethylamine, but they are basically wrong.

In fact, since you made your posting, they have made a nomenclature correction. Still wrong, as in imprecise, but closer.

[Edited on 22-9-2012 by zed]
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