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Author: Subject: new phenethylamine?
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[*] posted on 1-4-2009 at 04:44
new phenethylamine?


Does anyone know of the existance of the following compound has it ever been tested or made?

Insted of having N-methylphenylisopropylamine
N-methyl-1-phenylpropan-2-amine

Have: N-methoxyphenylisopropylamine...
So insted of that methyl next to the NH have a OCH3...
I think the correct name would be:

O-methyl-N-(1-phenylpropan-2-yl)hydroxylamine
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[*] posted on 1-4-2009 at 05:11
DNA's Designer Amphetamine thread


It would have been clearer just to say N-methoxyamphetamine as compared to N-methylamphetamine? (Methedrine)

Restating your question:

Ph-CH2-CH(-NHMe)-CH3

is the normal structure of N-methylamphetamine, and instead you propose

Ph-CH2-CH(NH-OMe)-CH3

and you want to know whether this has similar properties?

The answers are all in the literature.

The parent compound would be an oxime made from the ketone (in this case phenylacetone, methyl benzyl ketone, P2P) and hydroxylamine hydrochloride then O-alkylated.

Calculate the empirical formula and look in Beilstein.

I would say the chances are very high that it has been prepared, but very low that it will have stimulant CNS effects of the sort that methamphetamine has.

First ask yourself how toxic it will be?

Then ask if any related stimulants posess a methyloximino moiety.

There will have been in the last century God knows how many structure-activity studies of this series.

Big Pharma are not stupid.



[Edited on 1-4-2009 by Sauron]




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[*] posted on 1-4-2009 at 23:55


Or you could insted of making the oxime by hydroxylamine use o-methoxyhydroxylamine immediately.
Same goes for preparing the N-methylated variant, insted of making it with hydroxylamine and then methylating, one could use N-methylhydroxylamine...and reduce that nitrone.
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[*] posted on 2-4-2009 at 01:20


Quote: Originally posted by Sauron  
The parent compound would be an oxime made from the ketone (in this case phenylacetone, methyl benzyl ketone, P2P) and hydroxylamine hydrochloride then O-alkylated.


No Sauron, the parent compound would be the hydroxylamine, N-hydroxyamphetamine, which would then be O-alkylated. The parent compound could be made by selective reduction from either phenylacetone oxime or phenyl-2-nitropropane.
I know I have seen this compound mentioned in the litterature. But I cannot remember where. I'm quite sure it is active though, since the parent compound is active.
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[*] posted on 2-4-2009 at 03:17


Damn it, you still make it from the ketone via the oxime, REDUCE that to the N-hydroxy, and O-alkylate that. The parent is still P2P - just as it is for meth.

Ketone >C=O
oxime >C=N-OH
N-hydroxy >C-NH-OH
Target .C-NH-OMe

And yes DNA you could use those already alkylated reagents if you have them. Saves a step.

[Edited on 2-4-2009 by Sauron]




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[*] posted on 2-4-2009 at 05:50


Quote: Originally posted by Sauron  
The parent is still P2P - just as it is for meth.


I think you mean that phenylacetone is just one of several possible precursors for methamphetamine. Legal commercial production of methamphetamine starts with phenylacetone but the illegal dito seems to favor ephedrine.
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[*] posted on 2-4-2009 at 06:11


Not if you look at the ceised drug labs then most of them 90% uses phenylacetone, but anyway I don't know if this is still a viable discussion for this board.
Another weird thing, I'm preparing the N-methyl oxime of phenylacetone and the company has a license for it to prepare these compounds.
But the weird thing is when I run a TLC on phenylacetone and also from the reaction mixture with N-methylhydroxylamine then I don't see the phenylacetone spot anymore in the reaction mixture but there is a spot at the baseline...
Then I stained it with 2,4-dinitrophenylhydrazine to have the ketone form the hydrazone, but the spot at the baseline also gets stained...while this isn't a ketone (at least it shouldn't be :) ).
Would one expect the N-methylphenylacetone nitrone to be at the baseline?

[Edited on 2-4-2009 by DNA]
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[*] posted on 2-4-2009 at 07:22


Toxicity data for dl-N-Methoxy-alpha-methyl-phenethylamine

http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHa...


It has been a research subject for so long that you would be hard pressed to find a novel phenethylamine whos effects are unknown.

[edit] Hmm link doesnt seem to be working maybe this one will.

[Edited on 2-4-2009 by Sedit]





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[*] posted on 2-4-2009 at 07:51


Just so. As I stated upthread.



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[*] posted on 2-4-2009 at 09:02


i always thought people were talking about math when they wrote meth, i assumed a typo.

edit-that was a joke, i'm that naive, lol

[Edited on 2-4-2009 by Panache]




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[*] posted on 2-4-2009 at 11:00


Take a look at J. Med. Chem 4: 51 (1961) and you will find the compound your looking for.
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[*] posted on 2-4-2009 at 11:28


Here it is so everyone can see what this thread is about.

That's the nice thing about having 5 major ACS journals on my destop. Thanks, alter!

And thanks, bronstein. All my best to Leon.

[Edited on 2-4-2009 by Sauron]

Attachment: jm50017a005.pdf (181kB)
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[*] posted on 6-4-2009 at 01:18


Does anyone know if from a nitrone one could form a salt?
Like when you would form the nitrone with phenylacetone and N-methylhydroxylamine to get the corresponding nitrone.
Would it be possible to seperate the nitrone from the N-methylhydroxylamine by washing the extract with HCl solution? Or would the nitrone also form a salt...
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