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Chemical idea

dread

dread

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Chemical ideas

I was playing with chemsketch this one night, and I came up with this.

The idea came from phenmetrazine, which is an amphetamine with the carbon tail & amine twisted into a morpholine.

Now if you'd do the same to the tail of a tryptamine?

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looks a bit like the pyr- and mor-T's, but with the morpholine locking the 'tail' into one position a bit better.

I doubt it'll have much activity though.
 
I don't. There are some similarities with tryptamines & phenethylamines, eg. alpha-methylation works potentiating and protecting from MAO:s in both. Generally, most things concerning the ethylamine-tail work similarly in both chemical types, but additions on the aromatic ring don't - 2 dimethoxy groups in certain positions works for phens, but not for trypts.

So, if "twisting" the carbon-tail to a morpholine works in phenmetrazine, I very much believe this would work with a tryptamine too. Only, tryptamines need to be tertiary amines to be any good, so I moved the methyl from the alpha-carbon to the amine. In a way, this is a distant analogue of MET, with the end of the ethyl-group connected with an oxygen to the beta-carbon. The DET analogue of this chemical would have an ethyl in the amine instead of the methyl. Or you could add a carbon to the 3-position of the morpholine, next to the indole, it would be in the same position as the alpha-methyl in AMT. This compound would be very interesting, since it'd have 2 stereocenters.

And of course, there are the possible 4-HO, 5-MeO, 4-AcO etc. groups. So if this chemical would be active, it could create a whole new group of psychedelic tryptamines.
 
you just blew my mind, lol! i need to take a chem course so i get involved in some of these discussions as im very interested.
 
The compound would most likely be orally active but with a low potency compared to, say, AMT.
 
oh yea and the indolic nitrogen in the tryptamine series of drugs corresponds roughly with a 2-methoxy substituent in the phenethylamine class of drugs. AMT is basically a 1-winged DR-FLY analog with the sidechain connected to the pyrrole ring versus the benzene ring.
 
True.
I don't know if these compounds would be potent by weight, but very likely they'd be long lived, as morpholine is a quite stable structure.

What I'd like to know, is there a possibility of the morpholine ring breaking, like non-cyclic ethers, which break easily by metabolization? Morpholine should be more stable since it's a cyclic ether, but if it could break, the compound would become beta-hydroxy-MET. Which could also be an active metabolite.
 
ethers, cyclic or not, are actually quite metabolically inert...diethyl ether is mostly excreted unchanged...
 
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