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Have amphetamines with double/triple bonds substituted been tried?

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bupropion

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Feb 29, 2008
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Have amphetamines with double/triple bonds substituted been tried? Such as:

Double bond to the alpha-methyl group
Double bond connecting the alpha carbon to nitrogen
Double bond connecting the extra carbon to the nitrogen on methamphetamine


What about an analog of both amphetamine and phenelzine (i.e. amphetamine with a second nitrogen attached to the first)? Would this be called alpha-methyl- or beta-methyl-phenelzine?
 
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Not quite double bond to the alpha aton, but a vinyl group produces aletamine (alpha allylphenethylamine), a rather mild CNS stimulant, but with decent analgesic activity.

Everything else you mention would be an unstable compound; carbon-nitrogen double bonds quickly hydrolyses to a ketone (benzyl methyl ketone/phenylacetone in this case) & ammonia. Again a double bond between two cabons, one containing the amine will rearrange to an imine in a manner similar to keto-enol tautomerism & hydrolyse - and hello more benzyl methyl ketone!). Rearrangements will occur for the variations you're suggesting
 
What about amphetamine with a second nitrogen added to the first one? Would this be called alpha-methyl- or beta-methyl-phenelzine?
 
Sorry for bringing up such an old thread but I'm really interested in the a-vinyl-PEAs, perhaps even a-vinyl-tryptamine? Does anyone know anything more about them?
Also I've been looking everywhere but does anyone have any info on a-hydroxy, a-methoxy and a-methanol-PEAs?
 
I think I actually remember seeing that somewhere. I'll try find out.

EDIT: Nevermind it was with the essential oils and I can't seem to delete the post. However thinking about it 2-PTC and DMCPA come close with the cyclopropyl bit, I guess. But really it's not that close at all and they were complete washouts.

I reckon though, you could be onto something there. Possible loss of potency but only a tiny bit and the effects could be a lot better (i.e smoother or more euphoric, richer visuals, that sort of thing).

EDIT2: However, could a double bond there (on an amp compound) turn into something like 2-PTC or DMCPA after it's metabolised? Could be a nasty comedown. I reckon, if so, it'd be the same with the a-vinyl.
 
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blueberries said:
I think I actually remember seeing that somewhere. I'll try find out.

EDIT: Nevermind it was with the essential oils and I can't seem to delete the post. However thinking about it 2-PTC and DMCPA come close with the cyclopropyl bit, I guess. But really it's not that close at all and they were complete washouts.

I reckon though, you could be onto something there. Possible loss of potency but only a tiny bit and the effects could be a lot better (i.e smoother or more euphoric, richer visuals, that sort of thing).

EDIT2: However, could a double bond there (on an amp compound) turn into something like 2-PTC or DMCPA after it's metabolised? Could be a nasty comedown. I reckon, if so, it'd be the same with the a-vinyl.
Click to expand...

What if it was double bond on alpha to beta, then a beta-hydroxy. Cathinone prodrug?

PxiJjtV.png
 
That will tautomerize to cathinone because it's an enol.

gz1jQz4.png


Generally double bonds are not seen because they provide a metabolic handle to react with - epoxidation, diol formation, ketone formation, other oxidative cleavage. Not the sort of thing you want to see in a drug if you want it to persist in the body.

Besides, double bonds near aromatic rings can be activated towards metabolic attack. that compound you drew might go retro-aldol to 4-methyl benzaldehyde. or just dehydrate to a ketone. either way it's not very stable. even if it's protected as an ester. it will still eliminate.
 
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sekio said:
That will tautomerize to cathinone because it's an enol.

gz1jQz4.png


Generally double bonds are not seen because they provide a metabolic handle to react with - epoxidation, diol formation, ketone formation, other oxidative cleavage. Not the sort of thing you want to see in a drug if you want it to persist in the body.

Besides, double bonds near aromatic rings can be activated towards metabolic attack. that compound you drew might go retro-aldol to 4-methyl benzaldehyde. or just dehydrate to a ketone. either way it's not very stable. even if it's protected as an ester. it will still eliminate.
Click to expand...
Would it be able to stay stable as a hydroxy until consumed? Or will it just tautomerize upon synthesis?

The idea is a mephedrone prodrug.
I realize its an enol
 
It would tautomerize upon standing. No matter what you do the chemical equilibrium is always present and is why you don't see acetone as an enol either, even though it's isomeric and the two can interconvert.

WzZ2i7h.png
 
Again, bringing up this issue of alpha-vinyl bonds. What happens? Tautomerisation ala the alpha-beta double bond?
 
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