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Phenylsulfanylethylamines ?

T

Turing Machine

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I apologize if this is in the wrong forum. I remember reading a decades old paper a while ago describing stimulant properties of 1-phenylsulfanylethanamine, amphetamine with the beta carbon replaced with a sulfur, and comparing it to amphetamine but I can no longer locate it. Does anyone have this paper, or any information about this compound or phenylsulfanylethanamine analogs of substituted amphetamines? Maybe my memory is finally dying on me or I'm thinking of the sulfur being bonded on the other side of the alpha carbon or something else, but I'm pretty sure it was this compound. If necessary, I'll draw up a picture of the molecular structure, but I'd assume most people here know what I'm referring to.
 
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I was just thinking about this but I didnt know there was any articals out there. It seems reasonable cuz sulphor is next to oxygen. So beta-keto amphetamines mean theres oxygens at the beta phenyl position so this would mean replacing the oxygens with sulphor. Sometimes proper positioning of sulphors increases potency sometimes subing it for oxygens can reduce it. I was also wondering if N-Methyl-3,4-MethyleneDiSulphanylamphetamine had ever been tested or was even worth it. Also I was thinking about 2-(2-Chlorophenyl)-2-ethylamino-1-sulphanylcyclohexane (sorry, not sure if that's the proper way to write it out) basically an analog of ketamine with a sulphor in place of the ketone. My mind just goes off on these tangents sometimes...
 
Actually, I'm talking about sulfur in place of the beta carbon, as opposed to attached to the beta carbon, or maybe I've misunderstood you.
 
You are talking about different things. Zonk is referring to a thioketone. Cuz sulphor is next to oxygen, you know.
 
I took it that way also, seems like a thioketone (learned a new word, how many scrabble points is that?) should be active.
 
He's talking about a sulfide: the sulfur analog of an ether:

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Although maybe you're thinking along the lines of 2-(phenylsulfanyl)ethanamine, which has been written about in various contexts (including as an antidote for mustard gas).

fryingsquirrel said:
thioketone (learned a new word, how many scrabble points is that?)
Click to expand...

xero! It's not in Webster's 4th.
 
I misread the original post, I thought u said phenylsulphanylpropanamine, I was thinking of beta-sulphonyl or beta-thio-amphetamine
 
This is a rather unstable looking molecule, as a thiohemiaminal. It would break down in water rapidly to give thiophenol, acetaldehyde and ammonia.
 
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