• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

Thioketones

MagickalKat777

MagickalKat777

Bluelight Crew
Joined
Feb 4, 2004
Messages
7,020
Location
Denver, CO
I take no responsibility for the original author but thought I would post this here to see what you all think... Personally I think the sulfur may abolish activity but I wanted to see what the brains here think. Also, wouldn't these technically get around the UK blanket cathinone ban?

"If you replace the oxygen atom in a ketone with sulphur, you get a thioketone. You could do this with any of the currently available beta-ketone amphetamines and get new analogues. And anyone that is knowledgeable in pharmacology, how do you think this will alter effects of the compounds?"

Discuss - I am deeply curious on this one.
 
Well methiedrone has already been seen (no idea why they chose that one) for sale... So in your mind they would be entirely unstable? What do you think they would break down to?
 
To my knowledge, they usually dimerize. So you'd get some sort of disulfide. In vivo this would reduce to beta-sulfhydryl-methamphetamine.

Frankly I wouldn't trust anything sold by Eric to be what he says it is. The vendor who stocks this is likely getting duped -- they also sell such ridiculous stuff as "eric-2".

Further is methiedrone the methedrone analog, not the mephedrone analog. If active, expect MAO inhibition and hyperthermia.
 
Not really all that interested in consuming thiones/thiols -- if you think you smelled bad after taking mephedrone, wait until you try that stuff. There may be enough steric hindrance here to prevent rapid polymerization/cyclization of the compound, but I doubt you'd be left with something you'd still want to take, anyway. It's possibly these compounds may also irreversibly bind to enzymes/receptors to which they are substrates.
 
Ouch. Yeah no thank you. 24/7 DA and NE surges... ffs... I won't touch these with a 1000000000000 foot pole. Thanks nuke :)
 
Why would you suspect irreversible binding? there are lots of compounds which contain such features that don't do so (I can't think of any that do, but that's meaningless on this subject).

It wouldn't be 24/7. It would only last for a period of time because of down-regulation and receptor pruning (which would result in new receptors growing over a few hours to days).

I think naloxazone bind irreversibly with opioid receptors, but I don't know anything about it off hand.
 
there are plenty of approved drugs that contain a thioketone moiety, e.g.


sulazepam
180px-Sulazepam.svg.png


prothionamide
220px-Protionamide.png


thiopental
247px-Thiopental.svg.png


what worries me is that usually thioketones are found in drugs as a part of a thioamide moiety, which probably serves to stabilize (reduce reactivity) of the C=S .
 
...Atara beats me to it.

'Irreversible' (or maybe we better call it what it really is: covalent) binding is still not from the table. The thioketone is prone to tautomerisation, e.g. lets consider the thio-version of cathinone (i.e. 2-amino-1-phenylpropane-1-thione), which is in a equilibrium with 2-amino-1-phenylprop-1-ene-1-thiol. This one is actually able to dimerize.
As Nuke already suggested, steric hindrance could slow this down. Nonetheless, with another thiol in sufficient proximity, covalent (...irreversible; oh this sounds just so lethal ;) ) binding is possible.

Anyone having the proposed amino acids responsible for cathinone-binding at hand?


Peace! - Murphy
 
Last edited:
Hammilton said:
Why would you suspect irreversible binding? there are lots of compounds which contain such features that don't do so (I can't think of any that do, but that's meaningless on this subject).

It wouldn't be 24/7. It would only last for a period of time because of down-regulation and receptor pruning (which would result in new receptors growing over a few hours to days).

I think naloxazone bind irreversibly with opioid receptors, but I don't know anything about it off hand.
Click to expand...

The thioketones are so highly reactive that one would expect them to react with either the protein backbones or side chains of whatever they bind too. It would be partially stabilized by the aromatic group, but I still think it would be dangerous. Thioketones are sometimes produced by the body as metabolites and are considered to be toxic metabolites (generally nephrotoxic).

I still think it will smell so horrific that no one would consume it anyway, though. See this article on thioacetone: http://pipeline.corante.com/archives/2009/06/11/things_i_wont_work_with_thioacetone.php
 
^By the way, I love that blog, In the Pipeline. His articles titled Things I Will Never Work With (or something like that) is always highly entertaining. He`s actually considering publishing a book of them.
 
I'm aware of the smell issue, but the binding thing wasn't one I'd even have considered.
 
maybe compounds of this type might be worth investigating?

20rs8ea.jpg


or the corresponding sulfone
 
You must log in or register to reply here.
Top