Sulphur GHB analogue??

[Reminisant B]

I Can't upload files at the moment but does anyone know if any sulphur analogues of GHB have been made?

Looking at this....
http://www.wormbook.org/chapters/www_gaba/gabafig1.jpg

which highlights "saclofen" a new baclofen analogue.

What about taking off the phenyl ring, the NH and replacing with OH - I.e GHB with sulphur?

 

[bigmac74]

Saclofen is a GABA-B antagonist [http://www.ncbi.nlm.nih.gov/entrez/...ve&db=PubMed&list_uids=2559370&dopt=Abstract], so I'd assume the sulphinic acid analogue of GHB is no good either (except possibly for GHB overdose).

 

[haribo1]

There are some new sleepers based on the muscimol skeleton that look interesting...

 

[fastandbulbous]

The 4-thio analogue of GHB may well work, but if my experience of mercatoethanol (2-hydroxyeyhanethiol) in the lab is anything to go by, bo one is going to go anywhere near it as it will stink to high heaven. If the carboxylic acid function were fully reduced to a CH3 group you get butanethiol, which is the main component of eau de skunk and after having made some out of curiosity when bored in the lab many years ago, I wouldn't want to be anywhere in a room containing it. The thiol derivative had chance to make your bodily secretions absolutely rancid (just think how garlic or fenugreek gets into sweat, then substitute in the smell of skunk)

 

[haribo1]

I was also under the impression that the thiols are rather volatile & explosive.

 

[fastandbulbous]

Nah, just incredibly stinky (like make you throw up sort of stinky!)

 

[vecktor]

Nah, just incredibly stinky (like make you throw up sort of stinky!)

there is some current research into repulsive smells being carried out in the US as part of an army project,it seems that some cultures are repelled by different smells buty seleno mercaptan and the isopropyl telluro mercaptan are reviled by western noses but asians are rather less repulsed. the same applied to indole.
I havebeen told of a warehouse where circa 10g of ethyl mercaptan was spilled and it was so vile that no one could enter for several weeks. thank god al quaeda don't get some into the london underground.... hard to believe but it would be worse than a million bankers armpits.

thiomuscimol has been quite heavily investigated but doesn't work in the same way as GHB, lacks the dopaminergic effects.

thio GHB is CAS Registry Number 13095-73-3 cannot yet find any references to the pharmacology or toxicology just synthetic refs

 

[fastandbulbous]

I havebeen told of a warehouse where circa 10g of ethyl mercaptan was spilled and it was so vile that no one could enter for several weeks.

After my butyl mercaptan synthing exercise (only about 2g out of skunkish curiosity), people commented for weeks afterwards about the strange smell in my lab (which I had to come clean about before they got the drains thoroughly cleaned etc). The lab where they use mercaptoethanol for denaturing proteins always had the reputation for being a vile place to have to work.

Worst thing about mercaptans is their fat solubility, which means if you get some on your skin the smell follows you for days and there's nothing you can do about it (again found that out after an accident with mercaptoethanol)

PS. Vecktor, isn't it actually 3-methylindole (skatole - how appropriate) that gives indole it's vile smell (eua de merde - skatole gives dhit a lot of it's smell!) - I've smelled some analar grade indole and it was only a fraction of the stench of ordinary reagent quality.

I agree though, if you wanted to carry out a non lethal attack on an underground transport system, a quarter of a litre of ethyl or butyl mercaptan would be incredibly efficient. Noone would use it on warm days

 

[vecktor]

indeed my mistake, skatole is the nasty smelling thing in impure indole although apparrently it is a flavouring added to ice cream
http://www.chm.bris.ac.uk/motm/skatole/skatolec.htm

 

[vecktor]

ok the ref to 4-mecapto butyric acid or rather the thiolactone GBL analogue I could find in a really short search was
http://www.ncbi.nlm.nih.gov/entrez/...t_uids=1256638&query_hl=2&itool=pubmed_docsum

someone with scifinder could do better and much quicker

the abstract is

Abstract

The present study evaluated in the rat the gross behavioural and electroencephalographic activity produced by several short chain aliphatic alcohols, fatty acids, some of their derivatives and some heterocyclic 5-ring compounds that have structural similarities mainly to 4-hydroxybutyric acid and butyrolactone.

4-Hydroxybutyric acid (and butyrolactone) produced a progression of EEG and behavioural changes characteristic of generalized non-convulsive epilepsy. During the period of continuous EEG high amplitude slow wave activity, the rat was cataleptoid and during periods of spiking with electrical silence, the righting reflex was lost.

Non-convulsive epileptoid activity with some characteristics similar to that produced by 4-hydroxybutyric acid and butyrolactone was observed following administration of butanol, 2-butanol, 1,4-butane-diol, 4-chlorobutanol, 4-methoxybutyric acid, 4-chlorobutyric acid, tetrahydrofuran and 2-deoxy-Image-glucose. Convulsive seizures were observed following 4-mercaptobutyric acid thiolactone and pyrrolidine.

The results are discussed with regard to the structural components necessary to elicit epileptoid activity and the possible mechanism of action. It is suggested that part of the mechanism of action of these substances may involve inhibition of the enzymes involved in brain glutamate and aspartate metabolism.

 

[hussness]

What's 2-deoxy-Image-glucose?

 

[vecktor]

What's 2-deoxy-Image-glucose?

no idea I just cut n pasted the abstract... I guess its a fuck up.
2-DG is a glycolysis inhibitor, though quite why they decided to investigate it along with GHB and others I am not sure, though I do know that GBL is quite potent at altering dopamine metabolism so perhaps they were looking for metabolic inhibitors?