• 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

thiobutryolactone/GTB

kidamnesiac

kidamnesiac

Bluelighter
Joined
Oct 19, 2006
Messages
533
anyone have any direct experience with this? my SAR knowledge of these guys is minimal, more or less potent?
 
Thiols? You'll not get invited to any meet ups if you go ingesting things like that! In my lab, with the cullusion of the technicians, we once made about 0.25g of butyl mercaptan (1-butanethiol) as that's the 'essence of skunk (small black & white mammal!)' and we wanted to see just how bad it was. The place smelled rancid for over two weeks - nothing would shift the smell.

And you propose ingesting several grams of a thiol related coimpound? 8o

Actually, it might interfere with the citric acid/Krebs cycle - best to find out first as that's not something you want fucked up in your body
 
How do you make a thiol? alkyl bromide and hydrogen sulphide?

I was using thiophenol before and noticed the lab stunk, thought i must have thrown out the wrong syringe (half the syringes in my hood had been used to measure it or ethanedithiol), turned out i got a drop on my t-shirt! Most people i walked past in the corridor after that turned their heads as they passed, probably thought i farted!
 
it doesnt smell that bad, a little like H2S.

I thought dithiothreitol was the smell o skunk. we use it to keep proteins from coagulatin' and i kinda like it. I also like beta-mercaptoethanol as well. mabye i'm weird.

why do you suspect issues with the krebs cycle?
 
Ugh yuk, no thanks on ingesting this one, thiols stink WAY worse than H2S.

The good thing about H2S/H2Se, apart from its insidious toxicity as an inhibitor of cytochrome oxidase (ala cyanide), is the stench is volatile, as is the gas, I have had bad experience with mercaptans, after ingesting a lot more chlormethiazole than I should, that smell came out in all my bodily fluids, inside my mouth and all, and the fleece I was wearing at the time, well, I had to wear the same set of clothes for three days or so so as not to contaminate any other clothes, the smell hung around for days, I washed the clothes, but the smell wouldn't come out and I had to chuck the fleece, my favourite leather belt, the synthetic fiber shirts came out better, and stopped stinking after a few washes.

Fast, doesn't the sulfhydryl group in thiols complex with proteins, making the stench stick to the surface layer of hair, nails and skin until it grows out?
I recall reading that somewhere but I may be mistaken.

Either ways I would rather work with H2S over mercaptans any day.
 
I'd choose the mercaptans over H2S, that's what the fume hood is for. The benzyl is the worst IMO, like a very unclean lion cage, and quite persistent, along with the aryl ones. NaOCl does wonders on such clothes (and on you).

I would certainly not go even close to thiobutyrolactone, but hey - it could almost be abbreviated G. BuSH.
 
I just took a look at the bottle from Sigma-Aldrich and it says as a warning:

Stench!

first time I've ever seen that on a chemical bottle :)
 
How do you make a thiol? alkyl bromide and hydrogen sulphide?

That would overalkylate.. chemists usually use a substance that looks like urea, except with a sulphur atom replacing the imine.
 
kidamnesiac said:
I just took a look at the bottle from Sigma-Aldrich and it says as a warning:

Stench!

first time I've ever seen that on a chemical bottle :)
Click to expand...

that's funny that it uses that warning and that term in particular...i guess you will take what those have said here into greater liight =D
 
Yeah all the thiols i've seen are labelled stench, i think diphenyldiselenide too.

Acyl, thiourea u mean, what it'll react with an alkyl halide? Lawessons reagent on the alcohol might work i guess, not sure about that though.

Edit: I quite like the smell of the (di)selenide though, in low concentrations anyway.
 
Thiols are easily made by adding S8 to grignard reagents. good yield.

I remember a chemist bought some thiocresol and Methanethiol from Sigma. The MeSH glass bottle was wrapped in a plastic bag and packed in a can. We can smell the specific stench of mercaptans through the can !!!

Trimethylamine is very foul, too.
I remember a friend told me that he smelled the TMA before the FID detected it ... I dont know if he lies but the olfactive threshold of TMA is very very low...

In PiHKAL Sulgin talk about a chemist who broked a flask of dibutyl telluride in a bus. restoring a brethable athmosphere was impossible...

The MOST horrible chemical I ever smelled is certainly "Thioacetamide" ! The only chemical worst than cadaverine.
 
One guy at the company I worked for rotavaped a t-BuSH containin solution in the lab-the company got complaints from civilians from Another part of the city!You can smell the tiniest concentrations,really,FID and such suck indeed as indicator.But the smell of mercaptans is not that bad (some even don't smell at all!) if you are a bit lab experienced,neither is cadaverin.You somehow can get used to it,at least to a certain degree.I knew one old chemist who actually enjoyed H2S smell...

Myself,I was even a bit dissappointed by Cacodyloxid ...

If you wanna know REAL stench chemicals,try Cyclopentanecarbonicacid and such (you'll get sensitized and hate it from the on even more!),or certain isocyanides like Methyl-isocyanoacetat,they CAN make you puke instantly, believe me!

Maybe GTB won't smell at all,who knows,or will be the next great thing at Givaudan (in tiny concentrations...)...
 
Cacodyl compounds aren't really suitable for producing stenches for amusement purposes, its highly toxic.
 
It is actually usually the disulfide that stinks the most.

Freshly distilled pure mercaptoethanol is essentially odorless. It rapidly oxidizes to the bis(2-hydroxyethyl)disulfide which is responsible for the stench.

I would guess GTB is probably the same - hydrolysis -> oxidation to the disulfide = bad stench.
 
Butyl mercaptan - 1-chlorobutanol & sodium hydrogen sulphide in excess (no more synthesis talk!). I think the vilest smell of all is 3-methylindole - it doesn't get ca;;ed skatole for nothing (conc. essence of shit!). It's what makes tryptamines smell dodgy.

They actually add ethyl mercaptan (ethanethiol)to natural gas so that you can detect leaks (it's in te Guinness book of records as the smelliest substance in the world. You can smell a teaspoonfull if you released it in a covered football stadium! 8o )

I thought dithiothreitol was the smell o skunk. we use it to keep proteins from coagulatin' and i kinda like it. I also like beta-mercaptoethanol as well. mabye i'm weird.
Click to expand...

Never, ever design any room fresheners! =D Yes very weird as mercaptoethanol is vile (6M urea is far better ie. more pleasant for denaturing proteins)

Ps ref for skunk juice here

why do you suspect issues with the krebs cycle?
Click to expand...

Replacing oxygen with sulphur in a lot of things leads to enzyme inhibitors (re@ 2C-T-X & Aleph series effects on MAO), as the sulphur doesn't allow conformational change of enzymes to active form;just being very cautious
 
You must log in or register to reply here.
Top