Metabolization of 2-Methyl-2-butanol

[kakti]

There's a thread over on OD about 2-Methyl-2-butanol, which was apparently used in the early 20th century and possibly earlier in medical settings, with comparisons to other depressants of the day such as chloral hydrate.

Can anyone speculate as to what, if any, toxic metabolites would be produced from consuming this?

[dread]

It is active in doses of 2,000-4,000 mg, making it some 20 times more potent than regular ethanol.

http://en.wikipedia.org/wiki/2-Methyl-2-butanol

Yeah, sounds like fun...

[LabRatNW]

Maybe a good substitute for GHB.

[Pomzazed]

please check this.
Collins, A., Sumner, S., Borghoff, S., and Medinsky, M. (1999). A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures. Toxicol. Sci. 49, 15–28.
http://toxsci.oxfordjournals.org/cgi...nt/49/1/15.pdf

It's metabolized by 1) P-450 oxidation to 2,3-dihydroxy-2-methylbutane and 2)gluconoride conjugation.

[mutter]
meh, at first a search with 2-methyl-2-butanol yields nothing except saying it's a metabolite of isopentane, and once i put in the trivail name tert-amyl alcohol the info suddenly pops out a bunch!
[/mutter]

I'll add an image to make reading in the thread easier:

[flacky]

(...)

[kakti]

Thank you pomzazed I appreciate that file, and you're right tert-amyl alcohol produces a ton more results. Now, can anyone speculate as to whether either of those metabolites, or the glucoronide conjugate of 2,3-dihydroxy-2-methyl-butane may be harmful? This kinda stuff isn't really my forte

[vecktor]

Is this stuff in fusel oil? the hangover inducing toxics in fermented beverages?

[kakti]

I think you're referring to isobutyl carbinol, which is a different isomer of amyl alcohol produced in ciders, ales, whiskeys, etc.

http://en.wikipedia.org/wiki/Amyl_alcohol

[Hammilton]

tert-Amyl alcohol is also produced as a by product of fermentation. Not sure to what level, though.

Would be hard to schedule something like this, though.

[vecktor]

IIRC one of the earliest SAR investigations was on the narcotic effects of alcohols, from methanol to longchainahols, there was a nice correlation between lipophilicity/chain length and activity up to a maximum after whch the alcohols became less active (due to poor availability I guess)

nothing wrong with ethanol IMHO.
the higher alcohols smell bad, and as the vapour is going to be excreted on the breath you might get a narcotic effect with the similutanous side effect of no one wanting to be in the same room.
at least it doesn't oxidise to a carboxylic acid, as higher carboxylic acids are truly repulsive if they have any volatility from butanoic onwards the smell gets worse and worse.
looks like an ideal drug for antisocial people or those who only have friends with anosmia.

A quick look at the analysis of fusel oils does seem that the tert alcohols are only very minor components of fusel oils most are the primary and secondary alcohols, which makes sense because they are amino acid derived, (deamination and decarboxylation) phenylalanine give phenylethanol, etc etc

wonder if yeast fermentation of Glutamic gives anything interesting it would if only the carboxylic acid next to the amino is decarboxylated???

[Tryptamine*Dreamer]

The smell of this chemical isn't bad, IMO. It does have a somewhat strong smell if you stick your nose pretty close to the bottle, but the smell is a sort of mint or menthol like smell.

I would guess that many people would mistake the smell on someones breath for something minty. I however can't say what it smells like on a person's breath.

I just don't think the smell is unpleasant. I guess that is a matter of opinion though.

please check this.
Collins, A., Sumner, S., Borghoff, S., and Medinsky, M. (1999). A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures. Toxicol. Sci. 49, 15–28.
http://toxsci.oxfordjournals.org/cgi...nt/49/1/15.pdf

It's metabolized by 1) P-450 oxidation to 2,3-dihydroxy-2-methylbutane and 2)gluconoride conjugation.

[mutter]
meh, at first a search with 2-methyl-2-butanol yields nothing except saying it's a metabolite of isopentane, and once i put in the trivail name tert-amyl alcohol the info suddenly pops out a bunch!
[/mutter]

I'll add an image to make reading in the thread easier:

Thank you for this information. I was wondering what the metabolic products were. I'll have to see if I can find anything on the toxicity of these chemicals. This was definitely some information I was wanting.

[kakti]

Thank you pomzazed I appreciate that file, and you're right tert-amyl alcohol produces a ton more results. Now, can anyone speculate as to whether either of those metabolites, or the glucoronide conjugate of 2,3-dihydroxy-2-methyl-butane may be harmful? This kinda stuff isn't really my forte

Just wanted to bump this. Can anyone speculate what the toxicity of any of these would be

2,3 dihydroxy-2-methylbutane
2-methyl-2butyl gluconoride
gluconoride conjugate of 2,3-dihydroxy-2-methyl-butane (what would the IUPAC name of this be?)

Also, any speculation on what further metabolites could be produced?

According to This thread beenhead has suggested "Chemicals with similar structure are known to be carcinogenic, including ethanol" and there was also something about it containing strain alkyl chains and those generally not being good for human consumption.

Thanks in advance

[ballstoyousir!]

So it doesn't seem to produce E Glucuronide or E Sulf. through glucuronidation, interesting.