Ketones and aldehyde dehydrogenase, chlorbutol

[Limpet_Chicken]

In short,how does chlorobutanol metabolize? does the resulting metabolite get processed by aldehyde dehydrogenase And most importantly, can one take chlorobutanol if on an aldehyde dehydrogenase inhibitor such as the nitroimidazole antibiotics (E.g metro)?

Going to need something for seizure prophylaxis, and wondering if I can safely use chlorbutol, because it is quick and simple to prepare, to keep me on my feet whilst a haloform rxn goes to completion and the resulting chloroform is condensed w. acetone to give chlorbutol? basically to give me time for the simple, but more demanding chlormethiazole synth, because the extraction of these particular thiamine tablets is a nuisance.

 

[sekio]

You know, I think chlorobutanol is best relegated to use as a preservative. Easy as it is to make, I've never heard anything good about it.
I suspect it works as a prodrug to chloral, when all is said and done, so in a real emergency maybe it's useful, but seriously, consider phenobarbital a better alternative, and that's saying a lot.

Please, try not to poison yourself too badly - I know you're dealing with an infection and what not but you should be careful

 

[Pomzazed]

I cant remember the study, but I've read before that chlorbutol exhibits its effect without metabolizing to chloral hydrate or chloral

 

[Synaps3]

It is metabolized to a diol and/or glucuronide (VERY slowly). 10 day half-life. Not worth it.

I addition, the glucuronidation process is shown to inhibit itself after a certain level. So if you take too much the half-life will increase more than 10 days.

https://www.ncbi.nlm.nih.gov/pubmed/7159691

does the resulting metabolite get processed by aldehyde dehydrogenase

It is a tertiary alcohol, so there are no aldehydes involved like there are for chloral hydrate. It does not get converted to chloral hydrate btw despite the similar structure.

 

[sekio]

Its half-life in vitro is 37 days at pH 7.4. The long terminal half-life of chlorbutol makes it unsuitable as a sedative drug

yeah no fucking kidding. Similar pharmacology to bromide then. This actually makes phenobarbital look like baby aspirin.

 

[Limpet_Chicken]

Only reason that it was potentially going to be used was as a one-time dose of GABAergic, I'd lost a couple of my chloremethiazole caps, recovered them later, after they rolled under the sofa. But in the meantime they had kinda deflated, much of the volatile freebase inside the buggers was absent.

Meant I needed an emergency anticonvulsant. Wish I'd have thought of bromide actually haha. As it was, had to swallow a bottle of valerian extract tablets whilst in the middle of a myoclonic seizure, before it turned to totally atonic and I could do nothing about it at al. Not very fun. Worked though once they kick in.

Had to come up with an improvization and quickly. Didn't make the chlorbutol as it happens, since I didn't find out about replies to this post until just now.

 

[Limpet_Chicken]

Also I have a thought. Probably infinitely more useful than for in vivo purposes.

Could this be used as a substitute for chloral hydrate when making Melzer's reagent? I suspect so, but am not 100% sure whether the aldehyde portion of the chloral molecule takes part in the color reaction of Melzer's

 

[sekio]

I doubt it, the chloral hydrate there is used for its optical properties.

 

[Limpet_Chicken]

Yeah, its the clearing agent is it not?