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Ketamine salts solubility

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(1-Trichloromethyl)ethanol, a derivative of chloral and chlorbutanol, has two stereoisomers and it would be interesting to see if there's a difference in their CNS depressant effects. I think this compound was used as a sedative some 100 years ago or so, but I can't remember what name it was called.

Ethyl 2-butyl ether also has an R and S isomer. Ethyl propenyl ether can exist in cis and trans forms, but there's a risk that it is toxic in some way even though divinyl ether was also used as an anesthetic in the past and the C-C double bonds didn't cause any extra toxicity in that case. A benefit of the double bond there is that it's probably destroyed metabolically much faster than Et2O, so it doesn't make you stink of volatile solvent for the next 24 hours.

Some chiral volatile anesthetics have actually been observed to have a difference in potency between R and S forms, but the subjective psychoactive effects haven't been tested in humans.
 
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(1-Trichloromethyl)ethanol?

I knew that some inhalational anesthetics were chiral but it's interesting that they demonstrate differing MAC numbers. Desflurane, enflurane and methoxyflurane are also chiral. Since the fluorinated ethers display hepatotoxicity, it MAY be a methodology of reducing said toxicity, but I imagine a chiral synthesis would be costly and the difference in MAC numbers isn't vast - or at least not in the examples I know of.
 
(1-Trichloromethyl)ethanol?
Yeah, a typo, should have read 1-(trichloromethyl)ethanol or 1,1,1-trichloro-2-hydroxypropane.

I believe the chloral like compounds and also paraldehyde act by a mechanism similar to ethanol, 2m2b and volatile anesthetics.
 
Clenbuterol. Yes, it was used to dope greyhounds. Apparently their was a famous case in the UK in which every dog was doped with the material apart from a 25/1 outsider. Apparently the bookmakers lost £100,000 which in 1952, was a LOT of money. It was referred to as the 'White City Scandal' but given the limited ability to test for doping, even the police were unable to press charges.

Eddie Chapman (Agent Zigzag) was famously behind it. He got about 60 people to spread bets across the 60 odd bookies. Normally bookmakers will offset their risk among other bookmakers but that night, their was no way to 'lay off' their risk and it bankrupted about 12 of them.

So I think it's reasonable to suggest that it is indeed a CNS depressant... or, at least, it reliably makes greyhounds run significantly more slowly.
 

This was created to be an alternative for chloral hydrate, but it has a half-life of several days due to the difficulty of oxidizing a tertiary alcohol and therefore accumulates in your system. Much like trying to use phenobarbital as a hypnotic.
 
Does it accumulate? I thought it was simply excreted unchanged. While unusual, it's not alone in that. Even things like pregabalin are excreted by the kidneys 97% unchanged.
 
Some article I now can't immediately find had a case report of someone having been in stupor state for more than two weeks after using chlorobutanol excessively and accumulating it in his system. They measured the half life of the drug to be more than a week long, but it's possible that it's less when it's not an overdose situation.
 
I would certainly be interested to read. As with all drug excretion, their is a limiting step. If intake is huge, it could well take a long time for it to be excreted.

I wonder if that rate is faster in dogs? One would imagine that if dozens of them were doped and the effects lasted for weeks, it would be quite evident. Sadly, although the news media of the time reported on the 'White City Scandal', in 1952 I doubt any testing would be possible - especially since the precise nature of the material was unknown.

If memory serves, the bis-sulfonyl class of hypnotic (Sulfonal, Trional, Tetranol) had a very slow onset and very long duration of action. The latter were more lipophilic (so faster acting) and I suspect had a shorter duration of action since those alkyl chains can be more readily oxidized.
 
Well, it's the result of evolution. The human body wouldn't encounter halogenated alcohols in nature so we aren't adapted to deal with it. It's interesting that in certain parts of Africa the water contains large amounts of fluoride salts - far above the amounts added to water in some nations, but the peoples of those regions don't seem to suffer any ill effects. I presume the water has had those fluoride levels for tens of thousands of years and since this all occurs in some fairly remote regions, it's peoples will have been around for a long, long time.

If memory serves, in Australia they use fluoroacetic acid derivatives to selectively poison invasive species because again, native species are adapted to higher levels of such compounds.
 
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