Pharmacology Of Haloalkanes

[PerpetualAnhedonic]

Greetings,
I wonder if any of the best minds of Bluelight might be able to answer this:

I'm interested in learning the pharmacological points of the most common Haloalkanes.
More specifically, it is the pharmacodynamics that I am curious about. Though pharmacokinetics and any other pieces of info are also absolutely welcome and encouraged.

I have done some searching across several different sources, but absolutely nothing to be found....perhaps someone has better sources of information or even personal knowledge on this specifically than I do.

It is a very curious class of substances, though I have absolutely no interest in ever consuming them.
I inquire purely for curiousity's sake and educational purposes.
It's of no real concern to me if there aren't answers available, but it would be real cool if anyone knows and can assist me in satisfying/quenching my thirst for random, useless knowledge lol.
I thank you all in advance.

Oh, plus, it occurs to me that there ARE some people that do enjoy consuming these substances, so it may also be of interest to them.

-Perpetual Anhedonic

 

[sekio]

Presumably the haloalkanes act as halfway-points between the lower alkyl alcohols and the hydrocarbons. See also: halogenated ethers like isoflurane, sevoflurane, desflurane. Potency correlates with logP, the octanol/water partition coefficient.

I know that ethyl chloride is abused in Brazil as "lanca-perfume", logically it should act as an intoxicant not that dissimilar to a cross between ether/chloroform and ethyl alcohol.

However, if you know your chemistry, you'll figure out that everything save fluoroalkanes are too reactive to be good drugs; generally haloalkanes are alkylating agents under the right conditions and as a result can damage DNA and protiens. And fluoroalkanes of the wrong chain length/substitution pattern (even number of carbons) will get chewed up to fluoroacetic acid, a known citric acid cycle toxin.

 

[Jabberwocky]

There is one haloalkane anesthetic molecule containing bromine, and as far as I know, its the only one:

https://en.wikipedia.org/wiki/Halothane

 

[Solipsis]

Well the only one being really used, there is also roflurane and teflurane.

What are some rules.. terminal haloalkyl groups (not F) are supposedly a problem because of alkylation, and fluoroalkyl groups of even number of carbons will get cleaved to fluoroacetic acid (not sure what the toxic levels are?). But that is for aliphatic functions, I imagine it can get complicated with more branched structures or does this rule only hold for unbranched aliphatic chains?

But anaesthetics like those are they really so compelling? If you have to, why not ether.. But I see you have no interest in consuming..

Personally I am theoretically interested in things like chlorobutanol. And I have to wonder about chloral hydrate with other halogens..

Apparently as expected bromal hydrate does exist - still have to check on I and F analogues..

Snippets like these are pretty interesting IMO:

1. When bromal hydrate is administered to dogs, neither tribromoethanol nor tribromoacetic acid can be demonstrated in the plasma.

2. Under physiological conditions in vitro bromal hydrate reacts rapidly with serum albumin and with cysteine, the latter substance being oxidized to cystine.

3. It is suggested that the "positive halogen" properties of bromal hydrate are responsible for its high toxicity.

http://jpet.aspetjournals.org/content/94/4/401

 

[Pomzazed]

Fluoroacetate is potent rat poison (and other mammals too)

 

[Solipsis]

Even so, it's fucking tedious trying to administer gases to the rats to make fluoroacetate in vivo, anaesthetic or not...

 

[sekio]

Any even-chain N-fluoroalkane will metabolize to fluoroacetate, it's also sold as the sodium salt of fluoroacetate as "1080", a pesticide banned in many areas.