Misc Different ethers

[pino]

I was reading about higher chain an branched alcohols and read that many have recreational effects and have a more favorable profile than ethanol.

I was interested if different ethers than diethyl ether have more desirable effects. Such as less smelly, or better safety ratio, not inflammable or less irritant.

I already found out these were used in medicine:

• diethyl ether
• vinyl ether

Where vinyl ether is possible hepatoxic. I didn't include isoflurane and others, because they seem to have the same problems.

There are more potential candidates:

• demethyl ether - which is a gas, so not ideal, but narcotic
• dipropyl ether
• ethyl vinyl ether
• iso-propenyl ether

The last two I found here:
http://ebm.sagepub.com/content/28/2/151.extract

Are there more ethers? And are there dangers like with alcohols, such as methanol which metabolizes to formic acid?

 

[sekio]

"Ether" is just a term for a molecule with the carbon-oxygen-carbon linkage in it. Even drugs like codeine are technically "ethers"! So there are a lot of possible ones...

Most of those candidates are inferior to diethyl ether for narcotic usage, because of diffculty in handling (lower boiling points) or, occasionally, toxicity concerns. Divinyl ether decomposes to acetaldehyde (the compound responsible for hangovers). Most ethers, but especially di-isopropyl ether will also form ether peroxides if stored for too long, which are contact explosives (!). This is made even worse by the very high vapour pressure of the lower ethers (they love to evaporate), and immense flammability.

Simple ethers like diethyl ether are not metabolised extensively; they leave the body via the lungs and skin (especially diethyl ether, which boils below human body temperature).

The new-generation halogenated ethers like isoflurane, sevofulrane, desflurane are popular because they have low to moderate toxicity, rapid removal from the body, and most importantly they are nonflammable.

Dibutyl ether is also known as a solvent, but it is not used as an inhalant. Ethyl ether and the halogenated ethers are pretty much the only game in town.

 

[pino]

Ah yes, I meant simple ethers. I was hoping there was some non smelly one, which won't explode or engulf you in flames, but I checked a couple of them and they all form peroxides and are flammable. Isoflurane and those others are probably out of reach for most of us.

I did some research, which was pretty random, but still interesting.

I found this document, which states that most simple ethers causes anaesthesia:

http://ilocis.org/documents/chpt104e.htm

The principal physiological effect of the unhalogenated ethers shown in the accompanying tables is anaesthesia. At high exposures, such as repeated exposures in excess of 400 ppm to ethyl ether, nasal irritation, loss of appetite, headache, dizziness and excitation, followed by sleepiness may result. Repeated contact with the skin may cause it to become dry and cracked. Following long-term exposures, it has been reported that mental disorders may occur.

It regards halogenated ethers as an hazard, because of carcinogenicity

Unless there is evidence to the contrary, it is prudent to treat all halogenated ethers prudently and to consider all alkylating agents potential carcinogens unless there is evidence to the contrary. The glycidyl ethers are considered in the family entitled “Epoxy compounds”.

Methyl tert-butyl ether works also as an anaesthesic, but is also suspected to cause renal failure and was also tried as treatment for gall stones .
http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5847

It is metabolised to tert-butyl alcohol and 2-methyl-1,2-propanediol and 2-hydroxyisobutyric acid:
www.who.int/water_sanitation_health/dwq/chemicals/MTBE200605.pdf

Tert-butyl alcohol seems to be under suspicion to cause kidney cancer. Would tert-amyl alcohol (2-methyl-2-butanol) also cause that? I read some people are enjoying that lately.

But I couldn't find any research about other simple ethers used in anaesthesia than diethyl-ether or divinyl ether -which isn't used very extensively-, which probably means diethyl ether is already good enough.

Thanks for your help.