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Diethyl Ether metabolism

Comes out as potentially explosive "elephantine flattus" as well. Quite a problem if you're smoking too...

I could have sworn somewhere that I saw it was hydrated(hydrolyzed? same thing in this situation?) to 2 ethanols, but haven't ever been able to find the source.
 
Diethyl ether (DEE) is primarily converted in humans to acetaldehyde and ethanol through the action of the enzyme CYP450 2E1, which deethylates the DEE, and in the aqueous environment of the blood stream adds water (H+ OH-)to the highly reactive products, oxidizing one molecule into the aldehyde and reducing the other into the alcohol. In addition, CYP450 2B1 and CYP450 2A6 are minor substrates for DEE, and a finally a significant amount of the remaining DEE is exhaled through the lungs unchanged.

MobiusDick
 
fastandbulbous said:
None at all?

Most is removed from the body in the breath though, that's why if someone uses diethyl ether their breath reeks of it for about 2-3 hours afterwards
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makes sense. the boiling point of ether is lower than human body temperature, so it would diffuse readily back into the lungs.
I suppose ethers must be cleaved somehow because the great and very cheap solvent methyl tert butyl ether, MTBE is regarded as a formaldehyde source in vivo and therefore nasty. ETBE would form acetaldehyde instead which is less reactive and nasty.
 
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makes sense. the boiling point of ether is lower than human body temperature, so it would diffuse readily back into the lungs.
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Acetaldehyde has an even lower boiling point ~21 deg C, yet most produced from ethanol metabolism isn't released through the breath is it? I guess it's related to enzyme kinetics involved in formation of acetyl co-enzyme A and further oxidation to acetic acid...
 
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phase_dancer said:
Acetaldehyde has an even lower boiling point ~21 deg C, yet most produced from ethanol metabolism isn't released through the breath is it?
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which is water soluble???
how long before the acetaldehyde is further metabolised??
acetone from isopropanol ingestion is excreted through the breath.
 
phase_dancer said:
Acetaldehyde has an even lower boiling point ~21 deg C, yet most produced from ethanol metabolism isn't released through the breath is it? I guess it's related to enzyme kinetics involved in formation of acetyl co-enzyme A and further oxidation to acetic acid...
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well like mobius said, ether wont go much into the bladder cuz of its nonpolarity, and its vapor pressure is so high it easily goes out the lungs

acetaldehyde has other ways to exit the body or be metabolized right
 
acetaldehyde dehydrogenase converts it to the acetate and it is quickly connected to CoA, forming acetyl CoA, which, unless you are hurting for calories otherwise, ends up going into the synthesis of fatty acids instead of the CAC, and hence, beer belly.

acetaldehyde is a wildly volatile product but there are lots of enzymes around to make use of it so it doesn't diffuse too far most of the time, unlike formaldehyde.
 
vecktor said:
which is water soluble???
how long before the acetaldehyde is further metabolised??
acetone from isopropanol ingestion is excreted through the breath.
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Acetaldehyde is oxidized to acetate; it is the acetaldehyde that causes many of the hangover symptoms associated with ethanol. Antabuse (disulfiram ) blocks oxidation at this step by inhibition of aldehyde dehydrogenase (acetaldehyde builds up and causes dysphoria in most people.)

MobiusDick
 
MobiusDick said:
Acetaldehyde is oxidized to acetate; it is the acetaldehyde that causes many of the hangover symptoms associated with ethanol. Antabuse (disulfiram ) blocks oxidation at this step by inhibition of aldehyde dehydrogenase (acetaldehyde builds up and causes dysphoria in most people.)

MobiusDick
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I didn't see the above post, but the acetyl-CoA component is correct.

MobiusDick
 
I have long suspected that the reason why I don't like drinking alcohol that much is because of acetaldehyde buildup. Is there a way to induce this enzyme?
 
hussness said:
I have long suspected that the reason why I don't like drinking alcohol that much is because of acetaldehyde buildup. Is there a way to induce this enzyme?
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Well, you can increase the regeneration rate of NAD+ with fructose. With larger quantities of alcohol this should increase oxidation rates of both ethanol and acetaldehyde.


vecktor said:
which is water soluble???
how long before the acetaldehyde is further metabolised??
acetone from isopropanol ingestion is excreted through the breath.
Click to expand...

Thanks. Yes, that's what you get for posting without thinking while running out the door. I just dug out a chart on the characteristics of inhalation anaesthetics which gives a theoretical blood:gas partition coefficient of 12.0 for ether. Rates of equilibrium (reflective of lipid solubility) show ~75% of initial alveolar concentration of ether is present after 50 minutes (Rang et al).
 
hussness said:
I have long suspected that the reason why I don't like drinking alcohol that much is because of acetaldehyde buildup. Is there a way to induce this enzyme?
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i had to use yeast alcohol dehydrogenase, which actually takes acetaldehyde to alcohol, (the nomenclature on these things kill me sometimes) for a biochemical assay recently. I was thinking what a great way it would be to beat someone in a drinking contest, ie. add a little bit of your alcohol dehydrogenase (the human variety that makes acetaldehyde) to your beverage, along with NADH, and bam, you're drinking water and most of the aldehyde goes away to the atmosphere, leaving only a slightly fruity taste to your beverage.

so if you're ever in a real life drinking contest or being hazed or whatever...

I doubt you're experiencing a buildup of the aldehyde, unless you are a super skinny person, or you have enzyme (genetic) issues. It might have more to do with a blocking of the positive effects from other drugs you may be on that prevent you from feeling the mellow buzz of a few drinks and only the nasty effects of too much.
 
qwe said:
well like mobius said, ether wont go much into the bladder cuz of its nonpolarity, and its vapor pressure is so high it easily goes out the lungs

acetaldehyde has other ways to exit the body or be metabolized right
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Also note that compounds that are very lipophilic are not able to be removed by the kidneys, and during phase I biotransformation, it is the "job" of some of the CYP450 enzymes and mixed function oxidases to "look" for susceptible sites or groups on lipophilic molecules to oxidize so that phase II molecules like UDPGT (uridine diphosphate-glucuronyltransferase) can add an extremely water soluble molecule like glucuronic acid. This then allows absorbtion at the proximal tubules of the kidney. In the case of ether, no phase II reaction is necessary for urinary excretion.

Also, just because the boiling point of a substance is less than the body does not mean that all of the substance will be excreted in the breath. A significant amount of ether is exhaled. This goes against some of the principles of the anesthesiology of the inhalation agents, many of which have boiling points less than the normal body temperature.

MobiusDick
 
MobiusDick said:
Also, just because the boiling point of a substance is less than the body does not mean that all of the substance will be excreted in the breath. A significant amount of ether is exhaled. This goes against some of the principles of the anesthesiology of the inhalation agents, many of which have boiling points less than the normal body temperature.

MobiusDick
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Can you elaborate on that paragraph at all?
thanks for all the info MobiusDickus
 
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