3 ms·

Methyl groups play heavily in organic chemistry. As an organic compound, it allows otherwise fairly inert metals to be easily absorbed into body tissues and int

Methyl groups play heavily in organic chemistry. As an organic compound, it allows otherwise fairly inert metals to be easily absorbed into body tissues and interfere with the chemical processes therein. To take mercury for example, you can stick your hand in a vat of elemental mercury and be fine. A few drops of dimethylmercury on your skin can be fatal.

Bluestein 2y ago
> A few drops of dimethylmercury on your skin can be fatal. Sounds like a state actor's weapon of choice ...
- deleted 2y ago
  [deleted]
- Ekaros 2y ago
  Only if your agents are ready to commit painful suicide... Dimethylmercury can pass through gloves...
  - Bluestein 2y ago
    Nasty stuff.-
  - btilly 2y ago
    My ex knew the woman who discovered that by accident. https://cen.acs.org/safety/lab-safety/25-years-Karen-Wetterhahn-died-dimethylmercury-poisoning/100/i21 https://cen.acs.org/safety/lab-safety/25-years-Karen-Wetterh... has the story. A few drops on the outside of the latex gloves was enough to kill her. Maybe she would have survived if she'd changed the gloves immediately? Regardless, she didn't do that, and so didn't survive.
    - TeMPOraL 2y ago
      Worth noting is that it took almost a year for that exposure to kill her, and half that before they even realized something happened that day. From the article: On Aug. 14, 1996, Karen Wetterhahn was exposed to dimethylmercury while making a standard for nuclear magnetic resonance studies related to DNA damage. (...) It was 5 full months before the consequences of that spill became apparent. Wetterhahn developed stomach problems, then began having trouble walking and speaking clearly. A friend, nurse Cathy Johnson, recalls a lunch date in early January 1997 when she urged Wetterhahn to see a doctor. Within a few weeks, Wetterhahn was in a coma. On June 8, 1997, she died. She was 48 years old. I always imagined all such nasty chemicals kill you in a matter of minutes to hours, days at the most. I never imagined they could turn you into a walking corpse. It's up there with Rabies.
    - Anotheroneagain 2y ago
      She would be fine if she ate brazil nuts. Mercury only hurts you by depleting selenium.
      - btilly 2y ago
        My first reaction to this was to get angry. If there was such a simple solution, wouldn't she still be alive? But, luckily, I hit Google first. https://edis.ifas.ufl.edu/publication/FS437 https://edis.ifas.ufl.edu/publication/FS437 showed that selenium does protect against mercury. Even dimethylmercury. And https://www.webmd.com/diet/health-benefits-brazil-nuts https://www.webmd.com/diet/health-benefits-brazil-nuts shows that Brazil nuts are an excellent way to get selenium. In fact it is comparable to a supplement, and a sustained diet of 3 nuts per day is already in the toxic range. I had no idea. So it appears to be correct, there's a good chance that eating Brazil nuts could have saved her life!
        Bluestein 2y ago
        That's incredible.- (Was going to say it was "nuts" but abstained :)
- astrange 2y ago
  It's long acting and very obvious. The famous case of someone dying from a two-drop spill took a year after exposure IIRC.
User23 2y ago
Methylating is like acetylating. It's kind of a go-to thing to try in medicinal chemistry.
- Bluestein 2y ago
  > kind of a go-to thing to try in medicinal chemistry. May I ask why?
  - zdragnar 2y ago
    Acetyl groups are made of carbonyl and methyl groups. To improve bioavailability of a compound, attempting to add on either a methyl or acetyl group may help. Depending on the compound, skipping this step may cause the compound to be relatively inert. This is why, for example, calcium carbonate is a poor source of calcium as a nutritional supplement, but calcium citrate is readily absorbed- the citrate itself is an organic compound, so the body more readily takes it up out of the digestive system and the calcium can be used.
    - andrewflnr 2y ago
      Maybe a dumb question, but from this should I conclude that calcium citrate does not fully dissociate in solution the way e.g. NaCl does? Because otherwise how would it matter what the counter-ion was for the calcium? Then again I've always been hazy on why ions seem to behave differently depending on what they originally dissolve from, so if there's something weird going on there I'd love to know about it.
      - LM358 2y ago
        Chelation is the keyword you're looking for: https://en.wikipedia.org/wiki/Chelation https://en.wikipedia.org/wiki/Chelation
      - zdragnar 2y ago
        Calcium carbonate is entirely insoluble. Calcium citrate is only slightly soluble in water. Calcium carbonate will react with stomach acid to form calcium chloride (along with CO2 and water). When given intravenously, calcium chloride is perfectly bioavailable. However, within the small intestines, it has very poor uptake, both through the intestines' active and passive mechanisms. Any remaining calcium carbonate has no uptake at all.

Bluestein 2y ago

> A few drops of dimethylmercury on your skin can be fatal. Sounds like a state actor's weapon of choice ...

deleted 2y ago
[deleted]
Ekaros 2y ago
Only if your agents are ready to commit painful suicide... Dimethylmercury can pass through gloves...
- Bluestein 2y ago
  Nasty stuff.-
- btilly 2y ago
  My ex knew the woman who discovered that by accident. https://cen.acs.org/safety/lab-safety/25-years-Karen-Wetterhahn-died-dimethylmercury-poisoning/100/i21 https://cen.acs.org/safety/lab-safety/25-years-Karen-Wetterh... has the story. A few drops on the outside of the latex gloves was enough to kill her. Maybe she would have survived if she'd changed the gloves immediately? Regardless, she didn't do that, and so didn't survive.
  - TeMPOraL 2y ago
    Worth noting is that it took almost a year for that exposure to kill her, and half that before they even realized something happened that day. From the article: On Aug. 14, 1996, Karen Wetterhahn was exposed to dimethylmercury while making a standard for nuclear magnetic resonance studies related to DNA damage. (...) It was 5 full months before the consequences of that spill became apparent. Wetterhahn developed stomach problems, then began having trouble walking and speaking clearly. A friend, nurse Cathy Johnson, recalls a lunch date in early January 1997 when she urged Wetterhahn to see a doctor. Within a few weeks, Wetterhahn was in a coma. On June 8, 1997, she died. She was 48 years old. I always imagined all such nasty chemicals kill you in a matter of minutes to hours, days at the most. I never imagined they could turn you into a walking corpse. It's up there with Rabies.
  - Anotheroneagain 2y ago
    She would be fine if she ate brazil nuts. Mercury only hurts you by depleting selenium.
    - btilly 2y ago
      My first reaction to this was to get angry. If there was such a simple solution, wouldn't she still be alive? But, luckily, I hit Google first. https://edis.ifas.ufl.edu/publication/FS437 https://edis.ifas.ufl.edu/publication/FS437 showed that selenium does protect against mercury. Even dimethylmercury. And https://www.webmd.com/diet/health-benefits-brazil-nuts https://www.webmd.com/diet/health-benefits-brazil-nuts shows that Brazil nuts are an excellent way to get selenium. In fact it is comparable to a supplement, and a sustained diet of 3 nuts per day is already in the toxic range. I had no idea. So it appears to be correct, there's a good chance that eating Brazil nuts could have saved her life!
      - Bluestein 2y ago
        That's incredible.- (Was going to say it was "nuts" but abstained :)
astrange 2y ago
It's long acting and very obvious. The famous case of someone dying from a two-drop spill took a year after exposure IIRC.

User23 2y ago

Methylating is like acetylating. It's kind of a go-to thing to try in medicinal chemistry.

Bluestein 2y ago
> kind of a go-to thing to try in medicinal chemistry. May I ask why?
- zdragnar 2y ago
  Acetyl groups are made of carbonyl and methyl groups. To improve bioavailability of a compound, attempting to add on either a methyl or acetyl group may help. Depending on the compound, skipping this step may cause the compound to be relatively inert. This is why, for example, calcium carbonate is a poor source of calcium as a nutritional supplement, but calcium citrate is readily absorbed- the citrate itself is an organic compound, so the body more readily takes it up out of the digestive system and the calcium can be used.
  - andrewflnr 2y ago
    Maybe a dumb question, but from this should I conclude that calcium citrate does not fully dissociate in solution the way e.g. NaCl does? Because otherwise how would it matter what the counter-ion was for the calcium? Then again I've always been hazy on why ions seem to behave differently depending on what they originally dissolve from, so if there's something weird going on there I'd love to know about it.
    - LM358 2y ago
      Chelation is the keyword you're looking for: https://en.wikipedia.org/wiki/Chelation https://en.wikipedia.org/wiki/Chelation
    - zdragnar 2y ago
      Calcium carbonate is entirely insoluble. Calcium citrate is only slightly soluble in water. Calcium carbonate will react with stomach acid to form calcium chloride (along with CO2 and water). When given intravenously, calcium chloride is perfectly bioavailable. However, within the small intestines, it has very poor uptake, both through the intestines' active and passive mechanisms. Any remaining calcium carbonate has no uptake at all.