4 ms·

Are dimethyls with wrong sort of metals all really nasty stuff? Just wondering as dimethylmercury is also nasty stuff.

by Ekaros 2y ago

ta988 2y ago
It seem so, but it is a bit more complex in reality https://pubs.acs.org/doi/10.1021/acs.organomet.7b00605 https://pubs.acs.org/doi/10.1021/acs.organomet.7b00605
zdragnar 2y ago
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!
  - 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.
monktastic1 2y ago
Indeed. I am reminded of the sad and horrible story of https://en.m.wikipedia.org/wiki/Karen_Wetterhahn https://en.m.wikipedia.org/wiki/Karen_Wetterhahn
culi 2y ago
Yeah I find this interesting too. A methyl group separates the street drug meth from the prescribed drug amphetamine. The main role that methyl group plays is the way it crosses the blood brain barrier. During the process of crossing the methyl group is lost. Which means with both meth and regular amphetamine the chemical that reaches your brain is the same. I wonder if the dimethyl plays the same role here. Allowing it to cross the blood brain barrier faster
- scotteric 2y ago
  As an aside, methamphetamine is also a prescribed drug in the US, called Desoxyn.
  - culi 2y ago
    Fascinating. In ww2 the Allies used methamphetamine heavily to keep their soldiers awake and able to fight. When those soldiers got back they missed the drug and for a while it was something you could just buy at any old drug store
    - lazide 2y ago
      The Germans did it first and ‘more better’. It was one of the forces behind the blitzkreig. Their brand name was ‘Pervitin’. [https://en.m.wikipedia.org/wiki/Drug_policy_of_Nazi_Germany#:~:text=Nazi%20military%20doctor%20Otto%20Friedrich,speed%20of%20Germany's%20initial%20blitzkrieg https://en.m.wikipedia.org/wiki/Drug_policy_of_Nazi_Germany#....] “Drug use in the German military during World War II was actively encouraged and widespread, especially during the war's later stages as the Wehrmacht became depleted and increasingly dependent on youth as opposed to experience.[4]” A lot of things make more sense about WW2 if you realize most major combatants were on heavy duty drugs during large portions of it.
abound 2y ago
From the article: > The general rule is, if you're looking for the worst organic derivatives of any metal, you should hop right on down to the methyl compounds.

Are dimethyls with wrong sort of metals all really nasty stuff? Just wondering as dimethylmercury is also nasty stuff.

by Ekaros 2y ago

Are dimethyls with wrong sort of metals all really nasty stuff? Just wondering as dimethylmercury is also nasty stuff.

It seem so, but it is a bit more complex in reality https://pubs.acs.org/doi/10.1021/acs.organomet.7b00605 https://pubs.acs.org/doi/10.1021/acs.organomet.7b00605

zdragnar 2y ago

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!
- 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.

monktastic1 2y ago

Indeed. I am reminded of the sad and horrible story of https://en.m.wikipedia.org/wiki/Karen_Wetterhahn https://en.m.wikipedia.org/wiki/Karen_Wetterhahn

culi 2y ago

Yeah I find this interesting too. A methyl group separates the street drug meth from the prescribed drug amphetamine. The main role that methyl group plays is the way it crosses the blood brain barrier. During the process of crossing the methyl group is lost. Which means with both meth and regular amphetamine the chemical that reaches your brain is the same. I wonder if the dimethyl plays the same role here. Allowing it to cross the blood brain barrier faster

scotteric 2y ago
As an aside, methamphetamine is also a prescribed drug in the US, called Desoxyn.
- culi 2y ago
  Fascinating. In ww2 the Allies used methamphetamine heavily to keep their soldiers awake and able to fight. When those soldiers got back they missed the drug and for a while it was something you could just buy at any old drug store
  - lazide 2y ago
    The Germans did it first and ‘more better’. It was one of the forces behind the blitzkreig. Their brand name was ‘Pervitin’. [https://en.m.wikipedia.org/wiki/Drug_policy_of_Nazi_Germany#:~:text=Nazi%20military%20doctor%20Otto%20Friedrich,speed%20of%20Germany's%20initial%20blitzkrieg https://en.m.wikipedia.org/wiki/Drug_policy_of_Nazi_Germany#....] “Drug use in the German military during World War II was actively encouraged and widespread, especially during the war's later stages as the Wehrmacht became depleted and increasingly dependent on youth as opposed to experience.[4]” A lot of things make more sense about WW2 if you realize most major combatants were on heavy duty drugs during large portions of it.

abound 2y ago

From the article: > The general rule is, if you're looking for the worst organic derivatives of any metal, you should hop right on down to the methyl compounds.