Friday, January 15, 2016

The Sleepy Lab Worker urban legend (needs debunking)

This Reddit thread about old synthesis stories (one being the classic "the dust in the lab was the actual catalyst for the reaction" tale) brought to mind a story I once heard. I doubt if it is actually true. This was told to me over a decade ago, and so the story is quite hazy and I may have added some details:
There was a new graduate student or postdoc who was new to a total synthesis lab that was working on some sort of marine natural product. The student seemed like a reasonable sort and dove into their new project (which may have been a project they inherited from someone else?) with gusto. After a few weeks, though, they started not showing up to work for a week at a time, and acting as if nothing had happened.  
After a few episodes of absenteeism, the lab got together and figured out that the new lab worker had accidentally ingested some of the compound they were working on, and it was having the effect of making them sleep for a week at a time at home, and then waking up as if nothing had happened. 
So a couple of caveats:
  1. Obviously, 99+% of this story is probably false, either through retelling, or CJ's mind adding details.
  2. This could have been one of CJ's coworkers telling chemistry urban legends.
  3. or, this story has a tiny seed of truth in it somewhere, from the many years of stories from chemical academia
So which one is it, readers? Have a great weekend. 

15 comments:

  1. No takers, huh?

    Well, for what it's worth, your story is bullshit. Nobody can not notice they were asleep for a week at a time, as they would wake up really hungry, dehydrated, and surrounded by a pool of their own urine (or more likely crusty bedsheets reeking of urea) and/or other nasty things. Plus they would probably notice the date change at some point. Maybe when reading the newspaper or seeing it was an unusual day of the week, unless they slept for exactly seven days. Also, it's unlikely that the boss would not want to kill them if they were missing for a week from a typical organic synthesis lab.

    There was a comment on 'In the Pipeline' a few years ago, maybe even more than five years ago that I can't find right now. It was one of those 'culture in total synthesis labs' posts or 'does total synthesis still have a useful purpose?'. The commenter said that the work environment in their lab was toxic and nobody talked to each other and they just came in and did columns for hours on end. They also said that they were working on some marine toxin, and one day, maybe they had a hole in the glove when they were isolating an intermediate, they fell asleep at the lab bench for ten hours. The commenter was very sure it was due to this intermediate. He/she was very angry at the labmates and angrily confronted them as to why they didn't do anything and were just working around them, and they just said "well, I thought you were tired so you were just resting (for ten hours)".

    Maybe this is where it comes from?

    ReplyDelete
  2. Is there a natural product known that has crazy sedative/memory loss effects?

    This sounds like one of those urban legends serving as a parable/social commentary - like when the office worker died at his desk and nobody noticed for 2 weeks, etc. Something about grad school's culture of crazy work hours and how you wouldn't notice if your colleague was seriously ill, poisoned or just acting like a typical student...

    ReplyDelete
    Replies
    1. St Andrews Lynx--due to the wiring in the brain, there's substantial crossover between sedation and memory loss. Positive modulators of GABAa receptors will generally give you both. You can get some degree of both with ethanol; I think valerian is also reported to do both.

      Delete
  3. It’s possible this story was inspired by the disaster in Saul Weinstein’s lab with 7-anti-bromonorbornene? The similarity in the two stories is that after the two chemists were exposed, they stopped coming into work. This was noted but again without alarm. Tragically the Weinstein story did not have such a benign ending. I wonder If it is not something about UCLA?

    ReplyDelete
    Replies
    1. Do you have a link? I'm not familiar with the Winstein story.

      Delete
  4. I've only read the published account (JACS 83(1961), p. 1516). Two students died and one was injured (minor) while working on norbornadiene bromination in Winstein's lab, presumably via a hydrolysis product. There are some Turkish daredevils who worked on the same stuff: JOC 61(1996), pp. 8297-8300.

    ReplyDelete
    Replies
    1. Surprised I had not heard about this before, and also how casual it all seems to be with these two papers. Single author JACS, because the other authors died doing the work?

      Delete
    2. PSA: this is probably not a good, legal way to reduce the number of coauthors on a paper.

      Delete
    3. Physical organic chemistry, the nonclassical years: taking intragroup competition to new lows? On one hand, that would have cut down on the joy of lab, but on the other hand, I'm sure the survivors would be welcome to work for the DOD or the CIA (pre-Church).

      Delete
    4. Thanks for the reference. I'm just wondering how something with this structure could kill someone? Some kind of inhibition of a crucial enzyme? I know, for example, how fluorophosphonates kill (blockage of acetylcholine esterase). But norborane derivatives? I'm a dumb biochemist, BTW.

      Delete
    5. I don't think the Winstein group had any idea, and they were working with them a lot. I think the second olefin contributes to making the norbornene bromide reactive (it may act as a assistant, in the same way that the sulfur of mustard gas (ClCH2CH2)2S helps push out the chlorides [via a three-membered sulfonium salt (CH2CH2S+)CH2CH2Cl Cl-]), but again, they were working with these compounds, and didn't anticipate that kind of reactivity. They don't seem like they would be that volatile, but maybe something with the physical state enables absorption much more effectively than related structures. Lung damage implies breathing as the method of administration, but I guess I assumed the lung damage was progressive and not the 12-24h type of phosgene/Magic Methyl/dimethyl sulfate/methyl fluorosulfonate or triflate poisoning from hydrolysis, lung damage and drowning. I don't know why (maybe if it were that quick, they'd have known what the cause was before the second person died).

      We learned about it when going through safety stuff for undergrad research, I think, the lesson being that if you don't know what the compound can do, assume that it could kill you, because we don't know everything, and sometimes it can.

      Delete
    6. Yes, I heard about this in Grad school as well. The Dept Chair wryly told us that Winstein suspected there was something dangerous about a compound they were working with after a 2nd grad student died on the same project. I always wondered what molecules they were working on, so thanks again for the ref.

      Delete
    7. The folklore is that people did know they were missing but it was a more laid back time (and near the beach) so no one worried about it. Winstein did contact both separately but because they both had slurred speech, Winstein concluded they both had been drinking.
      The syn-isomer is commercially available and is a well behaved secondary bromide. I have always felt this was the conclusive evidence which convinced everyone of the reality of π-bond participation in Sn2 reactions. The accident was widely known and more compelling than all of those rate constants. It took longer for the reality of σ-bond participation to be accepted.

      Delete
  5. On the subject of dust-is-the-catalyst tales, I'm fond of this one - reactions run with older syringe needles gave better yields, eventually leading to Cu being identified as a catalyst: http://dx.doi.org/10.1016/S0040-4039(00)78231-1

    ReplyDelete
  6. Wow. The summer prior to starting MSc work at Michigan State U, I worked for a faculty member who (I think) was doing contract synthesis. Project #2 was to produce perchlorodibenzodioxane from chlorination of dibenzodioxane. Fortunately, a cousin of mine was a health activist with the local union. He brought over a lot of literature and told me that I should not, under any circumstances, continue on that project. OK, 2,3,7,8-TCDE is toxic because the alpha positions have H, and the beta ones were chlorinated, but still. That project was then given to a PhD student on his 6th year. He apparently poisoned himself with chlorine gas.

    There are more interesting stories available, also concerning project #1, the grad student and the professor (I didn't work for him on my thesis).

    ReplyDelete