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Derek Lowe The 2002 Model

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Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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September 18, 2005

A Sensitive Guy

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Posted by Derek

Well, my poison ivy has abated, which is good news on several fronts. Besides the obvious one, it also means that I wasn't exhibiting a reaction to a particular reagent that I was using a lot of at the same time, an aryl isocyanate. Those are reactive little creatures, and they're known to bother some people. I'm very glad it wasn't an immune response to it, because (a) I still need to do reactions with the stuff and (b) I've never become sensitized to any lab reagent, and I'd hate to start now.

Probably the closest I've ever come was back in graduate school. I had a long synthesis that started with a tosylation reaction of a protected sugar. For the non-chemists, that's a way to convert an alcohol group into something much more reactive, and it uses a reagent called para-toluenesulfonyl chloride. Since even organic chemists don't like wandering around all day saying mouthfuls like that, it's abbreviated in the lingo as tosyl chloride.

And it reeks. It has a peculiar nasty sweetish smell, penetrating and hard to get out of your nose, particularly when you're crystallizing a kilo of the stuff. As I wrote in passing here, it was very easy to get fed up with that step. It got to the point that the smell gave me an instant headache, right up between the eyes. That's no longer the case, but I don't enjoy working with it to this day.

The other reagent that I couldn't take for a while isn't known as a sensitizer. When I was a teaching assistant during my first year, one of the sophomore organic labs was the preparation of phenyl Grignard reagent. They did that in good ol' diethyl ether, probably because it's cheap as dirt. Never mind that it's one of the most volatile (and flammable) solvents you can possibly use, and never mind that there were about two fume hoods for thirty students, so everyone just banged away out on the benchtops. The air practically got wavery with ether fumes, and why the whole place didn't go up is a real stumper.

I was teaching three lab sections a week that term, as fate would have it. After the first one, I had a headache from all that damned ether. That kicked in immediately during the second lab section the next afternoon, and I was really feeling awful by the end. Came the third section, and when the first gust of ether hit me I nearly hurled my lunch into the nearest sink. I just couldn't take it. I spent the whole afternoon teaching from out in the hall, asking people to hold up their flasks while I squinted at them and yelled encouraging advice. I only came into the lab to cruise from one side of the room to the other while holding my breath.

No, I couldn't take the smell of ether for a while after that one (it doesn't bother me now at all). But then, I spent my first week as an summer undergrad in Dale Boger's group (1982) surviving mostly on the contents of a jar of peanut butter, and it was a year or so before I could face that again, too. Academic chemistry does toughen you up.

Comments (6) + TrackBacks (0) | Category: Life in the Drug Labs


1. Jason Rush on September 18, 2005 11:00 PM writes...

Diethyl ether is innocuous enough that you can drink it in quantity. It has been popular as an intoxicant in the past, particularly in Russia and Ireland. Apparently it makes you smell like ether.

"A surgeon visiting Draperstown in 1878 remarked that the main street smelled like his surgery, where ether was used as an anesthetic. Old ether topers, he added, could finish off a three-ounce wineglassful at a single swig, without even water for a chaser."

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2. Chris Hoess on September 19, 2005 12:49 AM writes...

I've had an experience sort of like that. In my first undergraduate lab, we used to do these gargantuan preps: every 2 liters of distillate extracted with 0.5 liters of ether...six times over. (We'd recycle the ether we roto-vaped off, of course.) Anyway, I noticed a similar phenomenon: the smell of ether would register as quite pleasant for a while, and then suddenly my body would shout "Enough!" and it would become sickening.

(Postscript: the next year, I was taking organic lab and, while waiting in line with our 10-ml graduated cylinders to receive our ration of ether for Grignards or whatever we were doing, one of the students confided to her friend, "I'm scared of ether!" Amazingly, I did not laugh.)

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3. Tom Bartlett on September 19, 2005 9:12 AM writes...

Lots of people are really sensitive to phospines-- diphenyl phosphine, tributyl phosphine, etc. I am not, but I have to admit, they smell awful. My current least-favorite odor is indole. Smells like burning tires to me.

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4. Derek Lowe on September 19, 2005 10:30 AM writes...

No argument on the phosphines - I'm just glad that triphenylphosphine is too big to have any vapor pressure, or it would probably reek, too. The alkyl phosphites are no prize in the odor department, either, I have to say.

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5. Timothy on September 20, 2005 11:23 AM writes...

The last chemistry course I took was in high school, but I remember doing something with cyclohexane that made me so ill I ended up vomiting out the window. Smells like rotting raw chicken, that stuff.

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6. Bizot on August 31, 2007 1:13 PM writes...

Derek ,
do you know id Tosylation in DMF or DMSO may be applied to the surface of solid particles with OH groups ?

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