Why Organic Chemistry should always be taken (and passed) by pre-meds — part II

Chapter 25 of Clayden is all about synthesis, and as an old Woodward grad student, I loved it.  Ingenuity and elegance on display many times.  Everything in the previous 24 chapters was brought to bear on each problem at hand.  

Just like medicine.

You start in medical school with anatomy and biochemistry, then move on to pathology and pharmacology, then to endocrinology which uses much of the above, then physical diagnosis.  All this in the 2 years before you really get involved with patients.  The handbook for entering med students at Duke is reported to have started with:   “Like to read?  Good, you’ve come to the right place.”

Having spent 2 years reading about the diseases flesh is heir to, at the start of the third year, you are then plunked down in front of a patient to take a history, do a physical exam, come to some sort of understanding about what’s wrong and propose a course of action.  All this to a cynical intern over which stands a even more cynical resident, and above that an attending physician.  

The first few patients take several hours each.  They don’t come with labels saying I’ve got a liver problem, any more than a target molecule says why don’t you try the aldol condensation. Almost invariably, the patients have multiple problems, and you have to be careful that your therapy for one doesn’t adversely affect another — does this remind you of protecting groups?  It should.  

The fact that you have to bring everything you know and have ever studied to bear on an unfamiliar situation is typical of synthesis and medicine.  Even if you’re a specialist, the problems you see don’t necessarily have origins in what you specialize in.  Organic chemistry teaches you to think this way, and if you can’t, you don’t belong in medicine.  For an earlier rumination on this topic see the link at the end.

One example, for any docs reading this.  As a neurologist you get called on to see people who pass out.  One young woman I saw had passed out several times on a hot summer day.  She was thin, but otherwise appeared healthy.   On physical examination (she’d been hospitalized), she had a gorgeous tan.  Moreover, it was all over her body, including the breasts and pelvis.   This was Montana in the 70’s (which was like the US in the 50’s) and there was very little nude sunbathing going on.  That gave the diagnosis away. See the next paragraph for the denouement. I’ve put in some white space so you can think about it before scrolling down.

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She had Addison’s disease and was in adrenal crisis.  Even though it was late evening, I called in an endocrinologist (stat) who drew tons of blood and started treatment immediately.  He told me I’d saved her life.  He said she was on her way out and would have been gone by morning.   She was fainting because she couldn’t maintain her blood pressure when erect.  No intellectual achievement ever gave me satisfaction like this (not even the Woodward seminars). 

For the non MDs:  The total body tan gave things away for the following reason.  To a first approximation, the pituitary gland controls most of the other endocrine glands (adrenal, thyroid, ovaries, testis, but not the pancreas).  It samples the blood to make sure the glands are secreting what they should.  When they aren’t, it pumps out the appropriate hormone (ACTH, TSH, FSH, LH) which tells them to secrete more.  ACTH stands for AdrenoCorticoTrophic Hormone which drives the adrenal cortex to secrete.  However, ACTH is but a part of a larger protein (pro-opiomelanocortin) which contains at least 10 biologically active peptides in its 265 amino acids (ACTH accounts for only 39).  One group is the endorphins, but the clue to the diagnosis is that another peptide contained by both pro-opiomelanocortin and ACTH  is alpha melanocyte stimulating hormone, which makes the pigment cells in your skin (the melanocytes) produce more pigment, darkening the skin (and giving the young woman her great tan).  It doesn’t seem terribly efficient to pump out 10 biologically active peptides when you really want just one, but that’s the way we’re built. 

The link to the earlier rumination

 https://luysii.wordpress.com/2009/09/01/why-organic-chemistry-should-always-be-taken-and-passed-by-pre-meds/