NMR on the X-Files

I was watching the X-Files last night — because bing-watching 1990’s television is how I opt to spend my free time — when the show mentioned a particular analytical technique readers will be well familiar with: NMR.

One of the reasons I love this show so much is because the blatant pseudo-science presented has a glimmer of real science somewhere embedded in it.  Sure it’s fiction; but I’ve never seen them put up a structure containing a Texas carbon (and I’ve been looking!).

In last night’s episode, Special Agent Dana Scully shows her partner, Special Agent Fox Mulder, a “nuclear magnetic resonance spectra [sic].”  This then comes on screen for a couple seconds (click to embiggen):

Screen cap from The X-Files S4E19 “Synchrony”, approximately 14:30 into the episode

A Proton NMR spectrum indeed!  The protagonist explains the analyte in question is a drop of blood from a murder victim; that’s an awfully clean spectrum from such a complex source.  The compound we are looking at is an experimental super toxin which “catalytically” induces freezing — and subsequent death — in it victims.

Obviously, no such catalyst exists, but this is a real NMR spectrum of something.  The solvent appears to be deutero-chloroform spiked with TMS.  There’s an aromatic signal almost directly on top of the chloroform singlet.  It gets complicated in the 6.5-5.5 region with olefins aplenty.  A singlet at ~4.1 could belong to some kind of substituted anisole, or a chloromethyl group?  The doublet at 3.3 has me stumped.  My first guess would be methylene adjacent to NH, but alas, no NH proton visible.  Down around 2-1 ppm we have a mess of methyl groups and what looks like a t-butyl at 1.2 ppm.

I am awarding a bounty of 10 internet points to the commenter who can propose the most plausible structure for this spectrum.  For historical context, the episode was filmed in 1996-97 in Cambridge, MA using MIT for some of the shots.  So it’s a possibility that the spectrum was pulled from an MIT lab.

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