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Oct 20

Meth and mirror images: errors in Nick Reding’s “Methland”

by Chemjobber | Categories: general chemistry | (20329 Views)

meth-3

I recently picked up Nick Reding’s book Methland, which is about the blight of a small Iowa town due to methamphetamine use. I was interested in it because I had heard about it from NPR; I was interested in what Reding had to say about the chemistry of meth synthesis. What I found was pretty amusing.

I should pause to say that Reding was not focused on the chemistry at all — rather, his thesis was that meth was a mere symptom of the devastating effects of global economic forces on a small Iowa town. It’s well written and pretty gripping stuff.

I’m sure I’m not the only chemist who can get distracted by chemical explanations that’s just obviously wrong. But some of the explanations were just terribly, terribly wrong:

“Mirror imaging is a process whereby a chemical’s molecular structure is reversed, moving, for example, electrons from the bottom of a certain ring to the top, and vice versa. Pseudoephedrine, ephedrine, and methamphetamine are already near mirror images of one another. To make meth from ephedrine, it is necessary to remove a single oxygen atom from the outer electron ring. Thus ephedrine and methamphetamine not only look the same under a mass spectrometer, but both dilate the alveoli in the lungs and shrink blood vessels in the nose-hence ephedrine’s use as a decongestant while raising blood pressure and releasing adrenaline. The key difference is that meth, unlike ephedrine, prompts wide-scale releases of the neurotransmitters dopamine and epinephrine.

What the 1997 tests at the University of North Texas showed was that, at least in lab animals, mirror-image pseudoephedrine was equally as effective as regular pseudoephedrine as a decongestant. Unlike regular pseudo, however, the mirror-image version didn’t cause any side effects to the central nervous system, such as high blood pressure and a racing heart: the common “buzz” that one associates with cold medicine. Better yet for Warner-Lambert, mirror-image pseudoephedrine could only be synthesized into mirror-image methamphetamine, which, according to the Oregonian, had no stimulant effects and could not then be made into regular meth.” (quote thanks to Mike the Mad Biologist.)

Where to begin? First of all, “mirror imaging” is not a term; the word you’re looking for is, of course, enantiomers. The explanation about electrons is not correct; you can’t move electrons willy-nilly around rings. The comparison of ephedrine and methamphetamine as mirror images is wrong — they’re not even structural isomers. To make meth from ephedrine, you don’t “remove a single oxygen atom from the outer electron ring” (that sounds like something you do on the planet Zefu), you remove an oxygen and a hydrogen from a side chain by reduction. Ephedrine and methamphetamine most certainly DO NOT look the same under a mass spectrometer; I imagine it’s quite easy to distinguish the peaks from one another. Did Reding’s editor basically make a pass on the science stuff?

Reding’s book relies heavily on a series of articles on the meth epidemic written by Steve Suo of the Portland Oregonian. (If you look in Suo’s articles, you’ll see that Reding basically reworded the somewhat-more-correct chemistry explanation from Suo’s article.) Reding and Suo’s larger point  is that (-)-pseudoephedrine does not generate CNS-active methamphetamine, and that Warner-Lambert (and subsequently, Pfizer) were not interested enough in the larger public health issues to spend the money to push (-)-psuedoephedrine through the FDA approval process when the enantiomer they had was already quite lucrative.

So now that we’ve had a laugh about bad chemistry explanations, a question for everyone: how easy is it to get (-)-pseudoephedrine? The companies in India contacted by Suo said that they could supply ton quantities, no problem. I’m skeptical, but not that skeptical. Anyone out there know about this?

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  1. Andre

    Technically, the hydroxy group reduction is the net loss of a single oxygen atom (replacement of OH with H), so the writer is correct there. But everything else you point out is utter nonsense. I noticed all this a while ago when I first read that quote that you gave, and I’m glad I wasn’t the only one who was annoyed by it.

  2. Markos Strofyllas

    Plus, if you want to get *really* pedantic, epinephrine is the exact same thing as adrenaline ;)

  3. We Hate Your Blog

    No particular offense, but we hate your blog.

    http://wehateyourblog.com/2009/10/21/we-hate-chemistryblog/

    It’s just what we do.

    1. azmanam

      I dunno… I’m kinda honored. :)

      The only real beef he has with you is your sense of humor (twice). Sounds like projection to me.

      Guess what? We hate you back. Let’s go have a beer.

      1. We Hate Your Blog

        We’d love to have a beer. You’re paying.

    2. Chemjobber

      Wow — I think I’m honored. And yes, my sense of humor sucks. But there you are!

  4. Chemjobber

    Oh, heck. While I’m at it, why don’t I just add more pedantry:

    This is one of the opening passages of the book, where a meth addict burns his house down:

    “So bottle by bottle, container by container, he poured down the floor drain in the floor of his mother’s basement the chemicals he had stored there: anhydrous ammonia, Coleman lantern fluid denatured alcohol and kerosene. Finally, he poured 2 gallons of hydrochloric acid down the drain. Then he lit his cigarette.

    It took about a quarter of a second for the ionized hydrogen in the hydrochloric acid to propagate from the lighter’s flame and into the drain. This made the entire basement into a vacuum. Jarvis [the meth cook - CJ] heard a soft Whoosh! Then came the blast…”

    Huh? Ionized what? Propagating from where? Who is Reding’s scientific adviser and why does he or she stink?

  1. We hate ChemistryBlog « We hate your blog.

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