2012: Advent Chemistry: Sumatriptan

by on December 14, 2012

Sticking with the medical theme, this is sumatriptan:

The structure of sumatriptan, a multifunctionalised molecule.

It’s a migraine cure, and it’s marvellous. It works. When I have a migraine attack, I spray twenty milligrams of this up my nose, and the pain goes away. It’s not perfect – in particular, it doesn’t cure the whole migraine. I still get the fuzzy-brain problem and can’t think well enough to work for a few hours, and I still get the disrupted sleep patterns that knock me out the next day. So it doesn’t actually cure the migraines. It just stops them hurting and that’s good enough for me.

Sumatriptan is a dicyclic molecule – it contains two cyclic bits, two rings. They’re glued together, as you can see, but still count as separate for naming purposes.

It also contains something I didn’t know the name of, and had to look up. I hang my head in shame. It turns out that a sulfonyl (SO2) group adjacent to an amide (NH2, NRH or NR2) group is called a sulfonamide. It’s a component of several antibacterial drugs and, as sumatriptan illustrates, several other drugs as well. I’m not familiar with the details of how sumatriptan works, but I know what it does in a rough sense. It’s a vasoconstrictor – that is, it causes blood vessels to narrow, which relieves the excess pressure on the brain cells that causes my migraines.

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