Author Topic: Reduction of pregnenolone  (Read 53 times)

Tsathoggua

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Reduction of pregnenolone
« on: May 21, 2011, 06:41:25 PM »
So, bees'n'girls, thinking of what to do next time I get bored...got me wondering about stuff to keep my hands busy, has anybody ever considered reduction of the double bond in pregnenolone to pregnanolone?  think protection of the carbonyl as the bisulfite adduct followed by reduction with LAH or borohydride would do it?

Catalytic hydrogenation with precious metal catalysts is out, due to the poisoning effect of sulfur  on Pd/Pt etc. Followed by deprotection, assuming something like LAH wouldn't immediately reduce a sulfonate to SO2, which wouldn't at all surprise me.

The sulfate ester is available as a nootropic/so-called 'diet supplement' etc. Pregnanolone however, should be a potent GABAa agonist, with perhaps a barbiturate-like character, rather than benzo-like, it is most unselective, binding to pretty much every heteropentamer combination (perhaps excluding GABAc, which is more properly a GABAa homopentamer consisting entirely of Rho-type subunits, although it activates those pentameric ion channels containing delta subunits more strongly than others IIRC)

Any ideas, people? and for that matter, has anyone here ever taken a neurosteroid site selective GABAa agonist?
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