Ritter - 7-7-2008 at 10:32
Analogously to the metabolism of BDO to GHB, I checked on the metabolism of 2-buten-1,4-diol. This compound is also metabolized via oxidation.
Attached is the theoretical scheme presented by the EPA on this. See http://www.epa.gov/hpv/pubs/summaries/2butene1/c14224tp.pdf.
Due to it being an allylic alcohol & therefore more prone to oxidation than BDO, the final metabolite is maleic acid. But you can see the
structure of 4-hydroxcrotonic acid as a postulated intermediate in their scheme (their 'half acid.') Since they report that 2-buten-1,4-diol has a
very low toxicity, either the 4-hydroxycrotonic acid is in the biologically inactive cis form or it is transient enough to not accumulate to
the levels required to significantly affect the GHB receptors. (Most references to 2-buten-1,4-diol show it as the cis or Z isomer
as shown in the EPA graphic).
[Edited on 7-7-2008 by Ritter]
