(4) SCHEDULE IV.--A substance in Schedule IV has a low potential for abuse relative to the substances in Schedule III and has a currently accepted medical use in treatment in the United States, and abuse of the substance may lead to limited physical or psychological dependence relative to the substances in Schedule III. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation, are controlled in Schedule IV:
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The double bond of cycloartenol (compound 7 in diagram) is methylated by SAM to give a carbocation that undergoes a hydride shift and loses a proton to yield a compound with a methylene side-chain. Both of these steps are catalyzed by sterol C-24 methyltransferase (Step E1 in diagram). Compound 8 is then catalyzed by sterol C-4 demethylase (E2) and loses a methyl group to produce cycloeucalenol. Subsequent to this, the cyclopropane ring is opened with cycloeucalenol cycloisomerase (E3) to form 10 . Compound 10 loses a methyl group and undergoes an allylic isomerization to form Gramisterol 11 . This step is catalyzed by sterol C-14 demethylase (E4), sterol Δ14-reductase (E5), and sterol Δ8-Δ7-isomerase (E6). The last methyl group is removed by sterol demethylase (E7) to form episterol 12 . Episterol 12 is methylated by SAM to produce a second carbocation, which loses a proton to yield 13 . This step is catalyzed by 24-methylenesterol C-methyltransferase (E8). Compound 13 now undergoes reduction by NADPH and modifications in the β-ring to form β-sitosterol.