Levomefolic acid

31690-09-2151533-22-1(calcium salt) Interactive image CHEBI:136009 392351 D09353 44441215341110(calcium salt) 8S95DH25XCYA9R10K3F2F(calcium salt)Y DTXSID00185583 InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1Key: ZNOVTXRBGFNYRX-STQMWFEESA-NInChI=1/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1Key: ZNOVTXRBGFNYRX-STQMWFEEBP CN1c2c([nH]c(nc2=O)N)NC[C@@H]1CNc3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O US:OTC Levomefolic acid(INN, also known asL-5-MTHF,L-methylfolateandL-5-methyltetrahydrofolateand(6S)-5-methyltetrahydrofolate, and(6S)-5-MTHF) is the primary biologically active form offolateused at the cellular level forDNAreproduction, thecysteinecycle and the regulation ofhomocysteine. It is also the form found in circulation and transported across membranes into tissues and across theblood–brain barrier. In the cell,L-methylfolate is used in themethylationofhomocysteineto formmethionineandtetrahydrofolate(THF). THF is the immediate acceptor of one carbon unit for the synthesis ofthymidine-DNA,purines(RNAandDNA) andmethionine. The un-methylated form,folic acid(vitamin B9), is a synthetic form offolate, and must undergo enzymatic reduction bydihydrofolate reductase(DHFR) to become biologically active.Systematic reviews suggest thatadjunctiveL-methylfolate modestly improves symptoms inmajor depressive disorder. It is synthesized in the absorptive cells of the small intestine from polyglutamylated dietaryfolate. It is a methylated derivative oftetrahydrofolate. Levomefolic acid is generated bymethylenetetrahydrofolate reductase(MTHFR) from5,10-methylenetetrahydrofolate(MTHF) and used to recyclehomocysteineback tomethioninebymethionine synthase(MS). L-methylfolate is water-soluble and primarily excreted via the kidneys. In a study of 21 subjects with coronary artery disease, peak plasma levels were reached in one to three hours followingoralorparenteraladministration. Peak concentrations were found to be more than seven times higher thanfolic acid(129ng/ml vs. 14.1 ng/ml). Patients at risk forvitamin B12deficiency should consult with their medical provider prior to taking L-Methylfolate. The interrelationship between these two vitamins (L-Methylfolate and B12) is best explained by the methyl trap hypothesis.