lubazodone lubazodone lubazodone (developmental code names ym-992, ym-35995) is an experimental antidepressant which was under development by yamanouchi for the treatment for major depressive disorder in the late 1990s and early 2000s but was never marketed. it acts as a serotonin reuptake inhibitor (ki for sert = 21 nm) and 5-ht2a receptor antagonist (ki = 86 nm), and hence has the profile of a serotonin antagonist and reuptake inhibitor (sari). the drug has good selectivity against a range of other monoamine receptors, with its next highest affinities being for the α1-adrenergic receptor (ki = 200 nm) and the 5-ht2c receptor (ki = 680 nm). lubazodone is structurally related to trazodone and nefazodone, but is a stronger serotonin reuptake inhibitor and weaker as a 5-ht2a receptor antagonist in comparison to them and is more balanced in its actions as a sari. it reached phase ii clinical trials for depression, but development was discontinued in 2001 reportedly due to the "erosion of the ssri market in the united states". lubazodoneclinical dataother namesym-992; ym-35995routes ofadministrationoralatc codenoneidentifiers iupac name (2s)-2-morpholine cas number161178-07-0 ypubchem cid157919chemspider138947 nunii850tb2b172comptox dashboard (epa)dtxsid30167074 chemical and physical dataformulac14h18fno2molar mass251.301 g·mol−13d model (jsmol)interactive image smiles c1cc2=c(c=cc(=c2c1)f)oc3cncco3 inchi inchi=1s/c14h18fno2/c15-13-4-5-14(12-3-1-2-11(12)13)18-9-10-8-16-6-7-17-10/h4-5,10,16h,1-3,6-9h2/t10-/m0/s1 nkey:htodiqzhvchvgm-jtqlqieisa-n n ny (what is this?) (verify) synthesis patent: thus reaction of 7-fluoro-4-indanol (1) with (s)-glycidyl methanesulfonate, cid:12461090 (2) in the presence of base leads to the epoxypropyl ether, cid:139677486 (3). treatment with aminoethyl sulfate (4) closes the morpholine ring giving lubazodone (5).