title: Photophysics and photochemistry of z-chlorprothixene in acetonitrile.
abstract: Chlorprothixene (CPTX, Taractan) is a low potency antipsychotic mainly used for the treatment of psychotic disorders (e.g. schizophrenia) and acute mania occurring as part of bipolar disorders. As in the case of other numerous drugs used in the treatment of psychiatric disorders, CPTX presents geometric isomerism. Therefore, in vitro irradiation induces a rapid Z/E isomerization, which can affect its pharmacokinetic properties. This photoisomerization is not dependent on the oxygen concentration. The Z/E quantum yields determined for zCPTX in acetonitrile are 0.22 and 0.21 in anaerobic and aerobic environments, respectively. In the presence of water, both isomers decompose to produce 2-chlorothioxanthone (CTX) after prolonged irradiation. This process strongly depends on the water concentration and the irradiation time, i.e. it is autocatalyzed by the CTX through a triplet-energy transfer mechanism. The protonation state of the terminal amino group, on the other hand, has no effect on the isomerization process, but inhibits the formation of CTX. These results indicate that the phototoxicity of zCPTX is somehow affected by the formation of CTX.
authors.affiliation: Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico.
authors.forename: Luis E
authors.initials: LE
authors.lastname: Piñero
authors.forename: Carmelo
authors.initials: C
authors.lastname: García
authors.forename: Virginie
authors.initials: V
authors.lastname: Lhiaubet-Vallet
authors.forename: Rolando
authors.initials: R
authors.lastname: Oyola
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Miranda
mesh_terms: D000097:Acetonitriles / Q000737:chemistry*; D014150:Antipsychotic Agents / Q000737:chemistry*; D002749:Chlorprothixene / Q000737:chemistry*; D010777:Photochemistry
chemical_list: D000097:Acetonitriles; D014150:Antipsychotic Agents; D002749:Chlorprothixene; C032159:acetonitrile