| Identification | Back Directory | [Name]
8-hydroxyloxapine | [CAS]
61443-77-4 | [Synonyms]
8-hydroxyloxapine
Loxapine 8-Hydroxy Impurity
2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,f][1,4]oxazepin-8-ol
8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepin-3-ol
Dibenz[b,f][1,4]oxazepin-8-ol, 2-chloro-11-(4-methyl-1-piperazinyl)- | [Molecular Formula]
C18H18ClN3O2 | [MOL File]
61443-77-4.mol | [Molecular Weight]
343.81 |
| Chemical Properties | Back Directory | [Melting point ]
212-215°C | [storage temp. ]
Amber Vial, -20°C Freezer, Under Inert Atmosphere | [solubility ]
DMSO: soluble | [form ]
A solid | [Stability:]
Light Sensitive |
| Hazard Information | Back Directory | [Description]
8-hydroxy Loxapine (8-OH loxapine) is a metabolite formed when loxapine , an atypical antipsychotic, is metabolized by the cytochrome P450 isoform CYP1A2. Loxapine displays high affinity for histamine, serotonin (5-HT), dopamine, and α1-adrenergic receptors (Ki values = 7, 7.7, 9.5, 12, and 31 nM for H1, 5-HT2A, 5-HT2C, D2, and α1A-adrenergic receptors, respectively). It reduces agitation associated with schizophrenia or bipolar disorder. 8-OH Loxapine is considered inactive as it has relatively low affinity to dopamine and 5-HT receptors compared to the parent compound, however, 8-OH loxapine inhibits [14C]5-HT uptake in vitro (IC50 = 2 μM in human platelets). | [Chemical Properties]
Pale Yellow Solid | [Uses]
The inactive | [storage]
Store at -20°C | [References]
[1] MD P S, PH.D Hubert H M V T Ph D Roy Corbett Ph D. Atypical Neuroleptics Have Low Affinity for Dopamine D2 Receptors or Are Selective for D4 Receptors[J]. Neuropsychopharmacology, 1997, 16 2: 93-110. DOI: 10.1016/s0893-133x(96)00187-x
[2] YIN CHEONG WONG Zhong Z Siu Kwan Wo. Investigation of the disposition of loxapine, amoxapine and their hydroxylated metabolites in different brain regions, CSF and plasma of rat by LC–MS/MS[J]. Journal of pharmaceutical and biomedical analysis, 2012, 58: Pages 83-93. DOI: 10.1016/j.jpba.2011.09.020
[3] ANDREW J GOUDIE. H1-histamine Receptor Affinity Predicts Short-term Weight Gain for Typical and Atypical Antipsychotic Drugs[J]. Neuropsychopharmacology, 2003, 28 12: 2209-2209. DOI: 10.1038/sj.npp.1300291
[4] JUSTIN FADEN L C. Examining the safety, efficacy, and patient acceptability of inhaled loxapine for the acute treatment of agitation associated with schizophrenia or bipolar I disorder in adults[J]. Neuropsychiatric Disease and Treatment, 2019, 15 1: 2273-2283. DOI: 10.2147/ndt.s173567
[5] A. FULTON G. D B T Norman. Ligand binding and platelet uptake studies of loxapine, amoxapine and their 8-hydroxylated derivatives[J]. Journal of affective disorders, 1982, 4 2: Pages 113-119. DOI: 10.1016/0165-0327(82)90041-6 |
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