A loxapine metabolite
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Parent Compound(s)
20760Loxapine (succinate)
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8-hydroxy Loxapine

Item No. 21786

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-chloro-11-(4-methyl-1-piperazinyl)-dibenz[b,f][1,4]oxazepin-8-ol
CAS Number
61443-77-4
Synonyms
  • 8-OH Loxapine
Molecular Formula
C18H18ClN3O2
Formula Weight
343.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
ClC1=CC2=C(C=C1)OC3=C(C=C(O)C=C3)N=C2N4CCN(C)CC4
InChi Code
InChI=1S/C18H18ClN3O2/c1-21-6-8-22(9-7-21)18-14-10-12(19)2-4-16(14)24-17-5-3-13(23)11-15(17)20-18/h2-5,10-11,23H,6-9H2,1H3
InChi Key
VNJRIWXLPIYFGI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $169

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    1 mg

    $319

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    Product Description

    8-hydroxy Loxapine (8-OH loxapine) is a metabolite formed when loxapine (Item No. 20760), an atypical antipsychotic, is metabolized by the cytochrome P450 isoform CYP1A2.1,2 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).1,3 It reduces agitation associated with schizophrenia or bipolar disorder.4 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).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seeman, P., Corbett, R., and Van Tol, H.H. Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors. Neuropsychopharmacology 16(2), 93-110 (1997).

    2. Wong, Y.C., Wo, S.K., and Zuo, Z. 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. Pharm. Biomed. Anal. 58, 83-93 (2012).

    3. Kroeze, W.K., Hufeisen, S.J., Popadak, B.A., et al. H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. Neuropsychopharmacology 28(3), 519-526 (2003).

    4. Zeller, S.L., and Citrome, L. Managing agitation associated with schizophrenia and bipolar disorder in the emergency setting. West J. Emerg. Med. 17(2), 165-172 (2016).

    5. Fulton, A., Norman, T., and Burrows, G.D. Ligand binding and platelet uptake studies of loxapine, amoxapine and their 8-hydroxylated derivatives. J. Affect. Disord. 4(2), 113-119 (1982).