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Amoxapine

Amoxapine is a tricyclic antidepressant that acts as an antagonist at 5-HT2/3/6/7 receptors, D2/3/4 receptors, H1 histamine receptors, α1-adrenergic receptors, and also on the serotonin transporter (SERT) and norepinephrine transporter (NET). Amoxapine also acts as an antagonist at hERG K+ channels, potentially prolonging the cardiac QT interval. Amoxapine exhibits antidepressant, antipsychotic, and antibacterial activities. Amoxapine inhibits GABA- and NMDA-induced increases in intracellular Ca2+ levels and increases leu-enkephalin levels in vivo. This compound exhibits antibiotic activity through inhibition of bacterial β-glucuronidase.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18838256

Cas No.

14028-44-5

Purity

≥98%

Formula

C17H16ClN3O

Formula Wt.

313.78

Chemical Name

8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine

IUPAC Name

8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine

Melting Point

175.5C

Appearance

Yellow crystalline powder

Ahmad S, Hughes MA, Yeh LA, et al. Potential repurposing of known drugs as potent bacterial β-glucuronidase inhibitors. J Biomol Screen. 2012 Aug;17(7):957-65. PMID: 22535688.

Yang G, Zhou MH, Ren Z, et al. Amoxapine inhibits delayed outward rectifier K(+) currents in cerebellar granule cells via dopamine receptor and protein kinase A activation. Cell Physiol Biochem. 2011;28(1):163-74. PMID: 21865859.

Obers S, Staudacher I, Ficker E, et al. Multiple mechanisms of hERG liability: K+ current inhibition, disruption of protein trafficking, and apoptosis induced by amoxapine. Naunyn Schmiedebergs Arch Pharmacol. 2010 May;381(5):385-400. PMID: 20229012.

Chaudhry IB, Husain N, Khan S, et al. Amoxapine as an antipsychotic: comparative study versus haloperidol. J Clin Psychopharmacol. 2007 Dec;27(6):575-81. PMID: 18004123.

Takebayashi M, Kagaya A, Inagaki M, et al. Effects of antidepressants on gamma-aminobutyric acid- and N-methyl-D-aspartate-induced intracellular Ca(2+) concentration increases in primary cultured rat cortical neurons. Neuropsychobiology. 2000;42(3):120-6. PMID: 11015029.

Roth BL, Craigo SC, Choudhary MS, et al. Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. PMID: 7908055.

Gozlan H, Saddiki-Traki F, Merahi N, et al. Preclinical pharmacology of amoxapine and amitriptyline. Implications of serotoninergic and opiodergic systems in their central effect in rats. Encephale. 1991 Dec;17 Spec No 3:415-22. PMID: 1666997.

Hamon M, Gozlan H, Bourgoin S, et al. Opioid receptors and neuropeptides in the CNS in rats treated chronically with amoxapine or amitriptyline. Neuropharmacology. 1987 Jun;26(6):531-9. PMID: 3037421.

Rocaglamide