8-Hydroxyamoxapine

8-Hydroxyamoxapine
Pharmacokinetic data
Elimination half-life	30 hours
Identifiers
	IUPAC name 8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepin-3-ol;
CAS Number	61443-78-5;
PubChem CID	43656;
ChemSpider	39784;
UNII	0D4T741I48;
ChEBI	CHEBI:143289;
CompTox Dashboard (EPA)	DTXSID40210388;
Chemical and physical data
Formula	C17H16ClN3O2
Molar mass	329.78 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1)C2=NC3=C(C=CC(=C3)O)OC4=C2C=C(C=C4)Cl;
	InChI InChI=1S/C17H16ClN3O2/c18-11-1-3-15-13(9-11)17(21-7-5-19-6-8-21)20-14-10-12(22)2-4-16(14)23-15/h1-4,9-10,19,22H,5-8H2; Key:QDWNOKXUZTYVGO-UHFFFAOYSA-N;

8-Hydroxyamoxapine is an active metabolite of the antidepressant drug amoxapine (Asendin). It contributes to amoxapine's pharmacology.^[1]^[2] It is a serotonin-norepinephrine reuptake inhibitor (SNRI) with similar norepinephrine, but more serotonin, reuptake inhibition as its parent compound. It plays a part in balancing amoxapine's ratio of serotonin to norepinephrine transporter blockage.^[3]

References

^ Jue SG, Dawson GW, Brogden RN (July 1982). "Amoxapine: a review of its pharmacology and efficacy in depressed states". Drugs. 24 (1): 1–23. doi:10.2165/00003495-198224010-00001. PMID 7049659. S2CID 7279867.
^ Calvo B, García MJ, Pedraz JL, Mariño EL, Domínguez-Gil A (April 1985). "Pharmacokinetics of amoxapine and its active metabolites". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 23 (4): 180–185. PMID 3997304.
^ Midha KK, Hubbard JW, McKay G, Rawson MJ, Hsia D (September 1999). "The role of metabolites in a bioequivalence study II: amoxapine, 7-hydroxyamoxapine, and 8-hydroxyamoxapine". International Journal of Clinical Pharmacology and Therapeutics. 37 (9): 428–38. PMID 10507241.

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