Amoxapine
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MedKoo CAT#: 317186

CAS#: 14028-44-5

Description: Amoxapine is the N-demethylated metabolite of the antipsychotic agent loxapine that works by blocking the reuptake of norepinephrine, serotonin, or both. It also blocks dopamine receptors. Amoxapine is a tetracyclic antidepressant of the dibenzoxazepine family, though it is often classified as a secondary amine tricyclic antidepressant. It first received marketing approval in the US in 1992.


Chemical Structure

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Amoxapine
CAS# 14028-44-5

Theoretical Analysis

MedKoo Cat#: 317186
Name: Amoxapine
CAS#: 14028-44-5
Chemical Formula: C17H16ClN3O
Exact Mass: 313.09819
Molecular Weight: 313.78
Elemental Analysis: C, 65.07; H, 5.14; Cl, 11.30; N, 13.39; O, 5.10

Price and Availability

Size Price Availability Quantity
50.0mg USD 85.0 2 Weeks
100.0mg USD 90.0 2 Weeks
200.0mg USD 150.0 2 Weeks
500.0mg USD 250.0 2 Weeks
1.0g USD 350.0 2 Weeks
2.0g USD 550.0 2 Weeks
5.0g USD 950.0 2 Weeks
10.0g USD 1850.0 2 Weeks
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Synonym: Asendin; Asendis; Defanyl; Demolox; Oxamine; Amolife; Oxcap; Adisen; Amoxan

IUPAC/Chemical Name: 8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine

InChi Key: QWGDMFLQWFTERH-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

SMILES Code: C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl

Appearance: White to off-white solid powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 313.78 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Bhardwaj RM, Raval V, Oswald ID, Florence AJ. Crystal structure of a mixed solvated form of amoxapine acetate. Acta Crystallogr E Crystallogr Commun. 2015 Jan 10;71(Pt 2):139-41. doi: 10.1107/S2056989014028096. eCollection 2015 Feb 1. PubMed PMID: 25878802; PubMed Central PMCID: PMC4384552.

2: Kong R, Liu T, Zhu X, Ahmad S, Williams AL, Phan AT, Zhao H, Scott JE, Yeh LA, Wong ST. Old drug new use--amoxapine and its metabolites as potent bacterial β-glucuronidase inhibitors for alleviating cancer drug toxicity. Clin Cancer Res. 2014 Jul 1;20(13):3521-30. doi: 10.1158/1078-0432.CCR-14-0395. Epub 2014 Apr 29. PubMed PMID: 24780296; PubMed Central PMCID: PMC4079752.

3: Reeves KC, Virk S, Niedermier J, Duchemin AM. Addition of amoxapine improves positive and negative symptoms in a patient with schizophrenia. Ther Adv Psychopharmacol. 2013 Dec;3(6):340-2. doi: 10.1177/2045125313499363. PubMed PMID: 24294487; PubMed Central PMCID: PMC3840811.

4: Karasakal A, Ulu ST. Development and validation of a sensitive spectrofluorimetric method for the determination of amoxapine in human plasma and urine. Luminescence. 2014 May;29(3):284-7. doi: 10.1002/bio.2541. Epub 2013 Jun 19. PubMed PMID: 23780763.

5: Wong YC, Wo SK, 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. 2012 Jan 25;58:83-93. doi: 10.1016/j.jpba.2011.09.020. Epub 2011 Sep 22. PubMed PMID: 21993198.

6: Yang G, Zhou MH, Ren Z, Xu JJ, Mei YA. 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. doi: 10.1159/000331725. Epub 2011 Aug 16. PubMed PMID: 21865859.

7: Zimmer JS, Needham SR, Christianson CD, Piekarski CM, Sheaff CN, Huie K, Reed AR, Takahashi L. Validation of HPLC-MS/MS methods for analysis of loxapine, amoxapine, 7-OH-loxapine, 8-OH-loxapine and loxapine N-oxide in human plasma. Bioanalysis. 2010 Dec;2(12):1989-2000. doi: 10.4155/bio.10.156. PubMed PMID: 21110742.

8: Gupta M, Jain A, Verma KK. Determination of amoxapine and nortriptyline in blood plasma and serum by salt-assisted liquid-liquid microextraction and high-performance liquid chromatography. J Sep Sci. 2010 Dec;33(23-24):3774-80. doi: 10.1002/jssc.201000434. PubMed PMID: 21082678.

9: Takechi K, Abe T, Yorozuya T, Watanabe T, Nagaro T. Refractory hypotension during general anaesthesia caused by the long-term use of amoxapine. Anaesth Intensive Care. 2010 Sep;38(5):965-6. PubMed PMID: 20865899.

10: Obers S, Staudacher I, Ficker E, Dennis A, Koschny R, Erdal H, Bloehs R, Kisselbach J, Karle CA, Schweizer PA, Katus HA, Thomas D. 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. doi: 10.1007/s00210-010-0496-7. Epub 2010 Mar 13. PubMed PMID: 20229012.