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A7861

Sigma-Aldrich

Asenapine maleate

≥98% (HPLC)

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Synonym(s):
(3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12btetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c]pyrrole (2Z)-2-butenedioate, Org 5222, trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole maleate
Empirical Formula (Hill Notation):
C17H16ClNO ·C4H4O4
CAS Number:
85650-56-2
Molecular Weight:
401.84
EC Number:
288-064-8
UNSPSC Code:
12352200
PubChem Substance ID:
329770943
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

H2O: ≥10 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.CN1C[C@H]2[C@H](C1)c3cc(Cl)ccc3Oc4ccccc24

InChI

1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1

InChI key

GMDCDXMAFMEDAG-CHHFXETESA-N

General description

Asenapine maleate acts as an antimanic. It belongs to the family of dibenzoxepinopyrrolidines. Asenapine is considered to be a weak inhibitor of cytochrome P450 2D6 (CYP2D6). It increases the level of dopamine, norepinephrine and acetylcholine in brain.

Application

Asenapine maleate has been used as a stressor in studying the Fos expression in forebrain structures of rat models.
Asenapine maleate is a serotonin 5-HT and dopamine D2 receptor antagonist. Asenapine maleate can be used to treat schizophrenia and bipolar mania.

Biochem/physiol Actions

Asenapine maleate is a 5-HT receptor antagonist (5-HT1A,1B, 5-HT2A, 2B, 2C, 5-HT5A, 5-HT6 and 5-HT7), a D2 antagonist, and an antipsychotic.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H400

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ahmed A Abu-Hassan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 239, 118474-118474 (2020-05-26)
Asenapine maleate was approved by the FDA for the treatment of schizophrenia and mania or mixed episodes with bipolar I disorder. In the present article, two spectroscopic methods were developed and validated for the determination of asenapine. Both methods depend
Jakub Trawiński et al.
Ecotoxicology and environmental safety, 162, 272-286 (2018-07-11)
The photolytic and photocatalytic transformation of an antipsychotic drug asenapine with the use of H2O2 and TiO2 was studied. A method employing irradiation with a simulated full solar spectrum in the photostability chamber was applied, then the reverse-phase ultra high
The preclinical profile of asenapine: clinical relevance for the treatment of schizophrenia and bipolar mania
Tarazi FI and Neill JC
Expert Opinion on Drug Discovery, 8(1), 93-103 (2013)
Asenapine: a clinical review of a second-generation antipsychotic
Stoner SC and Pace HA
Clinical Therapeutics, 34(5), 1023-1040 (2012)
Felice Iasevoli et al.
International journal of molecular sciences, 21(15) (2020-08-07)
Antipsychotic agents modulate key molecules of the postsynaptic density (PSD), including the Homer1a gene, implicated in dendritic spine architecture. How the antipsychotic receptor profile, dose, and duration of administration may influence synaptic plasticity and the Homer1a pattern of expression is
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