85650-56-2 Usage
Description
Asenapine Maleate is a novel atypical antipsychotic agent, chemically known as a white solid. It is a dual antagonist of dopamine D2 and serotonin 5-HT2 receptors, exhibiting high affinity for a range of serotonin and dopamine receptors, as well as adrenergic and histamine receptors. Asenapine is marketed under the trade names Saphris and Sycrest, and is used for its efficacy in treating schizophrenia and acute mania associated with bipolar disorder. This certified solution standard is suitable for applications in clinical toxicology, forensic testing, or pharmaceutical research.
Uses
Used in Pharmaceutical Industry:
Asenapine Maleate is used as an antipsychotic medication for the treatment of acute schizophrenia and bipolar mania. Its application is based on its antagonist activity at D2 and 5-HT2A receptors, which helps in managing the symptoms of these mental health conditions.
Used in Research and Development:
Asenapine Maleate is used as a research compound for studying the Fos expression in forebrain structures of rat models, providing insights into its mechanism of action and potential applications in neuroscience.
Used in Clinical Toxicology and Forensic Testing:
Asenapine Maleate is used as a solution standard in liquid chromatography-mass spectrometry (LC/MS) or gas chromatography-mass spectrometry (GC/MS) applications, aiding in the identification and quantification of the drug in biological samples for clinical and forensic purposes.
Originator
Organon (US)
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.
Side effects
The most common adverse effects associated with asenapine treatment include insomnia, somnolence, nausea, anxiety, agitation, headache, vomiting, constipation, and psychosis. In placebo-controlled trials with risperidone, aripiprazole, and olanzapine in elderly subjects with dementia, there was a higher incidence of cerebrovascular adverse reactions (cerebrovascular accidents and transient ischemic attacks) including fatalities compared to placebo-treated subjects. Asenapine is not approved for the treatment of patients with dementia-related psychosis.
Synthesis
The chemical synthesis of asenapine can be achieved by several different methods. A concise synthesis of asenapine begins with the Horner-Emmons condensation of diethyl (5-chloro-2-fluoro)benzyl phosphonate with salicylaldehyde to produce the corresponding stilbene derivative, which undergoes a 1,3-dipolar cycloaddition reaction with trimethylamine-N-oxide in the presence of lithium diisopropylamide to furnish a trans-3,4-diarylpyrrolidine intermediate. Then, a base-catalyzed intramolecular cyclization involving the nucleophilic displacement of the fluoro group by the phenolic hydroxyl group affords asenapine, which
is finally treated with maleic acid in ethanol to yield the corresponding
maleate salt.
Check Digit Verification of cas no
The CAS Registry Mumber 85650-56-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,6,5 and 0 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 85650-56:
(7*8)+(6*5)+(5*6)+(4*5)+(3*0)+(2*5)+(1*6)=152
152 % 10 = 2
So 85650-56-2 is a valid CAS Registry Number.
InChI:InChI=1/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
85650-56-2Relevant articles and documents
A PROCESS FOR THE PREPARATION OF ASENAPINE AND NOVEL SALTS THEREOF
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Page/Page column 24, (2013/03/26)
A process for preparation of asenapine of formula (1) or its acid addition salts; The said process comprises preparation of trans racemate of asenapine by reacting trans- 1 1-chloro-2,3,3a, 12b-tetrahydro-2-methyl-lH-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-l-one with mixture of aluminium chloride and lithium aluminium hydride in solvent followed by converting it into acid addition salt of asenapine followed by hydrolyzing the acid addition salt into trans racemate asenapine base and converting the asenapine base into acid addition salt. Asenapine sulphate of formula (Via) and asenapine maleate of formula (IVb) are also disclosed. The co-precipitate of acid addition salt of asenapine with a pharmaceutically acceptable excipient of formula (V); is also disclosed.
CRYSTAL FORM OF ASENAPINE MALEATE
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Page/Page column 17; 18, (2013/04/10)
The present invention relates to a form of Asenapine Maleate with XRPD peaks at about 5.5,12.5,19.0 and 25.3 and to methods for the preparation thereof. Furthermore the invention relates to a reproducible process for the preparation of pure monoclinic form of Asenapine Maleate in crystalline form and to pharmaceutical compositions comprising the pure monoclinic form of asenapine maleate.
PROCESS FOR THE PREPARATION OF TETRACYCLIC DERIVATIVES AND INTERMEDIATE PRODUCTS USED IN THE PROCESS
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Page/Page column 20-22, (2012/04/17)
A process for preparation of a compound of formula I or a pharmaceutically acceptable salt thereof, is disclosed. The process involves subjecting a compound of formula II to Ullmann-type conditions to effect an intra-molecular ring closure reaction to form the compound of formula I. The different substituents are as described in the specification. Further, the process can provide an alternate route for the synthesis of asenapine from starting materials that can be readily available.
