5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

Base Information

• Chemical Name: 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate
• CAS No.: 65576-45-6
• Molecular Formula: C17H16ClNO
• Molecular Weight: 285.773
• Hs Code.: 2934999090
• Pharos Ligand ID: 96LHHAUR1QQ9
• Metabolomics Workbench ID: 149685
• ChEMBL ID: CHEMBL3544974
• Mol file: 65576-45-6.mol

Synonyms:5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole;Asenapine;asenapine maleate;ORG 5222;ORG-5222;saphris;Secuado;trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole

Chemical Property of 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 2.65E-05mmHg at 25°C
• Refractive Index: 1.609
• Boiling Point: 357.9 °C at 760 mmHg
• PKA: 9.50±0.20(Predicted)
• Flash Point: 170.2 °C
• PSA: 12.47000
• Density: 1.231 g/cm³
• LogP: 4.19640
• Storage Temp.: Store at +4°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 401.1030004
• Heavy Atom Count: 28
• Complexity: 482

Purity/Quality:

99% ^*data from raw suppliers

Asenapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2C(C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: CN1CC2C(C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=C\C(=O)O)\C(=O)O
• Recent EU Clinical Trials: A randomized, parallel group, multiple dose, 6 week study to evaluate safety, tolerability, and pharmacokinetics of asenapine in elderly subjects with psychosis.
• Description: (±)-Asenapine is an atypical antipsychotic. It binds to dopamine D1-4, α-adrenergic, and histamine receptors (Kis = 0.42-1.45, 0.32-1.26, and 1-6.17 nM, respectively), as well as the serotonin (5-HT) receptor subtypes 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT5A, 5-HT6, and 5-HT7 (Kis = 0.03-3.98 nM). (±)-Asenapine inhibits the suppression of neuron firing induced by the 5-HT2A, dopamine D2, and α2-adrenergic receptor agonists 2,5-dimethoxy-4-iodoamphetamine (DOI), apomorphine, and clonidine , respectively, in rat brain (ED50s = 75, 40, and 85 μg/kg, respectively). In vivo, (±)-asenapine (0.05-0.2 mg/kg, s.c.) increases extracellular dopamine levels in the medial prefrontal cortex (mPFC), nucleus accumbens (NAc), and lateral striatum and suppresses the conditioned avoidance response in rats. It prevents acute and chronic phencyclidine-induced deficits in cued reversal learning in rats when administered at a dose of 0.075 mg/kg. Formulations containing asenapine have been used in the treatment of schizophrenia and bipolar I disorder.
• Uses: Combined serotonin (5HT2) and dopamine (D2) receptor antagonist; structurally related to Mianserin. Antipsychotic
• Clinical Use: Atypical antipsychotic Treatment of schizophrenia and bipolar disease
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids. Anti-arrhythmics: increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval; avoid with amiodarone, disopyramide and procainamide (risk of ventricular arrhythmias). Antidepressants: concentration possibly increased by fluvoxamine; possibly increased paroxetine concentration; concentration of tricyclics possibly increased. Antiepileptics: antagonises anticonvulsant effect. Antimalarials: avoid with artemether/lumefantrine. Antivirals: concentration possibly increased by ritonavir. Anxiolytics and hypnotics: increased sedative effects.

Technology Process of 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

There total 71 articles about 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

asenapine sulphate → asenapine (65576-45-6,65621-78-5)

Guidance literature:

With ammonia; In water; ethyl acetate; at 0 - 5 ℃; for 0.25h; pH=7.5 - 8.5; Reagent/catalyst; Solvent;

Reference yield: 100.0%

trans-(3a,12b)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-C]pyrrol-1-one (129385-59-7,1180843-77-9,165890-26-6) → asenapine (65576-45-6,65621-78-5)

Guidance literature:

With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at -25 - -20 ℃; for 1h; Solvent;

Reference yield: 100.0%

trans-8-chloro-10,11-dihydro-11-[(methyl-amino)methyl]-dibenz[b,f]oxepin-10-carboxylic acid hydrochloride → asenapine (65576-45-6,65621-78-5)

Guidance literature:

trans-8-chloro-10,11-dihydro-11-[(methyl-amino)methyl]-dibenz[b,f]oxepin-10-carboxylic acid hydrochloride; With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at -10 - 0 ℃; for 0.5h;

With water; In tetrahydrofuran; Product distribution / selectivity;

upstream raw materials:

trans-5-chloro-2,3,3a,12b-tetrahydro-1H-dibenz<2,3:6,7>oxepino<4,5-c>pyrrole

methyl iodide

5-chloro-2-methoxybenzaldehyde

trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

Downstream raw materials:

trans-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole hydrochloride

trans-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz<2,3:6,7>oxepino<4,5-c>pyrrolidine maleate

trans-5-chloro-2,3,3a,12b-tetrahydro-1H-dibenz<2,3:6,7>oxepino<4,5-c>pyrrole

Refernces

• 1、 -. "For the preparation of asenapine and used for preparing intermediates of asenapine". Paragraph 0211; 0253-0257. . Retrieved 2019/01/22.
• 2、 -. "PROCESS FOR THE PREPARATION OF ASENAPINE MALEATE". Paragraph 0055; 0056. . Retrieved 2015/04/28.