(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7,9,11,14,16-hexaene; but-2-enedioic acid

• ChemBase ID: 154797
• Molecular Formular: C21H20ClNO5
• Molecular Mass: 401.8402
• Monoisotopic Mass: 401.10300043
• SMILES: CN1C[C@@H]2c3ccccc3Oc3ccc(cc3[C@H]2C1)Cl.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: Clc1ccc2c(c1)[C@H]1CN(C[C@@H]1c1c(O2)cccc1)C.OC(=O)/C=C/C(=O)O
• InChI: 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)/t14-,15-;/m1./s1
• InChIKey: GMDCDXMAFMEDAG-CTHHTMFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^2,^6.0^7,^1^2]octadeca-1(18),7,9,11,14,16-hexaene; but-2-enedioic acid
• IUPAC Traditional name: asenapine; butenedioic acid
• Synonyms: (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; Asenapine maleate

Database IDs

• CAS Number: 85650-56-2
• EC Number: 288-064-8
• PubChem SID: 162248935
• PubChem CID: 71311991

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9322492
• LogD (pH = 7.4): 3.4735167
• Log P: 3.7246065
• Molar Refractivity: 81.6499 cm^3
• Polarizability: 31.63231 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38-50/53
• Safety Statements: 26-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P301 + P310-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H16ClNO ·C4H4O4

DETAILS

Sigma Aldrich - A7861

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.
Application
Asenapine maleate is a serotonin 5-HT and dopamine D2 receptor antagonist. Asenapine maleate can be used to treat schizophrenia and bipolar mania.