13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene; butanedioic acid

• ChemBase ID: 155326
• Molecular Formular: C22H24ClN3O5
• Molecular Mass: 445.89606
• Monoisotopic Mass: 445.14044856
• SMILES: CN1CCN(CC1)C1=Nc2ccccc2Oc2c1cc(cc2)Cl.C(CC(=O)O)C(=O)O
• Canonical SMILES: CN1CCN(CC1)C1=Nc2ccccc2Oc2c1cc(Cl)cc2.OC(=O)CCC(=O)O
• InChI: InChI=1S/C18H18ClN3O.C4H6O4/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18;5-3(6)1-2-4(7)8/h2-7,12H,8-11H2,1H3;1-2H2,(H,5,6)(H,7,8)
• InChIKey: YQZBAXDVDZTKEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene; butanedioic acid; 13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,9,12,14-heptaene; butanedioic acid
• IUPAC Traditional name: loxapine; succinic acid
• Synonyms: 2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine, Succinate; Oxilapine; CL-62362; S-805; SUM-3170; Loxapine, Succinate; Loxapine Succinate; Loxapine succinate salt

Database IDs

• CAS Number: 27833-64-3
• EC Number: 248-682-0
• MDL Number: MFCD00069298
• PubChem SID: 24277719; 162249464
• PubChem CID: 71399

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.3977866
• LogD (pH = 7.4): 3.0634365
• Log P: 3.4606025
• Molar Refractivity: 95.1111 cm^3
• Polarizability: 35.46127 Å^3
• Polar Surface Area: 28.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble; Water
• Apperance: white solid; White to Of-White Solid
• Melting Point: 150-152°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: WM5750000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Gene Information: human ... DRD2(1813), DRD4(1815), HTR2A(3356), HTR2B(3357), HTR7(3363)

Product Information

• Salt Data: Succinate
• Empirical Formula (Hill Notation): C18H18ClN3O · C4H6O4

DETAILS

Sigma Aldrich - L106

Biochem/physiol Actions
D2/D4 dopamine receptor antagonist; 5-HT2A/2B, 5-H7 serotonin receptor antagonist; dibenzoxazepine antipsychotic agent.

Toronto Research Chemicals - L472750

A D2/D4-Dopamine receptor antagonist. A serotonergic receptor antagonist. A dibenzoxazepine antipsychotic agent.

REFERENCES

• Shen, Y., et al.: J. Biol. Chem., 268, 18200 (1993)
• Fiorella, D., et al.: Psychopharmacology, 121, 347 (1993)
• Glusa, E., et al.: Br. J. Pharmacol., 130, 692 (2000)