N-(4-{2-[(2S,6R)-12-cyano-8-oxa-4-azatricyclo[7.4.0.02,6]trideca-1(13),9,11-trien-4-yl]ethyl}phenyl)acetamide

• ChemBase ID: 177666
• Molecular Formular: C22H23N3O2
• Molecular Mass: 361.43692
• Monoisotopic Mass: 361.17902699
• SMILES: c1(ccc2c(c1)[C@@H]1[C@@H](CO2)CN(C1)CCc1ccc(cc1)NC(=O)C)C#N
• Canonical SMILES: N#Cc1ccc2c(c1)[C@H]1CN(C[C@@H]1CO2)CCc1ccc(cc1)NC(=O)C
• InChI: InChI=1S/C22H23N3O2/c1-15(26)24-19-5-2-16(3-6-19)8-9-25-12-18-14-27-22-7-4-17(11-23)10-20(22)21(18)13-25/h2-7,10,18,21H,8-9,12-14H2,1H3,(H,24,26)/t18-,21+/m1/s1
• InChIKey: ZDZWIQDJFWTDAM-NQIIRXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-{2-[(2S,6R)-12-cyano-8-oxa-4-azatricyclo[7.4.0.0^2,^6]trideca-1(13),9,11-trien-4-yl]ethyl}phenyl)acetamide
• IUPAC Traditional name: N-(4-{2-[(2S,6R)-12-cyano-8-oxa-4-azatricyclo[7.4.0.0^2,^6]trideca-1(13),9,11-trien-4-yl]ethyl}phenyl)acetamide
• Synonyms: rel-N-[4-[2-[(3aS,9bR)-8-Cyano-1,3a,4,9b-tetrahydro[1]benzopyrano[3,4-c]pyrrol-2(3H)-yl]ethyl]phenyl]acetamide; rac S 33138

Database IDs

• CAS Number: 220647-56-3
• PubChem SID: 164233576
• PubChem CID: 9820327

CALCULATED PROPERTIES

• Acid pKa: 14.655187
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.79837173
• LogD (pH = 7.4): 0.6194844
• Log P: 2.5324414
• Molar Refractivity: 106.5513 cm^3
• Polarizability: 40.110676 Å^3
• Polar Surface Area: 65.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S080700

A preferential dopamine D3 versus D2 receptor antagonist and potential antipsychotic agent; it does not interact with histamine H1 and muscarinic receptors.

REFERENCES

• Ichikawa, J., et al.: Brain Res., 939, 34 (2002)
• Clements, R., et al.: Neuropharmacology, 49, 1007 (2002)
• Day, M., et al.: Biochem. Pharmacol., 73, 1123 (2002)
• Gyertyan, I., et al.: Eur. J. Pharmacol., 572, 171 (2002)
• Millan, M., et al.: J. Pharmacol.