10-[(3S)-1-azabicyclo[2.2.2]octan-3-yl(13C,2H2)methyl]-10H-phenothiazine

• ChemBase ID: 172676
• Molecular Formular: C20H22N2S
• Molecular Mass: 323.45973484
• Monoisotopic Mass: 323.15372455
• SMILES: c1ccc2c(c1)Sc1c(N2[13CH2][C@H]2[C@H]3CCN(CC3)C2)cccc1
• Canonical SMILES: c1ccc2c(c1)N([13CH2][C@@H]1CN3CC[C@H]1CC3)c1c(S2)cccc1
• InChI: InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2/t16-/m0/s1/i14+1
• InChIKey: HOKDBMAJZXIPGC-BOWKUJMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[(3S)-1-azabicyclo[2.2.2]octan-3-yl(^1^3C,^2H₂)methyl]-10H-phenothiazine
• IUPAC Traditional name: 10-[(1S,3S,4s)-1-azabicyclo[2.2.2]octan-3-yl(^1^3C,^2H₂)methyl]phenothiazine
• Synonyms: 10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine-13C,d2; 10-(3-Quinuclidinylmethyl)phenothiazine-13C,d2; Butix-13C,d2; Metaplexan-13C,d2; Mircol-13C,d2; NSC 303612-13C,d2; Nipolazin-13C,d2; Primalan-13C,d2; Quitadrill-13C,d2; Zesulan-13C,d2; rac Mequitazine-13C,d2

Database IDs

• PubChem SID: 164228586
• PubChem CID: 71749966

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2331452
• LogD (pH = 7.4): 2.961917
• Log P: 4.1948013
• Molar Refractivity: 99.0543 cm^3
• Polarizability: 38.214188 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 130-131°C

DETAILS

Toronto Research Chemicals - M225112

It is a labelled antihistamine.

REFERENCES

• Uzan, A., et al.: Xenobiotica, 6, 633 (1976)
• Persi, L., et al.: Alergy, 52, 451 (1976)
• Nakamura, K., et al.: J. Pharmacol. Exp. Ther., 284, 437 (1976)
• Theunissen, E., et al.: Clin. Exp. Allergy, 34, 250 (1976)