10-[3-(dimethylamino)propyl]-2-(1-hydroxyethyl)-10H-5λ4,10-phenothiazin-5-one

• ChemBase ID: 170580
• Molecular Formular: C19H24N2O2S
• Molecular Mass: 344.47106
• Monoisotopic Mass: 344.15584902
• SMILES: c1ccc2c(c1)S(=O)c1c(N2CCCN(C)C)cc(cc1)C(O)C
• Canonical SMILES: CN(CCCN1c2ccccc2S(=O)c2c1cc(cc2)C(O)C)C
• InChI: InChI=1S/C19H24N2O2S/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)24(19)23/h4-5,7-10,13-14,22H,6,11-12H2,1-3H3
• InChIKey: PMRKLUFRQDNKCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[3-(dimethylamino)propyl]-2-(1-hydroxyethyl)-10H-5λ^4,10-phenothiazin-5-one
• IUPAC Traditional name: 10-[3-(dimethylamino)propyl]-2-(1-hydroxyethyl)-5λ^4,10-phenothiazin-5-one
• Synonyms: 10-[3-(Dimethylamino)propyl]-α-methyl-10H-phenothiazine-2-methanol 5-Oxide; 2-(1-Hydroxyethyl) Promazine Sulfoxide (mixture of diastereomers)

Database IDs

• CAS Number: 73644-42-5
• PubChem SID: 164226490
• PubChem CID: 71749043

CALCULATED PROPERTIES

• Acid pKa: 14.753878
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.8804183
• LogD (pH = 7.4): 0.7953928
• Log P: 2.2060387
• Molar Refractivity: 101.5579 cm^3
• Polarizability: 39.12422 Å^3
• Polar Surface Area: 43.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 148-152°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - H942290

A metabolite of Promazine (P756300).

REFERENCES

• Dewey, E.A., et al.: Drug Metab. Dispos., 9, 30 (1981)
• Kronstrand, R., et al.: J. Anal. Toxicol., 27, 464 (1981)