(2Z)-but-2-enedioic acid; 1-(10-{3-[bis(2H3)methylamino]propyl}-10H-phenothiazin-2-yl)ethan-1-one

• ChemBase ID: 158843
• Molecular Formular: C23H26N2O5S
• Molecular Mass: 442.52794
• Monoisotopic Mass: 442.15624294
• SMILES: c1cccc2c1N(c1c(S2)ccc(c1)C(=O)C)CCCN(C)C.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CN(CCCN1c2ccccc2Sc2c1cc(cc2)C(=O)C)C
• InChI: InChI=1S/C19H22N2OS.C4H4O4/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)23-19;5-3(6)1-2-4(7)8/h4-5,7-10,13H,6,11-12H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: FQRHOOHLUYHMGG-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 1-(10-{3-[bis(^2H₃)methylamino]propyl}-10H-phenothiazin-2-yl)ethan-1-one
• IUPAC Traditional name: 1-(10-{3-[bis(^2H₃)methylamino]propyl}phenothiazin-2-yl)ethanone; maleic acid
• Synonyms: 1-[10-[3-(Dimethylamino-d6)propyl]-10H-phenothiazin-2-yl]ethanone (2Z)-2-Butenedioate; 10-[3-(Dimethylamino-d6)propyl]phenothiazin-2-yl Methyl Ketone Maleate; Acepran-d6; Acepromazine-d6 Monomaleate; Acetylpromazine-d6 Maleate; Anatran-d6; Atravet-d6; Calmivet-d6; NSC 264522-d6; Notensil-d6; Notenzil-d6; Plegicil-d6; Sedalin-d6; Soprontin-d6; Acepromazine-d6 Maleate

Database IDs

• PubChem SID: 162252978
• PubChem CID: 71312711

CALCULATED PROPERTIES

• Acid pKa: 16.055948
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.6094632
• LogD (pH = 7.4): 2.3599155
• Log P: 3.488603
• Molar Refractivity: 99.3543 cm^3
• Polarizability: 37.856915 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A130902

Labelled Acepromazine (A130900). A tranquilizer.

REFERENCES

• Wirth, W., et al.: Arch. Int. Pharmacodyn, 123, 78 (1959)
• Dyson, H., et al.: Can.Vet. J., 33, 462 (1959)