(2Z)-but-2-enedioic acid; [(2S)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine

• ChemBase ID: 166729
• Molecular Formular: C23H28N2O5S
• Molecular Mass: 444.54382
• Monoisotopic Mass: 444.17189301
• SMILES: c1ccc2c(c1)N(c1c(S2)ccc(c1)OC)C[C@H](CN(C)C)C.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.COc1ccc2c(c1)N(C[C@H](CN(C)C)C)c1c(S2)cccc1
• InChI: InChI=1S/C19H24N2OS.C4H4O4/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21;5-3(6)1-2-4(7)8/h5-11,14H,12-13H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-;/m0./s1
• InChIKey: IFLZPECPTYCEBR-FXSDFHGDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; [(2S)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine
• IUPAC Traditional name: [(2S)-3-(2-methoxyphenothiazin-10-yl)-2-methylpropyl]dimethylamine; maleic acid
• Synonyms: (+)-10-[3-(Dimethylamino)-2-methylpropyl]-2-methoxyphenothiazine; (+)-Methotrimeprazine; Dextromepromazine; d-Methotrimeprazine; Dextro Mepromazine Maleate; (βS)-2-Methoxy-N,N,β-trimethyl-10H-phenothiazine-10-propanamine

Database IDs

• PubChem SID: 162260862
• PubChem CID: 71315857

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.89110804
• LogD (pH = 7.4): 2.2412717
• Log P: 4.252608
• Molar Refractivity: 99.8311 cm^3
• Polarizability: 38.484814 Å^3
• Polar Surface Area: 15.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D299250

The (S) optical isomer of Methotrimeprazine (M260785), an analgesic/neuroleptic.

REFERENCES

• Kandagal, P., et al.: J. Pharm. Biomed. Anal., 47, 260 (2008)
• Iorns, E., et al.: Biochem. J., 417, 361 (2008)