(2Z)-2-{3-[bis(2H3)methylamino]propylidene}tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol

• ChemBase ID: 170397
• Molecular Formular: C20H21NO
• Molecular Mass: 291.38684
• Monoisotopic Mass: 291.1623143
• SMILES: C\1(=C/CCN(C)C)/c2c(C=Cc3c1cccc3)ccc(c2)O
• Canonical SMILES: CN(CC/C=C\1/c2ccccc2C=Cc2c1cc(O)cc2)C
• InChI: InChI=1S/C20H21NO/c1-21(2)13-5-8-19-18-7-4-3-6-15(18)9-10-16-11-12-17(22)14-20(16)19/h3-4,6-12,14,22H,5,13H2,1-2H3/b19-8-
• InChIKey: UHLPYBQGKLHIFK-UWVJOHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2-{3-[bis(^2H₃)methylamino]propylidene}tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol
• IUPAC Traditional name: (2Z)-2-{3-[bis(^2H₃)methylamino]propylidene}tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-ol
• Synonyms: 5-[3-(Dimethylamino)propylidene]-5H-dibenzo[a,d]cyclohepten-3-ol-d6; 3-Hydroxy Cyclobenzaprine-d6

Database IDs

• PubChem SID: 164226307
• PubChem CID: 71748957

CALCULATED PROPERTIES

• Acid pKa: 9.215558
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.8836396
• LogD (pH = 7.4): 2.008798
• Log P: 3.4322684
• Molar Refractivity: 104.6047 cm^3
• Polarizability: 35.87688 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H926002

A labelled metabolite of Cyclobenzaprine (C987750).

REFERENCES

• Hucker, H.B., et al.: Drug Metab. Dispos., 6, 184-92 (1978)