9,10-dimethoxy-3-[2-(2H3)methyl(3,3,3-2H3)propyl]-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

• ChemBase ID: 178236
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: c1(c(cc2c(c1)C1N(CC2)CC(C(=O)C1)CC(C)C)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
• InChI: InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3
• InChIKey: MKJIEFSOBYUXJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9,10-dimethoxy-3-[2-(^2H₃)methyl(3,3,3-^2H₃)propyl]-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
• IUPAC Traditional name: 9,10-dimethoxy-3-[2-(^2H₃)methyl(3,3,3-^2H₃)propyl]-1H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
• Synonyms: (3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl-d6)-2H-benzo[a]quinolizin-2-one; cis-2-Oxo-3-(isobutyl-d6)-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine; (+/-)-Tetrabenazine-d6; NSC 169886-d6; NSC 172187-d6; Ro 1-9569-d6; Rubigen-d6; Tetrabenazine-d6

Database IDs

• PubChem SID: 164234146
• PubChem CID: 71752399

CALCULATED PROPERTIES

• Acid pKa: 18.239992
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.4955962
• LogD (pH = 7.4): 3.094543
• Log P: 3.4010618
• Molar Refractivity: 91.3074 cm^3
• Polarizability: 35.678963 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T284002

Labelled Tetrabenazine. Dopamine depleting agent. An antidyskinetic; antipsychotic.

REFERENCES

• Schwartz, et al.: Biochem. Pharmacol., 15, 645 (1966)
• Janovic, J., et al.: Ann. Neurol., 11, 41 (1966)
• Janovic, J., et al.: Neurology, 38, 391 (1966)