(2S,3S,11bS)-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-ol

• ChemBase ID: 167729
• Molecular Formular: C19H29NO3
• Molecular Mass: 319.43846
• Monoisotopic Mass: 319.21474379
• SMILES: c1(c(cc2c(c1)[C@H]1N(CC2)C[C@@H]([C@H](C1)O)CC(C)C)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)CCN1[C@H]2C[C@H](O)[C@H](C1)CC(C)C
• InChI: InChI=1S/C19H29NO3/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/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16-,17-/m0/s1
• InChIKey: WEQLWGNDNRARGE-XIRDDKMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,11bS)-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-ol
• IUPAC Traditional name: (2S,3S,11bS)-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-ol
• Synonyms: (2R,3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl-d6)-2H-benzo[a]quinolizin-2-ol; (2α,3β,11bβ)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl-d6)-2H-benzo[a]quinolizin-2-ol; trans (2,3)-Dihydro Tetrabenazine-d6

Database IDs

• CAS Number: 1346604-77-0
• PubChem SID: 162261862
• PubChem CID: 71316205

CALCULATED PROPERTIES

• Acid pKa: 14.847957
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.020527132
• LogD (pH = 7.4): 1.752485
• Log P: 2.6724951
• Molar Refractivity: 92.3982 cm^3
• Polarizability: 36.226173 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449657

A labelled metabolite of Tetrabenazine in vivo. The trans izomer of Dihydrotetrabenazine is used for the treatment of hyperkinetic movement disorders.

REFERENCES

• Kilbourn, M., et al.: Eur. J. Pharmacol., 278, 249 (1995)
• Perera, R., et al.: J. Med. Chem., 46, 2599 (1995)
• Mager, D., et al.: J. Pharm. Sci., 94, 2475 (1995)
• Zheng, G., et al.: Bioorg. Med. Chem., 16, 5018 (1995)