(3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

• ChemBase ID: 154021
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: CC(C)C[C@@H]1CN2CCc3cc(c(cc3[C@H]2CC1=O)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)CCN1[C@@H]2CC(=O)[C@@H](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/t14-,16-/m1/s1
• InChIKey: MKJIEFSOBYUXJB-GDBMZVCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
• IUPAC Traditional name: (+)-tetrabenazine
• Synonyms: 9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one; Tetrabenazine

Database IDs

• CAS Number: 58-46-8
• EC Number: 200-383-6
• MDL Number: MFCD08461052
• Beilstein Number: 40090
• PubChem SID: 162248160
• PubChem CID: 667453

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

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: solid

Safety Information

• RTECS: DK2275000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H27NO3

DETAILS

Sigma Aldrich - T2952

Biochem/physiol Actions
Tetrabenazine is a reversible type 2 vesicular monoamine transporter (VMAT) inhibitor. It depletes dopamine stores.