CAS 1026016-83-0 (3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-one (HCID 667453)

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Basic information

CAS: 1026016-83-0
Standard SMILES: COc1cc2c(cc1OC)[C@H]1CC(=O)[C@H](CC(C)C)CN1CC2
InChIKey: MKJIEFSOBYUXJB-GDBMZVCRSA-N
Molecular formula: C19H27NO3
Average molar mass: 317.4 g/mol
Monoisotopic mass: 317.19909372

Overview

(3R,11bR)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one is a 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one in which both stereocentres have R configuration. It is an enantiomer of a (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one.

Names & identifiers

Preferred name: (3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-one
IUPAC: (3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
English name: 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3R,11bR)-
Molecular formula: C19H27NO3
Molecular weight: 317.42

Names & synonyms

(+)-Tetrabenazine1026016-83-0(3R,11Br)-TetrabenazineTetrabenazine, (+)-(3R,11bR)-Tbz69ENL3U6BFDTXSID101117156(3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-one2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3R,11bR)-(3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-oneTetrabenazine R,R-RefChem:1050259

Show more names

11bR)-TBZ11bR)-Tetrabenazine(+)-Tetrabenazine (TBZ)(+)-Tetrabenazine, 10 mM in DMSO(+) Tetrabenazine,(+)Tetrabenazine(3R11BR)-TBZ(3R11BR)-TETRABENAZINE

DTXCID501548729Tetrabenazine (+)-(3R,11bR)-3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one(+)-TbzTetrabenazine R,R-form [MI]MFCD08461052CHEMBL61636(3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 38.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 23
Formal charge: 0
Complexity: 425

Experimental & physicochemical properties

LogP2.99

Physicochemical properties

Melting point: 108 · 108-110 °C
Boiling point: 448.9 · 448.9±45.0 °C(Predicted)
Density: 1.12 · 1.12
storage temp.: Inert atmosphere,Room Temperature
solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
pka: 6.46 · 6.46±0.40(Predicted)
form: Solid
color: White
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
SMILES: C12=CC(OC)=C(OC)C=C1CCN1[C@]2([H])CC(=O)[C@H](CC(C)C)C1
FDA UNII: 69 ENL3U6BF · 69ENL3U6BF

Safety & regulation

Safety data

Signal word: warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P264-P270-P301+P312-P330-P501-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405