(-)-Tetrabenazine

HCID 11634155
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Basic information

CAS
1026016-84-1
Standard SMILES
COc1cc2c(cc1OC)[C@@H]1CC(=O)[C@@H](CC(C)C)CN1CC2
InChIKey
MKJIEFSOBYUXJB-HOCLYGCPSA-N
Molecular formula
C19H27NO3
Average molar mass
317.4 g/mol
Monoisotopic mass
317.19909372

Overview

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

Names & identifiers

Preferred name
(-)-Tetrabenazine
IUPAC
(3S,11bS)-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)-, (3S,11bS)-
Molecular formula
C19H27NO3
Molecular weight
317.42

Names & synonyms

1026016-84-1(3S,11bS)-tetrabenazine(-)-tetrabenazine(3S,11bS)-3-Isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-oneTetrabenazine, (-)-(-)-Tbz(3S,11bS)-Tbz(3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one(3S,11bS)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one8A3NP33E5M(-)-Tetrabenazine (>75% ee)2H-BENZO[A]QUINOLIZIN-2-ONE, 1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-, (3R,11BR)-REL-
Show more names
75% ee)(3S,11bS)(-)-Tetrabenazine-d3(-)-Tetrabenazine (>(3S,11bS)-TetrabenazineTestosterone Impurity 39(3S,11bS)-Tetrabenazine-d72H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahyd
(-)-Ro 1-9569(3S,11bS)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one(3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3S,11bS)CAS-58-46-8(3S,5R,11bS)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one(S,S)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-oneTetrabenazinum [INN-Latin]

Database identifiers

CAS
1026016-84-1、58-46-8
PubChem CID
11634155
DTXSID
DTXSID0042614
ChEBI
CHEBI:64030
UNII
8A3NP33E5M、Z9O08YRN8O
Nikkaji
J2.792.295C

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
38.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
23

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
109 · 109-115°C
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility
Dichloromethane (Slightly), Chloroform (Slightly), Methanol (Slightly)
form
Solid
color
White to Off-White
FDA UNII
8 A3NP33E5M · 8A3NP33E5M

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

Chemistry & industry

Applications

Uses(-)-Tetrabenazine is a potent inhibitors of vascular monoamine transporter 2 (VMAT2) and may be applicable towards the treatment of chorea associated with Huntington’s disease.

Suppliers11 total

Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]
Aladdin Scientific[email protected]
南京药石科技股份有限公司4000255188 · [email protected]
泰州市众致生物科技有限公司[email protected] 15066129350 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]

Additional notes

DefinitionChEBI: 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 S configuration.

Related reactions

4 records
New reaction record

Compound notes

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