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Merck

T2952

Tetrabenazine

≥98% (HPLC), VMAT inhibitor, solid

Synonym(s):

9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-(rel 3R,11bR)-2H-benzo[a]quinolizin-2-one

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About This Item

Empirical Formula (Hill Notation):
C19H27NO3
CAS Number:
58-46-8
Molecular Weight:
317.42
NACRES:
NA.77
PubChem Substance ID:
329826731
UNSPSC Code:
12352200
EC Number:
200-383-6
MDL number:
MFCD08461052
Beilstein/REAXYS Number:
40090
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Tetrabenazine, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL, H2O: insoluble

originator

Roche

storage temp.

2-8°C

SMILES string

COc1cc2CCN3C[C@@H](CC(C)C)C(=O)CC3c2cc1OC

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

InChI key

MKJIEFSOBYUXJB-GDBMZVCRSA-N

Related Categories

Application

Tetrabenazine has been used for dopamine uptake assays in mouse brain cells1. Tetrabenazine has also been used for non-specific binding assays in postnuclear supernatants derived from PC-12 and CV-1 cells2.

Biochem/physiol Actions

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

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Tetrabenazine is soluble in DMSO at a concentration that is greater than 10 mg/ml and is insoluble in water.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000344938
0000344938
0000190435
0000190435
0000136427

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Yelena Ugolev et al.
The Journal of biological chemistry, 288(45), 32160-32171 (2013-09-26)
Vesicular monoamine transporter 2 (VMAT2) transports monoamines into storage vesicles in a process that involves exchange of the charged monoamine with two protons. VMAT2 is a member of the DHA12 family of multidrug transporters that belongs to the major facilitator
S A Stuart et al.
British journal of pharmacology, 174(19), 3200-3210 (2017-08-07)
Predicting the risk of drug-induced adverse psychiatric effects is important but currently not possible in non-human species. We investigated whether the affective bias test (ABT) could provide a preclinical method with translational and predictive validity. The ABT is a bowl-digging
Vikas Kotagal et al.
Neurology, 82(17), 1514-1520 (2014-04-01)
Cardiovascular comorbidities associate with neurodegeneration in the elderly and may contribute to extranigral pathologies and medically refractory axial motor features in Parkinson disease (PD). We explored differences in the estimated rate of axial motor feature accrual between patients with PD
Catarina A Owesson-White et al.
Journal of neurochemistry, 121(2), 252-262 (2012-02-03)
Mesolimbic dopamine neurons fire in both tonic and phasic modes resulting in detectable extracellular levels of dopamine in the nucleus accumbens (NAc). In the past, different techniques have targeted dopamine levels in the NAc to establish a basal concentration. In
Michael P Dalton et al.
eLife, 12 (2024-03-22)
The vesicular monoamine transporter 2 (VMAT2) is a proton-dependent antiporter responsible for loading monoamine neurotransmitters into synaptic vesicles. Dysregulation of VMAT2 can lead to several neuropsychiatric disorders including Parkinson's disease and schizophrenia. Furthermore, drugs such as amphetamine and MDMA are
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