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T2952

Sigma-Aldrich

Tetrabenazine

≥98% (HPLC), 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
Beilstein:
40090
EC Number:
200-383-6
MDL number:
MFCD08461052
UNSPSC Code:
12352200
PubChem Substance ID:
329826731
NACRES:
NA.77

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

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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. 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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicolaas I Bohnen et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 32(8), 1609-1617 (2012-05-10)
Parkinson's disease (PD) is a multisystem neurodegenerative disorder. Heterogeneous clinical features may reflect heterogeneous changes in different brain regions. In contrast to the pronounced nigrostriatal denervation characteristic of PD, cholinergic changes are less marked. We investigated cholinergic innervation activity in
Mahabuba Jahan et al.
EJNMMI research, 1(1), 33-33 (2012-01-05)
Fluorine-18 dihydrotetrabenazine [DTBZ] analogues, which selectively target the vesicular monoamine transporter 2 [VMAT2], have been extensively studied for in vivo quantification of beta cell mass by positron-emission tomography [PET]. This study describes a novel deuterated radioligand [18F]fluoroethyl [FE]-DTBZ-d4, aimed to
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
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
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
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