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T2952

Sigma-Aldrich

Tetrabenazine

≥98% (HPLC), solid

Sinónimos:

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

Fórmula empírica (notación de Hill):
C19H27NO3
Número de CAS:
58-46-8
Peso molecular:
317.42
Beilstein/REAXYS Number:
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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Victor L Villemagne et al.
Neuro-degenerative diseases, 10(1-4), 161-165 (2012-01-21)
The noninvasive evaluation of nigrostriatal dopaminergic integrity by PET can provide useful information for the differential diagnosis between dementia with Lewy bodies (DLB) and Alzheimer's disease (AD). To evaluate the diagnostic potential of imaging striatal monoaminergic terminal integrity with the
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
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
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
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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