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Merck

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:
Peso molecular:
317.42
Beilstein/REAXYS Number:
40090
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

signalword

Warning

hcodes

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


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Joseph Jankovic et al.
Expert review of neurotherapeutics, 11(11), 1509-1523 (2011-10-22)
Tetrabenazine (TBZ; Xenazine) is a potent, selective, reversible depletor of monoamines from nerve terminals. TBZ inhibits the vesicular monoamine transporter type 2 which, in humans, is expressed nearly exclusively in the brain. TBZ is rapidly metabolized in the liver by
Hongyu Wang et al.
Molecular neurodegeneration, 5, 18-18 (2010-04-28)
Huntington's disease (HD) is a neurodegenerative disorder caused by a polyglutamine (polyQ) expansion in Huntingtin protein (Htt). PolyQ expansion in Httexp causes selective degeneration of striatal medium spiny neurons (MSN) in HD patients. A number of previous studies suggested that
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
Nicolaas I Bohnen et al.
Neurology, 81(18), 1611-1616 (2013-10-01)
We investigated dopaminergic and cholinergic correlates of gait speed in Parkinson disease (PD) and non-PD control subjects to test the hypothesis that gait dysfunction in PD may result from multisystem degeneration. This was a cross-sectional study. Subjects with PD but
Roger L Albin et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 54(6), 887-893 (2013-04-11)
We evaluated PET-based classification of neurodegenerative pathology in mild cognitive impairment (MCI). Our study was a cross-sectional and prospective evaluation of a cohort of 27 MCI subjects drawn from a university-based cognitive disorders clinic. We compared expert clinical consensus classification

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