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Merck
CN

5.09892

Tetrabenazine, TBZ

Synonym(s):

Tetrabenazine, TBZ, VMAT2 Inhibitor, Xenazine

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About This Item

Empirical Formula (Hill Notation):
C19H27NO3
CAS Number:
Molecular Weight:
317.42
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
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SMILES string

N21C(CC(=O)C(C2)CC(C)C)c3c(cc(c(c3)OC)OC)CC1

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

InChI key

MKJIEFSOBYUXJB-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

DMSO: 25 mg/mL

storage temp.

2-8°C

Quality Level

Biochem/physiol Actions

Primary Target
VMAT2
Reversible: yes

Disclaimer

Toxicity: Harmful (C)

General description

A cell permeable benzoquinolizine based compound that acts as a monoamine-depleting agent by blocking the activity vesicular monoamine transporter 2. Promotes late-stage differentiation of Pdx1-positive pancreatic progenitor cells into Neurog3 (Ngn3)-positive endocrine precursors without increasing their proliferation. Increases the number of insulin expressing cells in a dose dependent manner (EC50 = 220 nM) and this effect is significantly enhanced when cells are simultaneously treated with dibutyryl cAMP. Embryonic stem cells treated with TBZ and/or dibutyryl cAMP and then grafted into kidney capsule of AKITA mice reduce hyperglycemia, improve fasting blood glucose levels, and show an increase in plasma C-peptide levels.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Other Notes

Sakano, D., et al. 2014. Nat. Chem. Bio.10,141.

Jankovic, J., et al. 1997. Neurobiology48,1358.
Gertrude, P.Q., et al. 1959. J. Pharm. Exp. Ther.127, 103.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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