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?????? ??? ???
?? ??:
58-46-8
???:
??????
???(??):
??????;??????????
???:
Tetrabenazine
???(??):
Xenazine;1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one;Nitoman;Rubigen;Ro 1-9569;Tetrabezine;TETRABENAZINE;(3R,11bR)-rel-;butylbenzeneazine;TBZ,racemic mixture
CBNumber:
CB5339246
???:
C19H27NO3
??? ??:
317.42
MOL ??:
58-46-8.mol
MSDS ??:
SDS

?????? ??

???
128-130C
?? ?
456.71°C (rough estimate)
??
1.12
???
1.5180 (estimate)
?? ??
2-8°C
???
DMSO: >10mg/mL
??? ??
??
??? ??
??? ??
?? ?? (pKa)
6.46±0.40(Predicted)
??
???
Merck
14,9182
BRN
40090
???
??? ?? ?????? 1? ?? ??????. DMSO ?? ??? ??? -20°?? ?? 1?? ?? ??? ? ????.
InChI
InChI=1/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-/s3
InChIKey
MKJIEFSOBYUXJB-UHFFFAOYSA-N
SMILES
C12=CC(OC)=C(OC)C=C1CCN1[C@]2([H])CC(=O)[C@H](CC(C)C)C1 |&1:13,18,r|
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xn
?? ???? ?? 22
????? 24/25
????(UN No.) 3249
WGK ?? 3
RTECS ?? DK2275000
?? ?? 6.1(b)
???? III
HS ?? 29339900
???? ??? 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Oral
?? ?? ??? 58-46-8(Hazardous Substances Data)
????(GHS): Exclamation Mark (GHS07)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H302 ??? ??? ?? ?? ?? - ?? ?? 4 ?? P264, P270, P301+P312, P330, P501
??????:
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P270 ? ??? ??? ??? ???, ???? ???? ???.
P301+P312 ??? ???? ??? ????(??)? ??? ????.
P501 ...? ??? / ??? ?? ???.
NFPA 704
0
1 0

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White to Off-White Solid

??

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.

??

ChEBI: A benzoquinolizine that is 1,2,3,4,4a,9,10,10a-octahydrophenanthrene in which the carbon at position 10a is replaced by a nitrogen and which is substituted by an isobutyl group at position 2, an oxo group at position 3, and methoxy groups at positions 6 an 7.

?? ??

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.

???? ??

Potent inhibitor of vesicular monoamine uptake; depletes stores of dopamine, serotonin and noradrenalin. Binds with high affinity (IC 50 = 3.2 nM) to vesicular monoamine transporter (VMAT) in chromaffin granule membranes and displays higher affinity for VMAT2 than VMAT1. Also reported to block dopamine receptors. Causes behavioral depression; inhibits locomotor activity and produces hypothermia upon systemic administration in rats and mice.

Purification Methods

Crystallise it from MeOH. The hydrochloride has m 208-210o, and the oxime has m 158o (from EtOH). [Beilstein 21 III/IV 6488.]

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