An active metabolite of tetrabenazine
Related Products
Isomer(s)
42116NBI 98782
Parent Compound(s)
20380Tetrabenazine
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Dihydrotetrabenazine

Item No. 27182

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol
CAS Number
3466-75-9
Synonyms
  • DTBZ
  • trans-(2,3)-Dihydro Tetrabenazine
Molecular Formula
C19H29NO3
Formula Weight
319.4
Purity
≥98% (mixture of isomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleMethanol: soluble
SMILES
OC1C(CC(C)C)CN2C(C(C=C(OC)C(OC)=C3)=C3CC2)C1
InChi Code
InChI=1S/C19H29NO3/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/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3
InChi Key
WEQLWGNDNRARGE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $134

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    1 mg

    $253

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    Product Description

    Dihydrotetrabenazine is an active metabolite of the vesicular monoamine transporter 2 (VMAT2) inhibitor tetrabenazine (Item No. 20380) that is generated by hepatic carbonyl reductases.1 Dihydrotetrabenazine binds to mouse pons medulla, hypothalamus, and striatum (Kds = 2.72, 2.28, and 2.4 nM, respectively) and inhibits synaptic vesicular serotonin (5-HT) uptake (IC50s = 2.2, 2.8, and 2.3 nM, respectively).2 It also binds to human caudate nucleus, hippocampus, and substantia nigra pars compacta (Kds = 2.9, 2.5, and 2.8 nM, respectively).3 Dihydrotetrabenazine stereoisomers bind to VMAT2 in rat striatum.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, J.J., Ondo, W.G., Dashtipour, K., et al. Tetrabenazine for the treatment of hyperkinetic movement disorders: A review of the literature. Clin. Ther. 34(7), 1487-1504 (2012).

    2. Scherman, D. Dihydrotetrabenazine binding and monoamine uptake in mouse brain regions. J. Neurochem. 47(2), 331-339 (1986).

    3. Scherman, D., Raisman, R., Ploska, A., et al. [3H]dihydrotetrabenazine, a new in vitro monoaminergic probe for human brain. J. Neurochem. 50(4), 1131-1136 (1988).

    4. Yao, Z., Wei, X., Wu, X., et al. Preparation and evaluation of tetrabenazine enantiomers and all eight stereoisomers of dihydrotetrabenazine as VMAT2 inhibitors. Eur. J. Med. Chem. 46(5), 1841-1848 (2011).