Dihydrotetrabenazine

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Dihydrotetrabenazine
DTBZ ambiguous.svg
Identifiers
3466-75-9
ChemSpider 110379 YesY
Jmol 3D model Interactive image
  • 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
    Key: WEQLWGNDNRARGE-UHFFFAOYSA-N
  • COC1=C(OC)C=C(C(CC(O)C(CC(C)C)C2)N2CC3)C3=C1
Properties
C19H29NO3
Molar mass 319.45 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dihydrotetrabenazine or DTBZ is an organic compound with the chemical formula C19H29NO3. It is a close analog of tetrabenazine. DTBZ and its derivatives, when labeled with positron emitting isotopes such as carbon-11 and fluorine-18, are used as PET radioligands for examining VMAT2.[1]

Use in Positron Emission Tomography

Carbon-11 labeled (+)DTBZ(right) and fluorine-18 labeled fluoropropylated (+)DTBZ(left)
Reconstructed data from PET scan of healthy human brain using [18F]Fluoropropyl-DTBZ indicating VMAT2 distribution[2]

[11C]DTBZ as a PET radioligand with affinity for VMAT2 was developed in the mid 1990s by David E. Kuhl and colleagues at the University of Michigan.[3] There are two enantiomers of alpha-dihydrotetrabenazine, and the dextrorotary(or (+) isomer) has a high affinity of about 1 nanomolar Ki whereas the levorotary (or (-) isomer) has approximately 1000 fold lower affinity with a Ki of about 2 micromolar.[4]

VMAT2 is a membrane bound protein and a biomarker for Parkinson's disease. Binding of DTBZ to VMAT2 in individuals with Parkinson's disease is significantly reduced.[5] Moreover, the VMAT2 density as determined by [18F]DTBZ has been shown to be well, inversely correlated with the severity of Parkinson's disease.[6]

Avid Radiopharmaceuticals is sponsoring clinical trials of [18F]AV-133 (or [18F]Fluoropropyl-(+)-DTBZ) to identify subjects with dopaminergic degeneration.[7]

See also

References

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