Dihydrotetrabenazine

For research use only. Not for therapeutic Use.

  • CAT Number: M020143
  • CAS Number: 3466-75-9
  • Molecular Formula: C19H29NO3
  • Molecular Weight: 319.44
  • Purity: ≥95%
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Dihydrotetrabenazine (Cat No.:M020143) is a chemical compound that acts as a reversible inhibitor of vesicular monoamine transporter 2 (VMAT2). It is used in the treatment of various neurological and psychiatric disorders, including Huntington’s disease and tardive dyskinesia. By inhibiting VMAT2, dihydrotetrabenazine reduces the uptake of neurotransmitters such as dopamine into synaptic vesicles, leading to a decrease in the release of these neurotransmitters. This can help alleviate symptoms associated with excessive dopamine activity, such as involuntary movements in tardive dyskinesia. Dihydrotetrabenazine plays a crucial role in managing these challenging conditions by regulating neurotransmitter levels in the brain.


Catalog Number M020143
CAS Number 3466-75-9
Synonyms

(+)-ALPHA-DIHYDROTETRABENAZINE;2H-BENZO[A]QUINOLIZINE-2-OL, 1,3,4,6,7,11B-HEXAHYDRO-3-ISOBUTYL-9,10-DIMETHOXY-;DIHYDROTETRABENAZINE;DTBZ;2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-;1,3,4,6,7,11b-Hexahydro-9,10-dimet

Molecular Formula C19H29NO3
Purity ≥95%
Storage Store at -20°C
IUPAC Name 9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol
InChI 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
InChIKey WEQLWGNDNRARGE-UHFFFAOYSA-N
SMILES CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1O)OC)OC
Reference

1: Skor H, Smith EB, Loewen G, O/’Brien CF, Grigoriadis DE, Bozigian H.
Differences in Dihydrotetrabenazine Isomer Concentrations Following
Administration of Tetrabenazine and Valbenazine. Drugs R D. 2017 Aug 3. doi:
10.1007/s40268-017-0202-z. [Epub ahead of print] PubMed PMID: 28776237; PubMed
Central PMCID: PMC5629142.

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2: Weng CC, Chen ZA, Chao KT, Ee TW, Lin KJ, Chan MH, Hsiao IT, Yen TC, Kung MP,
Hsu CH, Wey SP. Quantitative analysis of the therapeutic effect of magnolol on
MPTP-induced mouse model of Parkinson/’s disease using in vivo
18F-9-fluoropropyl-(+)-dihydrotetrabenazine PET imaging. PLoS One. 2017 Mar
3;12(3):e0173503. doi: 10.1371/journal.pone.0173503. eCollection 2017. PubMed
PMID: 28257461; PubMed Central PMCID: PMC5336287.
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3: Ding D, Nickell JR, Dwoskin LP, Crooks PA. Quinolyl analogues of norlobelane:
novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine
uptake at the vesicular monoamine transporter-2. Bioorg Med Chem Lett. 2015 Jul
1;25(13):2613-6. doi: 10.1016/j.bmcl.2015.04.105. Epub 2015 May 9. PubMed PMID:
25991431; PubMed Central PMCID: PMC4457633.
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4: Collantes M, Barajas M, Quincoces G, Ramos-Membrive R, Martí-Climent JM, Ecay
M, Rodríguez S, Escalada J, Pe&#241;uelas I. Lessons from 11C-dihydrotetrabenazine
imaging in a xenograft mouse model of rat insulinoma: is PET imaging of
pancreatic beta cell mass feasible? Q J Nucl Med Mol Imaging. 2017
Dec;61(4):447-455. doi: 10.23736/S1824-4785.17.02803-5. Epub 2015 Apr 17. PubMed
PMID: 25881691.
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5: Kumar A, Lo ST, &#214;z OK, Sun X. Derivatization of (±) dihydrotetrabenazine for
copper-64 labeling towards long-lived radiotracers for PET imaging of the
vesicular monoamine transporter 2. Bioorg Med Chem Lett. 2014 Dec
15;24(24):5663-5665. doi: 10.1016/j.bmcl.2014.10.070. Epub 2014 Oct 28. PubMed
PMID: 25467156; PubMed Central PMCID: PMC4341964.
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6: Li X, Chen Z, Tang J, Liu C, Zou P, Huang H, Tan C, Yu H. Synthesis and
biological evaluation of 10-(11) C-dihydrotetrabenazine as a vesicular monoamine
transporter 2 radioligand. Arch Pharm (Weinheim). 2014 May;347(5):313-9. doi:
10.1002/ardp.201300307. Epub 2014 Feb 3. PubMed PMID: 24497196.
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7: Liu C, Chen Z, Li X, Tang J, Qin X. (+)-9-Benzyloxy-α-dihydrotetrabenazine as
an important intermediate for the VMAT2 imaging agents: absolute configuration
and chiral recognition. Chirality. 2013 Apr;25(4):215-23. doi:
10.1002/chir.22126. PubMed PMID: 23532997.

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