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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:48:25 UTC
HMDB IDHMDB0015592
Secondary Accession Numbers
  • HMDB15592
Metabolite Identification
Common NameTetrabenazine
DescriptionTetrabenazine, also known as nitoman or xenazine, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Tetrabenazine is a very strong basic compound (based on its pKa). 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 and 7.
Structure
Data?1582753314
Synonyms
ValueSource
1,2,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-oneChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11BH-benzo[a]quinolizineChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizineChEBI
NitomanKegg
XenazineKegg
Ro 1-9569HMDB
TBZHMDB
Tetra benazinHMDB
TetrabenzaineHMDB
TetrabenzineHMDB
Tetrabenazine orphan brandHMDB
Cambridge laboratories brand OF tetrabenazineHMDB
Orphan brand OF tetrabenazineHMDB
Roche brand OF tetrabenazineHMDB
Shire brand OF tetrabenazineHMDB
TetrabenazineMeSH
Chemical FormulaC19H27NO3
Average Molecular Weight317.4226
Monoisotopic Molecular Weight317.199093735
IUPAC Name9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
Traditional Nametetrabenazine
CAS Registry Number58-46-8
SMILES
COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1
InChI Identifier
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 KeyMKJIEFSOBYUXJB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • Piperidinone
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Cyclic ketone
  • Ether
  • Azacycle
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point128 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.36 g/LNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM182.630932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP10(3.23) g/LALOGPS
logP10(3.4) g/LChemAxon
logS10(-2.9) g/LALOGPS
pKa (Strongest Acidic)18.24ChemAxon
pKa (Strongest Basic)7.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.31 m³·mol⁻¹ChemAxon
Polarizability36.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.40331661259
DarkChem[M-H]-172.02731661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetrabenazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-4292000000-399e16e38421335dc45d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrabenazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrabenazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 10V, Positive-QTOFsplash10-014i-0019000000-02d6ea72dcc42a44288e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 20V, Positive-QTOFsplash10-014i-5269000000-f1240b2a09dcced1c8992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 40V, Positive-QTOFsplash10-0a4i-9430000000-cd11325cad96834bf22b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 10V, Negative-QTOFsplash10-014i-0009000000-484fd7bae49c0273c3172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 20V, Negative-QTOFsplash10-014j-7059000000-cbb7a83dafd4d674e7532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 40V, Negative-QTOFsplash10-0uec-9270000000-5581f9758fcb31092e0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 10V, Positive-QTOFsplash10-014i-0009000000-0041714e9cb69e8982f22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 20V, Positive-QTOFsplash10-014i-0039000000-7d6e398b5d4a2227026e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 40V, Positive-QTOFsplash10-052f-9281000000-0c9b09c6cde8e368ca062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 10V, Negative-QTOFsplash10-014i-0009000000-f61e4684d2f91b1d10d62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 20V, Negative-QTOFsplash10-014i-0029000000-f7a121501bdf247273bc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrabenazine 40V, Negative-QTOFsplash10-03di-1297000000-9bf4c9dd8adc56e35bd72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04844 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04844 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04844
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5796
KEGG Compound IDC11168
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrabenazine
METLIN IDNot Available
PubChem Compound6018
PDB IDNot Available
ChEBI ID64028
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. [PubMed:9040721 ]
  2. Guay DR: Tetrabenazine, a monoamine-depleting drug used in the treatment of hyperkinetic movement disorders. Am J Geriatr Pharmacother. 2010 Aug;8(4):331-73. doi: 10.1016/j.amjopharm.2010.08.006. [PubMed:20869622 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Poon LH, Kang GA, Lee AJ: Role of tetrabenazine for Huntington's disease-associated chorea. Ann Pharmacother. 2010 Jun;44(6):1080-9. doi: 10.1345/aph.1M582. Epub 2010 May 4. [PubMed:20442355 ]
General function:
Involved in transmembrane transport
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
References
  1. Zheng G, Dwoskin LP, Crooks PA: Vesicular monoamine transporter 2: role as a novel target for drug development. AAPS J. 2006 Nov 10;8(4):E682-92. [PubMed:17233532 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Kim YS, Shin JH, Hall FS, Linden DJ: Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8. doi: 10.1523/JNEUROSCI.0468-09.2009. [PubMed:19571144 ]
  4. Goland R, Freeby M, Parsey R, Saisho Y, Kumar D, Simpson N, Hirsch J, Prince M, Maffei A, Mann JJ, Butler PC, Van Heertum R, Leibel RL, Ichise M, Harris PE: 11C-dihydrotetrabenazine PET of the pancreas in subjects with long-standing type 1 diabetes and in healthy controls. J Nucl Med. 2009 Mar;50(3):382-9. doi: 10.2967/jnumed.108.054866. Epub 2009 Feb 17. [PubMed:19223416 ]
  5. Gros Y, Schuldiner S: Directed evolution reveals hidden properties of VMAT, a neurotransmitter transporter. J Biol Chem. 2010 Feb 12;285(7):5076-84. doi: 10.1074/jbc.M109.081216. Epub 2009 Dec 10. [PubMed:20007701 ]
  6. Wimalasena K: Vesicular monoamine transporters: structure-function, pharmacology, and medicinal chemistry. Med Res Rev. 2011 Jul;31(4):483-519. doi: 10.1002/med.20187. Epub 2010 Feb 4. [PubMed:20135628 ]