CHEBI:9467 - tetrabenazine

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ChEBI Name tetrabenazine
ChEBI ID CHEBI:9467
Definition A racemate consisting of equal amounts of (3R,11bR)- and (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one. An adrenergic uptake inhibitor, it was formerly used as an antipsychotic, but it is now used mainly for the treatment of various movement disorders including chorea, ballism, dystonias, and tardive dyskinesia.
Stars This entity has been manually annotated by the ChEBI Team.
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Roles Classification
Biological Role(s): adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
Application(s): antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
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ChEBI Ontology
Outgoing tetrabenazine (CHEBI:9467) has part (3R,11bR)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one (CHEBI:64029)
tetrabenazine (CHEBI:9467) has part (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one (CHEBI:64030)
tetrabenazine (CHEBI:9467) has role adrenergic uptake inhibitor (CHEBI:35640)
tetrabenazine (CHEBI:9467) has role antipsychotic agent (CHEBI:35476)
tetrabenazine (CHEBI:9467) is a racemate (CHEBI:60911)
IUPAC Name
rac-(3S,11bS)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one
INNs Sources
tetrabenazina ChemIDplus
tetrabenazine ChemIDplus
tetrabenazinum ChemIDplus
Synonyms Sources
1,2,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one NIST Chemistry WebBook
1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo(a)quinolizin-2-one ChemIDplus
2-oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizine ChemIDplus
Ro 1-9569 ChemIDplus
TBZ ChEBI
Tetrabenazine KEGG COMPOUND
Brand Names Sources
Nitoman DrugBank
Xenazine DrugBank
Manual Xrefs Databases
C11168 KEGG COMPOUND
D08575 KEGG DRUG
DB04844 DrugBank
Tetrabenazine Wikipedia
US2830993 Patent
View more database links
Registry Numbers Types Sources
58-46-8 CAS Registry Number ChemIDplus
58-46-8 CAS Registry Number NIST Chemistry WebBook
9356999 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10686169 PubMed citation Europe PMC
19929707 PubMed citation Europe PMC
20442355 PubMed citation Europe PMC
20869622 PubMed citation Europe PMC
21487088 PubMed citation Europe PMC
9040721 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2012-02-27 A potent inhibitor of vesicular monoamine uptake; depletes stores of dopamine, serotonin and noradrenalin. Binds with high affinity (IC50 = 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.