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Substance Name: Tetrabenazine [INN:BAN]
RN: 58-46-8
UNII: Z9O08YRN8O
InChIKey: MKJIEFSOBYUXJB-HOCLYGCPSA-N

Note

  • A drug formerly used as an antipsychotic and treatment of various movement disorders. Tetrabenazine blocks neurotransmitter uptake into adrenergic storage vesicles and has been used as a high affinity label for the vesicle transport system.

Molecular Formula

  • C19-H27-N-O3

Molecular Weight

  • 317.4263
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Membrane Transport Modulators
  • Neuroleptic
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Tetrabenazine
  • Tetrabenazine [INN:BAN]

MeSH Heading

  • Tetrabenazine

Synonyms

  • 1,3,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo(a)quinolizin-2-one
  • 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11-beta-hexahydro-2H-benzoquinolizine
  • 5-21-13-00178 (Beilstein Handbook Reference)
  • AI3-52046
  • BRN 0040090
  • EINECS 200-383-6
  • Nitoman
  • NSC 169886
  • Ro 1-9569
  • Rubigen
  • Tetrabenazina
  • Tetrabenazina [INN-Spanish]
  • Tetrabenazine
  • Tetrabenazinum
  • Tetrabenazinum [INN-Latin]
  • UNII-Z9O08YRN8O
  • Xenazine

Systematic Names

  • 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-
  • 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)- (9CI)
  • Tetrabenazine

Registry Numbers

CAS Registry Number

  • 58-46-8

FDA UNII

  • Z9O08YRN8O

Other Registry Numbers

  • 2104-79-2
  • 39630-28-9

System Generated Number

  • 0000058468

Structure Descriptors

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/t14-,16-/m0/s1

InChIKey

MKJIEFSOBYUXJB-HOCLYGCPSA-N

Smiles

CC(C)C[C@H]1CN2CCc3cc(c(cc3[C@@H]2CC1=O)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 150mg/kg (150mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
mouse LD50 oral 550mg/kg (550mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 308, 1972.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 308, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 128 deg C   EXP
log P (octanol-water) 2.660 (none)   EST
Atmospheric OH Rate Constant 1.90E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.