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Tetrabenazine
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Name

Tetrabenazine

 EINECS 200-383-6
CAS No. 58-46-8 Density 1.127 g/cm3
PSA 38.77000 LogP 3.17600
Solubility N/A Melting Point 128-130 °C
Formula C19H27NO3 Boiling Point 448.941 °C at 760 mmHg
Molecular Weight 317.428 Flash Point 225.311 °C
Transport Information N/A Appearance white to off-white solid
Safety 24/25 Risk Codes 22
Molecular Structure Molecular Structure of 58-46-8 (Tetrabenazine) Hazard Symbols HarmfulXn
Synonyms

2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3S,11bS)-;(3S,11bS)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one;

Article Data 7

Tetrabenazine Synthetic route

67-56-1

methanol

89929-27-1

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 25 - 30℃; Mitsunobu Displacement; Large scale;96%
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

1069-62-1

2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; 2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide In ethanol at 80℃;
Stage #2: With sodium hydroxide; water In dichloromethane		75%
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

C12H18O3

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; C12H18O3 In ethanol at 60℃; for 72h; Diels-Alder Cycloaddition; Inert atmosphere;
Stage #2: With morpholine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol at 20℃; for 3h; Inert atmosphere;		69%

3-isobutyl-9,10-dimethoxy-2-methylene-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 3-isobutyl-9,10-dimethoxy-2-methylene-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline With osmium(VIII) oxide; water In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: With sodium periodate; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 0℃; for 5h; Inert atmosphere;		61%
3-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-tetrahydro-2H-pyrido<2,1-a>isoquinoline-1,3-carboxylic acid diethyl ester

3-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-tetrahydro-2H-pyrido<2,1-a>isoquinoline-1,3-carboxylic acid diethyl ester

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
With hydrogenchloride
1346909-18-9

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
2.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
3.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
3.2: 5 h / 0 °C / Inert atmosphere
View Scheme
1346909-10-1

6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
2.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
2.2: 5 h / 0 °C / Inert atmosphere
View Scheme
1346909-36-1

methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.58 h / -20 - -5 °C / Inert atmosphere
2.1: diethyl ether; hexane / 2 h / -78 - 20 °C / Inert atmosphere
3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.67 h / Inert atmosphere
4.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
5.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
5.2: 1 h / Inert atmosphere
6.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
7.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
8.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
9.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
9.2: 5 h / 0 °C / Inert atmosphere
View Scheme
1346909-38-3

N-methoxy-N,4-dimethyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentane amide

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: diethyl ether; hexane / 2 h / -78 - 20 °C / Inert atmosphere
2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere
3.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
4.2: 1 h / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
6.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
7.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
8.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
8.2: 5 h / 0 °C / Inert atmosphere
View Scheme
1346909-30-5

5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hexan-2-one

58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
1.2: 0.67 h / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
3.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
3.2: 1 h / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
5.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
6.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
7.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
7.2: 5 h / 0 °C / Inert atmosphere
View Scheme

Tetrabenazine Specification

The Tetrabenazine, with the CAS registry number 58-46-8, is also known as 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3S,11bS)-. It belongs to the product categories of APIs; Serotonin Receptor; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-383-6. This chemical's molecular formula is C19H27NO3 and molecular weight is 317.42. What's more, both its IUPAC name and systematic name are the same which is called (3S,11bS)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder. When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. 

Physical properties about Tetrabenazine are: (1)ACD/LogP: 3.476; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.48; (4)ACD/LogD (pH 7.4): 3.43; (5)ACD/BCF (pH 5.5): 25.96; (6)ACD/BCF (pH 7.4): 231.94; (7)ACD/KOC (pH 5.5): 186.36; (8)ACD/KOC (pH 7.4): 1665.24; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12) Polar Surface Area: 38.77 Å2; (13)Index of Refraction: 1.554; (14)Molar Refractivity: 90.255 cm3; (15)Molar Volume: 281.609 cm3; (16)Polarizability: 35.78×10-24cm3; (17)Surface Tension: 44.228 dyne/cm; (18)Density: 1.127 g/cm3; (19)Flash Point: 225.311 °C; (20)Enthalpy of Vaporization: 70.754 kJ/mol; (21)Boiling Point: 448.941 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C3[C@@H](CC(C)C)CN2[C@H](c1c(cc(OC)c(OC)c1)CC2)C3
(2) InChI: 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
(3) InChIKey: MKJIEFSOBYUXJB-HOCLYGCPSA-N

The toxicity data is as follows:

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.

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