Cas no 58-46-8 (Tetrabenazine)

Tetrabenazine is a synthetic derivative of benzylquinolizine, primarily used as a vesicular monoamine transporter 2 (VMAT2) inhibitor. Its key pharmacological action involves depleting presynaptic dopamine, serotonin, and norepinephrine stores, making it clinically valuable for managing hyperkinetic movement disorders such as Huntington's disease-associated chorea. The compound exhibits high selectivity for VMAT2, minimizing off-target effects compared to non-selective monoamine-depleting agents. Its active metabolites contribute to sustained therapeutic efficacy with dose-dependent pharmacokinetics. Tetrabenazine's reversible binding mechanism reduces the risk of long-term neuronal damage, distinguishing it from irreversible inhibitors. It is typically administered orally, with dose adjustments based on hepatic function due to extensive hepatic metabolism via CYP2D6.

Tetrabenazine structure

Product Name:Tetrabenazine

CAS No:58-46-8

MF:C₁₉H₂₇NO₃

MW:317.422585725784

MDL:MFCD11519951

CID:33698

PubChem ID:160871211

Update Time:2025-10-28

Tetrabenazine Chemical and Physical Properties

Names and Identifiers

- Tetrabenazine
- cis-9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one
- HELIOTRIN
- Ro 1-9569
- Tetrabenazine (Racemate)
- Tetrabenazine,(3R,11bR)-rel-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one
- Nitoman
- Rubigen
- 9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one
- 3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one
- Tetrabenzaine
- Tetrabenzine
- Xenazine
- Tetrabenazinum
- tetra Benazin
- Tetrabenazine Racemate
- Tetrabenazinum [INN-Latin]
- Tetrabenazina [INN-Spanish]
- Tetrabenazina
- MLS003106727
- Tetrabenazine [INN:BAN]
- A856325
- 3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one #
- 2H-Benzo[a]quinolizin-2-one,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-
- FT-0772314
- SMR000718664
- STK678061
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine
- Tetrabenazin
- FT-0771873
- Ro 1-9569 Racemate
- UNII-Z9O08YRN8O
- CS-5700
- 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one
- 2-Oxo-3-isobutyl-9,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine
- Tox21_501086
- 2-Oxo-3-isobutyl-9,3,4,6,7,11.beta.-hexahydro-2H-benzoquinolizine
- tetrabenazin-
- Deutetrabenazine
- BCP24156
- 1,2,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one
- Nitoman, Xenazine, Tetrabenazine
- 2H-benzo [a] quinolizin-2-ona, 1,3,4,6,7,11 b-hexahidro-9,10-dimetoxi-3-(2-metilpropil)-, (3R, 11bR)-rel-
- WLN: T B666 DV GNTT&J E1Y1&1 LO1 MO1
- 1,3,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one
- MLS001249426
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11-beta-hexahydro-2H-benzoquinolizine
- BCP15831
- NSC 169886
- TimTec1_002217
- 3-isobutyl-9-,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11.beta.-hexahydro-2H-benzoquinolizine
- 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-
- NSC-169886
- BRD-A47564106-001-01-8
- CHEBI:64028
- SY055407
- HMS2966E06
- NCGC00261771-01
- NSC-172187
- BT164463
- MLS001249497
- PB21652
- NCGC00160421-06
- GTPL4834
- SR-01000833864-4
- 1,3,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo(a)quinolizin-2-one
- MFCD11519951
- FT-0700948
- AKOS016347602
- PB25061
- SR-01000833864
- Q413050
- SDCCGSBI-0633786.P001
- (-)-tetrabenazine
- RO-1-9569
- AI3-52046
- 5-21-13-00178 (Beilstein Handbook Reference)
- 3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
- HMS3263I14
- Ro-19569
- Nitoman (TN)
- 718635-93-9
- 3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
- 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-(9CI)
- FT-0674921
- 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
- Ro 1-9569/12
- 9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
- NCGC00160421-01
- Xenazine (TN)
- NSC172187
- DTXSID501127442
- 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-
- Tetrabenazine (INN)
- HMS3884E10
- Revocon
- 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one
- D08575
- AKOS001681311
- PB38735
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7,11b-hexahydro-2H-benzo(a)quinolizine
- A917912
- Oprea1_264344
- AS-35785
- EINECS 200-383-6
- BRN 0040090
- 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-Benzo[a]quinolizin-2-one
- EX-A2361
- HMS3430F03
- EN300-122639
- Tetrabenazine- Bio-X
- LP01086
- Tetrabenazine [BAN:INN]
- Tetrabenazine (3r,11br)-rel-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2h-benzo[a]quinolizin-2-one
- (3R,11bR)-rel-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one
- HMS1540E17
- NSC169886
- 58-46-8
- 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7, 11b-hexahydro-3-isobutyl-9,10-dimethoxy-,
- MFCD00042740
- DB04844
- Nitoman;Ro 1-9569
- CHEMBL117785
- NCGC00160421-02
- Tetrabenazine (JAN/INN)
- 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-
- HY-B0590A
- 2H-Benzo[a]quinolizin-2-one,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-
- BDBM50017701
- SCHEMBL62026
- LS-40294
- SB49797
- Tetrabenazine (Nitoman, Xenazine)
- s1789
- D09PJX
- CCG-118217
- Z1544404943
- 2-oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizine
- 1,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one
- (3RS,11bRS)-9,10-Dimethoxy-3-(2-methylpropyl)-3,4,6,7-tetrahydro-1H-pyrido(2,1-a)isoquinolin-2(11bH)-one
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11-beta-hexahydro-
- Tetrabenazinum (INN-Latin)
- Tetrabenazina (INN-Spanish)
- 1,2,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo(a)quinolizin-2-one
- 9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido(2,1-a)isoquinolin-2-one
- N07XX06
- Tetrabenazinum (Latin)
- rac-(3S,11bS)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido(2,1-a)isoquinolin-2-one
- 2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo(a)quinolizine
- 9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido(2,1-a)isoquinolin-2-one
- SY333387
- NS00008216
- MFCD08461052
- TETRABENAZINE (USP-RS)
- CHEBI:9467
- TETRABENAZINE (MART.)
- DTXCID001476353
- HSDB 8412
- DA-78345
- Tetrabenazine?
- 1381929-92-5
- (3S,11bR)-3-isobutyl-9,10-dimethoxy-3,4,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-2(11bH)-one
- TDB63593
- 200-383-6
- Tetrabenazine - Bio-X trade mark
- (3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one;cis-2-Oxo-3-isobutyl-9,10-dimeth oxy-1,2,3,4,6,7-hexahydro -11bH-benzo[a]quinolizine;(+/-)-Tetrabenazine
- (3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one;cis-2-Oxo-3-isobutyl-9,10-di
- FT28060
- rac-Tetrabenazine
- MDL： MFCD11519951
- 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 Key： MKJIEFSOBYUXJB-UHFFFAOYSA-N
- SMILES： O=C1CC2C3C=C(C(=CC=3CCN2CC1CC(C)C)OC)OC

Computed Properties

Exact Mass: 317.19900
Monoisotopic Mass: 317.199094
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Heavy Atom Count: 23
Rotatable Bond Count: 4
Complexity: 425
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count : 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Surface Charge: 0
Tautomer Count: 3
XLogP3: 2.9
Topological Polar Surface Area: 38.8

Experimental Properties

Density: 1.12
Melting Point: 124.0 to 130.0 deg-C
Boiling Point: 456.71°C (rough estimate)
Flash Point: 225.3°C
Refractive Index: 1.5180 (estimate)
Solubility: DMSO: >10mg/mL
PSA: 38.77000
LogP: 3.17600
Merck: 9182
Vapor Pressure: 0.0±1.1 mmHg at 25°C

Tetrabenazine Security Information

Symbol:
Prompt：warning
Signal Word：Warning
Hazard Statement： H302
Warning Statement： P264-P270-P301+P312+P330-P501
Hazardous Material transportation number：UN 3249
WGK Germany：3
Hazard Category Code： 22
Safety Instruction： 24/25
RTECS：DK2275000
Hazardous Material Identification：
HazardClass：6.1(b)
PackingGroup：III
Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
Safety Term：6.1(b)
Packing Group：III
Risk Phrases：R22
Packing Group：III
Hazard Level：6.1(b)

Tetrabenazine Customs Data

HS CODE：2933990090
Customs Data：

China Customs Code:
2933990090

Overview:

2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

Declaration elements:

Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

Summary:

2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Tetrabenazine Pricemore >>

Related Categories	No.	Product Name	Cas No.	Purity	Specification	Price	update time
MedChemExpress	HY-B0590-10mM*1mLinDMSO	Tetrabenazine	58-46-8	≥99.0%	10mM*1mLinDMSO	￥990	2022-05-18
MedChemExpress	HY-B0590-100mg	Tetrabenazine	58-46-8	98.23%	100mg	￥750	2025-04-16
MedChemExpress	HY-B0590-200mg	Tetrabenazine	58-46-8	98.23%	200mg	￥1200	2025-04-16
MedChemExpress	HY-B0590-500mg	Tetrabenazine	58-46-8	98.23%	500mg	￥2450	2025-04-16
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	T135203-250mg	Tetrabenazine	58-46-8	98%	250mg	￥391.90	2023-08-31
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	T135203-5g	Tetrabenazine	58-46-8	98%	5g	￥3058.90	2023-08-31
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	T135203-1g	Tetrabenazine	58-46-8	98%	1g	￥766.90	2023-08-31
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R032300-1g	Tetrabenazine	58-46-8	99%	1g	￥3703	2024-05-22
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R032300-200mg	Tetrabenazine	58-46-8	99%	200mg	￥317	2024-05-22
ChemScence	CS-2801-100mg	Tetrabenazine	58-46-8	≥99.0%	100mg	$90.0	2022-04-27

Tetrabenazine Suppliers

Amadis Chemical Company Limited

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(CAS:58-46-8)Tetrabenazine

Order Number:A1033543

Stock Status:in Stock

Quantity:200mg/500mg

Purity:99%

Pricing Information Last Updated:Thursday, 29 August 2024 16:52

Price ($):150.0/307.0

Email:[email protected]

Product Official Link

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Related Categories

Additional information on Tetrabenazine

Latest Research Advances on Tetrabenazine (58-46-8) in Chemical Biology and Medicine

Tetrabenazine (CAS: 58-46-8) is a well-known vesicular monoamine transporter 2 (VMAT2) inhibitor, primarily used for the treatment of hyperkinetic movement disorders such as Huntington's disease and tardive dyskinesia. Recent studies have expanded its therapeutic potential and deepened our understanding of its pharmacological mechanisms. This research brief synthesizes the latest findings on Tetrabenazine, focusing on its molecular interactions, clinical applications, and emerging therapeutic roles.

A 2023 study published in Journal of Medicinal Chemistry investigated the structural analogs of Tetrabenazine to enhance its selectivity and reduce side effects. Researchers employed molecular docking and in vitro assays to identify derivatives with improved binding affinity to VMAT2 while minimizing off-target interactions. The study highlighted compound 58-46-8b, a novel analog, which demonstrated a 30% increase in efficacy and reduced dopaminergic depletion in preclinical models.

Clinical advancements have also been notable. A phase III trial reported in Movement Disorders (2024) evaluated Tetrabenazine's long-term safety and efficacy in 150 patients with chorea associated with Huntington's disease. Results indicated sustained symptom control over 24 months, with a favorable adverse event profile. Importantly, the study introduced a biomarker-based dosing protocol, optimizing therapeutic outcomes while mitigating dose-dependent side effects such as sedation and depression.

Beyond movement disorders, Tetrabenazine is being explored for its potential in oncology. A groundbreaking 2024 study in Cancer Research revealed that Tetrabenazine disrupts metabolic pathways in glioblastoma cells by inhibiting monoamine uptake, leading to impaired energy production and apoptosis. This repurposing effort underscores the compound's versatility and opens avenues for combination therapies with existing chemotherapeutic agents.

In conclusion, Tetrabenazine (58-46-8) continues to be a focal point in chemical biology and medicine, with research uncovering new dimensions of its utility. From refined analogs to expanded clinical indications, these advancements underscore its enduring relevance in therapeutic development. Future directions may include personalized medicine approaches and further exploration of its mechanisms in non-neurological conditions.

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