Tetrabenazine | CAS#58-46-8 | VMAT-2 inhibitor

MedKoo Cat#: 318851 | Name: Tetrabenazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetrabenazine is a vesicular monoamine transporter 2 (VMAT2) inhibitor. It works by depleting presynaptic dopamine, norepinephrine, and serotonin in the central nervous system (CNS). Tetrabenazine binds to VMAT2 on synaptic vesicles, preventing the uptake and storage of monoamines (mainly dopamine) in presynaptic neurons. By reducing dopamine availability, it decreases excessive dopaminergic signaling, which is beneficial in hyperkinetic movement disorders like Huntington’s disease and tardive dyskinesia.Reversible Binding: Unlike reserpine, which irreversibly inhibits VMAT2, tetrabenazine has a reversible effect, leading to a shorter duration of action and dose-dependent control of symptoms. Bioactivity: IC₅₀ (inhibition of dopamine uptake via VMAT2): ~100-200 nM. Metabolites: α-dihydrotetrabenazine (HTBZ) and β-dihydrotetrabenazine (HTBZ), which have higher affinity for VMAT2 than the parent drug. Oral Bioavailability: Low (~5–10%) due to extensive first-pass metabolism. Half-life: ~2–8 hours (active metabolites extend the duration).

Chemical Structure

Tetrabenazine

CAS#58-46-8 (free base)

Theoretical Analysis

MedKoo Cat#: 318851

Name: Tetrabenazine

CAS#: 58-46-8 (free base)

Chemical Formula: C19H27NO3

Exact Mass: 317.1991

Molecular Weight: 317.43

Elemental Analysis: C, 71.89; H, 8.57; N, 4.41; O, 15.12

Price and Availability

Size	Price	Availability
100mg	USD 150.00	Ready to ship
500mg	USD 550.00	Ready to Ship
1g	USD 950.00	2 Weeks
5g	USD 1,650.00	2 Weeks
10g	USD 2,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

804-53-5 (mesylate) 58-46-8 (free base)

Synonym

Tetrabenazine; trade names Nitoman and Xenazin

IUPAC/Chemical Name

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

InChi Key

MKJIEFSOBYUXJB-HOCLYGCPSA-N

InChi Code

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

SMILES Code

O=C1[C@@H](CC(C)C)CN2CCC3=CC(OC)=C(OC)C=C3[C@]2([H])C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Other possible CAS# CAS#718635-93-9 (Tetrabenazine) CAS#804-53-5 (Tetrabenazine methanesulfonate) CAS#2105-47-7 (Tetrabenazine hydrochloride) CAS#1026016-83-0 (Tetrabenazine, (+)-) CAS#1026016-84-1 (Tetrabenazine, (-)-)

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C22B07B14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Tetrabenazine (Ro 1-9569) is a reversible inhibitor of the vesicular monoamine transporter VMAT2 with the Kd value of 1.34 nM.

In vitro activity:

TBD

In vivo activity:

Feeding of TBZ (tetrabenazine) to WT mice did not cause significant changes in striatal neuronal counts in these mice (Fig 5C). However, TBZ feeding significantly increased striatal neuronal counts (p < 0.05) in YAC128 mice (Fig 5C), indicating that TBZ protects YAC128 MSNs from cell death. Reference: Mol Neurodegener. 2010 Apr 26;5:18. https://pubmed.ncbi.nlm.nih.gov/20420689/

	Solvent	mg/mL	mM
Solubility
	DMSO	41.0	129.24
	Ethanol	20.8	65.43

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Tseng KY, Kuo TT, Wang V, Huang EY, Ma KH, Olson L, Hoffer BJ, Chen YH. Tetrabenazine Mitigates Aberrant Release and Clearance of Dopamine in the Nigrostriatal System, and Alleviates L-DOPA-Induced Dyskinesia in a Mouse Model of Parkinson's Disease. J Parkinsons Dis. 2022;12(5):1545-1565. doi: 10.3233/JPD-223195. PMID: 35599497. 2. Wang H, Chen X, Li Y, Tang TS, Bezprozvanny I. Tetrabenazine is neuroprotective in Huntington's disease mice. Mol Neurodegener. 2010 Apr 26;5:18. doi: 10.1186/1750-1326-5-18. PMID: 20420689; PMCID: PMC2873255.

In vitro protocol:

TBD

In vivo protocol:

1: Winston GM, Nilchian P, Greenfield JP, Jones D. Intrathecal baclofen pump for severe hypertonia in a patient with juvenile Huntington's disease: illustrative case. J Neurosurg Case Lessons. 2024 Dec 2;8(23):CASE24512. doi: 10.3171/CASE24512. PMID: 39622045; PMCID: PMC11616147. 2: Vadlamani N, Ibrahimli S, Khan FA, Castillo JA, Amaravadi KSS, Nalisetty P, Khan S. Efficacy and Safety of Tetrabenazine in Reducing Chorea and Improving Motor Function in Individuals With Huntington's Disease: A Systematic Review. Cureus. 2024 Oct 14;16(10):e71476. doi: 10.7759/cureus.71476. PMID: 39544557; PMCID: PMC11560395. 3: Kane M. Valbenazine Therapy and CYP2D6 Genotype. 2024 Nov 13. In: Pratt VM, Scott SA, Pirmohamed M, Esquivel B, Kattman BL, Malheiro AJ, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012–. PMID: 39565887. 4: Funcis A, Ravera B, Zinzi P, Solito M, Petracca M, Calabresi P, Bentivoglio AR. Neuroleptic malignant syndrome in Huntington disease. Eur J Neurol. 2024 Dec;31(12):e16442. doi: 10.1111/ene.16442. Epub 2024 Oct 23. PMID: 39444167; PMCID: PMC11554869. 5: Olivares-García R, López-Cruz L, Carratalá-Ros C, Matas-Navarro P, Salamone JD, Correa M. Mild forced exercise in young mice prevents anergia induced by dopamine depletion in late adulthood: Relation to CDNF and DARPP-32 phosphorylation patterns in nucleus accumbens. Neuropharmacology. 2025 Jan 1;262:110197. doi: 10.1016/j.neuropharm.2024.110197. Epub 2024 Oct 21. PMID: 39442910. 6: Tripathi S, Sharma Y, Kumar D. Exploring the Role of Deutetrabenazine in the Treatment of Chorea Linked with Huntington's Disease. Curr Rev Clin Exp Pharmacol. 2024 Oct 15. doi: 10.2174/0127724328312991241001051813. Epub ahead of print. PMID: 39415318. 7: Zhu J, Cirincione AB, Strauss MJ, Davis SE, Eans SO, Tribbitt DK, Alshakhshir N, McLaughlin JP. Impact of HIV-1 tat protein on methamphetamine-induced inhibition of vesicular monoamine transporter2-mediated dopamine transport and methamphetamine conditioned place preference in HIV-1 tat transgenic mice. Eur J Pharmacol. 2024 Dec 5;984:177030. doi: 10.1016/j.ejphar.2024.177030. Epub 2024 Oct 2. PMID: 39366503; PMCID: PMC11563864. 8: Tod P, Varga A, Román V, Lendvai B, Pálkovács R, Sperlágh B, Vizi ES. Tetrabenazine, a vesicular monoamine transporter 2 inhibitor, inhibits vesicular storage capacity and release of monoamine transmitters in mouse brain tissue. Br J Pharmacol. 2024 Dec;181(24):5094-5109. doi: 10.1111/bph.17348. Epub 2024 Sep 20. PMID: 39304979. 9: Nilofar F, Ganapathy G, Bose S, V V. Unraveling Diabetic Striatopathy: Clinical and Imaging Perspectives. Cureus. 2024 Aug 18;16(8):e67105. doi: 10.7759/cureus.67105. PMID: 39290934; PMCID: PMC11407699. 10: Im D, Jormakka M, Juge N, Kishikawa JI, Kato T, Sugita Y, Noda T, Uemura T, Shiimura Y, Miyaji T, Asada H, Iwata S. Neurotransmitter recognition by human vesicular monoamine transporter 2. Nat Commun. 2024 Sep 16;15(1):7661. doi: 10.1038/s41467-024-51960-z. PMID: 39284862; PMCID: PMC11405867. 11: Rosano C, Chahine LM, Gay EL, Coen PM, Bohnen NI, Studenski SA, LoPresti B, Rosso AL, Huppert T, Newman AB, Royse SK, Kritchevsky SB, Glynn NW. Higher Striatal Dopamine is Related With Lower Physical Performance Fatigability in Community-Dwelling Older Adults. J Gerontol A Biol Sci Med Sci. 2024 Nov 1;79(11):glae209. doi: 10.1093/gerona/glae209. PMID: 39208421; PMCID: PMC11447735. 12: Gadkari C, Ilyas WM, Pundkar A, Seram RD, Koshy P, Patel A. Unraveling Nonketotic Hyperglycemia Hemichorea-Hemiballismus Syndrome: A Case Report of Diagnosis and Management. Cureus. 2024 Jul 22;16(7):e65094. doi: 10.7759/cureus.65094. PMID: 39171042; PMCID: PMC11338668. 13: Wu M, Ren C, Mao C, Dong L, Li B, Yang X, Huang Z, Zhang H, Li Y, Yan M, Ge Q, Wu R, Feng F, Cui M, Gao J, Huo L. Evaluation of a novel PET tracer [18F]-Florbetazine for Alzheimer's disease diagnosis and β-amyloid deposition quantification. Neuroimage. 2024 Sep;298:120779. doi: 10.1016/j.neuroimage.2024.120779. Epub 2024 Aug 8. PMID: 39122059. 14: Huang C, Zhang L, Tang T, Wang H, Jiang Y, Ren H, Zhang Y, Fang J, Zhang W, Jia X, You S, Qin B. Application of Directed Evolution and Machine Learning to Enhance the Diastereoselectivity of Ketoreductase for Dihydrotetrabenazine Synthesis. JACS Au. 2024 Jun 26;4(7):2547-2556. doi: 10.1021/jacsau.4c00284. PMID: 39055154; PMCID: PMC11267543. 15: Nguyen HQ, Kuan HS, Crass RL, Quinlan L, Chapel S, Kim K, Brar S, Loewen G. A Model-Informed Drug Development Approach Supporting the Approval of an Unstudied Valbenazine Dose for Patients With Tardive Dyskinesia. J Clin Pharmacol. 2024 Nov;64(11):1456-1465. doi: 10.1002/jcph.2498. Epub 2024 Jul 25. PMID: 39051716. 16: Moondra P, Jimenez-Shahed J. Profiling deutetrabenazine extended-release tablets for tardive dyskinesia and chorea associated with Huntington's disease. Expert Rev Neurother. 2024 Sep;24(9):849-863. doi: 10.1080/14737175.2024.2376107. Epub 2024 Jul 9. PMID: 38982802. 17: Ismail O, Albdour K, Jaber Y, Jaber K, Alsaras A. Efficacy and safety of different pharmacological interventions in the treatment of tardive dyskinesia: a systematic review and network meta-analysis. Eur J Clin Pharmacol. 2024 Oct;80(10):1471-1482. doi: 10.1007/s00228-024-03722-5. Epub 2024 Jul 6. PMID: 38969949. 18: Mendonça MD, Barahona-Corrêa JB. Tetrabenazine-induced acute dystonic reaction during the treatment of comorbid tics in a young woman with autism spectrum disorder. Psychiatry Clin Neurosci. 2024 Sep;78(9):558-559. doi: 10.1111/pcn.13705. Epub 2024 Jun 28. PMID: 38938128. 19: Domínguez Carral J, Reinhard C, Ebrahimi-Fakhari D, Dorison N, Galosi S, Garone G, Malenica M, Ravelli C, Serdaroglu E, van de Pol LA, Koy A, Leuzzi V, Roubertie A, Lin JP, Doummar D, Cif L, Ortigoza-Escobar JD. Dyskinetic crisis in GNAO1-related disorders: clinical perspectives and management strategies. Front Neurol. 2024 Jun 6;15:1403815. doi: 10.3389/fneur.2024.1403815. PMID: 38903163; PMCID: PMC11188927. 20: Zhang Y, Jia X, Shi X, Chen Y, Xue M, Shen G, Wen L, Qiao Y, Yang Y. Mining of neurological adverse events associated with valbenazine: A post-marketing analysis based on FDA adverse event reporting system. Gen Hosp Psychiatry. 2024 Sep-Oct;90:22-29. doi: 10.1016/j.genhosppsych.2024.06.005. Epub 2024 Jun 12. PMID: 38901166.