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

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

MedKoo CAT#: 318851

CAS#: 58-46-8

Description: Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntington's disease (HD), the first in the US. The precise mechanism of action of tetrabenazine is unknown. The antichorea effect is believed to be related to its effect as a reversible depletory of monoamines (such as dopamine, serotonin, norepinephrine and histamine)from nerve terminals) Tetrabenazine reversibly inhibits VMAT-2 resulting in decreased of monamines into synaptic vesicles

Chemical Structure

Tetrabenazine

CAS# 58-46-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318851
Name: Tetrabenazine
CAS#: 58-46-8
Chemical Formula: C19H27NO3
Exact Mass: 317.20
Molecular Weight: 317.429
Elemental Analysis: C, 71.89; H, 8.57; N, 4.41; O, 15.12

Price and Availability

Size	Price	Availability
50mg	USD 190	Ready to ship
100mg	USD 350	Ready to ship
200mg	USD 550	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

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

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. 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.

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1: [Tetrabenazine (tetrabenazine Orphan) orally]. J Pharm Belg. 2014 Dec;(4):49-50. Review. French. PubMed PMID: 25562927.

2: Machida K, Kawakami D, Miki M. [Pharmacological properties and clinical efficacy of tetrabenazine (Choreazine(®)Tablets 12.5 mg), a therapeutic agent for non-rhythmic involuntary movement]. Nihon Yakurigaku Zasshi. 2014 Mar;143(3):144-51. Review. Japanese. PubMed PMID: 24614638.

3: Chen JJ, Ondo WG, Dashtipour K, Swope DM. Tetrabenazine for the treatment of hyperkinetic movement disorders: a review of the literature. Clin Ther. 2012 Jul;34(7):1487-504. doi: 10.1016/j.clinthera.2012.06.010. Epub 2012 Jun 28. Review. PubMed PMID: 22749259.

4: Jankovic J, Clarence-Smith K. Tetrabenazine for the treatment of chorea and other hyperkinetic movement disorders. Expert Rev Neurother. 2011 Nov;11(11):1509-23. doi: 10.1586/ern.11.149. Review. PubMed PMID: 22014129.

5: Leung JG, Breden EL. Tetrabenazine for the treatment of tardive dyskinesia. Ann Pharmacother. 2011 Apr;45(4):525-31. doi: 10.1345/aph.1P312. Epub 2011 Apr 12. Review. Erratum in: Ann Pharmacother. 2011 May;45(5):690. PubMed PMID: 21487088.

6: Guay DR. Tetrabenazine, a monoamine-depleting drug used in the treatment of hyperkinetic movement disorders. Am J Geriatr Pharmacother. 2010 Aug;8(4):331-73. doi: 10.1016/j.amjopharm.2010.08.006. Review. PubMed PMID: 20869622.

7: Poon LH, Kang GA, Lee AJ. Role of tetrabenazine for Huntington's disease-associated chorea. Ann Pharmacother. 2010 Jun;44(6):1080-9. doi: 10.1345/aph.1M582. Epub 2010 May 4. Review. PubMed PMID: 20442355.

8: Fasano A, Bentivoglio AR. Tetrabenazine. Expert Opin Pharmacother. 2009 Dec;10(17):2883-96. doi: 10.1517/14656560903386292. Review. PubMed PMID: 19929707.

9: Setter SM, Neumiller JJ, Dobbins EK, Wood L, Clark J, DuVall CA, Santiago A. Treatment of chorea associated with Huntington's disease: focus on tetrabenazine. Consult Pharm. 2009 Jul;24(7):524-37. Review. PubMed PMID: 19689181.

10: Tetrabenazine (Xenazine) for Huntington's chorea. Med Lett Drugs Ther. 2009 Jan 26;51(1304):7-8. Review. PubMed PMID: 19172140.

11: Porta M, Sassi M, Cavallazzi M, Fornari M, Brambilla A, Servello D. Tourette's syndrome and role of tetrabenazine: review and personal experience. Clin Drug Investig. 2008;28(7):443-59. Review. PubMed PMID: 18544005.

12: Kenney C, Jankovic J. Tetrabenazine in the treatment of hyperkinetic movement disorders. Expert Rev Neurother. 2006 Jan;6(1):7-17. Review. PubMed PMID: 16466307.

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