7744-54-9

Upstream product

• 58-46-8 (3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one 
• 718635-93-9 tetrabenazine 
• 403804-65-9 rac-2-(hydroxymethyl)-4-methylpentanoic acid methyl ester 
• 1346909-44-1 4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentan-1-ol 
• 1346909-31-6 3-(hydroxymethyl)-5-methylhex-1-ene-2-yl trifluoromethanesulfonate 
• 1346909-40-7 5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hex-1-ene-2-yl trifluoromethanesulfonate 
• 1346909-30-5 5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hexan-2-one 
• 1346909-38-3 N-methoxy-N,4-dimethyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentane amide 
• 1346909-36-1 methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate 
• 1346909-10-1 6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline 
• 1346909-18-9 4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate 

Downstream Products

• 862287-32-9 C₂₉H₃₆F₃NO₅ 
• 862287-31-8 C₂₉H₃₆F₃NO₅ 
• 862287-34-1 C₂₉H₃₆F₃NO₅ 
• 862287-35-2 C₂₉H₃₆F₃NO₅ 

Relevant academic research and scientific papers

In vitro and in vivo studies of benzisoquinoline ligands for the brain synaptic vesicle monoamine transporter

Tetrabenazine is a high-affinity inhibitor of the vesicular monoamine transporter in mammalian brain. As part of a program to develop in vivo imaging agents for these transporters in human brain, a series of 2-alkylated dihydrototrabenazine ligands was synthesized and evaluated ia vitro and in vivo for binding to the brain vesicular monoamine transporter. Additions of organometallic reagents to tetrabenazine produced 2-methyl, 2-ethyl, 2-n- propyl, 2-isopropyl, and 2-isobutyl derivatives of dihydrotetrabenazine. The stereochemistry and conformation of the addition products were thoroughly verified by two-dimensional NMR techniques. All of these alkyl derivatives displayed in vitro affinity for the vesicular monoamine transporter binding site in rat brain using competitive assays with the radioligand [3H]methoxytetrabenazine. Except for the isopropyl derivative, all compounds when tested at 10 mg/kg iv showed an ability to inhibit in vivo accumulation of the radioligand [11C]methoxytetrabenazine in the mouse brain striatum. Derivatives with small alkyl groups (methyl, ethyl) were more effective than those with large groups (propyl, isobutyl). These studies suggest that large groups in the 2-position of the benzisoquinoline structure will significantly diminish both in vitro and in vivo binding of these compounds to the vesicular monoamine transporter.

Synthesis and X-ray analysis of dihydrotetrabenazine, a metabolite of tetrabenazine

The dihydrotetrabenazine (DTBZ) was synthesized by reduction of tetrabenazine with sodium borohydride in ethanol. Crystals suitable for X-ray analysis were obtained from a mixed solution of dichloromethane and ethanol in a five-to-one volume ratio. The crystal is monoclinic, space group P 21c with crystallographic parameters: a = 15.0129(14), b = 12.5677(12), c = 9.7715(9), = 98.556(2), = 0.078 mm1, V = 1823.1(3) 3, Z = 4, Dc = 1.164 g/cm3, F(000) = 696, T = 296(2) K. The X-ray analysis and the chiral HPLC show that the DTBZ prepared by our method consists of (2R,3R,11bR) and (2S,3S,11bS) enantiomers. Taylor and Francis Group, LLC.

A concise synthesis of tetrabenazine: An intramolecular aza-prins-type cyclization via oxidative c-h activation

A concise synthesis of tetrabenazine and dihydrotetrabenazine is described. The key feature of this synthesis is the intramolecular aza-Prins-type cyclization of an amino allylsilane via oxidative C-H activation. 2011 American Chemical Society.

Synthesis of (+)-and (-)-tetrabenazine from the resolution of-dihydrotetrabenazine

Tetrabenazine (1) was reduced with NaBH4 to-dihydrotetrabenazine (2) and then resolved with di-p-toluoyl-L-tartrate and di-p-toluoyl-D-tartrate to subsequently give (+)-and (-)-dihydrotetrabenazine. The enantiomers were oxidized under Swern conditions to prepare samples of (+)-tetrabenazine and (-)-tetrabenazine. The samples were optically pure by chiral HPLC analysis.

USE OF 3,1IB-CIS-DIHYDROTETRABENAZINE FOR THE TREATMENT OF SYMPTONS OF HUNTINGTON' S DISEASE

The invention provides 3,1 lb-cis-dihydrotetrabenazine for use in halting or slowing the progress of one or more symptoms of Huntington''s disease in a patient, and more particularly a symptom selected from involuntary movements such as involuntary chorea, tremors and twitches, and degeneration in gait.

DIHYDROTETRABENAZINES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The invention provides novel isomers of dihydrotetrabenazine, individual enantiomers and mixtures thereof wherein the dihydrotetrabenazine is a 3,11 b-cis- dihydrotetrabenazine. Also provided are methods for the preparation of the novel isomers, pharmaceutical compositions containing them and their use in treating hyperkinetic movement disorders such as Huntington's disease, hemiballismus, senile chorea, tic, tardive dyskinesia and Tourette's syndrome.