113627-25-1

Basic information

• Product Name: cis (2,3)-Dihydro Tetrabenazine
• Synonyms: cis (2,3)-Dihydro Tetrabenazine;(2R,3S,11bS)-rel-1,3,4,6,7,11b-Hexahydro-9,10-diMethoxy-3-(2-Methylpropyl)-2H-benzo[a]quinolizin-2-ol;(2α,3α,11bα)-1,3,4,6,7,11b-Hexahydro-9,10-diMethoxy-3 -(2-Methylpropyl)-2H-benzo[a]quinolizin-2-ol
• CAS NO: 113627-25-1
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.43846
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 113627-25-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 156-158°C (dec.)
• Boiling Point: 457.82°C at 760 mmHg
• Flash Point: 230.682°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.75±0.40(Predicted)
• CAS DataBase Reference: cis (2,3)-Dihydro Tetrabenazine(CAS DataBase Reference)
• NIST Chemistry Reference: cis (2,3)-Dihydro Tetrabenazine(113627-25-1)
• EPA Substance Registry System: cis (2,3)-Dihydro Tetrabenazine(113627-25-1)

Safety Data

• Hazardous Substances Data: 113627-25-1(Hazardous Substances Data)

Usage

Chemical Properties

cis (2,3)-Dihydro Tetrabenazine is White Solid

Uses

Different sources of media describe the Uses of 113627-25-1 differently. You can refer to the following data:
1. A metabolite of Tetrabenazine in vivo, which is likely the active pharmacological agent. The cis isomer of Dihydrotetrabenazine is used for the treatment of hyperkinetic movement disorders.
2. cis (2,3)-Dihydro Tetrabenazine is a metabolite of Tetrabenazine in vivo, which is likely the active pharmacological agent. The cis izomer of Dihydrotetrabenazine is used for the treatment of hyperkinetic movement disorders.

InChI:InChI=1/C19H29NO3/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/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16-,17+/m0/s1

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 articles and documents

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.

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.

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.