85081-18-1

Basic information

• Product Name: [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol
• Synonyms: Tetrabenazine metabolite A;Tetrabenazine metabolite B;2H-Benzo[a]quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-;[2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol;NBI-98782;(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol;(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol
• CAS NO: 85081-18-1
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.44
• Product Categories: Tetrabenazine;Impurities & Metabolites
• Mol File: 85081-18-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 106-108 °C(Solv: hexane (110-54-3))
• Boiling Point: 457.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.13
• PKA: 14.75±0.40(Predicted)
• CAS DataBase Reference: [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(85081-18-1)
• EPA Substance Registry System: [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol(85081-18-1)

Safety Data

• Hazardous Substances Data: 85081-18-1(Hazardous Substances Data)

Usage

Description

[2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol is a complex organic compound with a unique molecular structure. It is characterized by its hexahydroquinolizinol core, which is substituted with various functional groups, including methoxy and methylpropyl groups. [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol exhibits a range of biological activities and has potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
[2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol is used as a therapeutic agent for its potent inhibitory effects on vascular monoamine transporter 2 (VMAT2). This makes it a significant compound of interest for the development of drugs targeting various neurological disorders and conditions related to monoamine neurotransmission.
Used in Molecular Imaging Applications:
In addition to its therapeutic potential, [2R-(2a,3b,11bb)]-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol also serves as a valuable agent in molecular imaging. Its ability to modulate VMAT2 activity allows for the visualization and assessment of monoaminergic systems in the body, which can be crucial for diagnosing and monitoring the progression of certain diseases.

Upstream product

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

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.