(3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide

The title compound, C(21)H(26)NO(4) (+)·Br(−), also known as R-methyl­naltrexone (MNTX) bromide, is a selective peripher­ally acting μ-opioid receptor antagonist with a oroxymorphone skeleton, synthesized by hydroxyl protection, N-methyl­ation, deprotection and anion exchange of naltrexone. It compr...

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Autores principales: Chen, Xiangfeng, Zong, Zaiwei, Du, Youguo, Li, Jianguo, Sun, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3275079/
https://www.ncbi.nlm.nih.gov/pubmed/22347024
http://dx.doi.org/10.1107/S1600536812000645
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author Chen, Xiangfeng
Zong, Zaiwei
Du, Youguo
Li, Jianguo
Sun, Min
author_facet Chen, Xiangfeng
Zong, Zaiwei
Du, Youguo
Li, Jianguo
Sun, Min
author_sort Chen, Xiangfeng
collection PubMed
description The title compound, C(21)H(26)NO(4) (+)·Br(−), also known as R-methyl­naltrexone (MNTX) bromide, is a selective peripher­ally acting μ-opioid receptor antagonist with a oroxymorphone skeleton, synthesized by hydroxyl protection, N-methyl­ation, deprotection and anion exchange of naltrexone. It comprises a five-ring system A/B/C/D/E. Rings C and E adopt distorted chair conformations, whereas ring D is in half-chair conformation. The C/E ring junctions are trans fused. The dihedral angle between rings D and E is 82.3 (1)°, while the dihedral angles between the planes of rings C and A, and rings D and E are respectively 81.7 (1), 75.9 (1) and 12.2 (1)°. In the crystal, mol­ecules are linked by O—H⋯Br hydrogen bonds.
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spelling pubmed-32750792012-02-15 (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide Chen, Xiangfeng Zong, Zaiwei Du, Youguo Li, Jianguo Sun, Min Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(26)NO(4) (+)·Br(−), also known as R-methyl­naltrexone (MNTX) bromide, is a selective peripher­ally acting μ-opioid receptor antagonist with a oroxymorphone skeleton, synthesized by hydroxyl protection, N-methyl­ation, deprotection and anion exchange of naltrexone. It comprises a five-ring system A/B/C/D/E. Rings C and E adopt distorted chair conformations, whereas ring D is in half-chair conformation. The C/E ring junctions are trans fused. The dihedral angle between rings D and E is 82.3 (1)°, while the dihedral angles between the planes of rings C and A, and rings D and E are respectively 81.7 (1), 75.9 (1) and 12.2 (1)°. In the crystal, mol­ecules are linked by O—H⋯Br hydrogen bonds. International Union of Crystallography 2012-01-14 /pmc/articles/PMC3275079/ /pubmed/22347024 http://dx.doi.org/10.1107/S1600536812000645 Text en © Chen et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Chen, Xiangfeng
Zong, Zaiwei
Du, Youguo
Li, Jianguo
Sun, Min
(3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title_full (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title_fullStr (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title_full_unstemmed (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title_short (3R,4R,4aS,7aR,12bS)-3-Cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1H-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
title_sort (3r,4r,4as,7ar,12bs)-3-cyclo­propyl­methyl-4a,9-dihy­droxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octa­hydro-1h-4,12-methano­benzofuro[3,2-e]isoquinolin-3-ium bromide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3275079/
https://www.ncbi.nlm.nih.gov/pubmed/22347024
http://dx.doi.org/10.1107/S1600536812000645
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