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Two ortho-rhom-bic polymorphs of hydro-morphone.

ABSTRACT: Conditions to obtain two polymorphic forms by crystallization from solution were determined for the analgesic drug hydro-morphone [C17H19NO3; systematic name: (4R,4aR,7aR,12bS)-9-hy-droxy-3-methyl-1,2,4,4a,5,6,7a,13-octa-hydro-4,12-methano-benzofuro[3,2-e]iso-quinolin-7-one]. These two crystalline forms, designated as I and II, belong to the P212121 ortho-rhom-bic space group. In both polymorphs, the hydro-morphone mol-ecules adopt very similar conformations with some small differences observed only in the N-methyl amine part of the mol-ecule. The crystal structures of both polymorphs feature chains of mol-ecules connected by hydrogen bonds; however, in form I this inter-action occurs between the hydroxyl group and the tertiary amine N atom whereas in form II the hydroxyl group acts as a donor of a hydrogen bond to the O atom from the cyclic ether part.

SUBMITTER: Mazurek J

PROVIDER: S-EPMC4908523 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Two ortho-rhom-bic polymorphs of hydro-morphone.

Mazurek Jaroslaw J Hoffmann Marcel M Fernandez Casares Ana A Cox D Phillip DP Minardi Mathew D MD Sasine Josh J

Acta crystallographica. Section E, Crystallographic communications 20160426 Pt 5

Conditions to obtain two polymorphic forms by crystallization from solution were determined for the analgesic drug hydro-morphone [C17H19NO3; systematic name: (4R,4aR,7aR,12bS)-9-hy-droxy-3-methyl-1,2,4,4a,5,6,7a,13-octa-hydro-4,12-methano-benzofuro[3,2-e]iso-quinolin-7-one]. These two crystalline forms, designated as I and II, belong to the P212121 ortho-rhom-bic space group. In both polymorphs, the hydro-morphone mol-ecules adopt very similar conformations with some small differences observed ...[more]

PMID: 27308029

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