Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate

Gauchat, Eric; Nazarenko, Alexander Y.

doi:10.1107/s2056989016019939

Cited by 2 publications

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“…There is a need for new crystalline forms of naltrexone hydrochloride (Nichols et ISSN 2056-9890 al., 2013) as well for new analytical methods of its unambiguous identification. This communication is a continuation of our work on analytical crystallography of opiate compounds (Gauchat & Nazarenko, 2017).…”

Section: Chemical Contextmentioning

confidence: 81%

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

2017

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Naltrexone [systematic name: 17-(cyclopropylmethyl)-3,14-dihydroxy-4,5 -epoxymorphinan-6-one] is an opioid receptor competitive antagonist that has been widely used to prevent relapse in opioid-and alcohol-dependent subjects. Its chloride salt forms non-isomorphic solvates with ethanol (C 20 H 24 NO 4 + ÁCl À Á-ÁC 2 H 5 OH) (I), propan-2-ol (C 20 H 24 NO 4 + ÁCl À ÁC 3 H 7 OH) (II), and 2-methylpropan-2-ol (C 20 H 24 NO 4 + ÁCl À ÁC 4 H 9 OH) (III). The naltrexone cation can be described as a T-shape made out of two ring systems, a tetrahydro-2H-naphtho [1,8-bc]furan system and a decahydroisoquinolinium subunit, that are nearly perpendicular to one another. The flexible cyclopropylmethyl group can adopt various different conformations in response to its surroundings: an increase of available space around cyclopropylmethyl group may allow it to adopt a more favorable conformation. In all these structures, the alcohol molecules occupy infinite solvent-filled channels. All three compounds described are attractive crystalline forms for unambiguous identification of naltrexone chloride after isolation from a pharmaceutical form. Compound (III) was refined as a two-component twin. Chemical contextAlcohol and opiate dependence are potentially life-threatening disorders associated with adverse physical and societal effects including poor social functioning, familial problems, and crime (Compton & Volkow, 2006). One strategy suggested to address these issues is the inclusion of receptor antagonists that reduce, and can even reverse, the euphoric effects of the drug sought by abusers. Naltrexone [systematic name: 17-(cyclopropylmethyl)-3,14-dihydroxy-4,5 -epoxy-morphinan-6-one] is an opioid receptor competitive antagonist that has been widely used to prevent relapse in heroin and other opioiddependent subjects, and has been found to reduce cravings in alcohol-dependent subjects (Roozen et al., 2006). Its structurerelated analogue oxymorphone is a potent -agonist, which differs from naltrexone only in having an N-methyl group in place of an N-cyclopropylmethyl group (Amato et al., 1990). Elucidation of the conformational profile of naltrexone is of fundamental importance in order to determine molecular requirements for the specific binding affinities of this drug, particularly through the possible position of groups responsible for pharmacological action.The most common pharmaceutical form of this compound is naltrexone hydrochloride tablets. The introduction of new crystalline forms of an active pharmaceutical compound provides an opportunity to improve the performance characteristics of a pharmaceutical product. There is a need for new crystalline forms of naltrexone hydrochloride (Nichols et ISSN 2056-9890 al., 2013) as well for new analytical methods of its unambiguous identification. This communication is a continuation of our work on analytical crystallography of opiate compounds (Gauchat & Nazarenko, 2017). Structural commentaryIn all cases, interaction with the alcohol molecules does not affect the geometry of t...

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Section: Chemical Contextmentioning

confidence: 81%

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

2017

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“…While the latter has been reported previously [16], no hydrogen positions were determined which precludes discussions of inter-and intramolecular interactions. The molecular and crystal structures of tetrachlorido cuprate and cobaltate salts are known [17], as are the crystal and molecular structures of the neutral parent opioid dextromethorphan [18,19]. The latter has found use as cough medication and has received renewed attention as potential remedy for several symptoms of Alzheimer's disease [20].…”

Section: Commentmentioning

confidence: 99%

Structure redetermination of dextromethorphan hydrobromide monohydrate, C₁₈H₂₈BrNO₂ – localization of hydrogen atoms

Muller

Hosten

Betz

2021

Zeitschrift Für Kristallographie - New Crystal Structures

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Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate

Abstract: In the crystal structures of title compounds, two identical protonated dextromethorphan cations are connected to tetrachloridocobaltate (or tetrachloridocuprate) anions via strong N—H⋯Cl hydrogen bonds, forming neutral ion associates

Cited by 2 publications

References 10 publications

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

Structure redetermination of dextromethorphan hydrobromide monohydrate, C₁₈H₂₈BrNO₂ – localization of hydrogen atoms

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Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate

Abstract: In the crystal structures of title compounds, two identical protonated dextromethorphan cations are connected to tetra­chlorido­cobaltate (or tetra­chlorido­cuprate) anions via strong N—H⋯Cl hydrogen bonds, forming neutral ion associates

Cited by 2 publications

References 10 publications

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

Crystal structure of naltrexone chloride solvates with ethanol, propan-2-ol, and 2-methylpropan-2-ol

Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms

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Abstract: In the crystal structures of title compounds, two identical protonated dextromethorphan cations are connected to tetrachloridocobaltate (or tetrachloridocuprate) anions via strong N—H⋯Cl hydrogen bonds, forming neutral ion associates

Structure redetermination of dextromethorphan hydrobromide monohydrate, C₁₈H₂₈BrNO₂ – localization of hydrogen atoms